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Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside "River Room." The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

9020 Bozman Neavitt Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

228 Perry Cabin Dr Unit 228 / 226, Saint Michaels

$1,945,000

Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a chef-inspired gourmet kitchen designed for elevated entertaining and showcases premium appliances, including a 60-inch extra-large refrigerator/freezer, Wolf propane cooktop, and integrated refrigerated and freezer beverage drawers thoughtfully integrated into the cabinetry. The first-floor primary suite provides effortless main-level living with a private enclosed porch and spa-like bath retreat. This combined property conveys two deep-water boat slips (6' MLW) with water and electricity, each able to accommodate a 40-foot vessel. Community amenities include kayak launch; tennis courts lined for pickleball and a private beach. A fully owned solar energy system with integrated backup battery storage provides exceptional energy efficiency and resilience adding approximately $2,000/year offset to electricity bills as well as solar income. Just a short walk or boat ride to the shops and restaurants of historic Saint Michaels, and an easy drive to Easton, Annapolis, Washington, DC, and Philadelphia. Don't miss this rare offering in one of the Chesapeake Bay's premier boating destinations. Professional photography and media forthcoming.

6 Beds ⋅ 6 Baths

Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a chef-inspired gourmet kitchen designed for elevated entertaining and showcases premium appliances, including a 60-inch extra-large refrigerator/freezer, Wolf propane cooktop, and integrated refrigerated and freezer beverage drawers thoughtfully integrated into the cabinetry. The first-floor primary suite provides effortless main-level living with a private enclosed porch and spa-like bath retreat. This combined property conveys two deep-water boat slips (6' MLW) with water and electricity, each able to accommodate a 40-foot vessel. Community amenities include kayak launch; tennis courts lined for pickleball and a private beach. A fully owned solar energy system with integrated backup battery storage provides exceptional energy efficiency and resilience adding approximately $2,000/year offset to electricity bills as well as solar income. Just a short walk or boat ride to the shops and restaurants of historic Saint Michaels, and an easy drive to Easton, Annapolis, Washington, DC, and Philadelphia. Don't miss this rare offering in one of the Chesapeake Bay's premier boating destinations. Professional photography and media forthcoming.

228 Perry Cabin Dr Unit 228 / 226, Saint Michaels

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

$1,945,000

Your Custom Dream Waterfront Home Awaits! This rare, build-ready lot offers a blank canvas for you to craft your perfect Eastern Shore estate with spectacular, panoramic views! The 2.9 acre waterfront lot in the Bachelor Pt section of Oxford offers 180 degree panoramic views stretching across the majestic Choptank River. Enjoy the peace of mind of a recently installed rip-rap shoreline over an estimated 569 feet of protected waterfront, providing long-term erosion protection and maintaining your valuable waterfront. The property also includes a new dock setup, featuring a heavy-duty 16,000 lb boat lift and two additional lifts perfect for jet skis. The lot is located within Oxford town limits, offering the advantage of access to public water and sewer hook-ups. Final approval has been given from the Oxford Planning Board for the building plans the current owner proposed providing a massive head start on your construction timeline. Those plans can be included in the sale of the lot and while you may modify them to suit your taste, having approved plans means the property is truly "build-ready." Simply choose your builder and start constructing your dream!

4480 Bachelors Point Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,795,000

Two RT 50 parcels located in Easton on sought after O.C. bound side at corner of Rt 50 and Dutchman s Lane. Office on property in good condition but sold as-is. Zoned General Commercial with all utilities available at site.

7696 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,750,000

Unique parcel of ground in Easton. Sale does NOT include cell tower which will be sold separately. It is in the PRD District but is zoned BC by the Town of Easton with residential as a permitted use. Survey available. The property is not in the Town Historic District. Feel free to ride on the property but no access until January.

402 Brookletts Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,750,000

Back on the market due to Buyers unable to fulfill home sale contingency- Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting. Designed for both the passionate cook and the gracious host, the gourmet kitchen features professional-grade Wolf appliances, a Cambria quartz oversized island, and custom cabinetry. The main level primary suite offers panoramic views of Harris Creek, custom millwork, and a spa-worthy bath showcasing a deep soaking tub and beautifully tiled shower. An additional main-level bedroom with private ensuite provides ideal accommodations for guests. On the second floor, three spacious bedrooms await. One a second private primary suite with custom closet and balcony. Two bedrooms, sharing a thoughtfully designed Jack and Jill bath, all centered around a loft-style lounge. Additional amenities include a thoughtfully designed mudroom and a garage with epoxy-coated floors and sleek Clopay glass garage doors. The covered porch creates a seamless space for indoor-outdoor entertaining. Situated on a large, private lot within an exclusive HOA waterfront community, the property offers a rare sense of seclusion while still providing access to coveted amenities such as a community dock and pool. With all new electric, plumbing, HVAC and more, this house has been taken down to the studs and rebuilt to its timeless architecture. From its elevated finishes to its extraordinary setting, 21485 Island Club Drive captures the essence of luxury coastal living on Maryland’s Eastern Shore.

5 Beds ⋅ 5 Baths

Back on the market due to Buyers unable to fulfill home sale contingency- Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting. Designed for both the passionate cook and the gracious host, the gourmet kitchen features professional-grade Wolf appliances, a Cambria quartz oversized island, and custom cabinetry. The main level primary suite offers panoramic views of Harris Creek, custom millwork, and a spa-worthy bath showcasing a deep soaking tub and beautifully tiled shower. An additional main-level bedroom with private ensuite provides ideal accommodations for guests. On the second floor, three spacious bedrooms await. One a second private primary suite with custom closet and balcony. Two bedrooms, sharing a thoughtfully designed Jack and Jill bath, all centered around a loft-style lounge. Additional amenities include a thoughtfully designed mudroom and a garage with epoxy-coated floors and sleek Clopay glass garage doors. The covered porch creates a seamless space for indoor-outdoor entertaining. Situated on a large, private lot within an exclusive HOA waterfront community, the property offers a rare sense of seclusion while still providing access to coveted amenities such as a community dock and pool. With all new electric, plumbing, HVAC and more, this house has been taken down to the studs and rebuilt to its timeless architecture. From its elevated finishes to its extraordinary setting, 21485 Island Club Drive captures the essence of luxury coastal living on Maryland’s Eastern Shore.

21485 Island Club Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,695,000

Refined waterfront offering on Maryland’s Eastern Shore, 7871 Avon Court has been completely transformed into a sophisticated modern farmhouse blending timeless design and convenience. Thoughtfully renovated to a like-new standard, the residence offers approximately 2,000 square feet with 3 bedrooms, 2.5 baths and a private office/flex space. Dramatic vaulted living spaces, wide-plank flooring, custom finishes and a beautifully reimagined kitchen create interiors that feel both elevated and inviting. Expansive windows frame views of the Tred Avon River from nearly every room, seamlessly connecting the home to its exceptional waterfront setting. Set on a high-bank waterfront site with approximately 360± feet of shoreline and 3± feet MLW, the property is ideally suited for boating, kayaking, paddleboarding and waterfront entertaining. Private pier, sandy beach, mature trees and expansive lawn create a rare park-like setting just minutes from downtown Easton and within easy reach of Washington, Northern Virginia, Philadelphia and surrounding Mid-Atlantic destinations. A compelling waterfront retreat offering privacy, style and effortless Eastern Shore living. Room for pool subject approvals.

Refined waterfront offering on Maryland’s Eastern Shore, 7871 Avon Court has been completely transformed into a sophisticated modern farmhouse blending timeless design and convenience. Thoughtfully renovated to a like-new standard, the residence offers approximately 2,000 square feet with 3 bedrooms, 2.5 baths and a private office/flex space. Dramatic vaulted living spaces, wide-plank flooring, custom finishes and a beautifully reimagined kitchen create interiors that feel both elevated and inviting. Expansive windows frame views of the Tred Avon River from nearly every room, seamlessly connecting the home to its exceptional waterfront setting. Set on a high-bank waterfront site with approximately 360± feet of shoreline and 3± feet MLW, the property is ideally suited for boating, kayaking, paddleboarding and waterfront entertaining. Private pier, sandy beach, mature trees and expansive lawn create a rare park-like setting just minutes from downtown Easton and within easy reach of Washington, Northern Virginia, Philadelphia and surrounding Mid-Atlantic destinations. A compelling waterfront retreat offering privacy, style and effortless Eastern Shore living. Room for pool subject approvals.

7871 Avon Ct, Easton

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

$1,685,000

UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

5 Beds ⋅ 5 Baths

UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

9180 Saint Michaels, Saint Michaels

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

$1,595,000

Nestled in the prestigious Canterbury subdivision, this exquisite Cape Cod home offers a harmonious blend of luxury and comfort. Spanning over 4,600 square feet, the interior boasts elegant wood floors and an inviting layout, featuring a spacious kitchen with upgraded countertops and a six-burner stove, perfect for culinary enthusiasts. The dining area and cozy built-ins create an ideal setting for gatherings, while the three fireplaces, adorned with charming mantels, add warmth and sophistication. Retreat to the primary suite, complete with a luxurious bath, or enjoy the convenience of an entry-level bedroom. The thoughtful design includes a laundry chute for effortless living. Outside, the expansive 2.44-acre lot is beautifully landscaped, providing a serene backdrop for relaxation. With an attached two-car garage and a commitment to quality, this home embodies an exclusive lifestyle, inviting you to create cherished memories in a space that truly feels like home.

Nestled in the prestigious Canterbury subdivision, this exquisite Cape Cod home offers a harmonious blend of luxury and comfort. Spanning over 4,600 square feet, the interior boasts elegant wood floors and an inviting layout, featuring a spacious kitchen with upgraded countertops and a six-burner stove, perfect for culinary enthusiasts. The dining area and cozy built-ins create an ideal setting for gatherings, while the three fireplaces, adorned with charming mantels, add warmth and sophistication. Retreat to the primary suite, complete with a luxurious bath, or enjoy the convenience of an entry-level bedroom. The thoughtful design includes a laundry chute for effortless living. Outside, the expansive 2.44-acre lot is beautifully landscaped, providing a serene backdrop for relaxation. With an attached two-car garage and a commitment to quality, this home embodies an exclusive lifestyle, inviting you to create cherished memories in a space that truly feels like home.

6385 Canterbury Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,550,000

Great Investment Opportunity – This 5500+/- sq ft Commercial Condo has a long term Lease with a well-established Tenant. Zoned Commercial, ideal for Medical or related Business. Excellent condition, great visibility and plenty of parking.

503 Cynwood Dr Unit 1, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,500,000

A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact:

$1,495,000

Prime commercial location at the corner of Route 50 and Matthewstown Road, offering excellent visibility and convenient access from both roadways. Situated on approximately 0.66 acres, the property is currently operating as a restaurant and features ample on-site parking to accommodate customers and staff. The prominent corner location and dual ingress/egress provide added convenience and accessibility, making this an attractive opportunity for investors or owner-users seeking a strategically positioned commercial property. Investors will appreciate the long-term tenant who would like to stay. Lease is also flexible for seller if buyer is an end-user.

8305 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,495,000

Very rare opportunity to buy 36+/- acres with stunning views of the Chesapeake Bay. Approximately 2,100 feet of rip-rapped shoreline. Property is slated for county sewer. Conservation Easement applies but property is approved for a large main residence and a 4 bedroom detached guest house up to 1,500 sf.

Bar Neck Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,475,000

29 ± Acres | Easton, Maryland | Development Opportunity. Exceptional 29 ± acre development opportunity located along Maryland Route 331 Dover Rd in Easton, Maryland, directly bordering the Town of Easton limits and the Waylands subdivision. This tract of land offers excellent visibility and a strategic location with significant future development potential. Located within Priority Area 3 of Easton’s Comprehensive Growth Plan Map, the property presents an attractive opportunity for R10A zoning or higher-density residential/community development project, subject to applicable approvals and zoning requirements. The parcel is currently in row crop production, offering an immediate agricultural use while positioning the property for potential future development. Its proximity to established residential development, Town of Easton services, and major transportation routes makes this a compelling opportunity for developers, investors, and land planners.

Dover Road, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$1,465,000

Turn-key waterfront home with spectacular views from every room. The entire house has been taken down to the studs: exterior and interior walls reframed; shed dormers installed; glass doors and windows placed in every wall; renovated kitchen with quartz countertops, semi-custom cabinets, new appliances, a Butler's Pantry, two new staircases, all new plumbing, electric, HVAC, built-ins, hardi-plank siding, Azek trim, composite decking, custom garage doors -- the list goes on. "Tilghman on Chesapeake" has coveted amenities including a clubhouse and outdoor pool on the water, piers, boat-slips, and sweeping views of the watermen departing at sun-rise. Restaurants and daily amenities are nearby including groceries, liquor, a deli and the best cup of coffee on the Eastern Shore served at the Country Store. Spectacular views, and laid-back community charm, is the timeless appeal that makes Tilghman Island so special. The home can convey furnished if desired.

3 Beds ⋅ 2 Baths

Turn-key waterfront home with spectacular views from every room. The entire house has been taken down to the studs: exterior and interior walls reframed; shed dormers installed; glass doors and windows placed in every wall; renovated kitchen with quartz countertops, semi-custom cabinets, new appliances, a Butler's Pantry, two new staircases, all new plumbing, electric, HVAC, built-ins, hardi-plank siding, Azek trim, composite decking, custom garage doors -- the list goes on. "Tilghman on Chesapeake" has coveted amenities including a clubhouse and outdoor pool on the water, piers, boat-slips, and sweeping views of the watermen departing at sun-rise. Restaurants and daily amenities are nearby including groceries, liquor, a deli and the best cup of coffee on the Eastern Shore served at the Country Store. Spectacular views, and laid-back community charm, is the timeless appeal that makes Tilghman Island so special. The home can convey furnished if desired.

21525 Island Club Rd, Tilghman

Listing courtesy of Sell Your Home Services. Contact:

$1,450,000

Cooke's Hope - Elegant Colonial home with pond views. Situated on a 3 +/- acre lot, this home boasts 4 bedrooms and 3.5 baths. Spacious foyer, library/den, formal dining room, family room with cozy woodburning fireplace and kitchen with island. The second floor features a primary suite, dual closets and a sitting room. Two-car detached garage with a covered entry and a bonus area above it. Hardwood floors grace most of the house. Community amenities include exercise trails, a gym, tennis courts and a community pier. A must see!

Cooke's Hope - Elegant Colonial home with pond views. Situated on a 3 +/- acre lot, this home boasts 4 bedrooms and 3.5 baths. Spacious foyer, library/den, formal dining room, family room with cozy woodburning fireplace and kitchen with island. The second floor features a primary suite, dual closets and a sitting room. Two-car detached garage with a covered entry and a bonus area above it. Hardwood floors grace most of the house. Community amenities include exercise trails, a gym, tennis courts and a community pier. A must see!

6855 Cookes Hope Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,399,000

This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! Come by boat or by car. ACCESS BY APPT ONLY, surveillance cameras.

This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! Come by boat or by car. ACCESS BY APPT ONLY, surveillance cameras.

104 Mulberry St, Saint Michaels

Listing courtesy of RE/MAX One. Contact:

$1,399,000

Major Price Improvement! Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for enjoying life on the water. Fabulous gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 + feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Sold As Is

Major Price Improvement! Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for enjoying life on the water. Fabulous gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 + feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Sold As Is

104 Myrtle St, Oxford

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

$1,379,800

Finish date 1st week of November by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan delivers comfort and ease. High‑end finishes include Shaw luxury vinyl plank flooring, a gourmet kitchen with a 36" dual‑fuel range, custom tile backsplash, quartz countertops, stainless steel appliances, and a spacious walk‑in pantry. The inviting living area features a fireplace and seamless access to the covered front and rear porches. The primary suite offers a true retreat with a spa‑inspired ensuite bathroom, soaking tub, walk‑in shower, sitting area, and a large closet. Additional highlights include a dedicated laundry room, public sewer, and thoughtful craftsmanship throughout. This beautifully designed home is a must‑see for anyone seeking luxury living in one of Maryland’s most charming waterfront towns.

Finish date 1st week of November by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan delivers comfort and ease. High‑end finishes include Shaw luxury vinyl plank flooring, a gourmet kitchen with a 36" dual‑fuel range, custom tile backsplash, quartz countertops, stainless steel appliances, and a spacious walk‑in pantry. The inviting living area features a fireplace and seamless access to the covered front and rear porches. The primary suite offers a true retreat with a spa‑inspired ensuite bathroom, soaking tub, walk‑in shower, sitting area, and a large closet. Additional highlights include a dedicated laundry room, public sewer, and thoughtful craftsmanship throughout. This beautifully designed home is a must‑see for anyone seeking luxury living in one of Maryland’s most charming waterfront towns.

7865 Pea Nck, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

$1,350,000

Waterfront coastal cottage living at its finest. Come see what makes this 3-bedroom, 2.5-bathroom retreat feel like a secluded getaway, approximately 10 minutes from downtown St. Michaels and two hours from the DC, and Baltimore areas. Set on 16.45 peaceful acres on Leadenham Creek, this property offers southwestern exposure and over 900 feet of shoreline. Sit back and enjoy evening sunset views from the newly installed dock (2025). Two sheds on the property, provide additional storage capability. Step inside to find a cozy, open-concept layout. The kitchen flows directly into a breakfast nook/dining area with built-in seating and an adjoining living room with a wood-burning fireplace, all with waterfront views. On the main level, you’ll find a primary bedroom suite with a full bathroom and access to a bright, private sunroom. A spiral staircase leads to two additional bedrooms. Additional updates include a new HVAC system (2022) and a new roof (2021). Privacy, waterfront, and acreage, all within a short drive of the restaurants, shops, museums, and activities St. Michaels has to offer.

Waterfront coastal cottage living at its finest. Come see what makes this 3-bedroom, 2.5-bathroom retreat feel like a secluded getaway, approximately 10 minutes from downtown St. Michaels and two hours from the DC, and Baltimore areas. Set on 16.45 peaceful acres on Leadenham Creek, this property offers southwestern exposure and over 900 feet of shoreline. Sit back and enjoy evening sunset views from the newly installed dock (2025). Two sheds on the property, provide additional storage capability. Step inside to find a cozy, open-concept layout. The kitchen flows directly into a breakfast nook/dining area with built-in seating and an adjoining living room with a wood-burning fireplace, all with waterfront views. On the main level, you’ll find a primary bedroom suite with a full bathroom and access to a bright, private sunroom. A spiral staircase leads to two additional bedrooms. Additional updates include a new HVAC system (2022) and a new roof (2021). Privacy, waterfront, and acreage, all within a short drive of the restaurants, shops, museums, and activities St. Michaels has to offer.

7582 Leadenham Cove Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,325,000

Located in the desirable Cooke’s Hope community, this spacious home offers approximately 4,966 square feet of finished living space with 4 bedrooms and 4½ baths. Primary suites on both the first and second floors provide flexibility, while two additional bedrooms and a spacious landing complete the upper level. All four bedrooms feature private baths. Recently refinished hardwood floors and tile extend throughout the home. The kitchen, dining room, and living room flow together to create generous spaces for everyday living and entertaining. The kitchen features granite countertops, a center island, stainless steel appliances, abundant cabinetry, an adjoining pantry, and a wet bar. The living room includes a gas fireplace and opens to the rear screened porch. Upper and lower front porches give the home its distinctive presence, while the rear screened porch overlooks a private in-ground gunite pool with a waterfall feature. A spacious stone terrace, mature landscaping, a fully fenced backyard, and adjoining open space create a peaceful and private outdoor setting. Additional features include a main-level laundry room, an attached two-car garage with a finished storage or bonus room above, and a recently encapsulated crawlspace with French drains, sump pumps, and a dehumidifier. Cooke’s Hope amenities include a community dock, canoe storage and launch, walking and exercise trails, tennis and pickleball courts, a private community mailroom, and a fitness center. Convenient to downtown Easton while offering a quiet, established neighborhood setting. Effective August 2026, The Homeowners Association has approached those owners in Cooke’s Hope with property backing to open space along Hope Circle to offer additional lands in the form of a perpetual easement that may be purchased and used for additional private open space, yard, garden and the area may be fenced. Contact listing agent for additional information.

4 Beds ⋅ 5 Baths

Located in the desirable Cooke’s Hope community, this spacious home offers approximately 4,966 square feet of finished living space with 4 bedrooms and 4½ baths. Primary suites on both the first and second floors provide flexibility, while two additional bedrooms and a spacious landing complete the upper level. All four bedrooms feature private baths. Recently refinished hardwood floors and tile extend throughout the home. The kitchen, dining room, and living room flow together to create generous spaces for everyday living and entertaining. The kitchen features granite countertops, a center island, stainless steel appliances, abundant cabinetry, an adjoining pantry, and a wet bar. The living room includes a gas fireplace and opens to the rear screened porch. Upper and lower front porches give the home its distinctive presence, while the rear screened porch overlooks a private in-ground gunite pool with a waterfall feature. A spacious stone terrace, mature landscaping, a fully fenced backyard, and adjoining open space create a peaceful and private outdoor setting. Additional features include a main-level laundry room, an attached two-car garage with a finished storage or bonus room above, and a recently encapsulated crawlspace with French drains, sump pumps, and a dehumidifier. Cooke’s Hope amenities include a community dock, canoe storage and launch, walking and exercise trails, tennis and pickleball courts, a private community mailroom, and a fitness center. Convenient to downtown Easton while offering a quiet, established neighborhood setting. Effective August 2026, The Homeowners Association has approached those owners in Cooke’s Hope with property backing to open space along Hope Circle to offer additional lands in the form of a perpetual easement that may be purchased and used for additional private open space, yard, garden and the area may be fenced. Contact listing agent for additional information.

28658 Hope Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,295,000

Beautifully maintained 3–4 bedroom home set on lovely park-like grounds in the sought after community of Cooke’s Hope. From the welcoming foyer, the home opens to formal living and dining rooms, followed by an inviting great room with cathedral ceiling, fireplace and wet bar. The spacious kitchen offers an abundance of cabinetry, stainless steel appliances, breakfast bar and a cozy breakfast nook overlooking the beautifully landscaped rear yard. Hardwood floors, crown molding and recessed lighting add warmth and character throughout. The first floor primary suite offers a walk-in closet and spacious bath with separate soaking tub. Upstairs, two additional ensuite bedrooms along with a separate office and family/bonus room with a private balcony. Tons of attic storage. Outdoor living is easy here, with a screened and wraparound porch overlooking the mature landscaping and private rear yard with gazebo. Cooke’s Hope offers an exceptional array of amenities, including scenic walking trails, ponds, tennis and pickleball courts, fitness room, community gathering spaces and a waterfront dock with slips and kayak storage. It is a community that offers both an active lifestyle and a sense of space and privacy. A special property in a highly desirable setting, offering one level living with plenty of additional space for family, guests and hobbies.Close to downtown Historic Easton, YMCA, shopping, museums and grocery stores. Please note: Sellers require a mid-April 2027 settlement. A rent-back agreement will be required if an earlier settlement is requested.

3 Beds ⋅ 4 Baths

Beautifully maintained 3–4 bedroom home set on lovely park-like grounds in the sought after community of Cooke’s Hope. From the welcoming foyer, the home opens to formal living and dining rooms, followed by an inviting great room with cathedral ceiling, fireplace and wet bar. The spacious kitchen offers an abundance of cabinetry, stainless steel appliances, breakfast bar and a cozy breakfast nook overlooking the beautifully landscaped rear yard. Hardwood floors, crown molding and recessed lighting add warmth and character throughout. The first floor primary suite offers a walk-in closet and spacious bath with separate soaking tub. Upstairs, two additional ensuite bedrooms along with a separate office and family/bonus room with a private balcony. Tons of attic storage. Outdoor living is easy here, with a screened and wraparound porch overlooking the mature landscaping and private rear yard with gazebo. Cooke’s Hope offers an exceptional array of amenities, including scenic walking trails, ponds, tennis and pickleball courts, fitness room, community gathering spaces and a waterfront dock with slips and kayak storage. It is a community that offers both an active lifestyle and a sense of space and privacy. A special property in a highly desirable setting, offering one level living with plenty of additional space for family, guests and hobbies.Close to downtown Historic Easton, YMCA, shopping, museums and grocery stores. Please note: Sellers require a mid-April 2027 settlement. A rent-back agreement will be required if an earlier settlement is requested.

28751 Emanuel St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,289,000

8410 Bozman Neavitt Rd, Bozman

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

Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butler’s pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler’s pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butler’s pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler’s pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

202 E Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.

3 Beds ⋅ 4 Baths

A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.

115 W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Presenting 47+ acres of stunning land just minutes from Easton, perfectly positioned at the intersection of Unionville Road and Miles River Road, extending along Anchorage Road. This expansive property is currently leased for farming and hunting, offering both income potential and recreational opportunities. While it has not been perc tested, the property holds potential for multiple lots, subject to required approvals. A rare investment opportunity with endless possibilities in a highly desirable location. Please note the photos with the house and barn are AI generated. There are no buildings on this property.

Unionville Road, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Final section of Lakelands subdivision! Previously approved for up to 48 lots, road cut thru, some water & sewer installed. PUD approved by Town in 2010. See agent for plats, engineering and current status. Unique opportunity! Wetlands needs to be updated with possible additional land becoming available. Road needs completion. Some Capital fees already paid. Water lines partially installed along with sewer lines. Water lines needs upgrading for sprinklers.

Ocean Gateway, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Final section of Lakelands subdivision! Previously approved for up to 48 lots, road cut thru, some water & sewer installed. PUD approved by Town in 2010. See agent for plats, engineering and current status. Unique opportunity! Wetlands needs to be updated with possible additional land becoming available. Road needs completion. Some Capital fees already paid. Water lines partially installed along with sewer lines. Water lines needs upgrading for sprinklers.

Ocean Gateway, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,195,000

Welcome home to 28641 Hope Circle, an elegant 4BR/3.5BA Federal-style residence nestled in the highly sought after Village section of Cooke’s Hope. Spanning 4,772 sq ft of meticulously maintained living space, this property blends timeless Eastern Shore charm with modern luxury. The thoughtful layout offers unmatched flexibility, featuring dual primary suites with one on the main level and one on the upper level, making it perfect for multi-generational living or an exceptional guest arrangement. The upper primary suite serves as a true sanctuary boasting a luxury bath and a private outdoor deck overlooking the serene surroundings. A welcoming foyer leads to formal dining room (currently being used as a living room) with custom wainscoting, and a private home office/study complete with high-end built-in cabinetry. The heart of the home flows into a sunlit breakfast area, a bright laundry room, and a spacious mudroom with custom coat and shoe organizational shelving. From there, a second staircase leads to an incredible, fully equipped media/theater room featuring reclining stadium seating, a movie projector, and an integrated screen. Expanding the living space even further, a fully finished, heated and air-conditioned third-floor bonus room provides endless possibilities for a yoga studio, playroom, gym, or hobby shop. Outside your door, enjoy the prestigious Cooke’s Hope lifestyle, which offers miles of scenic walking trails, a fitness center, tennis courts, a kayak launch, and the community’s signature pastures home to resident Belted Galloway cows, all while being just minutes from historic downtown Easton’s premiers dining and shopping.

Welcome home to 28641 Hope Circle, an elegant 4BR/3.5BA Federal-style residence nestled in the highly sought after Village section of Cooke’s Hope. Spanning 4,772 sq ft of meticulously maintained living space, this property blends timeless Eastern Shore charm with modern luxury. The thoughtful layout offers unmatched flexibility, featuring dual primary suites with one on the main level and one on the upper level, making it perfect for multi-generational living or an exceptional guest arrangement. The upper primary suite serves as a true sanctuary boasting a luxury bath and a private outdoor deck overlooking the serene surroundings. A welcoming foyer leads to formal dining room (currently being used as a living room) with custom wainscoting, and a private home office/study complete with high-end built-in cabinetry. The heart of the home flows into a sunlit breakfast area, a bright laundry room, and a spacious mudroom with custom coat and shoe organizational shelving. From there, a second staircase leads to an incredible, fully equipped media/theater room featuring reclining stadium seating, a movie projector, and an integrated screen. Expanding the living space even further, a fully finished, heated and air-conditioned third-floor bonus room provides endless possibilities for a yoga studio, playroom, gym, or hobby shop. Outside your door, enjoy the prestigious Cooke’s Hope lifestyle, which offers miles of scenic walking trails, a fitness center, tennis courts, a kayak launch, and the community’s signature pastures home to resident Belted Galloway cows, all while being just minutes from historic downtown Easton’s premiers dining and shopping.

28641 Hope Cir, Easton

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

$1,195,000

Fabulous home in Oaklands, ideally located along the highly desirable Oxford Road corridor! Beautifully updated and designed for effortless entertaining, this four-bedroom Colonial offers light-filled interiors, hardwood floors, geothermal heating and cooling and exceptional indoor-outdoor living. The living room features a fireplace flanked by custom built-ins and a large bay window. A separate family room provides a more relaxed setting with exposed wood beams and raised-hearth brick fireplace. At the heart of the home, the renovated kitchen features an oversized island, abundant cabinetry, a gas range, generous storage and a dining area. Just beyond, the light-filled sunroom is a standout with a wet bar, beamed ceiling and custom built-ins making it an inviting space for gatherings throughout the year. Upstairs, the oversized primary suite includes an updated ensuite bath and expansive walk-in closet. The second bedroom features hardwood floors and its own sitting area, while two additional bedrooms and an updated full bath complete the second floor. Outside, the backyard is an entertainer’s dream, featuring a saltwater in-ground pool, outdoor kitchen, fire pit and an impressive 1,532 square feet of terraced patio space. Two sheds offer additional storage and versatility, while a separate pump house accommodates the pool equipment. An oversized attached two-car garage provides ample space for vehicles, storage and hobbies. A 26 kW whole-house generator provides added comfort and peace of mind. Residents of Oaklands also enjoy community water access and use of the community pier, completing this exceptional Oxford Road property. Please do not go down driveway without an appointment.