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Currently one of the largest Farm/Residential Estates available in the State of Maryland and a once in a lifetime opportunity to own it. This 662+ acres waterfront property with 1.8 miles of shoreline known as "Middleville" circa 1880 is truly a magnificent landholding. Located in Talbot County the property is improved with 5 Residents. A newly renovated Main Home that boasts Tidewater Colonial mature coastal charm and expansive views of the water, 3 Guests homes, a Caretakers home and numerous storage and outbuildings. The Land itself consists of 5 parcels making up 390+/- acres of fertile cropland, 175+/- acres of mature forest, 7+ acre waterfowl holding/stocked fishpond, and 6 well fed water-controlled waterfowl impoundments. The property is improved with a pier that has two boats lifts with additional mooring and over 1200' of shoreline revetment. Enormous effort has been directed toward wildlife habitat improvement with an emphasis on waterfowl and quality game. This 'turn -key’ farm on Maryland’s Eastern Shore is a rare find and opportunity, as land is timeless and the chance to own it is not.

4 Beds ⋅ 3 Baths

Currently one of the largest Farm/Residential Estates available in the State of Maryland and a once in a lifetime opportunity to own it. This 662+ acres waterfront property with 1.8 miles of shoreline known as "Middleville" circa 1880 is truly a magnificent landholding. Located in Talbot County the property is improved with 5 Residents. A newly renovated Main Home that boasts Tidewater Colonial mature coastal charm and expansive views of the water, 3 Guests homes, a Caretakers home and numerous storage and outbuildings. The Land itself consists of 5 parcels making up 390+/- acres of fertile cropland, 175+/- acres of mature forest, 7+ acre waterfowl holding/stocked fishpond, and 6 well fed water-controlled waterfowl impoundments. The property is improved with a pier that has two boats lifts with additional mooring and over 1200' of shoreline revetment. Enormous effort has been directed toward wildlife habitat improvement with an emphasis on waterfowl and quality game. This 'turn -key’ farm on Maryland’s Eastern Shore is a rare find and opportunity, as land is timeless and the chance to own it is not.

29031 Howell Point Rd, Trappe

Listing courtesy of Holiday Real Estate. Contact:

Selling Office: Meredith Fine Properties.

$7,000,000

Discover an extraordinary 6.8-acre waterfront estate on Morgans Point, meticulously crafted for those who seek modern luxury infused with timeless elegance. This custom-designed residence seamlessly blends sophistication, comfort, and exceptional craftsmanship. A private, tree-lined drive leads to an expansive motor court, setting the stage for the grand two-story foyer that welcomes you inside. Spanning over 24,000 square feet across three levels, this home is designed for both lavish entertaining and relaxed everyday living. The gourmet chef's kitchen (the heartbeat of this home) is equipped with top-tier appliances and custom cabinetry. It flows effortlessly into a spacious covered terrace, offering stunning water views and an ideal space for outdoor living. The main level features a gracious family room, formal dining room, serene sitting room, paneled library, fitness room, sauna, and a glass-enclosed heated indoor pool with a hot tub. A convenient main-level guest suite with patio access adds to the home's versatility, while an elevator connects all floors for ease of movement. The bedroom layout is thoughtfully designed as a private retreat, featuring two luxurious primary suites, three additional ensuite bedrooms, and a separate in-law/au pair suite. The main primary suite is a sanctuary, complete with dual bathrooms (one with heated floors and an "in-mirror TV"), a cozy sitting area, a fireplace, and a large covered balcony overlooking the serene river. Outdoor spaces are designed to maximize the breathtaking water views, with expansive covered areas and a resort-style terrace. The private pier, equipped with two boat lifts, four jet ski lifts, and a floating dock (5' MLW, buyer to verify), offers endless opportunities for waterfront enjoyment. The lower level is an entertainer's dream, featuring a full bar, wine cellar, game room, secondary kitchen, theater room, and a discreetly located safe room with a vault and full bath for added security. Car enthusiasts will appreciate the expansive 73x30 four-car garage with soaring ceilings, complemented by an additional in-law/au pair suite above, complete with a full kitchen and family room. Nestled in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC, Northern Virginia, Annapolis, and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

6 Beds ⋅ 13 Baths

Discover an extraordinary 6.8-acre waterfront estate on Morgans Point, meticulously crafted for those who seek modern luxury infused with timeless elegance. This custom-designed residence seamlessly blends sophistication, comfort, and exceptional craftsmanship. A private, tree-lined drive leads to an expansive motor court, setting the stage for the grand two-story foyer that welcomes you inside. Spanning over 24,000 square feet across three levels, this home is designed for both lavish entertaining and relaxed everyday living. The gourmet chef's kitchen (the heartbeat of this home) is equipped with top-tier appliances and custom cabinetry. It flows effortlessly into a spacious covered terrace, offering stunning water views and an ideal space for outdoor living. The main level features a gracious family room, formal dining room, serene sitting room, paneled library, fitness room, sauna, and a glass-enclosed heated indoor pool with a hot tub. A convenient main-level guest suite with patio access adds to the home's versatility, while an elevator connects all floors for ease of movement. The bedroom layout is thoughtfully designed as a private retreat, featuring two luxurious primary suites, three additional ensuite bedrooms, and a separate in-law/au pair suite. The main primary suite is a sanctuary, complete with dual bathrooms (one with heated floors and an "in-mirror TV"), a cozy sitting area, a fireplace, and a large covered balcony overlooking the serene river. Outdoor spaces are designed to maximize the breathtaking water views, with expansive covered areas and a resort-style terrace. The private pier, equipped with two boat lifts, four jet ski lifts, and a floating dock (5' MLW, buyer to verify), offers endless opportunities for waterfront enjoyment. The lower level is an entertainer's dream, featuring a full bar, wine cellar, game room, secondary kitchen, theater room, and a discreetly located safe room with a vault and full bath for added security. Car enthusiasts will appreciate the expansive 73x30 four-car garage with soaring ceilings, complemented by an additional in-law/au pair suite above, complete with a full kitchen and family room. Nestled in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC, Northern Virginia, Annapolis, and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

5369 Morgans Point Dr, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$6,000,000

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen with vaulted ceiling and excellent light, stainless steel commercial grade appliances, granite countertops. Beautiful draperies throughout the house, and gilded valances in LR. Old wing can serve as caretaker's quarters or home office/conference area or additional BR space. 17 x 16 second story deck off old wing, with outside staircase as well as interior access. Poolside screened porch 17 x 17 with adjacent brick terrace 12 x 26. Front brick floored open porch 12 x 48 with open porch of same size above. Elevator accesses all three stories and is designed for a wheelchair use. Primary bedroom suite has walk-in closets, two large bathrooms, and dressing room with fireplace. Bar off FR has built-ins, two wine refrigerators and an ice machine. Pool 22 x 44 plus apron and brick wall. Pool is long enough for lap swimming. Loop-lock cover is almost new. HIGH SPEED FIBEROPTIC INTERNET SERVICE is available from Easton Velocity. The line has just been run. Owner has not yet connected. Close to the amenities of St. Michaels, with shopping, restaurants and Chesapeake Bay Maritime Museum. Talbot County has an airport on the northwest edge of Easton. 2700 sq ft caretaker's/guest house remodeled 2004/2005. 9.5 ft ceilings; 15 x 6 foyer; 17x 12 eat-in K; 23' x 19' LR with f/p and built in bookcases; 16 ft sq screened porch with great water view;; half bath.; first floor BR 19 x 13 with f/p and en-suite bath; 2d story has 17x 13 BR with fireplace and en-suite bath, 15 x 13 sitting room, 15 x 14 BR. full bath. "B.A.T" (best available technology) septic system new in 2025. Guest house roof less than two years old. Flower cutting beds, vegetable garden and orchard. Art studio (16 ft square) on high ground close to Tilghman Creek. Extensive barns and sheds, including a barn with 5 stalls, tack room and hayloft. Horse caretaker's apartment near barns. Incredible camellias, flowering trees, Spring bulbs. Rich Neck Manor is Talbot County's earliest land grant (1649/1651), The main block of the house was built for Samuel Harrison ca. 1824, Original pine floors, late Federal paneled doors and surrounds, elegant three-story staircase, mantelpieces, etc. The brick dairy (12 x 22) is an architectural "folly" built by Harrison, now used as a chapel. Attached to the Harrison house is a ca. 1740 gambrel-roofed brick kitchen (16 x 36) dating to the days of Matthew Tilghman Ward, while the brick smokehouse (20 x 20), and caretaker/guest house date to ca 1790. Rich Neck Manor was also the home of Revolutionary War patriot Matthew Tilghman. See attachments for history. This property is protected by a land conservation easement and by a MHT historical easement (see documents attached to this listing). The easement holders are helpful with advice and share their knowledge and experience. Hunting is outstanding on this property and the hunting rights are available to buyer. Fishing is unsurpassed, and the Miles River crabs are said to be the largest, heaviest crabs on the Shore. WATER DEPTH: the deepwater harbor is on Tilghman Creek. The "dock" is next to the art studio and consists of a bulkheaded and backfilled area with pilings and slips. It is believed that this area was dredged, but the current depth is uncertain. There is an electronic boat lift here. It has been suggested that the new owner should construct a pier perpendicular to the shore, thereby securing very deep water. The mooring belongs to this property and according to chart has 16 ft mlw. Available partly furnished.

8 Beds ⋅ 5 Baths

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen with vaulted ceiling and excellent light, stainless steel commercial grade appliances, granite countertops. Beautiful draperies throughout the house, and gilded valances in LR. Old wing can serve as caretaker's quarters or home office/conference area or additional BR space. 17 x 16 second story deck off old wing, with outside staircase as well as interior access. Poolside screened porch 17 x 17 with adjacent brick terrace 12 x 26. Front brick floored open porch 12 x 48 with open porch of same size above. Elevator accesses all three stories and is designed for a wheelchair use. Primary bedroom suite has walk-in closets, two large bathrooms, and dressing room with fireplace. Bar off FR has built-ins, two wine refrigerators and an ice machine. Pool 22 x 44 plus apron and brick wall. Pool is long enough for lap swimming. Loop-lock cover is almost new. HIGH SPEED FIBEROPTIC INTERNET SERVICE is available from Easton Velocity. The line has just been run. Owner has not yet connected. Close to the amenities of St. Michaels, with shopping, restaurants and Chesapeake Bay Maritime Museum. Talbot County has an airport on the northwest edge of Easton. 2700 sq ft caretaker's/guest house remodeled 2004/2005. 9.5 ft ceilings; 15 x 6 foyer; 17x 12 eat-in K; 23' x 19' LR with f/p and built in bookcases; 16 ft sq screened porch with great water view;; half bath.; first floor BR 19 x 13 with f/p and en-suite bath; 2d story has 17x 13 BR with fireplace and en-suite bath, 15 x 13 sitting room, 15 x 14 BR. full bath. "B.A.T" (best available technology) septic system new in 2025. Guest house roof less than two years old. Flower cutting beds, vegetable garden and orchard. Art studio (16 ft square) on high ground close to Tilghman Creek. Extensive barns and sheds, including a barn with 5 stalls, tack room and hayloft. Horse caretaker's apartment near barns. Incredible camellias, flowering trees, Spring bulbs. Rich Neck Manor is Talbot County's earliest land grant (1649/1651), The main block of the house was built for Samuel Harrison ca. 1824, Original pine floors, late Federal paneled doors and surrounds, elegant three-story staircase, mantelpieces, etc. The brick dairy (12 x 22) is an architectural "folly" built by Harrison, now used as a chapel. Attached to the Harrison house is a ca. 1740 gambrel-roofed brick kitchen (16 x 36) dating to the days of Matthew Tilghman Ward, while the brick smokehouse (20 x 20), and caretaker/guest house date to ca 1790. Rich Neck Manor was also the home of Revolutionary War patriot Matthew Tilghman. See attachments for history. This property is protected by a land conservation easement and by a MHT historical easement (see documents attached to this listing). The easement holders are helpful with advice and share their knowledge and experience. Hunting is outstanding on this property and the hunting rights are available to buyer. Fishing is unsurpassed, and the Miles River crabs are said to be the largest, heaviest crabs on the Shore. WATER DEPTH: the deepwater harbor is on Tilghman Creek. The "dock" is next to the art studio and consists of a bulkheaded and backfilled area with pilings and slips. It is believed that this area was dredged, but the current depth is uncertain. There is an electronic boat lift here. It has been suggested that the new owner should construct a pier perpendicular to the shore, thereby securing very deep water. The mooring belongs to this property and according to chart has 16 ft mlw. Available partly furnished.

10770 Rich Neck Rd, Claiborne

Listing courtesy of Shoreline Realty. Contact:

Selling Office: Unrepresented.

$6,000,000

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen with vaulted ceiling and excellent light, stainless steel commercial grade appliances, granite countertops. Beautiful draperies throughout the house, and gilded valances in LR. Old wing can serve as caretaker's quarters or home office/conference area or additional BR space. 17 x 16 second story deck off old wing, with outside staircase as well as interior access. Poolside screened porch 17 x 17 with adjacent brick terrace 12 x 26. Front brick floored open porch 12 x 48 with open porch of same size above. Elevator accesses all three stories and is designed for a wheelchair use. Primary bedroom suite has walk-in closets, two large bathrooms, and dressing room with fireplace. Bar off FR has built-ins, two wine refrigerators and an ice machine. Pool 22 x 44 plus apron and brick wall. Pool is long enough for lap swimming. Loop-lock cover is almost new. HIGH SPEED FIBEROPTIC INTERNET SERVICE is available from Easton Velocity. The line has just been run. Owner has not yet connected. Close to the amenities of St. Michaels, with shopping, restaurants and Chesapeake Bay Maritime Museum. Talbot County has an airport on the northwest edge of Easton. 2700 sq ft caretaker's/guest house remodeled 2004/2005. 9.5 ft ceilings; 15 x 6 foyer; 17x 12 eat-in K; 23' x 19' LR with f/p and built in bookcases; 16 ft sq screened porch with great water view;; half bath.; first floor BR 19 x 13 with f/p and en-suite bath; 2d story has 17x 13 BR with fireplace and en-suite bath, 15 x 13 sitting room, 15 x 14 BR. full bath. "B.A.T" (best available technology) septic system new in 2025. Guest house roof less than two years old. Flower cutting beds, vegetable garden and orchard. Art studio (16 ft square) on high ground close to Tilghman Creek. Extensive barns and sheds, including a barn with 5 stalls, tack room and hayloft. Horse caretaker's apartment near barns. Incredible camellias, flowering trees, Spring bulbs. Rich Neck Manor is Talbot County's earliest land grant (1649/1651), The main block of the house was built for Samuel Harrison ca. 1824, Original pine floors, late Federal paneled doors and surrounds, elegant three-story staircase, mantelpieces, etc. The brick dairy (12 x 22) is an architectural "folly" built by Harrison, now used as a chapel. Attached to the Harrison house is a ca. 1740 gambrel-roofed brick kitchen (16 x 36) dating to the days of Matthew Tilghman Ward, while the brick smokehouse (20 x 20), and caretaker/guest house date to ca 1790. Rich Neck Manor was also the home of Revolutionary War patriot Matthew Tilghman. See attachments for history. This property is protected by a land conservation easement and by a MHT historical easement (see documents attached to this listing). The easement holders are helpful with advice and share their knowledge and experience. Hunting is outstanding on this property and the hunting rights are available to buyer. Fishing is unsurpassed, and the Miles River crabs are said to be the largest, heaviest crabs on the Shore. WATER DEPTH: the deepwater harbor is on Tilghman Creek. The "dock" is next to the art studio and consists of a bulkheaded and backfilled area with pilings and slips. It is believed that this area was dredged, but the current depth is uncertain. There is an electronic boat lift here. It has been suggested that the new owner should construct a pier perpendicular to the shore, thereby securing very deep water. The mooring belongs to this property Available partly furnished.

8 Beds ⋅ 5 Baths

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen with vaulted ceiling and excellent light, stainless steel commercial grade appliances, granite countertops. Beautiful draperies throughout the house, and gilded valances in LR. Old wing can serve as caretaker's quarters or home office/conference area or additional BR space. 17 x 16 second story deck off old wing, with outside staircase as well as interior access. Poolside screened porch 17 x 17 with adjacent brick terrace 12 x 26. Front brick floored open porch 12 x 48 with open porch of same size above. Elevator accesses all three stories and is designed for a wheelchair use. Primary bedroom suite has walk-in closets, two large bathrooms, and dressing room with fireplace. Bar off FR has built-ins, two wine refrigerators and an ice machine. Pool 22 x 44 plus apron and brick wall. Pool is long enough for lap swimming. Loop-lock cover is almost new. HIGH SPEED FIBEROPTIC INTERNET SERVICE is available from Easton Velocity. The line has just been run. Owner has not yet connected. Close to the amenities of St. Michaels, with shopping, restaurants and Chesapeake Bay Maritime Museum. Talbot County has an airport on the northwest edge of Easton. 2700 sq ft caretaker's/guest house remodeled 2004/2005. 9.5 ft ceilings; 15 x 6 foyer; 17x 12 eat-in K; 23' x 19' LR with f/p and built in bookcases; 16 ft sq screened porch with great water view;; half bath.; first floor BR 19 x 13 with f/p and en-suite bath; 2d story has 17x 13 BR with fireplace and en-suite bath, 15 x 13 sitting room, 15 x 14 BR. full bath. "B.A.T" (best available technology) septic system new in 2025. Guest house roof less than two years old. Flower cutting beds, vegetable garden and orchard. Art studio (16 ft square) on high ground close to Tilghman Creek. Extensive barns and sheds, including a barn with 5 stalls, tack room and hayloft. Horse caretaker's apartment near barns. Incredible camellias, flowering trees, Spring bulbs. Rich Neck Manor is Talbot County's earliest land grant (1649/1651), The main block of the house was built for Samuel Harrison ca. 1824, Original pine floors, late Federal paneled doors and surrounds, elegant three-story staircase, mantelpieces, etc. The brick dairy (12 x 22) is an architectural "folly" built by Harrison, now used as a chapel. Attached to the Harrison house is a ca. 1740 gambrel-roofed brick kitchen (16 x 36) dating to the days of Matthew Tilghman Ward, while the brick smokehouse (20 x 20), and caretaker/guest house date to ca 1790. Rich Neck Manor was also the home of Revolutionary War patriot Matthew Tilghman. See attachments for history. This property is protected by a land conservation easement and by a MHT historical easement (see documents attached to this listing). The easement holders are helpful with advice and share their knowledge and experience. Hunting is outstanding on this property and the hunting rights are available to buyer. Fishing is unsurpassed, and the Miles River crabs are said to be the largest, heaviest crabs on the Shore. WATER DEPTH: the deepwater harbor is on Tilghman Creek. The "dock" is next to the art studio and consists of a bulkheaded and backfilled area with pilings and slips. It is believed that this area was dredged, but the current depth is uncertain. There is an electronic boat lift here. It has been suggested that the new owner should construct a pier perpendicular to the shore, thereby securing very deep water. The mooring belongs to this property Available partly furnished.

10770 Rich Neck Rd, Claiborne

Listing courtesy of Shoreline Realty. Contact:

Selling Office: Unrepresented.

$5,250,000

Major price reduction! Welcome to Henry’s Retreat, an extraordinary 37-acre waterfront estate overlooking Quarter Cove off the Wye River. Offering over 2,700 feet of shoreline, this stunning property ensures ultimate privacy, breathtaking views, and unforgettable sunsets. Built in 2016, the 8,835 sq. ft. main residence is designed for luxurious living and seamless entertaining, featuring five bedrooms, six full baths, and two half baths. The main-level primary suite boasts sweeping water views, an expansive ensuite dressing room/closet, and a spa-like bath with a glass-enclosed walk-in shower, soaking tub, and private laundry. The heart of the home is the chef’s kitchen, bathed in natural light and equipped with a granite center island, Thermador stainless appliances, and a striking barrel-vaulted ceiling. The adjoining sunroom, with its octagonal pitched ceiling and 180-degree windows, is anchored by a beautiful stone fireplace. The great room impresses with soaring ceilings and a woodburning stone fireplace, while the dining room showcases custom barnwood accents and wine storage. The second level features four additional bedrooms (one currently an office), four full baths (three ensuite), a fitness room, secondary laundry, and a conservatory overlooking the great room. The finished lower level is an entertainer’s dream, complete with a theater room, billiard area, wet bar, full bath, and ample storage. Equestrian enthusiasts will love the thoughtfully designed five-stall barn, each with a private paddock. The barn also includes a heated wash stall, climate-controlled tack room, bathroom, laundry, hay storage, and an enclosed equipment shed. A regulation-sized dressage ring and four interlocking fenced pastures further enhance the property. Complementing the estate’s natural beauty are eight raised garden beds and a charming orchard with apple and peach trees. Waterfront amenities include a 125’ private pier with three slips, three boat lifts, water, electricity, and deep water (7’-8’+/- MLW). Rounding out this exceptional retreat are an attached three-car garage with a dedicated workshop, an inground saltwater pool, a covered pavilion with an outdoor kitchen, and a hot tub. Truly a one-of-a-kind offering, Henry’s Retreat is the perfect blend of luxury, recreation, and serenity. Close to fine dining, shopping, theater, galleries, and Easton’s jet airport, the property is conveniently located 1.5 hours from DC and Baltimore, and 2 hours from Philadelphia.

6 Beds ⋅ 8 Baths

Major price reduction! Welcome to Henry’s Retreat, an extraordinary 37-acre waterfront estate overlooking Quarter Cove off the Wye River. Offering over 2,700 feet of shoreline, this stunning property ensures ultimate privacy, breathtaking views, and unforgettable sunsets. Built in 2016, the 8,835 sq. ft. main residence is designed for luxurious living and seamless entertaining, featuring five bedrooms, six full baths, and two half baths. The main-level primary suite boasts sweeping water views, an expansive ensuite dressing room/closet, and a spa-like bath with a glass-enclosed walk-in shower, soaking tub, and private laundry. The heart of the home is the chef’s kitchen, bathed in natural light and equipped with a granite center island, Thermador stainless appliances, and a striking barrel-vaulted ceiling. The adjoining sunroom, with its octagonal pitched ceiling and 180-degree windows, is anchored by a beautiful stone fireplace. The great room impresses with soaring ceilings and a woodburning stone fireplace, while the dining room showcases custom barnwood accents and wine storage. The second level features four additional bedrooms (one currently an office), four full baths (three ensuite), a fitness room, secondary laundry, and a conservatory overlooking the great room. The finished lower level is an entertainer’s dream, complete with a theater room, billiard area, wet bar, full bath, and ample storage. Equestrian enthusiasts will love the thoughtfully designed five-stall barn, each with a private paddock. The barn also includes a heated wash stall, climate-controlled tack room, bathroom, laundry, hay storage, and an enclosed equipment shed. A regulation-sized dressage ring and four interlocking fenced pastures further enhance the property. Complementing the estate’s natural beauty are eight raised garden beds and a charming orchard with apple and peach trees. Waterfront amenities include a 125’ private pier with three slips, three boat lifts, water, electricity, and deep water (7’-8’+/- MLW). Rounding out this exceptional retreat are an attached three-car garage with a dedicated workshop, an inground saltwater pool, a covered pavilion with an outdoor kitchen, and a hot tub. Truly a one-of-a-kind offering, Henry’s Retreat is the perfect blend of luxury, recreation, and serenity. Close to fine dining, shopping, theater, galleries, and Easton’s jet airport, the property is conveniently located 1.5 hours from DC and Baltimore, and 2 hours from Philadelphia.

11977 Billys Point Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Unrepresented Buyer Office.

$3,950,000

Willow Oak Farm is a rare and storied waterfront estate set on 20.0+/- acres along the shores of Harris Creek in Bozman, Maryland. Originally established in 1892, the property offers approximately 983 feet of waterfront and expansive open water views, with exceptional privacy just minutes from St. Michaels and Easton. The 6,000-square-foot French Eclectic main residence, built in 1921, features four en-bedrooms, grand entertaining spaces, and a seamless balance of formal and casual living. A separate cottage provides additional accommodations or workspace. Extensively renovated and modernized by the current owners, the home and infrastructure have been comprehensively upgraded while preserving historic character, creating a turnkey estate designed for both everyday living and refined entertaining.

4 Beds ⋅ 6 Baths

Willow Oak Farm is a rare and storied waterfront estate set on 20.0+/- acres along the shores of Harris Creek in Bozman, Maryland. Originally established in 1892, the property offers approximately 983 feet of waterfront and expansive open water views, with exceptional privacy just minutes from St. Michaels and Easton. The 6,000-square-foot French Eclectic main residence, built in 1921, features four en-bedrooms, grand entertaining spaces, and a seamless balance of formal and casual living. A separate cottage provides additional accommodations or workspace. Extensively renovated and modernized by the current owners, the home and infrastructure have been comprehensively upgraded while preserving historic character, creating a turnkey estate designed for both everyday living and refined entertaining.

7288 Bozman Neavitt Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$3,950,000

Tucked within a canopy of trees along Maryland’s Eastern Shore, this remarkable home rests quietly beside the Choptank River. The setting feels worlds away, eighty acres of meadows and woodland that open gently to more than 1,800 feet of private shoreline, where a western exposure captures breathtaking sunsets reflected across the water. The residence at 5084 Ferry Neck Road was shaped by owners whose careers in fine contemporary art inspired a deeply thoughtful approach to design, one that explored geometry, light, and proportion with an almost abstract eye. The resulting octagonal plan draws the landscape into every room, creating a calm rhythm of space and view. A low, horizontal brick façade settles the home into its surroundings, while a lifted roofline and generous overhangs give shelter and balance. Inside, a sweeping staircase curves upward through the central volume, a graceful gesture that anchors the home with quiet strength. In 2024, the property underwent a comprehensive renewal. Porcelain countertops, new glazing, and refined lighting bring a fresh modern sensibility while honoring the original architecture. Approached by a long, tree-lined drive, the home reveals itself gradually, first a glimmer through the woods, then an opening to water and sky. Beyond its immediate beauty, the land itself offers a rare opportunity, with the potential to create a divisible waterfront homesite should the next owner wish to explore it. What remains most striking, however, is its sense of comfort, a home that is inviting, shaped by art, nature, and time.

4 Beds ⋅ 4 Baths

Tucked within a canopy of trees along Maryland’s Eastern Shore, this remarkable home rests quietly beside the Choptank River. The setting feels worlds away, eighty acres of meadows and woodland that open gently to more than 1,800 feet of private shoreline, where a western exposure captures breathtaking sunsets reflected across the water. The residence at 5084 Ferry Neck Road was shaped by owners whose careers in fine contemporary art inspired a deeply thoughtful approach to design, one that explored geometry, light, and proportion with an almost abstract eye. The resulting octagonal plan draws the landscape into every room, creating a calm rhythm of space and view. A low, horizontal brick façade settles the home into its surroundings, while a lifted roofline and generous overhangs give shelter and balance. Inside, a sweeping staircase curves upward through the central volume, a graceful gesture that anchors the home with quiet strength. In 2024, the property underwent a comprehensive renewal. Porcelain countertops, new glazing, and refined lighting bring a fresh modern sensibility while honoring the original architecture. Approached by a long, tree-lined drive, the home reveals itself gradually, first a glimmer through the woods, then an opening to water and sky. Beyond its immediate beauty, the land itself offers a rare opportunity, with the potential to create a divisible waterfront homesite should the next owner wish to explore it. What remains most striking, however, is its sense of comfort, a home that is inviting, shaped by art, nature, and time.

5084 Ferry Neck Rd, Royal Oak

Listing courtesy of TTR Sothebys International Realty. Contact:

Selling Office: Non Subscribing Office.

$3,900,000

*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* NOTE: Has public sewer and well. Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**

20 Beds ⋅ 24 Baths

*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* NOTE: Has public sewer and well. Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**

21384 Coopertown Rd, Tilghman

Listing courtesy of Compass. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$3,900,000

*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inn’s serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**

21384 Coopertown Rd, Tilghman

Listing courtesy of Compass. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$3,350,000

Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

5 Beds ⋅ 6 Baths

Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

25610 Chance Farm Ct, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Century 21 Redwood Realty.

$3,200,000

4 Beds ⋅ 6 Baths

703 Riverview Ter, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

$3,200,000

Welcome to Rivermark - a true waterfront retreat in St. Michaels on the Eastern Shore. This custom-built home is an artistic masterpiece with five octagonal interconnected wings, creating distinct yet flowing spaces and breathtaking panoramic views of Porters Creek, Miles River, Wye River and the Eastern Bay from every room. With architecture inspired by the French West Indies, this home has been thoughtfully designed with both entertainment and relaxation in mind. Entering through the foyer, the heart of the home is the Great Room which contains soaring ceilings. This opens to a sun-drenched solarium with travertine flooring and floor-to-ceiling windows that wrap around the interconnected spaces of the sunroom, dining room, and kitchen. Entertaining guests is effortless with the gourmet kitchen that is fully equipped with stainless steel appliances, an Aga stove, granite countertops, a large center island, and custom shelving/cabinetry. With both garden and water views the dual office/study spaces have custom floor-to-ceiling built-ins and wood paneling. The primary suite and a sanctuary unto itself, constructed with 18-foot ceilings and a spa-inspired en-suite bathroom fireplace and private outdoor patio. On the opposite wing of the home, you'll discover two additional bright bedrooms with custom lighting and a spacious shared bathroom. A unique feature of this property is the spa-inspired, glass enclosed swimming pool which overlooks the Miles River. The area is complete with an adjacent sunroom, green house, sauna, and full bath in this zen-like setting. A separate guest house provides privacy with its own entrance, offering two bedrooms, two bathrooms, a kitchen, and a comfortable living space. Outdoors, this property offers a rarely available opportunity of 750 feet of a rip-rapped waterfront, deep waters and a 150-foot private dock with boat lift - offering direct access to the Eastern Shore’s waterways and nearby waterfront dining. The extensive professionally manicured landscaped grounds feature a tranquil koi pond with a fountain, lush gardens, abundant verdant trees, and brick patio with grill area. Rivermark was featured by the Talbot County Garden Club in the Maryland House & Garden Pilgrimage. Don’t miss your chance to view this unique property in person to appreciate the incredible details. Experience the best of St. Michaels living at Rivermark—where luxury, comfort, and natural beauty converge in perfect harmony.

5 Beds ⋅ 6 Baths

Welcome to Rivermark - a true waterfront retreat in St. Michaels on the Eastern Shore. This custom-built home is an artistic masterpiece with five octagonal interconnected wings, creating distinct yet flowing spaces and breathtaking panoramic views of Porters Creek, Miles River, Wye River and the Eastern Bay from every room. With architecture inspired by the French West Indies, this home has been thoughtfully designed with both entertainment and relaxation in mind. Entering through the foyer, the heart of the home is the Great Room which contains soaring ceilings. This opens to a sun-drenched solarium with travertine flooring and floor-to-ceiling windows that wrap around the interconnected spaces of the sunroom, dining room, and kitchen. Entertaining guests is effortless with the gourmet kitchen that is fully equipped with stainless steel appliances, an Aga stove, granite countertops, a large center island, and custom shelving/cabinetry. With both garden and water views the dual office/study spaces have custom floor-to-ceiling built-ins and wood paneling. The primary suite and a sanctuary unto itself, constructed with 18-foot ceilings and a spa-inspired en-suite bathroom fireplace and private outdoor patio. On the opposite wing of the home, you'll discover two additional bright bedrooms with custom lighting and a spacious shared bathroom. A unique feature of this property is the spa-inspired, glass enclosed swimming pool which overlooks the Miles River. The area is complete with an adjacent sunroom, green house, sauna, and full bath in this zen-like setting. A separate guest house provides privacy with its own entrance, offering two bedrooms, two bathrooms, a kitchen, and a comfortable living space. Outdoors, this property offers a rarely available opportunity of 750 feet of a rip-rapped waterfront, deep waters and a 150-foot private dock with boat lift - offering direct access to the Eastern Shore’s waterways and nearby waterfront dining. The extensive professionally manicured landscaped grounds feature a tranquil koi pond with a fountain, lush gardens, abundant verdant trees, and brick patio with grill area. Rivermark was featured by the Talbot County Garden Club in the Maryland House & Garden Pilgrimage. Don’t miss your chance to view this unique property in person to appreciate the incredible details. Experience the best of St. Michaels living at Rivermark—where luxury, comfort, and natural beauty converge in perfect harmony.

9791 Pintail Pl, Saint Michaels

Listing courtesy of Compass. Contact:

Selling Office: Benson & Mangold, LLC.

$3,088,000

Originally constructed in 1970 and extensively renovated in 2018, the main residence embodies refined sophistication and modern comfort. The open-concept floor plan seamlessly connects living, dining, and kitchen spaces, highlighted by high-quality hardwood floors, custom built-ins, and shiplap detailing that harmonize timeless charm with contemporary luxury. A chef’s kitchen with premium custom cabinetry, upscale appliances, quartz countertops, and a striking center island flows effortlessly into the living room and casual dining space. Anchored by a double-sided wood-burning fireplace, these areas connect gracefully to a formal dining room. Expansive sliding glass doors and oversized windows frame tranquil water views of Gross Creek. The luxurious primary suite boasts panoramic waterfront vistas, an exceptional walk-in closet with sauna, and a spa-like en-suite bath featuring a freestanding soaking tub, expansive tiled shower, marble accents, and refined fixtures. Additional highlights include three guest suites with private baths, and a workshop within the oversized two-car garage. Outdoors, an inviting wraparound brick patio and covered porch provides serene space to relax, enjoying the waterfront views and lush landscape. The property's gentle elevation comfortably positions all structures above the floodplain, complementing its mature, peaceful setting. Two pastures, each approximately 3.5 ac, offer flexibility for livestock or natural habitat restoration. Mature Willow Oaks lining the paved driveway complete the property's picturesque Eastern Shore charm. The waterfront guest house offers both privacy and comfort, featuring a farmhouse-inspired kitchen with primary suite including private half bath. Sliding doors open onto a covered waterside porch and patio, ideal for tranquil mornings and scenic sunsets. Enhanced by modern HVAC, LVP flooring, and laundry, this residence is perfect for extended stays or guests desiring independent accommodations. The caretaker cottage is situated apart from the main residence and discreetly screened by farmland and mature greenery, including its own parking area and separate driveway. Fully renovated, it provides three bedrooms, two baths, efficient mini splits, and low-maintenance LVP flooring. The greenhouse and crafting workshop offers functionality and charm, delighting gardeners, crafters, and hobbyists alike. The greenhouse includes irrigation, raised beds, and a potting shed, while the adjacent crafting workshop provides a welcoming farmhouse aesthetic with ample workspace bordered by mature hydrangeas further enhancing this delightful space. The pole building provides extensive accommodations for woodworking, automotive projects, marine storage, or machinery. Equipped with three-phase power, 12-ft-tall garage doors, an automotive lift, durable interior finishes, and abundant workspace, it is ideal for hobbyists or professionals requiring a versatile, temperature controlled environment. Ideally located just 7 mi from Easton Airport (ESN), 9 mi from downtown Easton, and a leisurely seven-mile boat ride to St. Michaels, Court Road Farm represents an exceptional opportunity to acquire a distinctive waterfront estate.

4 Beds ⋅ 4 Baths

Originally constructed in 1970 and extensively renovated in 2018, the main residence embodies refined sophistication and modern comfort. The open-concept floor plan seamlessly connects living, dining, and kitchen spaces, highlighted by high-quality hardwood floors, custom built-ins, and shiplap detailing that harmonize timeless charm with contemporary luxury. A chef’s kitchen with premium custom cabinetry, upscale appliances, quartz countertops, and a striking center island flows effortlessly into the living room and casual dining space. Anchored by a double-sided wood-burning fireplace, these areas connect gracefully to a formal dining room. Expansive sliding glass doors and oversized windows frame tranquil water views of Gross Creek. The luxurious primary suite boasts panoramic waterfront vistas, an exceptional walk-in closet with sauna, and a spa-like en-suite bath featuring a freestanding soaking tub, expansive tiled shower, marble accents, and refined fixtures. Additional highlights include three guest suites with private baths, and a workshop within the oversized two-car garage. Outdoors, an inviting wraparound brick patio and covered porch provides serene space to relax, enjoying the waterfront views and lush landscape. The property's gentle elevation comfortably positions all structures above the floodplain, complementing its mature, peaceful setting. Two pastures, each approximately 3.5 ac, offer flexibility for livestock or natural habitat restoration. Mature Willow Oaks lining the paved driveway complete the property's picturesque Eastern Shore charm. The waterfront guest house offers both privacy and comfort, featuring a farmhouse-inspired kitchen with primary suite including private half bath. Sliding doors open onto a covered waterside porch and patio, ideal for tranquil mornings and scenic sunsets. Enhanced by modern HVAC, LVP flooring, and laundry, this residence is perfect for extended stays or guests desiring independent accommodations. The caretaker cottage is situated apart from the main residence and discreetly screened by farmland and mature greenery, including its own parking area and separate driveway. Fully renovated, it provides three bedrooms, two baths, efficient mini splits, and low-maintenance LVP flooring. The greenhouse and crafting workshop offers functionality and charm, delighting gardeners, crafters, and hobbyists alike. The greenhouse includes irrigation, raised beds, and a potting shed, while the adjacent crafting workshop provides a welcoming farmhouse aesthetic with ample workspace bordered by mature hydrangeas further enhancing this delightful space. The pole building provides extensive accommodations for woodworking, automotive projects, marine storage, or machinery. Equipped with three-phase power, 12-ft-tall garage doors, an automotive lift, durable interior finishes, and abundant workspace, it is ideal for hobbyists or professionals requiring a versatile, temperature controlled environment. Ideally located just 7 mi from Easton Airport (ESN), 9 mi from downtown Easton, and a leisurely seven-mile boat ride to St. Michaels, Court Road Farm represents an exceptional opportunity to acquire a distinctive waterfront estate.

27047 Presquile Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$3,015,000

SERENE VIEWS AWAIT YOU AT YOUR EXCLUSIVE WATERFRONT , GORGEOUS ACRES ON PRIVATE MAJESTIC PENINSULA IN BETWEEN THE COASTAL TOWNS ST MICHAELS , EASTON. JUST A SHORT DRIVE TO ITS SHOPS, RESTAURANTS, CAFES, MUSEUMS AND ALL THE AREA HAS TO OFFER. THIS FABULOUS PROPERTY LETS YOU EXPERIENCE EASTERN SHORE LIFE STYLE AS ITS BEST. OPERATED AS A SUCESSFUL VACATION RENTAL IT HAS GONE THRU VARIOUS RENOVATIONS, LASTLY A MAJOR ONE IN 2020 AND 2021. YOUR CHANCE TO PURCHASE A 6 BEDROOM 6 BATHROOM TURN KEY PROPERTY TO ENJOY WITH YOUR FAMILY AND SHARE AS A RENTAL WITH FAMILIES THAT COME TO VISIT . THE PROEPRTY IS BEING SOLD TURN KEY WITH ALL CONTENTS.

6 Beds ⋅ 7 Baths

SERENE VIEWS AWAIT YOU AT YOUR EXCLUSIVE WATERFRONT , GORGEOUS ACRES ON PRIVATE MAJESTIC PENINSULA IN BETWEEN THE COASTAL TOWNS ST MICHAELS , EASTON. JUST A SHORT DRIVE TO ITS SHOPS, RESTAURANTS, CAFES, MUSEUMS AND ALL THE AREA HAS TO OFFER. THIS FABULOUS PROPERTY LETS YOU EXPERIENCE EASTERN SHORE LIFE STYLE AS ITS BEST. OPERATED AS A SUCESSFUL VACATION RENTAL IT HAS GONE THRU VARIOUS RENOVATIONS, LASTLY A MAJOR ONE IN 2020 AND 2021. YOUR CHANCE TO PURCHASE A 6 BEDROOM 6 BATHROOM TURN KEY PROPERTY TO ENJOY WITH YOUR FAMILY AND SHARE AS A RENTAL WITH FAMILIES THAT COME TO VISIT . THE PROEPRTY IS BEING SOLD TURN KEY WITH ALL CONTENTS.

6448 Partridge Ln, Royal Oak

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Shore Living Real Estate.

$3,000,000

Beautifully sited on 17.7 acres along the Miles River in one of Easton’s most coveted locations, this quintessential coastal property embodies the essence of Eastern Shore living - casual elegance, timeless architecture, and a seamless connection to the water from nearly every vantage point. The 4,665 sq. ft. residence offers 4–5 bedrooms and 5.5 baths, with formal dining and living rooms, and a cozy den opening to a waterside sunroom and patio. The large kitchen, complete with center island, custom built-ins, and dining area, flows into a bright family room that leads to a covered porch overlooking the river. A butler’s kitchen, laundry area, and adjacent full and half baths add convenience, while a breezeway connects to the attached three-car garage with a guest apartment above. Outdoor living shines with a private dock (two slips, 3.5' MLW), 585 feet of bulkheaded shoreline, a large gunite pool with adjacent gazebo, mature landscaping, and extensive hardscaping. Additional improvements include a detached three-bay garage and a waterside shed for storage and equipment. Owned by the same family since 1978, this exceptional property presents a rare opportunity for a new buyer to personalize a legacy waterfront estate. Note: Approximately 15 acres are enrolled in a Forest Stewardship Plan. Applications have been submitted to Talbot County for a new 4-bedroom septic system and reconstructed pier.

5 Beds ⋅ 6 Baths

Beautifully sited on 17.7 acres along the Miles River in one of Easton’s most coveted locations, this quintessential coastal property embodies the essence of Eastern Shore living - casual elegance, timeless architecture, and a seamless connection to the water from nearly every vantage point. The 4,665 sq. ft. residence offers 4–5 bedrooms and 5.5 baths, with formal dining and living rooms, and a cozy den opening to a waterside sunroom and patio. The large kitchen, complete with center island, custom built-ins, and dining area, flows into a bright family room that leads to a covered porch overlooking the river. A butler’s kitchen, laundry area, and adjacent full and half baths add convenience, while a breezeway connects to the attached three-car garage with a guest apartment above. Outdoor living shines with a private dock (two slips, 3.5' MLW), 585 feet of bulkheaded shoreline, a large gunite pool with adjacent gazebo, mature landscaping, and extensive hardscaping. Additional improvements include a detached three-bay garage and a waterside shed for storage and equipment. Owned by the same family since 1978, this exceptional property presents a rare opportunity for a new buyer to personalize a legacy waterfront estate. Note: Approximately 15 acres are enrolled in a Forest Stewardship Plan. Applications have been submitted to Talbot County for a new 4-bedroom septic system and reconstructed pier.

8515 Deep Cove Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Monument Sotheby's International Realty.

$2,995,000

"Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that create a bright, airy feel throughout. Designed to embrace its waterfront setting, the home seamlessly connects spacious living areas with multiple outdoor entertaining spaces overlooking the river. The well-thought-out outdoor living space was designed to fully maximize the property’s incredible waterfront setting, complete with a pool, outdoor fireplace, and covered pavilion overlooking both the pool and the water. Whether hosting guests or enjoying a quiet evening at home, the outdoor spaces offer a seamless extension of the home’s contemporary design and relaxed Eastern Shore lifestyle. Additional exterior amenities include a private dock, private tennis court, and hot tub, all surrounded by mature landscaping and a peaceful setting that enhances the property’s sense of seclusion. Ideally located just outside of Easton, the property provides convenient access to Washington, D.C., Baltimore, and Philadelphia, making it an exceptional full-time residence or weekend getaway within reach of several major metropolitan areas.

3 Beds ⋅ 5 Baths

"Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that create a bright, airy feel throughout. Designed to embrace its waterfront setting, the home seamlessly connects spacious living areas with multiple outdoor entertaining spaces overlooking the river. The well-thought-out outdoor living space was designed to fully maximize the property’s incredible waterfront setting, complete with a pool, outdoor fireplace, and covered pavilion overlooking both the pool and the water. Whether hosting guests or enjoying a quiet evening at home, the outdoor spaces offer a seamless extension of the home’s contemporary design and relaxed Eastern Shore lifestyle. Additional exterior amenities include a private dock, private tennis court, and hot tub, all surrounded by mature landscaping and a peaceful setting that enhances the property’s sense of seclusion. Ideally located just outside of Easton, the property provides convenient access to Washington, D.C., Baltimore, and Philadelphia, making it an exceptional full-time residence or weekend getaway within reach of several major metropolitan areas.

6906 Travelers Rest Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$2,975,000

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

4 Beds ⋅ 4 Baths

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

23961 Lynnewood Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$2,950,000

8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21±acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500± square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront setting, where expansive Chesapeake Bay views and unforgettable western sunsets become part of everyday life. The home's classic architecture is highlighted by stacked waterfront porches, a spacious front balcony, and walls of windows that capture panoramic views from nearly every principal room. Two gas fireplaces add warmth to the generous living spaces, while abundant storage and a thoughtful floor plan provide comfort and functionality for both everyday living and entertaining. The main level is anchored by a spacious waterfront primary suite featuring a walk-in closet, oversized water closet, an en-suite bath with a tile walk-in shower and a separate tub, and a private enclosed porch overlooking the Bay. Upstairs, three generously sized en-suite bedrooms offer exceptional accommodations. Two bedrooms open to the front balcony, while the waterfront suite enjoys direct access to the upper waterfront porch. The third floor offers an additional en-suite bedroom along with a versatile bonus room ideal as a home office, craft room, playroom, fitness space, or additional storage. Outside, approximately 662± feet of riprapped Chesapeake Bay shoreline frames the property, while mature trees create a beautiful natural setting. Approximately four acres lie outside of the agricultural assessment, with the remaining acreage benefiting from agricultural tax status. Positioned along the Eastern Bay Water Trail, the property offers experienced kayakers direct access to one of the region's premier paddling routes and the opportunity to explore the Chesapeake Bay from your own shoreline. A detached garage offers exceptional flexibility and could serve as a future pool house, workshop, studio, or, where permitted, guest accommodations. The home is equipped with five-zone heat pumps with central air conditioning, along with separate ductless HVAC systems serving both waterfront porches and the detached garage, providing year-round comfort throughout the property. Combining quality craftsmanship, a premier Chesapeake Bay location, and over 21± acres of land, this exceptional waterfront estate offers an increasingly rare opportunity to enjoy privacy, space, and some of the Eastern Shore's most spectacular sunset views.

5 Beds ⋅ 6 Baths

8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21±acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500± square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront setting, where expansive Chesapeake Bay views and unforgettable western sunsets become part of everyday life. The home's classic architecture is highlighted by stacked waterfront porches, a spacious front balcony, and walls of windows that capture panoramic views from nearly every principal room. Two gas fireplaces add warmth to the generous living spaces, while abundant storage and a thoughtful floor plan provide comfort and functionality for both everyday living and entertaining. The main level is anchored by a spacious waterfront primary suite featuring a walk-in closet, oversized water closet, an en-suite bath with a tile walk-in shower and a separate tub, and a private enclosed porch overlooking the Bay. Upstairs, three generously sized en-suite bedrooms offer exceptional accommodations. Two bedrooms open to the front balcony, while the waterfront suite enjoys direct access to the upper waterfront porch. The third floor offers an additional en-suite bedroom along with a versatile bonus room ideal as a home office, craft room, playroom, fitness space, or additional storage. Outside, approximately 662± feet of riprapped Chesapeake Bay shoreline frames the property, while mature trees create a beautiful natural setting. Approximately four acres lie outside of the agricultural assessment, with the remaining acreage benefiting from agricultural tax status. Positioned along the Eastern Bay Water Trail, the property offers experienced kayakers direct access to one of the region's premier paddling routes and the opportunity to explore the Chesapeake Bay from your own shoreline. A detached garage offers exceptional flexibility and could serve as a future pool house, workshop, studio, or, where permitted, guest accommodations. The home is equipped with five-zone heat pumps with central air conditioning, along with separate ductless HVAC systems serving both waterfront porches and the detached garage, providing year-round comfort throughout the property. Combining quality craftsmanship, a premier Chesapeake Bay location, and over 21± acres of land, this exceptional waterfront estate offers an increasingly rare opportunity to enjoy privacy, space, and some of the Eastern Shore's most spectacular sunset views.

8781 Tilghman Island Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$2,950,000

The Ultimate Harris Creek Retreat—Unrivaled Views. Room to Spread Out. Sunsets You’ll Never Forget. Welcome to your family’s forever getaway: a fully renovated waterfront estate on 2.4 acres with 240+ feet of direct water frontage. Perfectly positioned for stunning western views over Harris Creek, this exceptional property includes a reimagined main residence, newly constructed three-bay garage with guest suite, and a thoughtfully designed pool house for seamless indoor-outdoor living. Enjoy water views from nearly every room. Inside, a welcoming foyer leads to a dramatic great room with panoramic vistas and open flow ideal for entertaining. The sleek kitchen features an oversized island, 48” fridge, six-burner range, drawer microwave, beverage cooler, and ample cabinetry. A cozy fireside game room and a whimsical nautical-themed powder room add charm. A main-level bedroom with en-suite bath offers comfort for guests or those with mobility needs. Step outside to a large WearDeck composite deck with views of the new 100’ pier, 10,000 lb boat lift, and jet ski lifts. The approx. 3-ft MLW (buyer to verify) allows for a variety of watercraft. Spend your days tubing, water skiing, or fishing from your backyard. Upstairs, the expansive primary suite spans nearly the full width of the home, with tranquil water views, spa-style bath, walk-in closet, and space for a future sixth bedroom (once public sewer arrives, expected in 2026). Two additional bedrooms—one en-suite and one with shared bath—plus laundry complete the upper level. Nearly every bedroom offers views of the water or pool. The brand-new 40' x 20' pool features a sunning ledge, bubbler, automatic cover, and is pre-plumbed for a slide. The pool house adds a full bath, kitchenette, lounge area, and pool equipment/storage room with room for a future heater. The detached garage offers even more flexibility: a finished guest suite with en-suite bath, mini-split HVAC, and wet bar rough-in. The lower garage level—also with water views—makes an ideal workshop, studio, or creative space. With an elevated lot above the floodplain, new 5-bedroom BAT septic system, and anticipated sewer connection, this home is future-ready. All systems have been updated: dual-zone HVAC, electrical, plumbing, and roof. Exterior upgrades include Hardiplank siding, composite trim, and low-maintenance decking. A new tar-and-chip road adds smooth, low-maintenance access, rounding out the property’s turnkey appeal. Set along the revitalized shores of Harris Creek—home to the largest oyster restoration project in Chesapeake Bay history—this legacy retreat blends eco-conscious living with timeless waterfront luxury.

5 Beds ⋅ 7 Baths

The Ultimate Harris Creek Retreat—Unrivaled Views. Room to Spread Out. Sunsets You’ll Never Forget. Welcome to your family’s forever getaway: a fully renovated waterfront estate on 2.4 acres with 240+ feet of direct water frontage. Perfectly positioned for stunning western views over Harris Creek, this exceptional property includes a reimagined main residence, newly constructed three-bay garage with guest suite, and a thoughtfully designed pool house for seamless indoor-outdoor living. Enjoy water views from nearly every room. Inside, a welcoming foyer leads to a dramatic great room with panoramic vistas and open flow ideal for entertaining. The sleek kitchen features an oversized island, 48” fridge, six-burner range, drawer microwave, beverage cooler, and ample cabinetry. A cozy fireside game room and a whimsical nautical-themed powder room add charm. A main-level bedroom with en-suite bath offers comfort for guests or those with mobility needs. Step outside to a large WearDeck composite deck with views of the new 100’ pier, 10,000 lb boat lift, and jet ski lifts. The approx. 3-ft MLW (buyer to verify) allows for a variety of watercraft. Spend your days tubing, water skiing, or fishing from your backyard. Upstairs, the expansive primary suite spans nearly the full width of the home, with tranquil water views, spa-style bath, walk-in closet, and space for a future sixth bedroom (once public sewer arrives, expected in 2026). Two additional bedrooms—one en-suite and one with shared bath—plus laundry complete the upper level. Nearly every bedroom offers views of the water or pool. The brand-new 40' x 20' pool features a sunning ledge, bubbler, automatic cover, and is pre-plumbed for a slide. The pool house adds a full bath, kitchenette, lounge area, and pool equipment/storage room with room for a future heater. The detached garage offers even more flexibility: a finished guest suite with en-suite bath, mini-split HVAC, and wet bar rough-in. The lower garage level—also with water views—makes an ideal workshop, studio, or creative space. With an elevated lot above the floodplain, new 5-bedroom BAT septic system, and anticipated sewer connection, this home is future-ready. All systems have been updated: dual-zone HVAC, electrical, plumbing, and roof. Exterior upgrades include Hardiplank siding, composite trim, and low-maintenance decking. A new tar-and-chip road adds smooth, low-maintenance access, rounding out the property’s turnkey appeal. Set along the revitalized shores of Harris Creek—home to the largest oyster restoration project in Chesapeake Bay history—this legacy retreat blends eco-conscious living with timeless waterfront luxury.

22540 Hardcastle Ln, Bozman

Listing courtesy of Urban Brokers, LLC. Contact:

Selling Office: Meredith Fine Properties.

$2,900,000

"Fox Haven" Privately sited on almost 10 acres with 900+ feet of protected waterfront, this impressive retreat captures breathtaking wide water views from nearly every vantage point. Offering approximately 4,800 square feet of living space across three finished levels, the home is designed for comfort and versatility, with wood flooring, a well-appointed kitchen with island, and distinct living and dining areas. Five bedrooms are complemented by an upper-level office or den and a third-floor craft room with cork flooring. A spacious game room with pool table, three fireplaces, wine room, and extensive storage enhance the interior. Outdoors, enjoy a screened porch, in-ground pool, detached garage, multiple outbuildings, and a private pier equipped with two lifts—an ideal setting for boating enthusiasts and those seeking a peaceful waterfront lifestyle.

5 Beds ⋅ 5 Baths

"Fox Haven" Privately sited on almost 10 acres with 900+ feet of protected waterfront, this impressive retreat captures breathtaking wide water views from nearly every vantage point. Offering approximately 4,800 square feet of living space across three finished levels, the home is designed for comfort and versatility, with wood flooring, a well-appointed kitchen with island, and distinct living and dining areas. Five bedrooms are complemented by an upper-level office or den and a third-floor craft room with cork flooring. A spacious game room with pool table, three fireplaces, wine room, and extensive storage enhance the interior. Outdoors, enjoy a screened porch, in-ground pool, detached garage, multiple outbuildings, and a private pier equipped with two lifts—an ideal setting for boating enthusiasts and those seeking a peaceful waterfront lifestyle.

5995 Elston Shore Rd, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$2,850,000

"WHITEHALL FARM" 99 +/- exclusive Talbot County waterfront acres. Property consists of four parcels including three platted SDA's and over 2000 ft of shoreline bordering Irish Creek. MLW water depth average 2-3 ft. Parcels 1 and 3 percs are currently in re-evaluation process with the county. Parcel 2 improvements include a 2784 sq ft 4 bd 3 bath farmhouse and an updated BAT septic along with two 40 x 35 storage barns. 37 +/- tillable ag acres make up the interior of the farm. Timberland acres span 38 +/- acres upon the entryway with a mix of loblolly pine and hardwood. A 2 acre freshwater pond and a 5 acre plant and flood impoundment serve as crucial habitat for wintering waterfowl. This property is well suited for a large family compound in a highly desirable area of Talbot County and offers unlimited amenities. Conveniently located 10 minutes from St. Michaels, 15 minutes from Easton, and a short drive to the Oxford/ Bellevue Ferry, you will find several restaurants, shops, and activities nearby.

4 Beds ⋅ 3 Baths

"WHITEHALL FARM" 99 +/- exclusive Talbot County waterfront acres. Property consists of four parcels including three platted SDA's and over 2000 ft of shoreline bordering Irish Creek. MLW water depth average 2-3 ft. Parcels 1 and 3 percs are currently in re-evaluation process with the county. Parcel 2 improvements include a 2784 sq ft 4 bd 3 bath farmhouse and an updated BAT septic along with two 40 x 35 storage barns. 37 +/- tillable ag acres make up the interior of the farm. Timberland acres span 38 +/- acres upon the entryway with a mix of loblolly pine and hardwood. A 2 acre freshwater pond and a 5 acre plant and flood impoundment serve as crucial habitat for wintering waterfowl. This property is well suited for a large family compound in a highly desirable area of Talbot County and offers unlimited amenities. Conveniently located 10 minutes from St. Michaels, 15 minutes from Easton, and a short drive to the Oxford/ Bellevue Ferry, you will find several restaurants, shops, and activities nearby.

25320 White Hall Rd, Royal Oak

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Anne Arundel Properties, Inc..

$2,845,000

Miles Away on Murphy’s Point – Discover an unparalleled waterfront retreat at 28092 Glebe Rd, Easton, MD, nestled on approximately ±2.7 picturesque acres. Thoughtfully designed for entertaining, relaxation, and convenient living, this luxurious estate offers expansive indoor and outdoor spaces, exceptional waterfront amenities, and easy access to nearby towns, beaches, and metropolitan areas. With impressive construction and thoughtful expansion, this property promises both comfort and elegance. The estate blends serene rural charm with unmatched convenience, situated just minutes from the vibrant heart of historic Easton. Known for its rich cultural scene, charming boutiques, award-winning restaurants, and year-round events, Easton offers residents a sophisticated yet laid-back lifestyle on Maryland's coveted Eastern Shore. This expansive estate features generous open spaces perfect for gatherings, multiple luxurious bedroom suites, a dedicated theatre room, versatile office spaces, and two substantial garages flanking the home—accommodating up to eight vehicles. Outside, the property unfolds into a private paradise with meticulously landscaped grounds, inviting outdoor living spaces surrounding the waterfront pool, a complete pool house, and a waterside firepit ideal for enjoying stunning sunset views. Exceptional elevation provides sweeping northwest views over Glebe Creek, complete with a private pier and boat lift, offering easy navigation to the Miles River and the iconic waterfront town of St. Michaels. Whether you're exploring the charming streets of Oxford or dining along historic waterfront, this location places you within a short, scenic drive or boat ride of the Eastern Shore's finest towns and attractions. Built in 1995 by Bay Country Builders, this impressive home was thoughtfully expanded in 2001 by renowned Lundberg Builders, resulting in approximately ±7,366 square feet of luxurious yet comfortable living space. With 7 bedrooms, 8 full baths, and 2 half baths, the layout is ideal for hosting guests and multi-generational living, while remaining easy to maintain. Strategically located, this estate is just a short drive from Route 50, connecting residents to nearby beaches such as Ocean City and Rehoboth Beach, as well as major metropolitan areas including Annapolis, Baltimore, and Washington D.C. Additionally, convenient access to Easton Airport (ESN) makes travel effortless. Come home to Miles Away on Murphy’s Point—a rare opportunity to embrace Eastern Shore living at its finest.

7 Beds ⋅ 10 Baths

Miles Away on Murphy’s Point – Discover an unparalleled waterfront retreat at 28092 Glebe Rd, Easton, MD, nestled on approximately ±2.7 picturesque acres. Thoughtfully designed for entertaining, relaxation, and convenient living, this luxurious estate offers expansive indoor and outdoor spaces, exceptional waterfront amenities, and easy access to nearby towns, beaches, and metropolitan areas. With impressive construction and thoughtful expansion, this property promises both comfort and elegance. The estate blends serene rural charm with unmatched convenience, situated just minutes from the vibrant heart of historic Easton. Known for its rich cultural scene, charming boutiques, award-winning restaurants, and year-round events, Easton offers residents a sophisticated yet laid-back lifestyle on Maryland's coveted Eastern Shore. This expansive estate features generous open spaces perfect for gatherings, multiple luxurious bedroom suites, a dedicated theatre room, versatile office spaces, and two substantial garages flanking the home—accommodating up to eight vehicles. Outside, the property unfolds into a private paradise with meticulously landscaped grounds, inviting outdoor living spaces surrounding the waterfront pool, a complete pool house, and a waterside firepit ideal for enjoying stunning sunset views. Exceptional elevation provides sweeping northwest views over Glebe Creek, complete with a private pier and boat lift, offering easy navigation to the Miles River and the iconic waterfront town of St. Michaels. Whether you're exploring the charming streets of Oxford or dining along historic waterfront, this location places you within a short, scenic drive or boat ride of the Eastern Shore's finest towns and attractions. Built in 1995 by Bay Country Builders, this impressive home was thoughtfully expanded in 2001 by renowned Lundberg Builders, resulting in approximately ±7,366 square feet of luxurious yet comfortable living space. With 7 bedrooms, 8 full baths, and 2 half baths, the layout is ideal for hosting guests and multi-generational living, while remaining easy to maintain. Strategically located, this estate is just a short drive from Route 50, connecting residents to nearby beaches such as Ocean City and Rehoboth Beach, as well as major metropolitan areas including Annapolis, Baltimore, and Washington D.C. Additionally, convenient access to Easton Airport (ESN) makes travel effortless. Come home to Miles Away on Murphy’s Point—a rare opportunity to embrace Eastern Shore living at its finest.

28092 Glebe Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

$2,795,000

Perfectly positioned along the prestigious shores of the Tred Avon River, this extraordinary waterfront estate offers breathtaking water views from nearly every room and an unparalleled blend of luxury, craftsmanship, and cutting-edge sustainability. Designed to embrace its spectacular setting, the three-level main residence features exceptional attention to detail throughout, including rich hardwood flooring, custom millwork, hidden built-in cabinetry, and exquisite finishes at every turn. A gracious main hallway draws your eye directly to the covered waterside porch, creating a seamless connection between the home's elegant interior and its stunning riverfront backdrop. The heart of the home is a chef's kitchen appointed with marble countertops, a spacious center island, and thoughtfully designed gathering spaces that flow effortlessly into the dining room and inviting sitting room with a fireplace. The second-floor primary suite serves as a private retreat, featuring access to its own waterfront balcony overlooking the Tred Avon River. The luxurious primary bath offers a beautiful tiled steam shower with water views, a dedicated vanity area, and an expansive custom walk-in closet with integrated laundry. Outside, an incredible overflow pool creates a resort-like setting where endless river views take center stage. Guests will enjoy complete privacy in the detached guest house, which includes a kitchenette and full bath. A detached one-car garage provides additional storage and convenience. Built with both comfort and efficiency in mind, the property showcases Tesla Solar Roof shingles on both the main residence and guest house, geothermal heating and cooling, radiant floor heating throughout the first and second levels, seven Tesla backup batteries providing power during outages, and elevator access serving the first and second floors. A rare offering in the heart of historic Oxford, 200 West Street represents waterfront living at its finest—where timeless elegance, modern innovation, and spectacular views come together in one unforgettable property. --- {Luxury & Special Features} Waterfront primary suite featuring a private balcony, rain shower, and steam bath | Chef's kitchen with two freezer drawers and built-in plate warmer | Continuous warm water circulation system throughout the home | Dedicated water pressure enhancement system | Elevator serving the first and second floors | Radiant floor heating throughout the first and second levels | Geothermal heating and cooling system | Tesla Solar Roof shingles on the main residence and guest house | Seven Tesla Powerwall backup batteries providing power during outages | Tesla electric vehicle charging station | Resort-style overflow pool overlooking the Tred Avon River | Electric retractable awnings | Detached guest house with kitchenette and full bath | Detached one-car garage

4 Beds ⋅ 4 Baths

Perfectly positioned along the prestigious shores of the Tred Avon River, this extraordinary waterfront estate offers breathtaking water views from nearly every room and an unparalleled blend of luxury, craftsmanship, and cutting-edge sustainability. Designed to embrace its spectacular setting, the three-level main residence features exceptional attention to detail throughout, including rich hardwood flooring, custom millwork, hidden built-in cabinetry, and exquisite finishes at every turn. A gracious main hallway draws your eye directly to the covered waterside porch, creating a seamless connection between the home's elegant interior and its stunning riverfront backdrop. The heart of the home is a chef's kitchen appointed with marble countertops, a spacious center island, and thoughtfully designed gathering spaces that flow effortlessly into the dining room and inviting sitting room with a fireplace. The second-floor primary suite serves as a private retreat, featuring access to its own waterfront balcony overlooking the Tred Avon River. The luxurious primary bath offers a beautiful tiled steam shower with water views, a dedicated vanity area, and an expansive custom walk-in closet with integrated laundry. Outside, an incredible overflow pool creates a resort-like setting where endless river views take center stage. Guests will enjoy complete privacy in the detached guest house, which includes a kitchenette and full bath. A detached one-car garage provides additional storage and convenience. Built with both comfort and efficiency in mind, the property showcases Tesla Solar Roof shingles on both the main residence and guest house, geothermal heating and cooling, radiant floor heating throughout the first and second levels, seven Tesla backup batteries providing power during outages, and elevator access serving the first and second floors. A rare offering in the heart of historic Oxford, 200 West Street represents waterfront living at its finest—where timeless elegance, modern innovation, and spectacular views come together in one unforgettable property. --- {Luxury & Special Features} Waterfront primary suite featuring a private balcony, rain shower, and steam bath | Chef's kitchen with two freezer drawers and built-in plate warmer | Continuous warm water circulation system throughout the home | Dedicated water pressure enhancement system | Elevator serving the first and second floors | Radiant floor heating throughout the first and second levels | Geothermal heating and cooling system | Tesla Solar Roof shingles on the main residence and guest house | Seven Tesla Powerwall backup batteries providing power during outages | Tesla electric vehicle charging station | Resort-style overflow pool overlooking the Tred Avon River | Electric retractable awnings | Detached guest house with kitchenette and full bath | Detached one-car garage

200 West St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$2,750,000

Set on a private point overlooking Boone Creek and the Choptank River in Oxford, this exceptional 4BR/2.5BA modern farmhouse offers panoramic water views and refined coastal living on 2.4 acres. Built in 2018, the home showcases high-end finishes, hardwood flooring throughout, and a light-filled, open design with walls of windows capturing the surrounding waterfront. A welcoming, expansive front porch introduces the main level, where the cathedral-ceiling living room with gas fireplace flows seamlessly into a gourmet kitchen with top-tier appliances—ideal for both everyday living and entertaining. The main-level primary suite enjoys water views and privacy, while the second level overlooks the living space below and features three additional bedrooms and a full hall bath. Outdoor amenities complete the offering, including a waterside deck, new gunite pool (Aqua Pool), private pier with two slips and floating dock, riprapped shoreline, detached two-car garage (transformed and finished into a large office), and beautifully landscaped grounds—perfectly capturing the relaxed elegance and timeless appeal of Eastern Shore living.

4 Beds ⋅ 3 Baths

Set on a private point overlooking Boone Creek and the Choptank River in Oxford, this exceptional 4BR/2.5BA modern farmhouse offers panoramic water views and refined coastal living on 2.4 acres. Built in 2018, the home showcases high-end finishes, hardwood flooring throughout, and a light-filled, open design with walls of windows capturing the surrounding waterfront. A welcoming, expansive front porch introduces the main level, where the cathedral-ceiling living room with gas fireplace flows seamlessly into a gourmet kitchen with top-tier appliances—ideal for both everyday living and entertaining. The main-level primary suite enjoys water views and privacy, while the second level overlooks the living space below and features three additional bedrooms and a full hall bath. Outdoor amenities complete the offering, including a waterside deck, new gunite pool (Aqua Pool), private pier with two slips and floating dock, riprapped shoreline, detached two-car garage (transformed and finished into a large office), and beautifully landscaped grounds—perfectly capturing the relaxed elegance and timeless appeal of Eastern Shore living.

4361 Bachelors Point Rd, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$2,750,000

Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation system.The superbly designed and crafted home offers an open floor-plan with 4 bedrooms and an office, 3.5 designer baths with heated floors,, a magnificent gourmet kitchen, upper and lower level living areas providing outstanding functionality. Breathtaking water- views and protected shoreline! This is an outstanding turn-key property that comes beautifully furnished !

4 Beds ⋅ 4 Baths

Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation system.The superbly designed and crafted home offers an open floor-plan with 4 bedrooms and an office, 3.5 designer baths with heated floors,, a magnificent gourmet kitchen, upper and lower level living areas providing outstanding functionality. Breathtaking water- views and protected shoreline! This is an outstanding turn-key property that comes beautifully furnished !

5837 Irish Creek Rd, Royal Oak

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$2,730,000

Travel along an enchanting and winding drive, through a park-like setting, across the bridge, to the grand reveal of a prairie-style home boasting coastal-meets-contemporary design elements, all situated in the desirable Bantry community of Easton! On a private cove feeding into the Miles River, this property offers expansive, breathtaking water views and, the opportunity for boating, kayaking and enjoying the flight of many types of waterfowl (and an occasional eagle!). The property has been completely reimagined by the current owners over the last three years--fully renovated kitchen with stainless appliances, quartzite leathered waterfall island; beautiful pantry; updated owners' suite inclusive of a water-view primary bedroom, sitting room, double- vanity primary bath and walk-in closet (all on the main floor); another large bedroom and flex space/exercise room on the main floor share a full bath; laundry room; and two more bedrooms upstairs (both with water views) which share another full bath. You can't miss the magnificent view from the vaulted-ceiling great room which overlooks the cove on one side and offers a grand brick fireplace for those chilly winter eves on the opposite end. The home also provides a formal dining room, office with built-ins, sitting room with garden-view, large mud room with custom wallpaper, a wood burning stove, and a fun bar/entertaining area with custom elements; half-bath; and an enclosed cedar-lined porch overlooking the water. New interior doors and flooring throughout. Updated landscaping, flagstone patios, deck with cable rails, and rock gardens are designed to be low-maintenance. The deep bronze Anderson doors and many of the windows are new, as is the deep blue siding on the home, a 60 ft pier w/200 sq ft platform dock with 8000 lb boat lift (dock/lift installed by Weems in 2023). Anderson windows on the water side of the property come with Tru-Scene invisible screens. Two 5-ton HVAC units and new duct work installed in the last three years. Beautiful new roof and skylights installed in 2025. The home is at 8' elevation and not in a federal flood zone. The water depth at the dock is 2-2.5' MLW. Living shoreline with native grasses and flowers. The 21' center console Sea Hunt boat with a 200 HP Yamaha motor with approximately 100 hours is kept on the dock lift and conveys with an acceptable offer. The property has numerous large closets for storage, but also a three-car garage at the main house. A detached three bay garage/workshop with electric, insulation, water and heat, is perfect for a car or boat enthusiast. The sides bays are two cars deep and the large center bay (functioning as a workshop) that is 35'x35' can store a boat or up to 4 cars. Easton MD is considered the New Hamptons per Forbes magazine; a culinary mecca and cultural destination featuring museums, shops, theater, art festivals and more! This property will be a short drive to the new regional hospital anticipated for 2028 and is approximately 1.5 hours to Baltimore and Washington D.C..

4 Beds ⋅ 4 Baths

Travel along an enchanting and winding drive, through a park-like setting, across the bridge, to the grand reveal of a prairie-style home boasting coastal-meets-contemporary design elements, all situated in the desirable Bantry community of Easton! On a private cove feeding into the Miles River, this property offers expansive, breathtaking water views and, the opportunity for boating, kayaking and enjoying the flight of many types of waterfowl (and an occasional eagle!). The property has been completely reimagined by the current owners over the last three years--fully renovated kitchen with stainless appliances, quartzite leathered waterfall island; beautiful pantry; updated owners' suite inclusive of a water-view primary bedroom, sitting room, double- vanity primary bath and walk-in closet (all on the main floor); another large bedroom and flex space/exercise room on the main floor share a full bath; laundry room; and two more bedrooms upstairs (both with water views) which share another full bath. You can't miss the magnificent view from the vaulted-ceiling great room which overlooks the cove on one side and offers a grand brick fireplace for those chilly winter eves on the opposite end. The home also provides a formal dining room, office with built-ins, sitting room with garden-view, large mud room with custom wallpaper, a wood burning stove, and a fun bar/entertaining area with custom elements; half-bath; and an enclosed cedar-lined porch overlooking the water. New interior doors and flooring throughout. Updated landscaping, flagstone patios, deck with cable rails, and rock gardens are designed to be low-maintenance. The deep bronze Anderson doors and many of the windows are new, as is the deep blue siding on the home, a 60 ft pier w/200 sq ft platform dock with 8000 lb boat lift (dock/lift installed by Weems in 2023). Anderson windows on the water side of the property come with Tru-Scene invisible screens. Two 5-ton HVAC units and new duct work installed in the last three years. Beautiful new roof and skylights installed in 2025. The home is at 8' elevation and not in a federal flood zone. The water depth at the dock is 2-2.5' MLW. Living shoreline with native grasses and flowers. The 21' center console Sea Hunt boat with a 200 HP Yamaha motor with approximately 100 hours is kept on the dock lift and conveys with an acceptable offer. The property has numerous large closets for storage, but also a three-car garage at the main house. A detached three bay garage/workshop with electric, insulation, water and heat, is perfect for a car or boat enthusiast. The sides bays are two cars deep and the large center bay (functioning as a workshop) that is 35'x35' can store a boat or up to 4 cars. Easton MD is considered the New Hamptons per Forbes magazine; a culinary mecca and cultural destination featuring museums, shops, theater, art festivals and more! This property will be a short drive to the new regional hospital anticipated for 2028 and is approximately 1.5 hours to Baltimore and Washington D.C..

9716 Bantry Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Benson & Mangold, LLC.

$2,700,000

Welcome to this stunning brick one -story house on Riverview Terrace that you've always admired. From the moment that the front door opens, you will be captivated by the breathtaking views of the Miles River. This home offers an open floor-plan with a large great-room, dining room; kitchen, a primary bedroom suite , 2 guest rooms sharing a full bathroom,, an office and a powder room. Lovely hardwood floors, 2 fireplaces , extra- wide hallways, and numerous waterside windows/doors are some of the features that make this home special. This property, conveniently located on the 900 block of Riverview Terrace , provides easy access into downtown St. Michaels. Public water, public sewer, no town taxes, an attached 2 car garage, a completely insulated attic, a new stone driveway, crawl space with concrete floor, pier, deck, and beautiful landscaping contribute to the desirability of this property. Most furniture will be included with the sale.

3 Beds ⋅ 3 Baths

Welcome to this stunning brick one -story house on Riverview Terrace that you've always admired. From the moment that the front door opens, you will be captivated by the breathtaking views of the Miles River. This home offers an open floor-plan with a large great-room, dining room; kitchen, a primary bedroom suite , 2 guest rooms sharing a full bathroom,, an office and a powder room. Lovely hardwood floors, 2 fireplaces , extra- wide hallways, and numerous waterside windows/doors are some of the features that make this home special. This property, conveniently located on the 900 block of Riverview Terrace , provides easy access into downtown St. Michaels. Public water, public sewer, no town taxes, an attached 2 car garage, a completely insulated attic, a new stone driveway, crawl space with concrete floor, pier, deck, and beautiful landscaping contribute to the desirability of this property. Most furniture will be included with the sale.

900 Riverview Ter, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Cummings & Co. Realtors.

$2,695,000

Set in the highly sought-after Patrick’s Plains community, 28211 Brick Row Drive is an exceptionally maintained and thoughtfully appointed waterfront residence overlooking the serene waters of Island Creek. Bathed in natural light, the home welcomes you with a stunning foyer and living room featuring floor-to-ceiling windows, skylights, and a gas fireplace, seamlessly connecting to the expansive deck. Designed for both everyday living and elegant entertaining, the home offers a formal dining area and beautiful hardwood flooring throughout. The gourmet kitchen is a true centerpiece, boasting a massive island, Viking gas range, Sub-Zero refrigerator, stainless steel appliances, and abundant pantry storage. Just off the kitchen, the family room impresses with cathedral ceilings, a gas fireplace, sweeping water views, and direct access to a screened-in porch. The main-level primary suite is a private retreat, complete with a spacious walk-in closet and direct access to the back deck, where you can enjoy tranquil poolside and waterfront views. The luxurious primary bath features a cathedral ceiling, a standalone soaking tub, and a glass-enclosed shower. The lower level offers incredible flexibility as a poolside retreat or in-law suite, with its own living room, recreation space, bedroom, full bath, and kitchenette. Completing the home is a rare three-car garage, adding both convenience and functionality. The owner has completed many upgrades, including a new pool, pier improvements, three new HVAC systems, a new driveway, and a water treatment system, along with many other enhancements (full list available). With its prime waterfront setting, abundant natural light, and exceptional living spaces, this home offers a truly elevated lifestyle in one of the area’s most desirable communities.

5 Beds ⋅ 6 Baths

Set in the highly sought-after Patrick’s Plains community, 28211 Brick Row Drive is an exceptionally maintained and thoughtfully appointed waterfront residence overlooking the serene waters of Island Creek. Bathed in natural light, the home welcomes you with a stunning foyer and living room featuring floor-to-ceiling windows, skylights, and a gas fireplace, seamlessly connecting to the expansive deck. Designed for both everyday living and elegant entertaining, the home offers a formal dining area and beautiful hardwood flooring throughout. The gourmet kitchen is a true centerpiece, boasting a massive island, Viking gas range, Sub-Zero refrigerator, stainless steel appliances, and abundant pantry storage. Just off the kitchen, the family room impresses with cathedral ceilings, a gas fireplace, sweeping water views, and direct access to a screened-in porch. The main-level primary suite is a private retreat, complete with a spacious walk-in closet and direct access to the back deck, where you can enjoy tranquil poolside and waterfront views. The luxurious primary bath features a cathedral ceiling, a standalone soaking tub, and a glass-enclosed shower. The lower level offers incredible flexibility as a poolside retreat or in-law suite, with its own living room, recreation space, bedroom, full bath, and kitchenette. Completing the home is a rare three-car garage, adding both convenience and functionality. The owner has completed many upgrades, including a new pool, pier improvements, three new HVAC systems, a new driveway, and a water treatment system, along with many other enhancements (full list available). With its prime waterfront setting, abundant natural light, and exceptional living spaces, this home offers a truly elevated lifestyle in one of the area’s most desirable communities.

28211 Brick Row Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$2,687,753

219.435+- Acres Of Prime Eastern Shore Hunting Land With Tillable Fields, T Located in sought-after Talbot County near Trappe, Maryland, this 219.435 acre property presents a rare opportunity to own a diverse and highly productive piece of Eastern Shore land. With approximately 150 acres of tillable ground and former CRP acreage, this farm offers both income potential and exceptional wildlife habitat. The balance of the property consists of mature timber, creating ideal cover, bedding areas, and natural travel corridors for wildlife. This property is a proven hunting tract that supports strong populations of whitetail deer, with the area well known for producing mature bucks. The combination of agricultural fields, timber edges, and secluded pockets provides excellent stand locations and consistent deer movement. Wild turkeys are frequently observed throughout the property, taking advantage of the open fields and wooded sections for feeding and roosting. Water features further enhance the recreational value of this tract. A pond located on the property attracts Canada geese during the winter months and provides additional opportunities for puddle duck hunting. The property also features frontage along Raccoon Creek, expanding waterfowl hunting potential with opportunities to target species such as mallards, wood ducks, and black ducks. This combination of field, timber, and water creates a well-rounded hunting environment that is increasingly difficult to find in one tract. Access to the property is convenient with road frontage on both Kates Point Road and Bambury Road, allowing for flexible entry points and ease of equipment movement. Despite this accessibility, the property offers a high level of privacy, with its size and layout providing seclusion for both recreational use and future improvements. One of the standout features of this property is a small, secluded field located toward the rear of the tract. This area offers excellent potential for a dedicated food plot, additional farming, or re-enrollment into conservation programs. Its location provides an ideal setting for attracting and holding wildlife away from pressure. Importantly, the property is not encumbered by a conservation easement, giving the next owner flexibility in how the land is utilized. Whether the goal is to continue farming operations, enhance wildlife habitat, or establish a private recreational retreat, this tract offers a wide range of possibilities. Large, contiguous parcels with this blend of tillable acreage, timber, water frontage, and strong wildlife presence are increasingly rare on Marylands Eastern Shore. This Talbot County property stands out as a premier opportunity for hunters, investors, and outdoor enthusiasts looking to secure a versatile and productive piece of land.

00 Kates Point Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$2,680,000

Just 5-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings (including a cathedral ceiling in the family room and tray ceiling in the primary bedroom); four (or 5) bedrooms; 4 full and 2 half baths; large primary suite w/recently updated bath; gourmet kitchen w/island and breakfast room connected to a wonderful family room w/fireplace. Generous waterside glass to maximize the water views from most rooms. Beautiful waterside swimming pool (heated), surrounded by a spacious multi-level patio. For Chesapeake bay boating, there is a substantial 6' wide x 200' dock w/electric boat lift. Water depth at the dock on a typical low tide (MLW) is over 5 ft. This is a great boating, fishing and crabbing location. Tilghman Island's waterside restaurants, marinas and the open waters of Chesapeake Bay are just a short, scenic boat ride downstream from the dock. By car, the Town of St. Michaels with its many fine restaurants and attractions is less than 10-minutes away (5-miles). The house is well-elevated and is NOT in a high risk flood zone (flood insurance not mandatory). Very private. No HOA!

4 Beds ⋅ 6 Baths

Just 5-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings (including a cathedral ceiling in the family room and tray ceiling in the primary bedroom); four (or 5) bedrooms; 4 full and 2 half baths; large primary suite w/recently updated bath; gourmet kitchen w/island and breakfast room connected to a wonderful family room w/fireplace. Generous waterside glass to maximize the water views from most rooms. Beautiful waterside swimming pool (heated), surrounded by a spacious multi-level patio. For Chesapeake bay boating, there is a substantial 6' wide x 200' dock w/electric boat lift. Water depth at the dock on a typical low tide (MLW) is over 5 ft. This is a great boating, fishing and crabbing location. Tilghman Island's waterside restaurants, marinas and the open waters of Chesapeake Bay are just a short, scenic boat ride downstream from the dock. By car, the Town of St. Michaels with its many fine restaurants and attractions is less than 10-minutes away (5-miles). The house is well-elevated and is NOT in a high risk flood zone (flood insurance not mandatory). Very private. No HOA!

9262 Macks Ln, Mcdaniel

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..