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‘Eagle’s Nest’ is an exceptional waterfront retreat overlooking Island Creek, just minutes from historic Oxford. Prime location with guest house and deep water (6.5' MLW). Privately sited on more than four acres amid mature trees and meticulously landscaped grounds, this impressive main residence (5324 SF)—completely rebuilt by Ilex Construction in 2008—offers four bedrooms, four full baths, and two half baths. Every room is generously sized and thoughtfully designed to capture expansive water views while providing elegant yet comfortable living. The main level features beautifully appointed living spaces, including a formal living room with coffered ceiling, wood-burning fireplace, custom built-ins, wet bar, and sliding doors opening to the waterside patio. A formal dining room, enclosed by French doors, offers an inviting setting for entertaining. At the heart of the home, the gourmet kitchen showcases a cathedral ceiling, large center island, top-of-the-line appliances, gas fireplace, spacious walk-in pantry, and custom built-ins—creating a warm and functional gathering space. The adjoining sunroom is filled with natural light and features vaulted ceilings, slate tile flooring, and sweeping water views, with glass doors opening to the patio and pool area. Nearby, a well-equipped mudroom, laundry room, and half bath add everyday convenience, along with a covered breezeway to the two-car garage. The desirable main-level primary suite serves as a private retreat with tranquil water views, dual walk-in closets, and a luxurious en suite bath. Just off the primary suite corridor, a private office with custom built-ins and an additional powder room enhance the home’s thoughtful design. Upstairs, three generously sized guest bedrooms each include en suite baths. A comfortable sitting area opens to a balcony overlooking Island Creek—an ideal place to relax and take in the serene setting. In addition, a coveted one-bedroom, one-and-a-half-bath guest house (968 SF) includes a full kitchen, living room, and attached two-car garage—perfect for visitors, extended family, or flexible use. Outdoor living is equally impressive, highlighted by a gunite swimming pool, expansive brick patio, mature landscaping, and extensive hardscaping designed to complement the waterfront setting. The private pier features two slips and a boat lift with 6.5' MLW along a protected, riprapped shoreline. ‘Eagle’s Nest’ presents a rare opportunity to enjoy refined Eastern Shore waterfront living just moments from Oxford. New roof on main house (2025). New pool cover: Aqua pool service contract paid for-2026

4 Beds ⋅ 6 Baths

‘Eagle’s Nest’ is an exceptional waterfront retreat overlooking Island Creek, just minutes from historic Oxford. Prime location with guest house and deep water (6.5' MLW). Privately sited on more than four acres amid mature trees and meticulously landscaped grounds, this impressive main residence (5324 SF)—completely rebuilt by Ilex Construction in 2008—offers four bedrooms, four full baths, and two half baths. Every room is generously sized and thoughtfully designed to capture expansive water views while providing elegant yet comfortable living. The main level features beautifully appointed living spaces, including a formal living room with coffered ceiling, wood-burning fireplace, custom built-ins, wet bar, and sliding doors opening to the waterside patio. A formal dining room, enclosed by French doors, offers an inviting setting for entertaining. At the heart of the home, the gourmet kitchen showcases a cathedral ceiling, large center island, top-of-the-line appliances, gas fireplace, spacious walk-in pantry, and custom built-ins—creating a warm and functional gathering space. The adjoining sunroom is filled with natural light and features vaulted ceilings, slate tile flooring, and sweeping water views, with glass doors opening to the patio and pool area. Nearby, a well-equipped mudroom, laundry room, and half bath add everyday convenience, along with a covered breezeway to the two-car garage. The desirable main-level primary suite serves as a private retreat with tranquil water views, dual walk-in closets, and a luxurious en suite bath. Just off the primary suite corridor, a private office with custom built-ins and an additional powder room enhance the home’s thoughtful design. Upstairs, three generously sized guest bedrooms each include en suite baths. A comfortable sitting area opens to a balcony overlooking Island Creek—an ideal place to relax and take in the serene setting. In addition, a coveted one-bedroom, one-and-a-half-bath guest house (968 SF) includes a full kitchen, living room, and attached two-car garage—perfect for visitors, extended family, or flexible use. Outdoor living is equally impressive, highlighted by a gunite swimming pool, expansive brick patio, mature landscaping, and extensive hardscaping designed to complement the waterfront setting. The private pier features two slips and a boat lift with 6.5' MLW along a protected, riprapped shoreline. ‘Eagle’s Nest’ presents a rare opportunity to enjoy refined Eastern Shore waterfront living just moments from Oxford. New roof on main house (2025). New pool cover: Aqua pool service contract paid for-2026

4573 Bringman Farm Rd, Oxford

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

Selling Office: Unrepresented.

$2,600,000

Generational Waterfront Farm. Magnificent Building site on the Miles River on 50+ acres. Private tree-lined driveway passing through productive fields, mature evergreen and deciduous trees. There is a brick cape cod on the property and an outbuilding that should be considered a footprint for future development. Existing well, pier and bulkhead area on the cove (Newcomb Creek). Over 1500 of shoreline. 4 miles from St. Michaels and 5 miles from Easton. Incredible Sunrises and Sunsets, Remarkable true point of land with panoramic views, great waterfowl and deer hunting. Property includes large block of woods on other side of Rt 33 (approx.. 30+ acres). Owner has approval to be hooked up to public Sewer!

3 Beds ⋅ 3 Baths

Generational Waterfront Farm. Magnificent Building site on the Miles River on 50+ acres. Private tree-lined driveway passing through productive fields, mature evergreen and deciduous trees. There is a brick cape cod on the property and an outbuilding that should be considered a footprint for future development. Existing well, pier and bulkhead area on the cove (Newcomb Creek). Over 1500 of shoreline. 4 miles from St. Michaels and 5 miles from Easton. Incredible Sunrises and Sunsets, Remarkable true point of land with panoramic views, great waterfowl and deer hunting. Property includes large block of woods on other side of Rt 33 (approx.. 30+ acres). Owner has approval to be hooked up to public Sewer!

26396 St Michaels Rd, Newcomb

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$2,600,000

Welcome to your private Eastern Shore retreat! This amazing 4-bedroom, 4.5-bath Cape Cod is perfectly situated on a secluded peninsula, offering unparalleled tranquility and breathtaking waterfront views of Boone Creek located in beautiful Oxford, Maryland. The home offers an incredible blend of traditional elegance and modern luxury. An open and airy floor plan is bathed in natural light, with expansive windows framing the stunning water views from nearly every room. The living room has beautiful brick floors and a wood burning fireplace. You will also find a gas fireplace in the spacious family room. The bright and inviting sunroom has cathedral ceilings and walls of glass doors with water, pool, garden and patio views. The gourmet kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and a large center island. It flows effortlessly into the formal dining area which includes an additional fireplace for cozy and intimate dining experiences. Beautiful hard wood floors flow into several rooms. The main floor also hosts two private sanctuaries: an ensuite bedroom and a primary bedroom, each with private decks offering stunning water views. The primary suite's closet is a truly incredible, separate dressing room. A laundry room, a full bath, and a half bath complete the main level. Upstairs, two large bedrooms and a shared bath provide comfort and privacy for guests or family. Outside you discover a true entertainer's paradise. The property's unique peninsula location offers a wide expanse of water frontage, perfect for enjoying the Eastern Shore lifestyle. A large, sparkling in-ground pool is the centerpiece of the manicured grounds, surrounded by extensive hardscaping and lush landscaping, creating a resort-like feel. The detached two-car garage is enormous. There are raised beds in a fully fenced garden with a garden shed. The climate-controlled dock house offers endless possibilities for a gym, office, art studio or storage. The private dock provides water access for boating, kayaking, paddleboarding, fishing and crabbing on Boone Creek. With quick water access to Choptank River, Tred Avon River, Chesapeake Bay & Miles River, you can explore the best areas of the shore. This home is more than a residence; it's a lifestyle. Located just minutes from the historic town of Oxford, you'll have easy access to charming shops, restaurants, parks, the beach strand and the Oxford-Bellevue Ferry. This is a rare opportunity to own a piece of paradise on the Eastern Shore.

4 Beds ⋅ 5 Baths

Welcome to your private Eastern Shore retreat! This amazing 4-bedroom, 4.5-bath Cape Cod is perfectly situated on a secluded peninsula, offering unparalleled tranquility and breathtaking waterfront views of Boone Creek located in beautiful Oxford, Maryland. The home offers an incredible blend of traditional elegance and modern luxury. An open and airy floor plan is bathed in natural light, with expansive windows framing the stunning water views from nearly every room. The living room has beautiful brick floors and a wood burning fireplace. You will also find a gas fireplace in the spacious family room. The bright and inviting sunroom has cathedral ceilings and walls of glass doors with water, pool, garden and patio views. The gourmet kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and a large center island. It flows effortlessly into the formal dining area which includes an additional fireplace for cozy and intimate dining experiences. Beautiful hard wood floors flow into several rooms. The main floor also hosts two private sanctuaries: an ensuite bedroom and a primary bedroom, each with private decks offering stunning water views. The primary suite's closet is a truly incredible, separate dressing room. A laundry room, a full bath, and a half bath complete the main level. Upstairs, two large bedrooms and a shared bath provide comfort and privacy for guests or family. Outside you discover a true entertainer's paradise. The property's unique peninsula location offers a wide expanse of water frontage, perfect for enjoying the Eastern Shore lifestyle. A large, sparkling in-ground pool is the centerpiece of the manicured grounds, surrounded by extensive hardscaping and lush landscaping, creating a resort-like feel. The detached two-car garage is enormous. There are raised beds in a fully fenced garden with a garden shed. The climate-controlled dock house offers endless possibilities for a gym, office, art studio or storage. The private dock provides water access for boating, kayaking, paddleboarding, fishing and crabbing on Boone Creek. With quick water access to Choptank River, Tred Avon River, Chesapeake Bay & Miles River, you can explore the best areas of the shore. This home is more than a residence; it's a lifestyle. Located just minutes from the historic town of Oxford, you'll have easy access to charming shops, restaurants, parks, the beach strand and the Oxford-Bellevue Ferry. This is a rare opportunity to own a piece of paradise on the Eastern Shore.

4500 Boone Creek Rd, Oxford

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$2,500,000

205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images in photos). The beautiful front lawn provides a park-like setting with one-of-a-kind water-views overlooking St. Michaels Harbor. There is also a 2 bedroom, 2 bath guest cottage on the property. The property directly across the street (FKA The Hambeleton Inn) was purchased as a private residence and serves as a second home to its owner. This is a wonderful opportunity to own a landmark historic inn or primary or second home in the heart of St. Michaels.

5 Beds ⋅ 9 Baths

205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images in photos). The beautiful front lawn provides a park-like setting with one-of-a-kind water-views overlooking St. Michaels Harbor. There is also a 2 bedroom, 2 bath guest cottage on the property. The property directly across the street (FKA The Hambeleton Inn) was purchased as a private residence and serves as a second home to its owner. This is a wonderful opportunity to own a landmark historic inn or primary or second home in the heart of St. Michaels.

205 Cherry St, Saint Michaels

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

Selling Office: Coldwell Banker Realty.

$2,500,000

Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room anchored by a large brick hearth and woodburning fireplace. The gourmet kitchen is the center of the home - outfitted with upgraded appliances, a center island with breakfast bar, and additional dining space. Adjacent is a second kitchen - ideal for effortless indoor/outdoor entertaining. A formal dining room and large waterside sunroom complete the main living spaces. Upstairs, two spacious primary suites anchor each end of the home, offering privacy and comfort, with two additional guest bedrooms (one with ensuite bath) and a hall bath in between. Step outside to enjoy westerly water views from the elevated deck, or gather on the enclosed screened porch, perfect for crab feasts and sunset dining. Outdoor amenities include a charming 2BR/1.5BA guest cottage (540 sq. ft.), a new dock with two slips, stunning waterside pool, waterside firepit, and barrel sauna. A 3-bay equipment garage is connected to an enclosed game room and workshop - creating a complete retreat for relaxation, recreation, and unforgettable waterfront living. The property with its acreage is also great for hunting. This is Eastern Shore living at its best – spacious, serene, and set up for year-round enjoyment. *Furnishings may be available for sale.

5 Beds ⋅ 6 Baths

Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room anchored by a large brick hearth and woodburning fireplace. The gourmet kitchen is the center of the home - outfitted with upgraded appliances, a center island with breakfast bar, and additional dining space. Adjacent is a second kitchen - ideal for effortless indoor/outdoor entertaining. A formal dining room and large waterside sunroom complete the main living spaces. Upstairs, two spacious primary suites anchor each end of the home, offering privacy and comfort, with two additional guest bedrooms (one with ensuite bath) and a hall bath in between. Step outside to enjoy westerly water views from the elevated deck, or gather on the enclosed screened porch, perfect for crab feasts and sunset dining. Outdoor amenities include a charming 2BR/1.5BA guest cottage (540 sq. ft.), a new dock with two slips, stunning waterside pool, waterside firepit, and barrel sauna. A 3-bay equipment garage is connected to an enclosed game room and workshop - creating a complete retreat for relaxation, recreation, and unforgettable waterfront living. The property with its acreage is also great for hunting. This is Eastern Shore living at its best – spacious, serene, and set up for year-round enjoyment. *Furnishings may be available for sale.

5440 Ferry Neck Rd, Royal Oak

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

Selling Office: Benson & Mangold, LLC.

$2,495,000

This exceptional waterfront cottage is set on two private acres and offers sweeping sunset views over the Choptank River to the Chesapeake Bay. Completely renovated from crawl space to roof, the home features over 2,600 square feet of beautifully finished living space with three bedrooms and three full baths. The interior showcases renovated kitchen and baths, complemented by extensive custom finish-work throughout. There is a detached garage with metal roof and second floor storage and gravel circular driveway with ample parking. Improvements on this home include an encapsulated crawl space, new roof, siding, multiple premium sliding glass doors and windows, all valuable upgrades that enhance both style and energy efficiency. The grounds have been thoughtfully transformed with curated shrubs, trees, and perennials that highlight the existing landscape, concrete pool, and pergola, creating an ideal setting for outdoor relaxation and entertaining. Enjoy easy boating access just 10 minutes to Oxford and 15 minutes to Tilghman, while by land the property is ideally situated between Easton and St. Michaels. Enjoy the protection of high property elevation (no flood insurance required) with a sturdy rip-rapped shoreline, beautiful sandy bottom, and a private L pier with two new boat lifts. 24878 W. Ferry Neck Road offers the perfect blend of privacy, comfort, and Eastern Shore waterfront living on the Choptank River. List of the many recent improvements in document section of this listing.

3 Beds ⋅ 3 Baths

This exceptional waterfront cottage is set on two private acres and offers sweeping sunset views over the Choptank River to the Chesapeake Bay. Completely renovated from crawl space to roof, the home features over 2,600 square feet of beautifully finished living space with three bedrooms and three full baths. The interior showcases renovated kitchen and baths, complemented by extensive custom finish-work throughout. There is a detached garage with metal roof and second floor storage and gravel circular driveway with ample parking. Improvements on this home include an encapsulated crawl space, new roof, siding, multiple premium sliding glass doors and windows, all valuable upgrades that enhance both style and energy efficiency. The grounds have been thoughtfully transformed with curated shrubs, trees, and perennials that highlight the existing landscape, concrete pool, and pergola, creating an ideal setting for outdoor relaxation and entertaining. Enjoy easy boating access just 10 minutes to Oxford and 15 minutes to Tilghman, while by land the property is ideally situated between Easton and St. Michaels. Enjoy the protection of high property elevation (no flood insurance required) with a sturdy rip-rapped shoreline, beautiful sandy bottom, and a private L pier with two new boat lifts. 24878 W. Ferry Neck Road offers the perfect blend of privacy, comfort, and Eastern Shore waterfront living on the Choptank River. List of the many recent improvements in document section of this listing.

24878 W Ferry Neck Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$2,450,000

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

4 Beds ⋅ 5 Baths

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

965 San Domingo, Saint Michaels

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

Selling Office: Benson & Mangold, LLC.

24830 Deepwater Point Dr, Saint Michaels

$2,435,000

DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS..... A treasure of vantage points and chic contemporary beauty, this Martingham waterfront retreat offers rare front-row views of Miles River happenings - including the historic Log Canoe Races, Fourth of July fireworks, daily passages of billowing sails,and, on crisp days, sightlines stretching for miles. Set on 2.32 acres with nearly 250 feet of sandy shoreline, life here moves with effortless rhythm; from morning beachfront strolls to afternoons shaped by regattas, summer pool partiesand in-town finds. Relax by the awe inspiring extra large 50 foot heated pool with jacuzzi with of space for sunbathing and relaxing. There is also a IGLUCRAFT sauna from Eastonia for the health concious resident. Within your home of contemporary coastal personality, 2,875 square feet are serene and elevated as walls of airy hues allow gridless-windows to compose ever-changing artwork of golden sunsets, lifting fog, and distant gliding hulls. Built-ins display collected shells and photographs from travels, while a glowing hearth anchors conversation with holiday guests. Spend unhurried Sundays in the landscaped-wrapped screened-in porch. Here, dream-up recipes for the weekend’s gatherings, while the kitchen’s updated stone surfaces and appliances prepare everything from perfect picnics to generous crab feasts. At day’s end, two and a half modern baths soothe, partnering with a main-level primary suite and two additional bedrooms—including airy loft. serving as a 4th bedroom. From your 125-foot pier with 8–10 feet MLW, welcome the seasonal residents that live on the Osprey platform, launch kayaks toward the picturesque edges of Long Haul Creek or set sail into the open reaches of the Chesapeake Bay. While on tour, spot sea glass along the shore, linger at the pier, and imagine the ease of your two-car garage. The dock - built by WHEEMS - offers 2 jet ski lifts, a 16K pound boatlift, electric and water and a platform area to sit over the water and relax . From home, St. Michaels charms just minutes away, where beloved shops, dining, and harbor life fill easy afternoons, while rounds at The Links at Perry Cabin, cycling routes, and scenic trails shape the days between. The roof has been replaced by MARASUN in 2022, new HVAC in 2021, pool build in 2022, new water heater 2023.

3 Beds ⋅ 3 Baths

DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS..... A treasure of vantage points and chic contemporary beauty, this Martingham waterfront retreat offers rare front-row views of Miles River happenings - including the historic Log Canoe Races, Fourth of July fireworks, daily passages of billowing sails,and, on crisp days, sightlines stretching for miles. Set on 2.32 acres with nearly 250 feet of sandy shoreline, life here moves with effortless rhythm; from morning beachfront strolls to afternoons shaped by regattas, summer pool partiesand in-town finds. Relax by the awe inspiring extra large 50 foot heated pool with jacuzzi with of space for sunbathing and relaxing. There is also a IGLUCRAFT sauna from Eastonia for the health concious resident. Within your home of contemporary coastal personality, 2,875 square feet are serene and elevated as walls of airy hues allow gridless-windows to compose ever-changing artwork of golden sunsets, lifting fog, and distant gliding hulls. Built-ins display collected shells and photographs from travels, while a glowing hearth anchors conversation with holiday guests. Spend unhurried Sundays in the landscaped-wrapped screened-in porch. Here, dream-up recipes for the weekend’s gatherings, while the kitchen’s updated stone surfaces and appliances prepare everything from perfect picnics to generous crab feasts. At day’s end, two and a half modern baths soothe, partnering with a main-level primary suite and two additional bedrooms—including airy loft. serving as a 4th bedroom. From your 125-foot pier with 8–10 feet MLW, welcome the seasonal residents that live on the Osprey platform, launch kayaks toward the picturesque edges of Long Haul Creek or set sail into the open reaches of the Chesapeake Bay. While on tour, spot sea glass along the shore, linger at the pier, and imagine the ease of your two-car garage. The dock - built by WHEEMS - offers 2 jet ski lifts, a 16K pound boatlift, electric and water and a platform area to sit over the water and relax . From home, St. Michaels charms just minutes away, where beloved shops, dining, and harbor life fill easy afternoons, while rounds at The Links at Perry Cabin, cycling routes, and scenic trails shape the days between. The roof has been replaced by MARASUN in 2022, new HVAC in 2021, pool build in 2022, new water heater 2023.

24830 Deepwater Point Dr, Saint Michaels

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

Selling Office: Benson & Mangold, LLC.

$2,405,000

Waterfront living at its finest in Pirate’s Cove, tucked along the serene waters of Trippe Creek. Set on 2.71 waterfront acres and beautifully sited across from a nature preserve, this property offers serenity, sophistication, and sweeping water views. Built in 1986 and thoughtfully reimagined with a custom renovation in 2016, the home blends elegant design and modern comforts in a meticulously maintained, one-level layout featuring three bedrooms and three full baths. Vaulted ceilings and walls of windows fill the living spaces with natural light, creating a bright, open atmosphere throughout. Overlooking the water, the gourmet kitchen is a chef’s delight, featuring a Wolf range with warming drawer, Sub-Zero refrigerator, double wall ovens, quartzite countertops, generous cabinetry, and a spacious island perfect for gathering. The living room, kitchen, and primary suite are all sun-drenched and open seamlessly to the deck, providing stunning water views and creating effortless indoor-outdoor living. The primary suite is a tranquil retreat with expansive water views, a large walk-in closet, and a spa-like en-suite bath highlighted by a stone soaking tub, glass-enclosed shower, and a unique laundry-chute window that connects directly to the laundry room for added convenience. Outside, enjoy summer days by the salt water, in-ground pool or stroll down to your private pier with approximately 4' MLW—ideal for boating, kayaking, or simply soaking in the peaceful setting. A large attached three-car garage provides ample space for vehicles, storage, and waterfront gear. This is the essence of Eastern Shore waterfront living—refined, relaxed, and ready to be enjoyed.

3 Beds ⋅ 3 Baths

Waterfront living at its finest in Pirate’s Cove, tucked along the serene waters of Trippe Creek. Set on 2.71 waterfront acres and beautifully sited across from a nature preserve, this property offers serenity, sophistication, and sweeping water views. Built in 1986 and thoughtfully reimagined with a custom renovation in 2016, the home blends elegant design and modern comforts in a meticulously maintained, one-level layout featuring three bedrooms and three full baths. Vaulted ceilings and walls of windows fill the living spaces with natural light, creating a bright, open atmosphere throughout. Overlooking the water, the gourmet kitchen is a chef’s delight, featuring a Wolf range with warming drawer, Sub-Zero refrigerator, double wall ovens, quartzite countertops, generous cabinetry, and a spacious island perfect for gathering. The living room, kitchen, and primary suite are all sun-drenched and open seamlessly to the deck, providing stunning water views and creating effortless indoor-outdoor living. The primary suite is a tranquil retreat with expansive water views, a large walk-in closet, and a spa-like en-suite bath highlighted by a stone soaking tub, glass-enclosed shower, and a unique laundry-chute window that connects directly to the laundry room for added convenience. Outside, enjoy summer days by the salt water, in-ground pool or stroll down to your private pier with approximately 4' MLW—ideal for boating, kayaking, or simply soaking in the peaceful setting. A large attached three-car garage provides ample space for vehicles, storage, and waterfront gear. This is the essence of Eastern Shore waterfront living—refined, relaxed, and ready to be enjoyed.

5728 Pirates Cove Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$2,400,000

The best of the best—perhaps the finest home ever offered in Cooke’s Hope. This spectacular, custom-built brick residence blends timeless craftsmanship with thoughtful updates and exceptional outdoor living. The bright and inviting, recently updated kitchen boasts new countertops, an elegant tile backsplash, and upgraded fixtures, while maintaining its generous layout with a large center island, walk-in pantry, and adjoining office nook.The main-level primary suite provides convenience and privacy, while four additional bedrooms upstairs each offer generous space for guests or family. Exquisite details are found throughout, including cherry wood floors, 10+ foot ceilings, extensive millwork, three fireplaces, and copper gutters. An elevator services the first and second floors, as well as the ground level of the oversized attached garage. Ample storage is available throughout, including a third-floor attic with a fixed staircase. Outside, the property has been transformed into a curated garden retreat. Extensive hardscaping frames a brick patio with an outdoor kitchen, complemented by a tranquil accent fountain and a stunning in-ground pool—creating a private oasis for entertaining or quiet enjoyment. The fencing and paver driveway complete the thoughtful exterior improvements. Enjoy the desirable amenities of Cooke’s Hope, including a tennis court, fitness room, walking trails, wildlife ponds, and concierge services—all just moments from the shops, dining, and conveniences of historic downtown Easton.

5 Beds ⋅ 6 Baths

The best of the best—perhaps the finest home ever offered in Cooke’s Hope. This spectacular, custom-built brick residence blends timeless craftsmanship with thoughtful updates and exceptional outdoor living. The bright and inviting, recently updated kitchen boasts new countertops, an elegant tile backsplash, and upgraded fixtures, while maintaining its generous layout with a large center island, walk-in pantry, and adjoining office nook.The main-level primary suite provides convenience and privacy, while four additional bedrooms upstairs each offer generous space for guests or family. Exquisite details are found throughout, including cherry wood floors, 10+ foot ceilings, extensive millwork, three fireplaces, and copper gutters. An elevator services the first and second floors, as well as the ground level of the oversized attached garage. Ample storage is available throughout, including a third-floor attic with a fixed staircase. Outside, the property has been transformed into a curated garden retreat. Extensive hardscaping frames a brick patio with an outdoor kitchen, complemented by a tranquil accent fountain and a stunning in-ground pool—creating a private oasis for entertaining or quiet enjoyment. The fencing and paver driveway complete the thoughtful exterior improvements. Enjoy the desirable amenities of Cooke’s Hope, including a tennis court, fitness room, walking trails, wildlife ponds, and concierge services—all just moments from the shops, dining, and conveniences of historic downtown Easton.

28613 Lois Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: ERA Martin Associates.

$2,400,000

This exceptional waterfront estate, nestled on approximately 4.25 private acres with sunset views of Plaindealing Creek, features a custom pier equipped with electric, water, along with a rip-rapped shoreline. Positioned just off the Tred Avon River, the property includes a fully irrigated lawn, a year round porch with brick flooring and separate HVAC. There is also a waterside composite deck. The meticulously maintained four-bedroom residence boasts antique wood flooring throughout, a stunning gourmet kitchen, waterside great room with fireplace and custom built-ins, and separate den/family room with beautiful built-ins. The main-level owner's suite offers custom closets and a luxurious bathroom with a freestanding soaking tub and a separate tiled shower. Upstairs, you'll find a cozy loft ideal for a library or sitting area, custom skylights with power shades, and a rooftop balcony that connects to a finished bedroom/craft room over the attached two car garage. Additional amenities include a detached two-car garage with a bonus area above, a detached RV garage, and a boat shed. Conveniently located just minutes from Historic Easton and St. Michaels.

4 Beds ⋅ 5 Baths

This exceptional waterfront estate, nestled on approximately 4.25 private acres with sunset views of Plaindealing Creek, features a custom pier equipped with electric, water, along with a rip-rapped shoreline. Positioned just off the Tred Avon River, the property includes a fully irrigated lawn, a year round porch with brick flooring and separate HVAC. There is also a waterside composite deck. The meticulously maintained four-bedroom residence boasts antique wood flooring throughout, a stunning gourmet kitchen, waterside great room with fireplace and custom built-ins, and separate den/family room with beautiful built-ins. The main-level owner's suite offers custom closets and a luxurious bathroom with a freestanding soaking tub and a separate tiled shower. Upstairs, you'll find a cozy loft ideal for a library or sitting area, custom skylights with power shades, and a rooftop balcony that connects to a finished bedroom/craft room over the attached two car garage. Additional amenities include a detached two-car garage with a bonus area above, a detached RV garage, and a boat shed. Conveniently located just minutes from Historic Easton and St. Michaels.

26362 Westerly Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

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

$2,300,000

135 +/- acres bordering Easton town limits.

29833 Dover Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Meredith Fine Properties.

$2,300,000

Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

4 Beds ⋅ 4 Baths

Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

3770 Leonard Cove Ln, Trappe

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

Selling Office: TTR Sotheby's International Realty.

$2,300,000

Situated on 2 acres in the sought-after North Point community, this waterfront Cape Cod offers over 5,400 square feet of space and sweeping views of the Tred Avon River. With 7 ft MLW at the private dock, it’s an exceptional opportunity for boaters seeking reliable deep-water access. The main level is highlighted by a waterfront primary suite complete with a walk-in closet and full en suite bath. The open living area with vaulted ceilings creates a spacious feel, while a screened porch and waterside deck invite you to take in the views. Upstairs, flexible space allows for additional entertaining or a custom retreat to suit your needs. The property also features a pool, mature landscaping, and a large garage with storage. Ready for its next chapter, the home offers buyers the chance to reimagine and personalize the interiors to match their own style and vision. Just minutes from both Easton and St. Michaels, this property combines convenience with privacy and remarkable water access—a rare opportunity on the Tred Avon. Property is being sold As-is.

4 Beds ⋅ 6 Baths

Situated on 2 acres in the sought-after North Point community, this waterfront Cape Cod offers over 5,400 square feet of space and sweeping views of the Tred Avon River. With 7 ft MLW at the private dock, it’s an exceptional opportunity for boaters seeking reliable deep-water access. The main level is highlighted by a waterfront primary suite complete with a walk-in closet and full en suite bath. The open living area with vaulted ceilings creates a spacious feel, while a screened porch and waterside deck invite you to take in the views. Upstairs, flexible space allows for additional entertaining or a custom retreat to suit your needs. The property also features a pool, mature landscaping, and a large garage with storage. Ready for its next chapter, the home offers buyers the chance to reimagine and personalize the interiors to match their own style and vision. Just minutes from both Easton and St. Michaels, this property combines convenience with privacy and remarkable water access—a rare opportunity on the Tred Avon. Property is being sold As-is.

26657 N Point Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$2,200,000

This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home’s appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.

4 Beds ⋅ 5 Baths

This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home’s appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.

962 San Domingo Ct, Saint Michaels

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

Selling Office: Meredith Fine Properties.

$2,200,000

Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for entertaining. Gleaming hardwood floors enhance the home's inviting ambiance. The primary suite is a serene escape with a stunning bath, while the upper level offers generous space ready to be transformed to match your vision. Outside, the property unfolds into a private waterfront playground, complete with a charming cottage ideal for guests or extended family, and a detached two-car garage with a one-bedroom apartment awaiting restoration. Bring your imagination! An exceptional opportunity for boating, entertaining, and relaxed coastal living. Just minutes from fabulous restaurants, boutique shopping, and the quaint charm of St. Michaels.

4 Beds ⋅ 5 Baths

Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for entertaining. Gleaming hardwood floors enhance the home's inviting ambiance. The primary suite is a serene escape with a stunning bath, while the upper level offers generous space ready to be transformed to match your vision. Outside, the property unfolds into a private waterfront playground, complete with a charming cottage ideal for guests or extended family, and a detached two-car garage with a one-bedroom apartment awaiting restoration. Bring your imagination! An exceptional opportunity for boating, entertaining, and relaxed coastal living. Just minutes from fabulous restaurants, boutique shopping, and the quaint charm of St. Michaels.

24645 Long Haul, Saint Michaels

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$2,190,000

Significant Price Reduction! Welcome to this exceptional waterfront retreat on 3.5 acres overlooking Solitude Creek in Royal Oak. From the moment you enter, expansive water views set the tone for gracious living. Renovated in 2023, this 3,248 sq. ft. residence offers 4 bedrooms and 3.5 baths, including a main-level waterside primary suite with spa-like bath. The gourmet kitchen with upgraded appliances flows to inviting gathering spaces—family/recreation room, bar and sitting area, dining area and a living room with beamed ceilings, stone fireplace, and a dramatic wall of windows framing the panoramic view. Upstairs, three guest bedrooms—each with water views—include one ensuite and a shared hall bath. Outdoor living is enhanced with two expansive decks, an inground waterside pool, new outdoor shower, kayak launch, and new private pier with lift, two slips, and 3.5'MLW. A 3-car attached garage completes this inviting Eastern Shore property along with a new septic and hook-up to sewer. *Complete list of updates available! Furnishings, boat, and other outdoor items may be available for purchase. Property has excellent rental history but new owner would have to go through county application and approval process.

4 Beds ⋅ 4 Baths

Significant Price Reduction! Welcome to this exceptional waterfront retreat on 3.5 acres overlooking Solitude Creek in Royal Oak. From the moment you enter, expansive water views set the tone for gracious living. Renovated in 2023, this 3,248 sq. ft. residence offers 4 bedrooms and 3.5 baths, including a main-level waterside primary suite with spa-like bath. The gourmet kitchen with upgraded appliances flows to inviting gathering spaces—family/recreation room, bar and sitting area, dining area and a living room with beamed ceilings, stone fireplace, and a dramatic wall of windows framing the panoramic view. Upstairs, three guest bedrooms—each with water views—include one ensuite and a shared hall bath. Outdoor living is enhanced with two expansive decks, an inground waterside pool, new outdoor shower, kayak launch, and new private pier with lift, two slips, and 3.5'MLW. A 3-car attached garage completes this inviting Eastern Shore property along with a new septic and hook-up to sewer. *Complete list of updates available! Furnishings, boat, and other outdoor items may be available for purchase. Property has excellent rental history but new owner would have to go through county application and approval process.

25500 Chance Farm Rd, Royal Oak

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

Selling Office: Benson & Mangold, LLC.

$2,125,000

Significant Price Improvement!!! Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully re-imagined through comprehensive renovations completed in 2023 and 2024. See virtual tours above. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms and 5 and a half baths, this home offers an elevated blend of sophistication, comfort, and timeless Eastern Shore charm— located on East Chew Street, the property is walking distance to the harbor, boutiques, and celebrated dining of St. Michaels. From the moment you enter, the quality is unmistakable. Clean sightlines and an open, interconnected floor plan create an ideal setting for both everyday living and effortless entertaining. Throughout the home, curated lighting, custom millwork, elegant crown molding, custom doors, and redesigned fireplaces reflect a commitment to thoughtful design and enduring craftsmanship. The main level features a primary suite with beautifully updated finishes and refined details, including a fully renovated primary bath. There is a second primary suite on the second level as well with a renovated bath. The main residence offers four en-suite bedrooms; all baths have been renovated each providing privacy and comfort for family and guests alike. A standout feature of the property is the fully independent renovated permitted apartment above the two-car heated garage. Complete with a full kitchen, bath, washer and dryer, office area, and sleeping loft, this versatile space is ideal for extended family, guests, a private studio, home office or potential rental income. At the heart of the home, with secure access to the main house from a two garage, providing off street parking and easy kitchen access, is both functional and thoughtful. The kitchen showcases high-end appliances with gas, exquisite finishes, and custom lighting. The kitchen flows seamlessly into the living and dining areas, where fireplaces add warmth and ambiance. Upstairs, an additional media lounge area, a second upper-level primary suite offers a serene retreat with updated bathroom cabinetry and fixtures, a fireplace, and a beautifully designed custom walk-in closet. A third en-suite bedroom along with a spacious laundry room adjacent to the media room, enhance convenience. The fourth en-suite bedroom is on the third level with additional living space and a renovated bathroom. Outside, professionally newly designed landscaping and a full irrigation system provide year-round beauty, while the blue slate terrace—framed by expertly trained David Austin climbing roses—a grilling area creates a private outdoor sanctuary for entertaining or quiet reflection. Modern conveniences include Wi-Fi broadband, advanced home monitoring systems, and a Hikvision doorbell with remote access, updated HVAC, Renaldi tankless hot water systems both add comfort and peace of mind. A concrete crawlspace with a dehumidification unit is part of this well-built home. Perfectly positioned near the waterfront and within easy reach of Easton and Oxford, this turnkey home is ideal as a full-time residence or a sophisticated weekend retreat. With flawless finishes, flexible living spaces, and an unrivaled location, this property represents the pinnacle of Eastern Shore living. Schedule your private showing and experience its exceptional character firsthand. On a price per sq. ft. basis this property represents an excellent value and the new two-level apartment above the heated garage is an exceptional rental investment opportunity, guest quarters, studio or office.

5 Beds ⋅ 6 Baths

Significant Price Improvement!!! Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully re-imagined through comprehensive renovations completed in 2023 and 2024. See virtual tours above. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms and 5 and a half baths, this home offers an elevated blend of sophistication, comfort, and timeless Eastern Shore charm— located on East Chew Street, the property is walking distance to the harbor, boutiques, and celebrated dining of St. Michaels. From the moment you enter, the quality is unmistakable. Clean sightlines and an open, interconnected floor plan create an ideal setting for both everyday living and effortless entertaining. Throughout the home, curated lighting, custom millwork, elegant crown molding, custom doors, and redesigned fireplaces reflect a commitment to thoughtful design and enduring craftsmanship. The main level features a primary suite with beautifully updated finishes and refined details, including a fully renovated primary bath. There is a second primary suite on the second level as well with a renovated bath. The main residence offers four en-suite bedrooms; all baths have been renovated each providing privacy and comfort for family and guests alike. A standout feature of the property is the fully independent renovated permitted apartment above the two-car heated garage. Complete with a full kitchen, bath, washer and dryer, office area, and sleeping loft, this versatile space is ideal for extended family, guests, a private studio, home office or potential rental income. At the heart of the home, with secure access to the main house from a two garage, providing off street parking and easy kitchen access, is both functional and thoughtful. The kitchen showcases high-end appliances with gas, exquisite finishes, and custom lighting. The kitchen flows seamlessly into the living and dining areas, where fireplaces add warmth and ambiance. Upstairs, an additional media lounge area, a second upper-level primary suite offers a serene retreat with updated bathroom cabinetry and fixtures, a fireplace, and a beautifully designed custom walk-in closet. A third en-suite bedroom along with a spacious laundry room adjacent to the media room, enhance convenience. The fourth en-suite bedroom is on the third level with additional living space and a renovated bathroom. Outside, professionally newly designed landscaping and a full irrigation system provide year-round beauty, while the blue slate terrace—framed by expertly trained David Austin climbing roses—a grilling area creates a private outdoor sanctuary for entertaining or quiet reflection. Modern conveniences include Wi-Fi broadband, advanced home monitoring systems, and a Hikvision doorbell with remote access, updated HVAC, Renaldi tankless hot water systems both add comfort and peace of mind. A concrete crawlspace with a dehumidification unit is part of this well-built home. Perfectly positioned near the waterfront and within easy reach of Easton and Oxford, this turnkey home is ideal as a full-time residence or a sophisticated weekend retreat. With flawless finishes, flexible living spaces, and an unrivaled location, this property represents the pinnacle of Eastern Shore living. Schedule your private showing and experience its exceptional character firsthand. On a price per sq. ft. basis this property represents an excellent value and the new two-level apartment above the heated garage is an exceptional rental investment opportunity, guest quarters, studio or office.

203 Chew Ave E, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Monument Sotheby's International Realty.

$2,125,000

It doesn't get any better than this ! Stunning brand-new ,one-story coastal residence with a contemporary flair! As soon as you enter this magnificent home, you will be captivated by 20'+ ceilings, superb craftsmanship , an extremely well-designed open floor-plan; breathtaking water-views on Dun Cove and a luxurious yet inviting kitchen. There are a total of 3 en-suite bedrooms as well as an office, laundry room, mud room, and a grand family room, dining area and kitchen, Some notable features include: Cast iron farmhouse kitchen sink ; cast iron claw-foot bath-tub : 3/4 " solid white oak flooring; 3/4" tongue and groove ceilings; solid interior doors; Azek shaker siding; heated floors in all bathrooms; marble tile in Primary suite bathroom; ILVE 48" gas range; 150 ft. pier and a large waterside deck. Perfect home for either a primary residence or a vacation home. The prestigious Langdon farm location offers convenience to both St. Michaels and Tilghman. Owner is not responsible for any road maintenance as their lot is still on County Road.

3 Beds ⋅ 4 Baths

It doesn't get any better than this ! Stunning brand-new ,one-story coastal residence with a contemporary flair! As soon as you enter this magnificent home, you will be captivated by 20'+ ceilings, superb craftsmanship , an extremely well-designed open floor-plan; breathtaking water-views on Dun Cove and a luxurious yet inviting kitchen. There are a total of 3 en-suite bedrooms as well as an office, laundry room, mud room, and a grand family room, dining area and kitchen, Some notable features include: Cast iron farmhouse kitchen sink ; cast iron claw-foot bath-tub : 3/4 " solid white oak flooring; 3/4" tongue and groove ceilings; solid interior doors; Azek shaker siding; heated floors in all bathrooms; marble tile in Primary suite bathroom; ILVE 48" gas range; 150 ft. pier and a large waterside deck. Perfect home for either a primary residence or a vacation home. The prestigious Langdon farm location offers convenience to both St. Michaels and Tilghman. Owner is not responsible for any road maintenance as their lot is still on County Road.

21825 Langdon Farm Rd, Sherwood

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

Selling Office: Taylor Properties.

$2,100,000

This Island Creek waterfront home located on deep water with a southern exposure and long shoreline is being sold for the first time since built in 1999. Situated on 3.8 acres, every detail was thought out and executed by the owners and a top rate builder. The house consists of 4,469 sq. ft. of living space plus a two car garage. The house has an open floor plan, featuring a large eat in kitchen with views over Island Creek, the dock and an expansive well landscaped lawn that drops to the shoreline. The kitchen is well appointed with top end appliances, tons of storage areas, pantry and is close to the laundry room and shop. There is a primary bedroom suite on the first floor, a second bath, and three bedrooms and two full baths on the second floor. There is a deck, patio and screened porch facing SW, all meticulously maintained. The property is located in the “X” flood zone. This is an extraordinary waterfront property located in the Oxford zip code on one of the best deep water creeks in Talbot County.

4 Beds ⋅ 4 Baths

This Island Creek waterfront home located on deep water with a southern exposure and long shoreline is being sold for the first time since built in 1999. Situated on 3.8 acres, every detail was thought out and executed by the owners and a top rate builder. The house consists of 4,469 sq. ft. of living space plus a two car garage. The house has an open floor plan, featuring a large eat in kitchen with views over Island Creek, the dock and an expansive well landscaped lawn that drops to the shoreline. The kitchen is well appointed with top end appliances, tons of storage areas, pantry and is close to the laundry room and shop. There is a primary bedroom suite on the first floor, a second bath, and three bedrooms and two full baths on the second floor. There is a deck, patio and screened porch facing SW, all meticulously maintained. The property is located in the “X” flood zone. This is an extraordinary waterfront property located in the Oxford zip code on one of the best deep water creeks in Talbot County.

27877 Bent Farm Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$2,100,000

Nestled on a gorgeous waterfront lot just minutes from St. Michaels, this exceptional property offers the perfect blend of privacy, comfort, and convenience. Enjoy an easy bike ride into town while coming home to a peaceful setting surrounded by mature, established trees and beautifully landscaped grounds. Built with quality and designed for comfortable living, the home features two spacious primary suites, including one conveniently located on the first floor. Large walk-in closets provide abundant storage throughout. An attached in-law suite offers flexibility for extended family, guests, or multi-generational living. The impressive foyer welcomes you into a thoughtfully designed floor plan featuring mostly hardwood floors throughout. Enjoy a spacious dining room perfect for large family gatherings, a comfortable living room anchored by a cozy brick fireplace, dedicated office space, and a separate craft room. A large utility room provides exceptional functionality with space for an extra freezer and refrigerator, while multiple HVAC zones ensure comfortable heating and cooling throughout the home. Outdoor amenities are equally impressive. Relax by the pool, entertain on the waterfront, or take advantage of the private dock with approximately 4 feet of mean low water depth. The property also includes a substantial workshop with tractor storage, ideal for hobbyists, boaters, or those needing extra workspace. Recent improvements provide peace of mind, including a roof that is just two years old and a paved driveway completed within the last year. This is a rare opportunity to own a solidly built waterfront retreat offering space, functionality, and timeless Eastern Shore charm just moments from the shops, restaurants, and waterfront attractions of St. Michaels.

5 Beds ⋅ 6 Baths

Nestled on a gorgeous waterfront lot just minutes from St. Michaels, this exceptional property offers the perfect blend of privacy, comfort, and convenience. Enjoy an easy bike ride into town while coming home to a peaceful setting surrounded by mature, established trees and beautifully landscaped grounds. Built with quality and designed for comfortable living, the home features two spacious primary suites, including one conveniently located on the first floor. Large walk-in closets provide abundant storage throughout. An attached in-law suite offers flexibility for extended family, guests, or multi-generational living. The impressive foyer welcomes you into a thoughtfully designed floor plan featuring mostly hardwood floors throughout. Enjoy a spacious dining room perfect for large family gatherings, a comfortable living room anchored by a cozy brick fireplace, dedicated office space, and a separate craft room. A large utility room provides exceptional functionality with space for an extra freezer and refrigerator, while multiple HVAC zones ensure comfortable heating and cooling throughout the home. Outdoor amenities are equally impressive. Relax by the pool, entertain on the waterfront, or take advantage of the private dock with approximately 4 feet of mean low water depth. The property also includes a substantial workshop with tractor storage, ideal for hobbyists, boaters, or those needing extra workspace. Recent improvements provide peace of mind, including a roof that is just two years old and a paved driveway completed within the last year. This is a rare opportunity to own a solidly built waterfront retreat offering space, functionality, and timeless Eastern Shore charm just moments from the shops, restaurants, and waterfront attractions of St. Michaels.

8240 Tricefield, Saint Michaels

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

Selling Office: Benson & Mangold, LLC.

$2,100,000

0-3750 Windy Hill Rd- 139 acre Tract Located in the heart of Maryland’s Eastern Shore, this 139± acre farm in Talbot County offers a rare combination of highly productive agricultural land, proven hunting opportunities, and long-term investment potential. With a strong history of crop production and no conservation easements, this property provides flexibility for farming, recreation, and future development. The property is predominantly comprised of fertile, tillable acreage that has been successfully farmed in a rotation of soybeans, corn, and wheat. The soils in this region are known for their productivity, making this tract well-suited for continued agricultural use. Portions of the property have previously been enrolled in CRP programs, presenting an opportunity for future income diversification through conservation programs while maintaining active farming operations. Access is a standout feature, with dual road frontage along both Kates Point Road and Clarks Wharf Road. This allows for efficient equipment movement, multiple entry points, and potential homesite, subject to local regulations. The layout of the property is functional and open, offering expansive fields with excellent visibility and ease of management. For outdoor enthusiasts and investors alike, the recreational value is significant. The farm includes an established pit specifically designed for Canada goose and snow goose hunting, with the surrounding area known for strong seasonal waterfowl migration. The open fields and agricultural setting create ideal feeding conditions, making this a reliable hunting destination. In addition to waterfowl, the property supports a consistent population of whitetail deer. Surrounded by large tracts of timber, this farm serves as a natural feeding and transition area, increasing deer movement throughout the property. This balance of agriculture and nearby cover creates an ideal setup for both hunting and wildlife observation. The rural and private setting offers peace and seclusion while still being conveniently located near the towns of Easton and Cambridge. These nearby hubs provide access to shopping, dining, healthcare, and other essential services, making the property both practical and accessible. With no conservation easements in place, the property maintains maximum flexibility for future use. Whether you are looking to expand a farming operation, establish a premier hunting property, or build a private residence, this tract offers multiple pathways to meet your goals.

3750 Windy Hill Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Meredith Fine Properties.

$2,075,000

Traditional center hall colonial remodeled in 2006 with glassed sunroom and family room overlooking the water. Gorgeous sunsets over the river. The lot is high and well drained, and the shoreline is rip-rapped.. Bailey's Neck and Peachblossom Point are off Rt 333 a/k/a "the Oxford Road," which has far less traffic than Rt 33 "the St. Michaels Road". Llandaff RD provides quick access to Route 50. Talbot Country Club nearby. 15' x 19' Ipe deck with built-in benches on water side pf house. 20 x 21 two car garage with overhead storage, radar garage door openers. Most rooms have recessed lighting Planking on dock can be slippery--- please be careful. "Spring Cove" has been dredged to 4 ft MLW right up to most of the docks. Was 4 ft when checked earlier this summer but arrange to do your own checking. Great views westward to the Tred Avon River. Deed restriction precludes short term vacation rentals at all Peachblossom Point residences. The kitchen and sunroom and family room are all heated and cooled by the heat pump that is located under the study window. The rest of the house has central air conditioning from the compressors on the north side of the house The rest of the house is heated by electric baseboard heat with individual controls in the various rooms.

3 Beds ⋅ 3 Baths

Traditional center hall colonial remodeled in 2006 with glassed sunroom and family room overlooking the water. Gorgeous sunsets over the river. The lot is high and well drained, and the shoreline is rip-rapped.. Bailey's Neck and Peachblossom Point are off Rt 333 a/k/a "the Oxford Road," which has far less traffic than Rt 33 "the St. Michaels Road". Llandaff RD provides quick access to Route 50. Talbot Country Club nearby. 15' x 19' Ipe deck with built-in benches on water side pf house. 20 x 21 two car garage with overhead storage, radar garage door openers. Most rooms have recessed lighting Planking on dock can be slippery--- please be careful. "Spring Cove" has been dredged to 4 ft MLW right up to most of the docks. Was 4 ft when checked earlier this summer but arrange to do your own checking. Great views westward to the Tred Avon River. Deed restriction precludes short term vacation rentals at all Peachblossom Point residences. The kitchen and sunroom and family room are all heated and cooled by the heat pump that is located under the study window. The rest of the house has central air conditioning from the compressors on the north side of the house The rest of the house is heated by electric baseboard heat with individual controls in the various rooms.

6680 Peachblossom Point Rd, Easton

Listing courtesy of Shoreline Realty. Contact:

Selling Office: Redfin Corp.

$2,000,000

Welcome to Terrapin Point, an extraordinary waterfront estate nestled in the heart of Royal Oak, Maryland—one of Talbot County’s most coveted and picturesque settings. Built in 1890, this timeless Victorian residence evokes the charm of a bygone era, blending old-world elegance with the serene beauty of Maryland’s Eastern Shore. Set gracefully on a private point along the tranquil waters of Oak Creek, the property offers sweeping, uninterrupted waterfront views and a rare sense of peace and seclusion. With minimal boat traffic and protected waters just off the Miles River, Terrapin Point is a true sanctuary for those seeking quiet coastal living and the wonders of nature. A long, tree-lined driveway creates a grand and memorable approach, opening to a storybook setting reminiscent of a Norman Rockwell painting. The home itself is filled with natural light and architectural character, including soaring ceilings, elegant archways, and a stunning dining room with exposed beams that overlooks the water—perfectly framing the estate’s breathtaking surroundings. Designed for both relaxation and entertaining, the home features a spacious kitchen and dining area ideal for hosting, along with an oversize screened porch that invites you to unwind while enjoying gentle breezes off the creek. Outdoors, a beautifully positioned in-ground pool sits just at the water’s edge, offering a resort-like vacation experience. On the edge of the trees sits a beautifully designed potential "glamping" cabin, art or music studio where you can enjoy the birds singing and watch the light through the trees. Perfectly located, the property sits equidistant between the charming towns of Easton and St. Michaels, allowing effortless access to renowned dining, shopping, and cultural attractions while maintaining a peaceful, tucked-away feel. The 12 acre point of land and home embodies the quintessential Eastern Shore lifestyle—refined yet relaxed, elegant yet inviting. A rare offering where timeless architecture, premier waterfront, and an exceptional location come together to create a truly unforgettable property. *Seller currently resides at the property in the main floor primary suite. Several pictures have been visually enhanced with virtual staging.

4 Beds ⋅ 5 Baths

Welcome to Terrapin Point, an extraordinary waterfront estate nestled in the heart of Royal Oak, Maryland—one of Talbot County’s most coveted and picturesque settings. Built in 1890, this timeless Victorian residence evokes the charm of a bygone era, blending old-world elegance with the serene beauty of Maryland’s Eastern Shore. Set gracefully on a private point along the tranquil waters of Oak Creek, the property offers sweeping, uninterrupted waterfront views and a rare sense of peace and seclusion. With minimal boat traffic and protected waters just off the Miles River, Terrapin Point is a true sanctuary for those seeking quiet coastal living and the wonders of nature. A long, tree-lined driveway creates a grand and memorable approach, opening to a storybook setting reminiscent of a Norman Rockwell painting. The home itself is filled with natural light and architectural character, including soaring ceilings, elegant archways, and a stunning dining room with exposed beams that overlooks the water—perfectly framing the estate’s breathtaking surroundings. Designed for both relaxation and entertaining, the home features a spacious kitchen and dining area ideal for hosting, along with an oversize screened porch that invites you to unwind while enjoying gentle breezes off the creek. Outdoors, a beautifully positioned in-ground pool sits just at the water’s edge, offering a resort-like vacation experience. On the edge of the trees sits a beautifully designed potential "glamping" cabin, art or music studio where you can enjoy the birds singing and watch the light through the trees. Perfectly located, the property sits equidistant between the charming towns of Easton and St. Michaels, allowing effortless access to renowned dining, shopping, and cultural attractions while maintaining a peaceful, tucked-away feel. The 12 acre point of land and home embodies the quintessential Eastern Shore lifestyle—refined yet relaxed, elegant yet inviting. A rare offering where timeless architecture, premier waterfront, and an exceptional location come together to create a truly unforgettable property. *Seller currently resides at the property in the main floor primary suite. Several pictures have been visually enhanced with virtual staging.

26090 Royal Oak Rd, Royal Oak

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$2,000,000

Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and cultural amenities—no car required. Designed for both comfort and entertaining, the light filled interior features an open floor plan with high ceilings, a well-appointed chef’s kitchen, and a welcoming fireplace. Four private bedroom suites – including a primary suite on the main level - make it a breeze to accommodate larger family gatherings and visiting friends. A spacious screened waterside porch, heated inground pool, deck and Bocce Court extend the living space to the outdoors for seasonal entertaining and warmer weather fun. A separate pool house/studio, connected by the screened porch and breezeway, includes a full bath and offers flexibility for use as a home office, creative space or additional guest quarters. The 2.3 acres lot is located at the edge of the San Domingo Cove community and is adjacent to protected woodlands, providing privacy, and offers with public water and sewer and a fully fenced backyard. Boating enthusiasts will appreciate the dock (shared with one neighboring property), offering two dedicated slips and a floating dock per owner and water depths of approximately 4–4.5 feet at the slips and 3 feet at the floating dock. From here it is easy to boat to Tilghman Island and Oxford, and San Domingo Creek is also great for kayaking and canoeing. An exceptional and rare opportunity to enjoy refined, in town waterfront living in one of Talbot County’s most sought after communities.

4 Beds ⋅ 6 Baths

Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and cultural amenities—no car required. Designed for both comfort and entertaining, the light filled interior features an open floor plan with high ceilings, a well-appointed chef’s kitchen, and a welcoming fireplace. Four private bedroom suites – including a primary suite on the main level - make it a breeze to accommodate larger family gatherings and visiting friends. A spacious screened waterside porch, heated inground pool, deck and Bocce Court extend the living space to the outdoors for seasonal entertaining and warmer weather fun. A separate pool house/studio, connected by the screened porch and breezeway, includes a full bath and offers flexibility for use as a home office, creative space or additional guest quarters. The 2.3 acres lot is located at the edge of the San Domingo Cove community and is adjacent to protected woodlands, providing privacy, and offers with public water and sewer and a fully fenced backyard. Boating enthusiasts will appreciate the dock (shared with one neighboring property), offering two dedicated slips and a floating dock per owner and water depths of approximately 4–4.5 feet at the slips and 3 feet at the floating dock. From here it is easy to boat to Tilghman Island and Oxford, and San Domingo Creek is also great for kayaking and canoeing. An exceptional and rare opportunity to enjoy refined, in town waterfront living in one of Talbot County’s most sought after communities.

938 Marea Ter, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Washington Fine Properties, LLC.

$1,975,000

Construction is complete on this beautiful new waterfront home by Laine Street Homes. With 5,000 + finished sqft, 480 sqft of cover outdoor living space, approx. 4.5 acres, and about 320 lnft of frontage on Peach Blossom Creek, with a main level owners suite this home is a must see. Luxury amenities include 7 ½” wide high end wood floors, gourmet kitchen, 48” dual fuel range, built in artisan hood, beverage center, farmhouse sink, quartz countertops, dual fireplaces with matching quartz surrounds, luxury main level owners suite, spa shower, upgraded tile in all bathrooms, freestanding tub, high end custom cabinetry, 2nd floor loft / rec room accessible from 2nd, 3rd and 4th bedrooms and with ensuite bathrooms, full walk up basement with finished rec room, bedroom and full bathroom, custom trim, black and bronze hardware, custom lighting fixtures and more. Additional features include, James Hardie siding, 30 year architectural singles, standing seam metal porch roof, stone water table, two zone 92% efficient Carrier HAVC, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, and the list goes on and on. ***Pier Permit in Process***

5 Beds ⋅ 6 Baths

Construction is complete on this beautiful new waterfront home by Laine Street Homes. With 5,000 + finished sqft, 480 sqft of cover outdoor living space, approx. 4.5 acres, and about 320 lnft of frontage on Peach Blossom Creek, with a main level owners suite this home is a must see. Luxury amenities include 7 ½” wide high end wood floors, gourmet kitchen, 48” dual fuel range, built in artisan hood, beverage center, farmhouse sink, quartz countertops, dual fireplaces with matching quartz surrounds, luxury main level owners suite, spa shower, upgraded tile in all bathrooms, freestanding tub, high end custom cabinetry, 2nd floor loft / rec room accessible from 2nd, 3rd and 4th bedrooms and with ensuite bathrooms, full walk up basement with finished rec room, bedroom and full bathroom, custom trim, black and bronze hardware, custom lighting fixtures and more. Additional features include, James Hardie siding, 30 year architectural singles, standing seam metal porch roof, stone water table, two zone 92% efficient Carrier HAVC, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, and the list goes on and on. ***Pier Permit in Process***

28838 Jennings Rd, Easton

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

Selling Office: TTR Sotheby's International Realty.

$1,975,000

Nestled along the Miles River with westerly sunset views, this exceptional house offers a blend of modern comfort and classic Eastern Shore charm. Boasting sweeping views of St. Michaels, this home features an expansive open floor plan designed for seamless indoor-outdoor living. Step inside to find a sun-drenched great room creating the perfect setting for both quiet relaxation and lively gatherings. The gourmet kitchen, complete with granite countertops, high-end stainless steel appliances, and a spacious island, flows effortlessly into the living and dining areas, making entertaining a breeze. Outside, the resort-style backyard is an entertainer's dream, highlighted by a sparkling waterside pool, waterside cabana/bar, and lush landscaping. Whether you’re hosting a sunset cocktail hour or enjoying a quiet morning coffee, the panoramic water views provide a stunning backdrop. Additional features include, whole house generator, detached garage for additional car storage, cedar siding, and an irrigated rear lawn, a luxurious primary suite with waterfront views, a spa-like bath, generous guest accommodations, and ample storage throughout. With direct water access, you can easily enjoy all the Miles River has to offer. Located just minutes from downtown Easton and a short boat ride to the historic charm of St. Michaels, this property offers the perfect blend of coastal living and small-town sophistication.

3 Beds ⋅ 5 Baths

Nestled along the Miles River with westerly sunset views, this exceptional house offers a blend of modern comfort and classic Eastern Shore charm. Boasting sweeping views of St. Michaels, this home features an expansive open floor plan designed for seamless indoor-outdoor living. Step inside to find a sun-drenched great room creating the perfect setting for both quiet relaxation and lively gatherings. The gourmet kitchen, complete with granite countertops, high-end stainless steel appliances, and a spacious island, flows effortlessly into the living and dining areas, making entertaining a breeze. Outside, the resort-style backyard is an entertainer's dream, highlighted by a sparkling waterside pool, waterside cabana/bar, and lush landscaping. Whether you’re hosting a sunset cocktail hour or enjoying a quiet morning coffee, the panoramic water views provide a stunning backdrop. Additional features include, whole house generator, detached garage for additional car storage, cedar siding, and an irrigated rear lawn, a luxurious primary suite with waterfront views, a spa-like bath, generous guest accommodations, and ample storage throughout. With direct water access, you can easily enjoy all the Miles River has to offer. Located just minutes from downtown Easton and a short boat ride to the historic charm of St. Michaels, this property offers the perfect blend of coastal living and small-town sophistication.

8320 Ingleton Cir W, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Realty.

$1,950,000

The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A What's special The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A long, pine-lined entrance drive carries you toward a first glimpse of Harris Creek ahead — water framed by tall pines, open and still. Then the drive sweeps gently to the left, and then, almost as a surprise, the cottage — modest, elegant, perfectly placed. It makes no attempt to impress. It doesn’t need to. The cottage is quiet and handsome — simply elegant in the way that only genuine character produces. Nothing oversized, nothing imposing. Just a well-proportioned, beautifully maintained home that belongs exactly where it sits. That first view of the house — unhurried, understated, perfectly at home in its setting — tells you everything about what kind of place this is. THE PROPERTY Few waterfront properties in Talbot County can offer what Rose’s Garden delivers: 6.87 private acres along Harris Creek, with approximately 400 feet of rip-rap shoreline in excellent condition. That kind of scale — within the Saint Michaels area — is simply not available anymore. And the west-facing orientation means sunsets over open water every evening, looking out across largely undeveloped land on the opposite shore. The views are clean, natural, and remarkably unspoiled. For a property this close to Saint Michaels, that is genuinely extraordinary. A private dock with 4 feet of water provides direct access to the creek and the Chesapeake Bay beyond. The home has been comprehensively renovated — new roof, refinished hardwood floors, updated kitchen, two fully remodeled baths, and complete HVAC throughout. A buyer arrives to something turnkey, not a project. THE LIFESTYLE Morning coffee on the primary bedroom deck with the creek glassy and still, nothing but natural shoreline across the water. Afternoons in the saltwater pool with the scent of pines and the sound of the water nearby. Evenings at the waterside pavilion as the sky turns orange over Harris Creek — unobstructed, undeveloped, all yours to take in. The rose garden and large, beautiful mature trees spread across the property give the grounds a park-like, tended quality that simply cannot be manufactured — it accumulates over decades, and here it already exists. At night, subtle landscape lighting illuminates those trees from below, casting the grounds in a quiet, warm glow. It is the kind of lighting that enhances rather than announces — a property that is just as inviting after dark as it is at sunset. And yet Saint Michaels — its restaurants, the Chesapeake Bay Maritime Museum, the Miles River Yacht Club — is just minutes away. The seclusion is real. The convenience is too. That combination is what makes Rose’s Garden so difficult to replicate. WHY THIS PROPERTY IS RARE Properties like Rose’s Garden do not come together by accident. The acreage, the frontage, the dock, the unspoiled views, the mature landscape — each of these alone would make a property noteworthy. Together, and this close to Saint Michaels, they represent something that simply does not come to market often. The renovation means a buyer inherits none of the headaches that typically accompany older waterfront homes — the deferred maintenance, the aging systems, the compromises. The work is done and done well. Rose’s Garden is ready for its next chapter. AT A GLANCE 6.87 private acres — Saint Michaels area — Waterside pavilion — Pine-lined entrance drive w/ creek views — New roof — Large mature trees throughout grounds — Primary bedroom deck w/ water views — Subtle up lighting on mature trees — Full HVAC — central + mini-splits — Unspoiled views — largely undeveloped opposite shore — Both baths fully remodeled — 400 ft Harris Creek frontage — Refinished hardwood floors — Rip-rap shoreline — excellent condition — Updated kitchen w/

3 Beds ⋅ 3 Baths

The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A What's special The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A long, pine-lined entrance drive carries you toward a first glimpse of Harris Creek ahead — water framed by tall pines, open and still. Then the drive sweeps gently to the left, and then, almost as a surprise, the cottage — modest, elegant, perfectly placed. It makes no attempt to impress. It doesn’t need to. The cottage is quiet and handsome — simply elegant in the way that only genuine character produces. Nothing oversized, nothing imposing. Just a well-proportioned, beautifully maintained home that belongs exactly where it sits. That first view of the house — unhurried, understated, perfectly at home in its setting — tells you everything about what kind of place this is. THE PROPERTY Few waterfront properties in Talbot County can offer what Rose’s Garden delivers: 6.87 private acres along Harris Creek, with approximately 400 feet of rip-rap shoreline in excellent condition. That kind of scale — within the Saint Michaels area — is simply not available anymore. And the west-facing orientation means sunsets over open water every evening, looking out across largely undeveloped land on the opposite shore. The views are clean, natural, and remarkably unspoiled. For a property this close to Saint Michaels, that is genuinely extraordinary. A private dock with 4 feet of water provides direct access to the creek and the Chesapeake Bay beyond. The home has been comprehensively renovated — new roof, refinished hardwood floors, updated kitchen, two fully remodeled baths, and complete HVAC throughout. A buyer arrives to something turnkey, not a project. THE LIFESTYLE Morning coffee on the primary bedroom deck with the creek glassy and still, nothing but natural shoreline across the water. Afternoons in the saltwater pool with the scent of pines and the sound of the water nearby. Evenings at the waterside pavilion as the sky turns orange over Harris Creek — unobstructed, undeveloped, all yours to take in. The rose garden and large, beautiful mature trees spread across the property give the grounds a park-like, tended quality that simply cannot be manufactured — it accumulates over decades, and here it already exists. At night, subtle landscape lighting illuminates those trees from below, casting the grounds in a quiet, warm glow. It is the kind of lighting that enhances rather than announces — a property that is just as inviting after dark as it is at sunset. And yet Saint Michaels — its restaurants, the Chesapeake Bay Maritime Museum, the Miles River Yacht Club — is just minutes away. The seclusion is real. The convenience is too. That combination is what makes Rose’s Garden so difficult to replicate. WHY THIS PROPERTY IS RARE Properties like Rose’s Garden do not come together by accident. The acreage, the frontage, the dock, the unspoiled views, the mature landscape — each of these alone would make a property noteworthy. Together, and this close to Saint Michaels, they represent something that simply does not come to market often. The renovation means a buyer inherits none of the headaches that typically accompany older waterfront homes — the deferred maintenance, the aging systems, the compromises. The work is done and done well. Rose’s Garden is ready for its next chapter. AT A GLANCE 6.87 private acres — Saint Michaels area — Waterside pavilion — Pine-lined entrance drive w/ creek views — New roof — Large mature trees throughout grounds — Primary bedroom deck w/ water views — Subtle up lighting on mature trees — Full HVAC — central + mini-splits — Unspoiled views — largely undeveloped opposite shore — Both baths fully remodeled — 400 ft Harris Creek frontage — Refinished hardwood floors — Rip-rap shoreline — excellent condition — Updated kitchen w/

8670 Bozman Neavitt, Saint Michaels

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

Selling Office: Unrepresented.

$1,875,000

Welcome to an amazing farm opportunity located 3 miles from Oxford, Maryland, one of the Eastern Shore’s most treasured waterfront towns, where timeless charm meets an exceptional opportunity to create your dream home. Set along the shores of Goldsborough Creek, this premier waterfront parcel offers northwestern exposure, delivering breathtaking sunset views across tranquil waters. The preferred waterfront building site allows for construction with a 100-foot setback, providing nearly 180 degrees of waterfront views on Goldsborough Creek. A proposed 150-foot private dock site would provide approximately 2.5 feet at mean low tide. A recent septic application with the Talbot County Health Department has been submitted for a four-bedroom residence. Soil evaluations indicate excellent conditions for a generous sewage disposal area, offering flexibility for a substantial home and the potential for future improvements. Engineering analysis also supports the possibility of identifying additional SDA locations should subdivision be pursued, subject to county approvals. Preliminary estimates show the potential for 2 waterfront and 1 inland building site, to be confirmed with Talbot County Planning and Zoning. The farm is located within a historic waterfowl staging area providing habitat for wintering Canada Geese and Ducks. Adjacent woodland and contiguous farm fields complement this coveted rural setting with ample opportunity to enhance the natural features and create a haven for the outdoors and nature enthusiasts. This unique waterfront farm opportunity provides an extraordinary setting to design and build a custom waterfront retreat in a location defined by the natural beauty where land and water combine.

Oxford Road, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Realty.

$1,840,000

Nestled on 2.3 private acres in the sought-after Martingham neighborhood, this beautifully updated waterfront home offers one level living with the perfect blend of comfort, style, and outdoor living. Overlooking Porter Creek, the property features a private pier with lift and rip-rapped shoreline, where you can enjoy breathtaking sunsets, and endless days enjoying the water. Inside, the open floor plan flows effortlessly from the spacious living areas, open dining area, to the fully renovated kitchen, complete with quartz countertops, custom cabinetry, and modern appliances. The expansive waterside owner’s suite has a luxurious bathroom with heated tile floors, and generous closet space. Two additional bedrooms, plus a den that could serve as a fourth bedroom and custom bathroom. Step outside to a screened porch with awning or lounge beside the tiled gunite heated saltwater pool, Pebblesheen finish and surrounded by a custom deck—perfect for entertaining or quiet relaxation. Additional highlights include a two-car garage with attic storage, a laundry room with utility sink, stacked washer/dryer, and a 4-ton Legacy heat pump for year-round comfort. This is a rare opportunity to own a meticulously maintained home in one of St. Michaels’ most desirable communities, where privacy, luxury, and a waterfront lifestyle come together beautifully. Experience life alongside one of Maryland’s finest golf courses - across the street of the award-winning Links at Perry Cabin Golf Course—a premier golf destination designed by the legendary Pete Dye.

4 Beds ⋅ 3 Baths

Nestled on 2.3 private acres in the sought-after Martingham neighborhood, this beautifully updated waterfront home offers one level living with the perfect blend of comfort, style, and outdoor living. Overlooking Porter Creek, the property features a private pier with lift and rip-rapped shoreline, where you can enjoy breathtaking sunsets, and endless days enjoying the water. Inside, the open floor plan flows effortlessly from the spacious living areas, open dining area, to the fully renovated kitchen, complete with quartz countertops, custom cabinetry, and modern appliances. The expansive waterside owner’s suite has a luxurious bathroom with heated tile floors, and generous closet space. Two additional bedrooms, plus a den that could serve as a fourth bedroom and custom bathroom. Step outside to a screened porch with awning or lounge beside the tiled gunite heated saltwater pool, Pebblesheen finish and surrounded by a custom deck—perfect for entertaining or quiet relaxation. Additional highlights include a two-car garage with attic storage, a laundry room with utility sink, stacked washer/dryer, and a 4-ton Legacy heat pump for year-round comfort. This is a rare opportunity to own a meticulously maintained home in one of St. Michaels’ most desirable communities, where privacy, luxury, and a waterfront lifestyle come together beautifully. Experience life alongside one of Maryland’s finest golf courses - across the street of the award-winning Links at Perry Cabin Golf Course—a premier golf destination designed by the legendary Pete Dye.

9788 Pintail Pl, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.