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Discover your own Eastern Shore retreat at 4491 Bachelors Point Road in Oxford, MD. This exceptional 29-acre waterfront estate offers unrivaled privacy, 2,100 feet of pristine shoreline on Boone Creek, and effortless access to the Choptank River. The thoughtfully designed residence—completed initially in 2003 and extensively updated—features over 2,000± sq. ft., three bedrooms, and a newly completed 2023 primary suite with a walk-in closet and spa-style bath. Enjoy sweeping water and wildlife views from the expansive screened porch and spacious deck. A separate apartment above the detached garage provides flexible space for guests, a home office, or rental income. The property also includes a 100-foot dock with water and electric (replanked in 2025) and sheltered waters ideal for small boats, kayaking, paddleboarding, and swimming. Set within the highly sought-after Bachelor’s Point community, residents enjoy proximity to deepwater boat slips, a full-service boatyard, and Oxford’s charming boutiques, restaurants, festivals, and recreational amenities. Mature trees, abundant wildlife, and protected conservation acreage create a serene, low-maintenance setting perfect for a private getaway, hunting retreat, or investment opportunity.

4491 Bachelors Point Rd, Oxford

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

"Whispering Pines" A beautiful waterfront escape on private 2.75 +/- acre lot located within walking and biking distance from historic downtown St Michaels. Spacious, light and airy 4000+ sq foot 3BR 3BA home, custom built in 1996 boasts a desirable large, entry-level, primary suite, 2 en-suite bathrooms upstairs, spacious family room with cathedral ceiling and cozy wood burning fireplace, open kitchen, den with beautiful built-ins, bonus room/4th bedroom above attached 2 car garage, and a terrific sun room. Shed with electric, outdoor lighting - including at driveway entrance. 260' +/- of protected shoreline with high elevation, 6-foot-wide pier with electric and water, 3+/-feet MLW , room for a pool. Backyard patio to enjoy amazing sunsets over Broad and Rolles Creek. Sewer line installation along primary road currently underway. Property sold as-is, inspections for informational purposes only.

$1,800,000

3 Beds ⋅ 4 Baths

"Whispering Pines" A beautiful waterfront escape on private 2.75 +/- acre lot located within walking and biking distance from historic downtown St Michaels. Spacious, light and airy 4000+ sq foot 3BR 3BA home, custom built in 1996 boasts a desirable large, entry-level, primary suite, 2 en-suite bathrooms upstairs, spacious family room with cathedral ceiling and cozy wood burning fireplace, open kitchen, den with beautiful built-ins, bonus room/4th bedroom above attached 2 car garage, and a terrific sun room. Shed with electric, outdoor lighting - including at driveway entrance. 260' +/- of protected shoreline with high elevation, 6-foot-wide pier with electric and water, 3+/-feet MLW , room for a pool. Backyard patio to enjoy amazing sunsets over Broad and Rolles Creek. Sewer line installation along primary road currently underway. Property sold as-is, inspections for informational purposes only.

23854 Mount Misery Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Nantucket-Style Waterfront Retreat on a Private Peninsula Near Oxford Discover this enchanting Nantucket-style cottage, gracefully positioned on its own private 2.6-acre peninsula at the confluence of the Choptank River and Boone Creek. Just minutes from the historic town of Oxford, this 3,196 sq ft home offers approximately 1,000 feet of pristine waterfront and panoramic western views—perfect for savoring Chesapeake Bay sunsets . Built in 1986, the residence has been thoughtfully updated by West and Callahan, featuring a new roof, siding, Trex decking, and numerous new windows to enhance both comfort and efficiency . Zillow Main Level Highlights: A spacious kitchen that flows into a large dining area, opening to a side screened porch—ideal for alfresco dining. A versatile double room serving as a living area and library/study or potential game room. A second screened porch overlooking the in-ground pool, offering a serene space to relax. Upper Level Features: Three bedrooms and two full baths. The primary suite boasts vaulted ceilings and breathtaking views across the Choptank River. The second bedroom features high ceilings and picturesque vistas. The third bedroom includes a cozy desk alcove and a charming sleeping porch . Additional Amenities: An artist's studio equipped with water and electricity, situated adjacent to the in-ground pool. A private pier on Boone Creek with an electric lift, accommodating small watercraft. This unique property combines timeless design with modern updates, offering a tranquil waterfront lifestyle just a short drive from Oxford's shops, dining, and cultural attractions.

$1,800,000

Nantucket-Style Waterfront Retreat on a Private Peninsula Near Oxford Discover this enchanting Nantucket-style cottage, gracefully positioned on its own private 2.6-acre peninsula at the confluence of the Choptank River and Boone Creek. Just minutes from the historic town of Oxford, this 3,196 sq ft home offers approximately 1,000 feet of pristine waterfront and panoramic western views—perfect for savoring Chesapeake Bay sunsets . Built in 1986, the residence has been thoughtfully updated by West and Callahan, featuring a new roof, siding, Trex decking, and numerous new windows to enhance both comfort and efficiency . Zillow Main Level Highlights: A spacious kitchen that flows into a large dining area, opening to a side screened porch—ideal for alfresco dining. A versatile double room serving as a living area and library/study or potential game room. A second screened porch overlooking the in-ground pool, offering a serene space to relax. Upper Level Features: Three bedrooms and two full baths. The primary suite boasts vaulted ceilings and breathtaking views across the Choptank River. The second bedroom features high ceilings and picturesque vistas. The third bedroom includes a cozy desk alcove and a charming sleeping porch . Additional Amenities: An artist's studio equipped with water and electricity, situated adjacent to the in-ground pool. A private pier on Boone Creek with an electric lift, accommodating small watercraft. This unique property combines timeless design with modern updates, offering a tranquil waterfront lifestyle just a short drive from Oxford's shops, dining, and cultural attractions.

26319 Chanticleer Rd, Oxford

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

*Furniture and decor included in sale* Experience elevated coastal living in this impeccably renovated 2,250 sq ft post-and-beam home, reimagined as a coastal modern contemporary masterpiece by interior designer Hollace Kutay. Known as Oyster Cove for its picturesque 2.5 acre location on Broad Creek, this home is perfectly situated for boaters and kayakers seeking both adventure and tranquility. Enjoy expansive water views from nearly every room, and take full advantage of the private dock outfitted with an electric boat lift—complete with both water and electric hookups for seamless waterfront living. Featuring 4 bedrooms and 3.5 baths—including dual primary suites upstairs and down—this designer showcase comes fully furnished (except 2 bedrooms) with curated, unique pieces included in the sale. The chef's kitchen features beautiful black and gold appliances, including a 48-inch duel fuel range. A stunning 9-foot island anchors the room, perfect for casual dining or entertaining, while the separate prep kitchen is equipped with a second refrigerator, sink, and dishwasher, ensuring both efficiency and style. The under-stair wine room with one-of-a-kind wallpaper as well as a dedicated office/lounge add both charm and function. The powder room features a custom artisan octopus sink crafted by designer and artist Hollace Kutay. Enjoy seamless indoor-outdoor living with generous dining spaces perfect for gatherings. This is a rare turnkey opportunity to own a furnished, design-forward home that’s as livable as it is luxurious. Owner is a Maryland licensed realtor.

$1,780,000

*Furniture and decor included in sale* Experience elevated coastal living in this impeccably renovated 2,250 sq ft post-and-beam home, reimagined as a coastal modern contemporary masterpiece by interior designer Hollace Kutay. Known as Oyster Cove for its picturesque 2.5 acre location on Broad Creek, this home is perfectly situated for boaters and kayakers seeking both adventure and tranquility. Enjoy expansive water views from nearly every room, and take full advantage of the private dock outfitted with an electric boat lift—complete with both water and electric hookups for seamless waterfront living. Featuring 4 bedrooms and 3.5 baths—including dual primary suites upstairs and down—this designer showcase comes fully furnished (except 2 bedrooms) with curated, unique pieces included in the sale. The chef's kitchen features beautiful black and gold appliances, including a 48-inch duel fuel range. A stunning 9-foot island anchors the room, perfect for casual dining or entertaining, while the separate prep kitchen is equipped with a second refrigerator, sink, and dishwasher, ensuring both efficiency and style. The under-stair wine room with one-of-a-kind wallpaper as well as a dedicated office/lounge add both charm and function. The powder room features a custom artisan octopus sink crafted by designer and artist Hollace Kutay. Enjoy seamless indoor-outdoor living with generous dining spaces perfect for gatherings. This is a rare turnkey opportunity to own a furnished, design-forward home that’s as livable as it is luxurious. Owner is a Maryland licensed realtor.

23857 Ebb Point Rd, Bozman

Listing courtesy of Meredith Fine Properties. Contact:

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

$1,750,000

Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 full/1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a secondary staircase provide access to the upper levels. All six bedrooms are located on the second floor. The owner’s suite includes a fireplace, ensuite bath, and access to a front-facing balcony. Front-facing secondary bedrooms also have balcony access. The third level offers additional living space, including a large bonus room, entertainment room, three additional rooms, completed drywall and electrical work, and a full bath with shower. Additional property features include a detached garage with parking and storage, an externally accessed basement for storage, a wide exterior pad suitable for boat or RV storage, hardwood floors, a waterside deck, and a private pier. This property combines acreage, extensive waterfront frontage, and a spacious residence ready for its next owner.

6 Beds ⋅ 5 Baths

Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 full/1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a secondary staircase provide access to the upper levels. All six bedrooms are located on the second floor. The owner’s suite includes a fireplace, ensuite bath, and access to a front-facing balcony. Front-facing secondary bedrooms also have balcony access. The third level offers additional living space, including a large bonus room, entertainment room, three additional rooms, completed drywall and electrical work, and a full bath with shower. Additional property features include a detached garage with parking and storage, an externally accessed basement for storage, a wide exterior pad suitable for boat or RV storage, hardwood floors, a waterside deck, and a private pier. This property combines acreage, extensive waterfront frontage, and a spacious residence ready for its next owner.

7421 Quaker Neck Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Porter House International Realty Group.

$1,723,750

Bridgewater Farm - 12633 CONNELLY ROAD, CORDOVA MD 21625 137± Acres - consisting of approximately 105± tillable, 20± acres of woodland, and the balance around the house, driveway, and hedges. The property is improved by a circa 1870 brick farmhouse with a basement and several sheds, barn, well, and septic. Health Department information on file showing 1980 septic and 1986 well. Property sold ‘as-is’. **Existing farm lease. Contact agent for details. The residence provides late-19th-century architecture that is remarkably intact for a rural brick farmhouse. Significant features include the 13 cornices along the northern portion of the house, thick masonry walls, and brick lintel detailing above the windows. Later additions include the kitchen wing with a bedroom above and a three-season porch. There are two basements with a dirt floor and shoring with an interior concrete block retaining wall. The underside of the house is accessible to witness the condition and assess for renovation. Additional structures include a period barn and sheds. Offers considered beginning 5.13.26 to allow adequate time on the market. Showing by appointment only.

Bridgewater Farm - 12633 CONNELLY ROAD, CORDOVA MD 21625 137± Acres - consisting of approximately 105± tillable, 20± acres of woodland, and the balance around the house, driveway, and hedges. The property is improved by a circa 1870 brick farmhouse with a basement and several sheds, barn, well, and septic. Health Department information on file showing 1980 septic and 1986 well. Property sold ‘as-is’. **Existing farm lease. Contact agent for details. The residence provides late-19th-century architecture that is remarkably intact for a rural brick farmhouse. Significant features include the 13 cornices along the northern portion of the house, thick masonry walls, and brick lintel detailing above the windows. Later additions include the kitchen wing with a bedroom above and a three-season porch. There are two basements with a dirt floor and shoring with an interior concrete block retaining wall. The underside of the house is accessible to witness the condition and assess for renovation. Additional structures include a period barn and sheds. Offers considered beginning 5.13.26 to allow adequate time on the market. Showing by appointment only.

12633 Connelly Rd, Cordova

Listing courtesy of Benson & Mangold, LLC. Contact:

Now Offered at $1,895,000 | Private Harris Creek Waterfront Private Harris Creek waterfront with pool, pier, boat lift and deep-water access—crafted for boating, kayaking and the best of Eastern Shore living. This five-bedroom, three-and-a-half-bath residence offers a rare blend of privacy, comfort and wide water views just minutes from St. Michaels and Easton. Sun-filled interiors feature red oak floors, custom built-ins, multiple fireplaces and an inviting layout designed for everyday living and entertaining. The kitchen is the heart of the home with KitchenAid appliances, granite countertops, oversized island seating, butler’s pantry and dry bar. Main-level living includes a waterside primary suite with fireplace, private guest suite, office or den, and additional gathering spaces. Upstairs offers three bedrooms, full bath and spacious family room. Outdoor living shines with a screened porch, expansive waterside deck, saltwater pool and firepit patio overlooking Harris Creek. Private pier with boat lift and deep-water access opens the door to endless days on the water. Additional features include a two-car garage with workshop, whole-house generator and new septic system (2025). An exceptional waterfront opportunity at an outstanding new price.

$1,700,000

5 Beds ⋅ 4 Baths

Now Offered at $1,895,000 | Private Harris Creek Waterfront Private Harris Creek waterfront with pool, pier, boat lift and deep-water access—crafted for boating, kayaking and the best of Eastern Shore living. This five-bedroom, three-and-a-half-bath residence offers a rare blend of privacy, comfort and wide water views just minutes from St. Michaels and Easton. Sun-filled interiors feature red oak floors, custom built-ins, multiple fireplaces and an inviting layout designed for everyday living and entertaining. The kitchen is the heart of the home with KitchenAid appliances, granite countertops, oversized island seating, butler’s pantry and dry bar. Main-level living includes a waterside primary suite with fireplace, private guest suite, office or den, and additional gathering spaces. Upstairs offers three bedrooms, full bath and spacious family room. Outdoor living shines with a screened porch, expansive waterside deck, saltwater pool and firepit patio overlooking Harris Creek. Private pier with boat lift and deep-water access opens the door to endless days on the water. Additional features include a two-car garage with workshop, whole-house generator and new septic system (2025). An exceptional waterfront opportunity at an outstanding new price.

22707 Marshall Ln, Wittman

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

Welcome to Tred Avon Point, an extraordinary waterfront property on a stunning point of land in the picturesque, historic town of Oxford, MD. Strategically sited only 25 feet to the waters edge on three sides to capture breathtaking views of the Tred Avon River & amazing western sunsets! Maritime inspired post & beam, open design visually connects the views to the space. The character & depth of the architecture blurs the lines between indoor & outdoor living. The abundance of the wood toned palette play with the hue & saturation of the natural landscape. The space easily transitions from entertaining friends & family to a respite for homeowners. The perfect vantage point to watch the boats, sailing races & watermen go by. Two primary suites on each level can be reached by the nautically designed wood spiral staircase or elevator. Gorgeous custom designed kitchen renovation done in 2019. The guest suite on the first level enjoys the views from its private deck. The rooftop cupula offers a stunning 360 degree birdseye view of the town & water. All season beauty can be enjoyed even in winter in front of the recently installed, high-end brick fireplace. The property includes a shared lot with a 7ft MLW deepwater multislip dock with lift. Perfectly located near dining, yacht club & marinas yet still invoking quiet & privacy. The included furniture, fine art & accessories create a move-in ready primary, 2nd home or vacation rental. Truly a one of a kind home!

$1,695,000

Welcome to Tred Avon Point, an extraordinary waterfront property on a stunning point of land in the picturesque, historic town of Oxford, MD. Strategically sited only 25 feet to the waters edge on three sides to capture breathtaking views of the Tred Avon River & amazing western sunsets! Maritime inspired post & beam, open design visually connects the views to the space. The character & depth of the architecture blurs the lines between indoor & outdoor living. The abundance of the wood toned palette play with the hue & saturation of the natural landscape. The space easily transitions from entertaining friends & family to a respite for homeowners. The perfect vantage point to watch the boats, sailing races & watermen go by. Two primary suites on each level can be reached by the nautically designed wood spiral staircase or elevator. Gorgeous custom designed kitchen renovation done in 2019. The guest suite on the first level enjoys the views from its private deck. The rooftop cupula offers a stunning 360 degree birdseye view of the town & water. All season beauty can be enjoyed even in winter in front of the recently installed, high-end brick fireplace. The property includes a shared lot with a 7ft MLW deepwater multislip dock with lift. Perfectly located near dining, yacht club & marinas yet still invoking quiet & privacy. The included furniture, fine art & accessories create a move-in ready primary, 2nd home or vacation rental. Truly a one of a kind home!

121 Pier, Oxford

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

Premier Car Wash Facility in Easton This is an exceptional opportunity to acquire a highly successful car wash business with a large and loyal customer base. Located on one of Easton's busiest arterial roads, the facility enjoys excellent visibility and a high traffic count, ensuring a steady flow of customers. Key Features: **New Tunnel Installed in 2016:** The car wash is equipped with a state-of-the-art tunnel system installed in 2016, offering efficient and high-quality cleaning services. The equipment is well-maintained, ensuring smooth operations and minimal downtime. **Cutting-Edge Washify POS System:** In 2023, the business upgraded to a modern Washify POS system, enhancing the customer experience with a streamlined payment process and efficient service management. This system also offers valuable data analytics for business optimization. **Prime Location:** The car wash boasts a strategic location on a highly trafficked arterial road in Easton, providing excellent visibility and accessibility. The location attracts a steady stream of both regular and new customers. **Ample Waiting Area:** The facility includes a spacious and comfortable waiting area for customers, enhancing their experience while they wait for their vehicles to be serviced. **Office and Storage Spaces:** The property features well-organized office and storage spaces, providing ample room for administrative tasks and inventory management. **Business Potential:** With its modern equipment, prime location, and established customer base, this car wash is poised for continued growth. The business has a strong reputation in the community, and its recent upgrades ensure it remains competitive in the market. **Investment Opportunity:** This is a turnkey operation with significant potential for expansion. The business is ideal for investors looking to enter the car wash industry or existing operators seeking to expand their portfolio. **Financial Information:** Detailed financial information is available upon request for serious inquiries with signed NDA.

$1,695,000

29328 Matthewstown Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Discover the rare opportunity to own one of the Eastern Shore's finest waterfront parcels: Lot 5, an exceptional 4.18-acre homesite in the exclusive Morgan's Point community of Oxford, Maryland. This home site has an approved prec, and flood insurance is not required. Tucked along the serene Tred Avon River, this buildable waterfront gem offers expansive privacy and boundless potential, thanks to its generous scale and direct river access with 389 feet of rip-rap shoreline. Perfect for your custom estate, family compound, or legacy retreat, this sanctuary marries natural splendor with the refined charm of Talbot County's coastal haven. Spanning 4.18 acres, a fully usable lot provides versatile space to build your future home with breathtaking river vistas. Boasting direct frontage on the Tred Avon River with ample mean low water depth In a market where waterfront estates command premiums, this rare 4+ acre offering represents an unparalleled canvas for your vision. Nestled in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC; Northern Virginia; Annapolis; and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

$1,650,000

Morgans Point Drive, Oxford

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

This charming cape cod is located in Oxford on Town Creek just outside the Historic District on a quiet dead end street. Downstairs is a home office (with full bath, could also be used as a primary), a built-in bar, cozy den with gas fireplace, bright sunroom and fabulous screened porch. Upstairs, freshly carpeted and painted, are four bedrooms and three full baths. The awning-covered deck just off the Primary gives the feeling of a tree house with expansive Creek views. In the backyard sits a waterside cottage, “The Boathouse,” with amazing breezes all summer and in the winter it’s a prime viewing spot for the spectacular Oxford Christmas Dock tree display. Got boats? The dock has 4 slips, one currently occupied by a floating dock (conveys). The fenced yard is perfect for your furry friends. The crawl space was recently encapsulated and the attic newly re-insulated (2025). This wonderful house has it all and is as charming as it gets.

$1,650,000

5 Beds ⋅ 5 Baths

This charming cape cod is located in Oxford on Town Creek just outside the Historic District on a quiet dead end street. Downstairs is a home office (with full bath, could also be used as a primary), a built-in bar, cozy den with gas fireplace, bright sunroom and fabulous screened porch. Upstairs, freshly carpeted and painted, are four bedrooms and three full baths. The awning-covered deck just off the Primary gives the feeling of a tree house with expansive Creek views. In the backyard sits a waterside cottage, “The Boathouse,” with amazing breezes all summer and in the winter it’s a prime viewing spot for the spectacular Oxford Christmas Dock tree display. Got boats? The dock has 4 slips, one currently occupied by a floating dock (conveys). The fenced yard is perfect for your furry friends. The crawl space was recently encapsulated and the attic newly re-insulated (2025). This wonderful house has it all and is as charming as it gets.

111 First St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished bonus space above, and a historic 40' x 63' barn. Additional highlights include a new metal roof, new windows, composite decking, updated kitchens and bathrooms, irrigation for the rear lawn and landscape beds, landscape lighting, and thoughtfully renovated living spaces, creating a truly move-in-ready retreat just minutes from downtown Easton. Built in 1824 on land first patented in 1663, the manor home has been thoughtfully renovated to preserve its historic character while embracing modern comfort. Wide-plank pine floors, original architectural details, and three wood-burning fireplaces create warmth and timeless elegance throughout. At the heart of the home, the beautifully renovated farmhouse kitchen is designed for gathering, featuring a large center island, professional 8-burner range, farmhouse sink, and recently updated fixtures that blend seamlessly with the home's period character. All kitchen and bathroom fixtures throughout the home have been thoughtfully updated within the past three years, offering today's conveniences while preserving the home's historic integrity. A spacious mudroom with utility sink adds everyday functionality, while the newly constructed sunroom addition showcases exposed wood beams and a cozy propane stove, creating the perfect space to relax and enjoy the surrounding landscape in every season. Outside, enjoy peaceful mornings from the composite deck overlooking eight scenic acres. The beautifully maintained rear lawn and landscape beds are serviced by an irrigation system, while landscape lighting highlights the mature trees, historic outbuilding, and walkways, creating an inviting setting well into the evening. Offered fully furnished, the home includes a beautifully curated collection of furnishings and lighting from Restoration Hardware, Arhaus, and Pottery Barn, allowing the next owner to enjoy a seamless transition into the Eastern Shore lifestyle.

$1,625,000

Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished bonus space above, and a historic 40' x 63' barn. Additional highlights include a new metal roof, new windows, composite decking, updated kitchens and bathrooms, irrigation for the rear lawn and landscape beds, landscape lighting, and thoughtfully renovated living spaces, creating a truly move-in-ready retreat just minutes from downtown Easton. Built in 1824 on land first patented in 1663, the manor home has been thoughtfully renovated to preserve its historic character while embracing modern comfort. Wide-plank pine floors, original architectural details, and three wood-burning fireplaces create warmth and timeless elegance throughout. At the heart of the home, the beautifully renovated farmhouse kitchen is designed for gathering, featuring a large center island, professional 8-burner range, farmhouse sink, and recently updated fixtures that blend seamlessly with the home's period character. All kitchen and bathroom fixtures throughout the home have been thoughtfully updated within the past three years, offering today's conveniences while preserving the home's historic integrity. A spacious mudroom with utility sink adds everyday functionality, while the newly constructed sunroom addition showcases exposed wood beams and a cozy propane stove, creating the perfect space to relax and enjoy the surrounding landscape in every season. Outside, enjoy peaceful mornings from the composite deck overlooking eight scenic acres. The beautifully maintained rear lawn and landscape beds are serviced by an irrigation system, while landscape lighting highlights the mature trees, historic outbuilding, and walkways, creating an inviting setting well into the evening. Offered fully furnished, the home includes a beautifully curated collection of furnishings and lighting from Restoration Hardware, Arhaus, and Pottery Barn, allowing the next owner to enjoy a seamless transition into the Eastern Shore lifestyle.

32137 Discovery Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Maryland Heritage Properties.

$1,625,000

Oxford Cove – A truly rare offering, this extraordinary waterfront property is a study in serenity, privilege, and timeless eastern shore beauty. Surrounded by sweeping, uninterrupted water views to the south and east, the property captures the beautiful sunrise, immersing you in the everchanging light and rhythm of the tides. The main residence- graciously scaled with four bedrooms-embraces a refined yet relaxed aesthetic, designed for effortless living and seamless indoor-outdoor flow. Expansive terrace with a waterside pool, creates an idyllic setting for both quiet reflection and elegant entertaining. A charming one bedroom guest house/pool house offers a private haven for visitors, while a separate workshop provides space for creativity or collection. For the avid mariner, the property is exceptionally equipped with a private pier with a boat lift and a floating dock for kayaks and canoes- delivering immediate access to the finest waters of the Chesapeake Bay. Set in the historic village of Oxford,, one of the Eastern Shore’s most treasured enclaves, “Oxford Cove” offers a rare balance of seclusion and proximity. Here, life is defined by understated luxury, natural beauty, and the enduring allure of the waterfront.

Oxford Cove – A truly rare offering, this extraordinary waterfront property is a study in serenity, privilege, and timeless eastern shore beauty. Surrounded by sweeping, uninterrupted water views to the south and east, the property captures the beautiful sunrise, immersing you in the everchanging light and rhythm of the tides. The main residence- graciously scaled with four bedrooms-embraces a refined yet relaxed aesthetic, designed for effortless living and seamless indoor-outdoor flow. Expansive terrace with a waterside pool, creates an idyllic setting for both quiet reflection and elegant entertaining. A charming one bedroom guest house/pool house offers a private haven for visitors, while a separate workshop provides space for creativity or collection. For the avid mariner, the property is exceptionally equipped with a private pier with a boat lift and a floating dock for kayaks and canoes- delivering immediate access to the finest waters of the Chesapeake Bay. Set in the historic village of Oxford,, one of the Eastern Shore’s most treasured enclaves, “Oxford Cove” offers a rare balance of seclusion and proximity. Here, life is defined by understated luxury, natural beauty, and the enduring allure of the waterfront.

106 E Division St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,600,000

Talbot County Farm With Country Home, Multiple Outbuildings And Tillable Ac This exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90 acre home farm offers a balanced mix of tillable acreage, improved structures, and wildlife habitat, making it well-suited for farming operations, outdoor recreation, and long-term land investment. The property has a proven track record of row crop production, including corn, soybeans, and wheat. A diverse and productive soil profile supports continued agricultural use, with primary soils consisting of Mattapex silt loam and Nassawango silt loam across the majority of the fields. Additional areas include Mattapex-Woodstown soils located within previously enrolled CRP sections and wooded portions of the farm. These soils are well regarded across the Eastern Shore for their consistency and productivity, providing a solid foundation for both commercial farming and conservation practices. The farm is zoned agricultural, allowing flexibility for a variety of uses, including crop production, recreational enjoyment, and potential enrollment in conservation programs. A large portion of the acreage is tillable, offering income potential or lease opportunities, while the remaining mix of timber and habitat enhances the property's recreational value. At the center of the property sits a well-maintained 1,966 square foot brick ranch-style home built in 1997. The residence offers three bedrooms and two full bathrooms and has been thoughtfully designed for both comfort and functionality. The main living area features a spacious living room with a knotty pine accent wall and bowed window that brings in natural light. The dining room includes chair rail detailing, tongue-and-groove paneling, and a built-in glass-front cabinet, creating a functional and inviting setting. The kitchen is well-appointed with wood cabinetry extending to the ceiling, crown molding, stainless steel appliances, and a center island with seating. A pass-through connects the kitchen to the dining area, improving flow for daily use and gatherings. French doors lead to a sunroom that overlooks the surrounding farmland and wooded edges, providing a consistent view of the property throughout the seasons. The primary suite includes a private bathroom with a deep jetted soaking tub. Additional features of the home include a covered front porch and an attached two-car garage. Supporting the agricultural operation are several outbuildings, including a milk house and two additional structures, highlighted by a custom-built steel building. These improvements provide space for equipment storage, workshop use, and potential game processing. From a recreational standpoint, this Talbot County farm offers strong hunting opportunities. A large pond, complete with a strategically placed hunting pit, is heavily utilized by migratory Canada geese during the season. The combination of open ground, water, and surrounding timber creates an ideal setup for waterfowl hunting. The property also supports a healthy population of whitetail deer, adding to its appeal for hunting and outdoor recreation. For buyers seeking additional acreage, an adjoining 82.54 acre tract is also available. This parcel includes a large portion of tillable ground, with sections previously enrolled in CRP. The additional tract provides an opportunity to expand the farming operation, increase recreational use, or secure additional investment acreage. It may be purchased together with the home farm or separately, offering flexibility for a range of buyers. It's l Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

Talbot County Farm With Country Home, Multiple Outbuildings And Tillable Ac This exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90 acre home farm offers a balanced mix of tillable acreage, improved structures, and wildlife habitat, making it well-suited for farming operations, outdoor recreation, and long-term land investment. The property has a proven track record of row crop production, including corn, soybeans, and wheat. A diverse and productive soil profile supports continued agricultural use, with primary soils consisting of Mattapex silt loam and Nassawango silt loam across the majority of the fields. Additional areas include Mattapex-Woodstown soils located within previously enrolled CRP sections and wooded portions of the farm. These soils are well regarded across the Eastern Shore for their consistency and productivity, providing a solid foundation for both commercial farming and conservation practices. The farm is zoned agricultural, allowing flexibility for a variety of uses, including crop production, recreational enjoyment, and potential enrollment in conservation programs. A large portion of the acreage is tillable, offering income potential or lease opportunities, while the remaining mix of timber and habitat enhances the property's recreational value. At the center of the property sits a well-maintained 1,966 square foot brick ranch-style home built in 1997. The residence offers three bedrooms and two full bathrooms and has been thoughtfully designed for both comfort and functionality. The main living area features a spacious living room with a knotty pine accent wall and bowed window that brings in natural light. The dining room includes chair rail detailing, tongue-and-groove paneling, and a built-in glass-front cabinet, creating a functional and inviting setting. The kitchen is well-appointed with wood cabinetry extending to the ceiling, crown molding, stainless steel appliances, and a center island with seating. A pass-through connects the kitchen to the dining area, improving flow for daily use and gatherings. French doors lead to a sunroom that overlooks the surrounding farmland and wooded edges, providing a consistent view of the property throughout the seasons. The primary suite includes a private bathroom with a deep jetted soaking tub. Additional features of the home include a covered front porch and an attached two-car garage. Supporting the agricultural operation are several outbuildings, including a milk house and two additional structures, highlighted by a custom-built steel building. These improvements provide space for equipment storage, workshop use, and potential game processing. From a recreational standpoint, this Talbot County farm offers strong hunting opportunities. A large pond, complete with a strategically placed hunting pit, is heavily utilized by migratory Canada geese during the season. The combination of open ground, water, and surrounding timber creates an ideal setup for waterfowl hunting. The property also supports a healthy population of whitetail deer, adding to its appeal for hunting and outdoor recreation. For buyers seeking additional acreage, an adjoining 82.54 acre tract is also available. This parcel includes a large portion of tillable ground, with sections previously enrolled in CRP. The additional tract provides an opportunity to expand the farming operation, increase recreational use, or secure additional investment acreage. It may be purchased together with the home farm or separately, offering flexibility for a range of buyers. It's l Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

3750 Windy Hill Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

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

$1,600,000

Talbot County Farm With Country Home, Multiple Outbuildings And Tillable Ac This exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90 acre home farm offers a balanced mix of tillable acreage, improved structures, and wildlife habitat, making it well-suited for farming operations, outdoor recreation, and long-term land investment. The property has a proven track record of row crop production, including corn, soybeans, and wheat. A diverse and productive soil profile supports continued agricultural use, with primary soils consisting of Mattapex silt loam and Nassawango silt loam across the majority of the fields. Additional areas include Mattapex-Woodstown soils located within previously enrolled CRP sections and wooded portions of the farm. These soils are well regarded across the Eastern Shore for their consistency and productivity, providing a solid foundation for both commercial farming and conservation practices. The farm is zoned agricultural, allowing flexibility for a variety of uses, including crop production, recreational enjoyment, and potential enrollment in conservation programs. A large portion of the acreage is tillable, offering income potential or lease opportunities, while the remaining mix of timber and habitat enhances the property's recreational value. At the center of the property sits a well-maintained 1,966 square foot brick ranch-style home built in 1997. The residence offers three bedrooms and two full bathrooms and has been thoughtfully designed for both comfort and functionality. The main living area features a spacious living room with a knotty pine accent wall and bowed window that brings in natural light. The dining room includes chair rail detailing, tongue-and-groove paneling, and a built-in glass-front cabinet, creating a functional and inviting setting. The kitchen is well-appointed with wood cabinetry extending to the ceiling, crown molding, stainless steel appliances, and a center island with seating. A pass-through connects the kitchen to the dining area, improving flow for daily use and gatherings. French doors lead to a sunroom that overlooks the surrounding farmland and wooded edges, providing a consistent view of the property throughout the seasons. The primary suite includes a private bathroom with a deep jetted soaking tub. Additional features of the home include a covered front porch and an attached two-car garage. Supporting the agricultural operation are several outbuildings, including a milk house and two additional structures, highlighted by a custom-built steel building. These improvements provide space for equipment storage, workshop use, and potential game processing. From a recreational standpoint, this Talbot County farm offers strong hunting opportunities. A large pond, complete with a strategically placed hunting pit, is heavily utilized by migratory Canada geese during the season. The combination of open ground, water, and surrounding timber creates an ideal setup for waterfowl hunting. The property also supports a healthy population of whitetail deer, adding to its appeal for hunting and outdoor recreation. For buyers seeking additional acreage, an adjoining 82.54 acre tract is also available. This parcel includes a large portion of tillable ground, with sections previously enrolled in CRP. The additional tract provides an opportunity to expand the farming operation, increase recreational use, or secure additional investment acreage. It may be purchased together with the home farm or separately, offering flexibility for a r Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

3750-A Windy Hill Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

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

$1,600,000

Welcome to Heron Cove Farm, a beautiful waterfront paradise situated on the banks of Broad Creek, just outside of Historic Saint Michaels, MD. This masterfully renovated home offers the convenience of one level living in a private setting of over 15 acres creating the feel of a peaceful escape, yet only two miles from the restaurants, shops and social network of town. Whether you enjoy relaxing on the deck, enjoying the pool, or spending the day boating along the Chesapeake Bay, this property is a complete show stopper! Three separate storage barns can store your toys and equipment, provide a base for horses, or create an opportunity for expansion. Bring your dreams and excitement alive for care free living!

Welcome to Heron Cove Farm, a beautiful waterfront paradise situated on the banks of Broad Creek, just outside of Historic Saint Michaels, MD. This masterfully renovated home offers the convenience of one level living in a private setting of over 15 acres creating the feel of a peaceful escape, yet only two miles from the restaurants, shops and social network of town. Whether you enjoy relaxing on the deck, enjoying the pool, or spending the day boating along the Chesapeake Bay, this property is a complete show stopper! Three separate storage barns can store your toys and equipment, provide a base for horses, or create an opportunity for expansion. Bring your dreams and excitement alive for care free living!

23869 New Land Dr, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Nestled beneath a canopy of mature pines along the protected waters of Solitude Creek, this beautifully renovated waterfront retreat captures the timeless appeal of Maryland's Eastern Shore. Occupying approximately 2.745 private acres with nearly 200 feet of shoreline, the property offers an exceptional blend of privacy, boating, and relaxed luxury—just minutes from the historic waterfront town of St. Michaels. Renovated in 2020, the residence pairs classic coastal architecture with bright, contemporary interiors designed to embrace natural light and peaceful water views. Spanning approximately 2,100 square feet, the home offers four bedrooms and two-and-a-half baths, all arranged on a single level for effortless everyday living. Warm hardwood floors, custom millwork, and an inviting fireplace create an atmosphere that is both elegant and welcoming, while expansive windows frame the surrounding landscape and shimmering creek beyond. At the heart of the home, a beautifully appointed gourmet kitchen features custom cabinetry, granite countertops, a generous center island, and vaulted ceilings that flow seamlessly into open dining and living spaces. Created for gathering with family and friends, these light-filled interiors extend naturally onto an expansive waterside composite deck—an ideal setting for morning coffee, sunset cocktails, or alfresco dinners overlooking the water. The primary suite offers a beautifully finished bath, while three additional guest bedrooms provide comfortable accommodations for family and visitors. Every room reflects a timeless aesthetic that complements the property's serene waterfront surroundings. A private pier with a 9,000-pound boat lift and approximately 6 feet of mean low water offers exceptional boating for a wide variety of vessels. The property's seamless connection to the Choptank River and surrounding tributaries creates a waterfront lifestyle defined by both privacy and adventure. Whether arriving by boat or by car, few locations offer such a remarkable balance of seclusion, convenience, and direct access to some of the Eastern Shore's most celebrated waterways. A detached two-car garage with loft space above provides abundant storage and flexibility for hobbies, a workshop, or future possibilities. Mature landscaping, towering pines, and exceptional privacy complete this rare waterfront offering. The adjacent 3.21± acre waterfront lot to the north is also available for purchase at $895,000. Additional information is available from the listing agent upon request

$1,595,000

4 Beds ⋅ 3 Baths

Nestled beneath a canopy of mature pines along the protected waters of Solitude Creek, this beautifully renovated waterfront retreat captures the timeless appeal of Maryland's Eastern Shore. Occupying approximately 2.745 private acres with nearly 200 feet of shoreline, the property offers an exceptional blend of privacy, boating, and relaxed luxury—just minutes from the historic waterfront town of St. Michaels. Renovated in 2020, the residence pairs classic coastal architecture with bright, contemporary interiors designed to embrace natural light and peaceful water views. Spanning approximately 2,100 square feet, the home offers four bedrooms and two-and-a-half baths, all arranged on a single level for effortless everyday living. Warm hardwood floors, custom millwork, and an inviting fireplace create an atmosphere that is both elegant and welcoming, while expansive windows frame the surrounding landscape and shimmering creek beyond. At the heart of the home, a beautifully appointed gourmet kitchen features custom cabinetry, granite countertops, a generous center island, and vaulted ceilings that flow seamlessly into open dining and living spaces. Created for gathering with family and friends, these light-filled interiors extend naturally onto an expansive waterside composite deck—an ideal setting for morning coffee, sunset cocktails, or alfresco dinners overlooking the water. The primary suite offers a beautifully finished bath, while three additional guest bedrooms provide comfortable accommodations for family and visitors. Every room reflects a timeless aesthetic that complements the property's serene waterfront surroundings. A private pier with a 9,000-pound boat lift and approximately 6 feet of mean low water offers exceptional boating for a wide variety of vessels. The property's seamless connection to the Choptank River and surrounding tributaries creates a waterfront lifestyle defined by both privacy and adventure. Whether arriving by boat or by car, few locations offer such a remarkable balance of seclusion, convenience, and direct access to some of the Eastern Shore's most celebrated waterways. A detached two-car garage with loft space above provides abundant storage and flexibility for hobbies, a workshop, or future possibilities. Mature landscaping, towering pines, and exceptional privacy complete this rare waterfront offering. The adjacent 3.21± acre waterfront lot to the north is also available for purchase at $895,000. Additional information is available from the listing agent upon request

6905 Pea Nck, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Lndg, Saint Michaels

$1,550,000

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Lndg, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact:

20 acres off St Michaels Rd overlooking Newcomb Creek and out to the Miles River. Partially cleared shoreline offering expansive views of the water with beautiful sandy beaches and high elevation. During the summer, enjoy a quick boat ride to St. Michaels and all that the town has to offer. In the fall and winter, enjoy great goose and duck hunting. Approved for 6 bedroom SDA.

$1,540,000

St Michaels Rd, Newcomb

Listing courtesy of Benson & Mangold, LLC. Contact:

PRICE REDUCED: Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is "move in ready" and ready to enjoy the Summer in Saint Michaels. 216 E Chew Ave. is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2-car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the "Conservatory". It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for spacious ground floor master suite as double closets and laundry plumbing already exist in addition to plumbing for a wet bar. Two sets of French doors open to either the front lawn or side yard for entertaining and outdoor grilling and dining. The side yard has a southern exposure and paver patios for a dining set and a fire pit. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the beautiful sunrises and sunsets. Now offered at a REDUCED PRICE, this home also has the lowest price per square foot for a Luxury, Waterview, in town home (under $450), making it a comparatively excellent value. This rare combination of location, quality, amenities and value cannot be replicated in the Saint Michaels market. Do not miss the opportunity to enjoy all that is special about Saint Michaels that comes with this special home.

$1,522,000

PRICE REDUCED: Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is "move in ready" and ready to enjoy the Summer in Saint Michaels. 216 E Chew Ave. is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2-car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the "Conservatory". It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for spacious ground floor master suite as double closets and laundry plumbing already exist in addition to plumbing for a wet bar. Two sets of French doors open to either the front lawn or side yard for entertaining and outdoor grilling and dining. The side yard has a southern exposure and paver patios for a dining set and a fire pit. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the beautiful sunrises and sunsets. Now offered at a REDUCED PRICE, this home also has the lowest price per square foot for a Luxury, Waterview, in town home (under $450), making it a comparatively excellent value. This rare combination of location, quality, amenities and value cannot be replicated in the Saint Michaels market. Do not miss the opportunity to enjoy all that is special about Saint Michaels that comes with this special home.

216 E Chew Ave, Saint Michaels

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Discover this stunning, custom-built waterfront Cape Cod nestled in Ferry Cove, Sherwood, a serene setting that is located right next door to a HGTV dream home! Newly constructed in 2024, this home offers the ultimate blend of luxury and comfort. Owners enjoy direct access to a beautiful sandy beach with 186 feet of waterfrontage on the Chesapeake Bay, creating the perfect space for both relaxation and entertaining guests. Step into the modern kitchen, which features ample storage, an oversized island, and an eye-catching glass backsplash. The open floor plan is designed for seamless entertaining, while a cozy fireplace provides warmth and ambiance on chilly evenings. The main level primary suite boasts breathtaking water views and an owner's suite that is sure to impress. Upstairs, a spacious loft opens to a second balcony deck that overlooks Ferry Cove—perfect for watching sunsets on warm evenings. Each of the two bedrooms includes a private bath, and the second room features a large bonus room situated above the oversized two-car garage. This flexible space offers numerous possibilities to suit your lifestyle needs. Set on over 5.5 acres, the property delivers privacy, water access, and the luxury of your own private sandy beach. There is also plenty of space for storage for your hobbies with a 36x42 pole barn added to the property in 2025. Experience modern amenities and an inviting coastal lifestyle in this exceptional retreat. Whether you seek a year-round residence or a getaway, this property offers an idyllic setting to enjoy the best of waterfront living.

$1,505,000

3 Beds ⋅ 4 Baths

Discover this stunning, custom-built waterfront Cape Cod nestled in Ferry Cove, Sherwood, a serene setting that is located right next door to a HGTV dream home! Newly constructed in 2024, this home offers the ultimate blend of luxury and comfort. Owners enjoy direct access to a beautiful sandy beach with 186 feet of waterfrontage on the Chesapeake Bay, creating the perfect space for both relaxation and entertaining guests. Step into the modern kitchen, which features ample storage, an oversized island, and an eye-catching glass backsplash. The open floor plan is designed for seamless entertaining, while a cozy fireplace provides warmth and ambiance on chilly evenings. The main level primary suite boasts breathtaking water views and an owner's suite that is sure to impress. Upstairs, a spacious loft opens to a second balcony deck that overlooks Ferry Cove—perfect for watching sunsets on warm evenings. Each of the two bedrooms includes a private bath, and the second room features a large bonus room situated above the oversized two-car garage. This flexible space offers numerous possibilities to suit your lifestyle needs. Set on over 5.5 acres, the property delivers privacy, water access, and the luxury of your own private sandy beach. There is also plenty of space for storage for your hobbies with a 36x42 pole barn added to the property in 2025. Experience modern amenities and an inviting coastal lifestyle in this exceptional retreat. Whether you seek a year-round residence or a getaway, this property offers an idyllic setting to enjoy the best of waterfront living.

7650 Ferry Cove Rd, Sherwood

Listing courtesy of Coldwell Banker Realty. Contact:

Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub, and double vanity. Upstairs, enjoy a private balcony with elevated water views, while the rear composite deck provides the perfect setting for everyday living and entertaining, all overlooking the Miles River. The outdoor space is designed to impress, complete with hardscaped pavers, a gas-connected grill, pizza oven, and propane fire table. A private dock offers direct water access, ideal for boating, kayaking, or simply enjoying the waterfront lifestyle. Additional highlights include new LVP flooring, a new furnace, encapsulated crawlspace, and a newly installed irrigation system to maintain the home’s mature landscaping and hydrangeas. A detached garage and access to a nearby community dock within walking distance further enhance the lifestyle this property offers. Tax record indicates wrong square footage, actual square footage of the home is 3,076 square feet of living space. *** Settlement cannot occur before September 10th, 2026***

$1,500,000

Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub, and double vanity. Upstairs, enjoy a private balcony with elevated water views, while the rear composite deck provides the perfect setting for everyday living and entertaining, all overlooking the Miles River. The outdoor space is designed to impress, complete with hardscaped pavers, a gas-connected grill, pizza oven, and propane fire table. A private dock offers direct water access, ideal for boating, kayaking, or simply enjoying the waterfront lifestyle. Additional highlights include new LVP flooring, a new furnace, encapsulated crawlspace, and a newly installed irrigation system to maintain the home’s mature landscaping and hydrangeas. A detached garage and access to a nearby community dock within walking distance further enhance the lifestyle this property offers. Tax record indicates wrong square footage, actual square footage of the home is 3,076 square feet of living space. *** Settlement cannot occur before September 10th, 2026***

602 Landing Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

This private retreat, ideally positioned between historic Easton and St. Michaels, offers the rare combination of privacy, acreage, and refined living that buyers seek on Maryland’s Eastern Shore. Set on more than six beautifully landscaped acres, the property includes a striking 4,800‑square‑foot all‑brick Colonial residence, an expansive concrete pool with a screened entertainment pavilion, a versatile 60' x 30' Morton building, and frontage on a freshwater pond with peaceful views extending toward the Miles River. The residence was just connected to our county sewer system which provides ultimate flexibility for future expansion of the home if desired. * The home’s exterior is designed for low‑maintenance living with full brick construction, a new roof, a paved drive and circular turnaround, generous parking, brick walkways, and a concrete pool surround. Inside, the first floor features oak hardwood floors, high ceilings, and impressive room sizes. The living room with fireplace, formal dining room, and private office or den with powder room create an elegant and functional layout. The renovated gourmet kitchen includes granite countertops, a tile backsplash, stainless appliances, and opens to a breakfast room and a spacious family room with a vaulted ceiling and cozy fireplace. The first‑floor primary suite serves as a true retreat with a vaulted ceiling, fireplace, oversized walk‑in closet, luxurious bath, and an adjoining flex room ideal for a gym, office, studio, or hobby space. A well‑designed mudroom, laundry with cabinetry and sink, and an additional powder room connect conveniently to the oversized two‑car garage. * The second floor offers a private guest suite with its own bath, two additional bedrooms, a hall bath, and a large bonus or game room. Dual staircases — a formal front staircase and a back staircase leading to the kitchen and family room — enhance both convenience and privacy. * Outdoor living is a highlight of this property. The large concrete pool and screened pavillion create an inviting setting for warm‑weather enjoyment. Mature, thoughtful landscaping surrounds the home, while the Morton building with four overhead doors provides exceptional flexibility for boats, RVs, car storage, or workshop needs. The freshwater pond at the edge of the property adds a serene natural element, with pondside views stretching toward the Miles River. * The home has been meticulously maintained and significantly improved. Recent upgrades include a renovated kitchen and dining area with new fixtures, backsplash, wallpaper, and stainless appliances; a 5‑ton Carrier high‑efficiency heat pump for 1st floor installed in 2011; Bryant 2.5‑ton upstairs AC unit installed in 2018; 2023 electric hot water heater; fresh exterior painting of the house, cabana, and barn trim in 2016; and a new GAF Weather Stopper 50‑year roof with transferable warranty added in 2018. The Morton building received a new steel roof in 2019. An 18.6 kW grid‑tied solar array was installed on the barn roof, covering approximately 90 percent of the home’s annual electric use. Atlantic Broadband service was extended to the property for reliable internet access. Additional enhancements include custom mosquito curtains for the cabana, a new pantry under the stairs, a fully remodeled downstairs bath, and an upgraded primary bath with new double vanity, granite, fixtures, and mirrors. Extensive landscaping improvements include new trees, raised garden beds with irrigation, refreshed poolside plantings, a new picket fence with hydrangeas and iris, and upgraded perennial gardens featuring a wide variety of seasonal blooms. Quarterly public sewer fee $231.25.

$1,500,000

4 Beds ⋅ 5 Baths

This private retreat, ideally positioned between historic Easton and St. Michaels, offers the rare combination of privacy, acreage, and refined living that buyers seek on Maryland’s Eastern Shore. Set on more than six beautifully landscaped acres, the property includes a striking 4,800‑square‑foot all‑brick Colonial residence, an expansive concrete pool with a screened entertainment pavilion, a versatile 60' x 30' Morton building, and frontage on a freshwater pond with peaceful views extending toward the Miles River. The residence was just connected to our county sewer system which provides ultimate flexibility for future expansion of the home if desired. * The home’s exterior is designed for low‑maintenance living with full brick construction, a new roof, a paved drive and circular turnaround, generous parking, brick walkways, and a concrete pool surround. Inside, the first floor features oak hardwood floors, high ceilings, and impressive room sizes. The living room with fireplace, formal dining room, and private office or den with powder room create an elegant and functional layout. The renovated gourmet kitchen includes granite countertops, a tile backsplash, stainless appliances, and opens to a breakfast room and a spacious family room with a vaulted ceiling and cozy fireplace. The first‑floor primary suite serves as a true retreat with a vaulted ceiling, fireplace, oversized walk‑in closet, luxurious bath, and an adjoining flex room ideal for a gym, office, studio, or hobby space. A well‑designed mudroom, laundry with cabinetry and sink, and an additional powder room connect conveniently to the oversized two‑car garage. * The second floor offers a private guest suite with its own bath, two additional bedrooms, a hall bath, and a large bonus or game room. Dual staircases — a formal front staircase and a back staircase leading to the kitchen and family room — enhance both convenience and privacy. * Outdoor living is a highlight of this property. The large concrete pool and screened pavillion create an inviting setting for warm‑weather enjoyment. Mature, thoughtful landscaping surrounds the home, while the Morton building with four overhead doors provides exceptional flexibility for boats, RVs, car storage, or workshop needs. The freshwater pond at the edge of the property adds a serene natural element, with pondside views stretching toward the Miles River. * The home has been meticulously maintained and significantly improved. Recent upgrades include a renovated kitchen and dining area with new fixtures, backsplash, wallpaper, and stainless appliances; a 5‑ton Carrier high‑efficiency heat pump for 1st floor installed in 2011; Bryant 2.5‑ton upstairs AC unit installed in 2018; 2023 electric hot water heater; fresh exterior painting of the house, cabana, and barn trim in 2016; and a new GAF Weather Stopper 50‑year roof with transferable warranty added in 2018. The Morton building received a new steel roof in 2019. An 18.6 kW grid‑tied solar array was installed on the barn roof, covering approximately 90 percent of the home’s annual electric use. Atlantic Broadband service was extended to the property for reliable internet access. Additional enhancements include custom mosquito curtains for the cabana, a new pantry under the stairs, a fully remodeled downstairs bath, and an upgraded primary bath with new double vanity, granite, fixtures, and mirrors. Extensive landscaping improvements include new trees, raised garden beds with irrigation, refreshed poolside plantings, a new picket fence with hydrangeas and iris, and upgraded perennial gardens featuring a wide variety of seasonal blooms. Quarterly public sewer fee $231.25.

8466 Aveley Farm Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Welcome to Saint Michaels Retreat—an extraordinary 6-acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and the Miles River. Just minutes from downtown Saint Michaels, this stunningly renovated residence offers over 4,100 sq. ft. of one-level living, thoughtfully designed for effortless indoor and outdoor entertaining. Inside, expansive living and dining areas feature 12-foot ceilings and abundant light. The custom kitchen and family room with gas fireplace anchor the home, while the welcoming foyer, formal living/dining rooms, and serene primary suite—with walk-in closet, built-ins, and a spa-like bath—all open to sweeping views of the pool, patio, and gardens. The gourmet kitchen showcases an oversized island with farm sink, walk-in pantry, wine cooler, extensive cabinetry, and top-of-the-line appliances, creating the perfect setting for both everyday living and memorable gatherings. Three additional bedrooms are well-appointed and share a spacious full hall bath. A private office with additional storage provides a quiet retreat for work or study. A mudroom with custom cabinetry and cedar closet, laundry room with new washer/dryer and utility sink, powder room, and a three-car garage provide both comfort and convenience. Renovated inside and out, the home highlights new flooring, upgraded fixtures and lighting, high-efficiency HVAC and water heater, and large Andersen windows that bathe each room in light. Outdoor living is equally inviting with a gunite pool (new filter and pump), expansive covered patio, pergola, paver-lined walkways, and a pool closet, plus a large shed for extra storage. A full bath just off the family room provides easy access to the pool area. Mature landscaping, a double-access driveway, and private pier (perfect for kayaking or paddle-boarding) complete the property. This remarkable home invites you to embrace the Eastern Shore lifestyle and all the beauty it has to offer. *A list of improvements is available in documents.

$1,500,000

Welcome to Saint Michaels Retreat—an extraordinary 6-acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and the Miles River. Just minutes from downtown Saint Michaels, this stunningly renovated residence offers over 4,100 sq. ft. of one-level living, thoughtfully designed for effortless indoor and outdoor entertaining. Inside, expansive living and dining areas feature 12-foot ceilings and abundant light. The custom kitchen and family room with gas fireplace anchor the home, while the welcoming foyer, formal living/dining rooms, and serene primary suite—with walk-in closet, built-ins, and a spa-like bath—all open to sweeping views of the pool, patio, and gardens. The gourmet kitchen showcases an oversized island with farm sink, walk-in pantry, wine cooler, extensive cabinetry, and top-of-the-line appliances, creating the perfect setting for both everyday living and memorable gatherings. Three additional bedrooms are well-appointed and share a spacious full hall bath. A private office with additional storage provides a quiet retreat for work or study. A mudroom with custom cabinetry and cedar closet, laundry room with new washer/dryer and utility sink, powder room, and a three-car garage provide both comfort and convenience. Renovated inside and out, the home highlights new flooring, upgraded fixtures and lighting, high-efficiency HVAC and water heater, and large Andersen windows that bathe each room in light. Outdoor living is equally inviting with a gunite pool (new filter and pump), expansive covered patio, pergola, paver-lined walkways, and a pool closet, plus a large shed for extra storage. A full bath just off the family room provides easy access to the pool area. Mature landscaping, a double-access driveway, and private pier (perfect for kayaking or paddle-boarding) complete the property. This remarkable home invites you to embrace the Eastern Shore lifestyle and all the beauty it has to offer. *A list of improvements is available in documents.

9171 Deepwater Point Rd, Saint Michaels

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

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$1,495,000

Nestled on a picturesque country setting, this exceptional and thoughtfully designed estate is perfect for both everyday living and entertaining. Featureing a beautifully appointed four-bedroom main residence, a private guest apartment, an inviting outdoor living area, and a spacious pole barn. The heart of the home is the stunning gourmet kitchen, complete with high-end appliances including a Viking range, a wine refrigerator, and an expansive center island with seating. The open design creates a seamless flow into the adjoining living and dining spaces, making it ideal for gatherings of any size. The luxurious main-level primary suite provides a peaceful retreat, while the covered front porch and screened porch offer the perfect places to enjoy the surrounding landscape throughout the seasons.Step outside to discover an extraordinary outdoor oasis featuring an in-ground pool, a charming pool house, and a covered outdoor kitchen and living area designed for effortless entertaining. Whether hosting family and friends or enjoying a quiet evening at home, the outdoor amenities create an unmatched resort-like atmosphere. Guests will appreciate the detached one-bedroom apartment, complete with a kitchenette and a cozy wood-burning stove, providing both privacy and comfort. A large pole barn offers abundant storage space and endless possibilities for hobbies, equipment, or workshop use. New GAF roof on main house, pole barn and garage has a fully transferable 50-year warranty on materials and a 30 year workmanship warranty. Offering an exceptional combination of elegance, functionality, and timeless appeal, this remarkable property presents a rare opportunity to enjoy the very best of Eastern Shore living.

5 Beds ⋅ 6 Baths

Nestled on a picturesque country setting, this exceptional and thoughtfully designed estate is perfect for both everyday living and entertaining. Featureing a beautifully appointed four-bedroom main residence, a private guest apartment, an inviting outdoor living area, and a spacious pole barn. The heart of the home is the stunning gourmet kitchen, complete with high-end appliances including a Viking range, a wine refrigerator, and an expansive center island with seating. The open design creates a seamless flow into the adjoining living and dining spaces, making it ideal for gatherings of any size. The luxurious main-level primary suite provides a peaceful retreat, while the covered front porch and screened porch offer the perfect places to enjoy the surrounding landscape throughout the seasons.Step outside to discover an extraordinary outdoor oasis featuring an in-ground pool, a charming pool house, and a covered outdoor kitchen and living area designed for effortless entertaining. Whether hosting family and friends or enjoying a quiet evening at home, the outdoor amenities create an unmatched resort-like atmosphere. Guests will appreciate the detached one-bedroom apartment, complete with a kitchenette and a cozy wood-burning stove, providing both privacy and comfort. A large pole barn offers abundant storage space and endless possibilities for hobbies, equipment, or workshop use. New GAF roof on main house, pole barn and garage has a fully transferable 50-year warranty on materials and a 30 year workmanship warranty. Offering an exceptional combination of elegance, functionality, and timeless appeal, this remarkable property presents a rare opportunity to enjoy the very best of Eastern Shore living.

4401 Grove Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

Welcome to this beautifully maintained 4/5 BR/3.5BA waterfront residence in desirable Oxford, offering timeless coastal appeal and the relaxed lifestyle that defines Maryland's Eastern Shore. Thoughtfully designed for both comfortable everyday living and gracious entertaining, the home features a desirable main-level primary suite with tranquil water views, a large walk-in closet, and a spacious ensuite bath with double-sink vanity. Upstairs, a second primary suite, two additional guest bedrooms, a full bath, and a versatile bonus room provide exceptional flexibility for family and guests. Filled with natural light, the home offers a seamless blend of traditional design and inviting gathering spaces. The gourmet kitchen features a center island, custom glass-front cabinetry, and opens to a charming breakfast room where peaceful water views create the perfect backdrop for morning coffee. A formal dining room is ideal for special occasions, while the dramatic vaulted living room showcases a gas-burning fireplace with custom surround and built-in entertainment center. Double sliding doors open to the patio and gardens, creating an effortless connection between indoor and outdoor living. A separate mudroom provides convenient interior access to the attached 2-car garage, which also offers a full staircase to wonderful attic storage above. Outside, a waterside screened porch invites you to relax and enjoy gentle Eastern Shore breezes and ever-changing views across Boone Creek. The beautifully landscaped grounds are enhanced by mature trees, flowering gardens, and expansive lawn leading to the water's edge. Complete with a private pier featuring two slips and a boat lift, approximately 3.5+ feet of MLW, riprapped shoreline, and picturesque views along Boone Creek, this exceptional waterfront property offers an ideal setting for boating, entertaining, and embracing the best of Oxford's waterfront lifestyle.

$1,495,000

Welcome to this beautifully maintained 4/5 BR/3.5BA waterfront residence in desirable Oxford, offering timeless coastal appeal and the relaxed lifestyle that defines Maryland's Eastern Shore. Thoughtfully designed for both comfortable everyday living and gracious entertaining, the home features a desirable main-level primary suite with tranquil water views, a large walk-in closet, and a spacious ensuite bath with double-sink vanity. Upstairs, a second primary suite, two additional guest bedrooms, a full bath, and a versatile bonus room provide exceptional flexibility for family and guests. Filled with natural light, the home offers a seamless blend of traditional design and inviting gathering spaces. The gourmet kitchen features a center island, custom glass-front cabinetry, and opens to a charming breakfast room where peaceful water views create the perfect backdrop for morning coffee. A formal dining room is ideal for special occasions, while the dramatic vaulted living room showcases a gas-burning fireplace with custom surround and built-in entertainment center. Double sliding doors open to the patio and gardens, creating an effortless connection between indoor and outdoor living. A separate mudroom provides convenient interior access to the attached 2-car garage, which also offers a full staircase to wonderful attic storage above. Outside, a waterside screened porch invites you to relax and enjoy gentle Eastern Shore breezes and ever-changing views across Boone Creek. The beautifully landscaped grounds are enhanced by mature trees, flowering gardens, and expansive lawn leading to the water's edge. Complete with a private pier featuring two slips and a boat lift, approximately 3.5+ feet of MLW, riprapped shoreline, and picturesque views along Boone Creek, this exceptional waterfront property offers an ideal setting for boating, entertaining, and embracing the best of Oxford's waterfront lifestyle.

26226 Langs Landing Rd, Oxford

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

A rare chance to own 44.28± acres of productive farmland located in the sought-after Chapel School District, just minutes northeast of Easton, Maryland. In a county where quality agricultural ground is rarely brought to market, this property presents a valuable opportunity for farmers, investors, and ag-focused buyers. The farm offers approximately 30± acres of tillable land, well-suited for row crops or rotational planting, along with 6± acres of timber and the remaining acreage in the homesite and agricultural improvements. The operation includes substantial infrastructure designed for dairy use: - 70± stall main barn with pasture access - Dry cow barn - 120' x 50' heifer barn - 10-cow swing parlor - 800-gallon milk tank - 350,000-gallon Slurrystone tank A 3,878± square-foot farmhouse (5 BR, 3 BA) accompanies the farm, offering ample space for family or farm staff. Both the residence and farm structures are sold As Is, giving the buyer an opportunity to repurpose or expand. Please note: Only the real property conveys. Cattle, machinery, and creamery processing equipment are available separately, outside of the property sale. With its tillable acreage, extensive dairy facilities, and prime Talbot County location, this is a rare opportunity to secure agricultural ground in one of Maryland’s most sought-after farming regions.

$1,450,000

5 Beds ⋅ 3 Baths

A rare chance to own 44.28± acres of productive farmland located in the sought-after Chapel School District, just minutes northeast of Easton, Maryland. In a county where quality agricultural ground is rarely brought to market, this property presents a valuable opportunity for farmers, investors, and ag-focused buyers. The farm offers approximately 30± acres of tillable land, well-suited for row crops or rotational planting, along with 6± acres of timber and the remaining acreage in the homesite and agricultural improvements. The operation includes substantial infrastructure designed for dairy use: - 70± stall main barn with pasture access - Dry cow barn - 120' x 50' heifer barn - 10-cow swing parlor - 800-gallon milk tank - 350,000-gallon Slurrystone tank A 3,878± square-foot farmhouse (5 BR, 3 BA) accompanies the farm, offering ample space for family or farm staff. Both the residence and farm structures are sold As Is, giving the buyer an opportunity to repurpose or expand. Please note: Only the real property conveys. Cattle, machinery, and creamery processing equipment are available separately, outside of the property sale. With its tillable acreage, extensive dairy facilities, and prime Talbot County location, this is a rare opportunity to secure agricultural ground in one of Maryland’s most sought-after farming regions.

10380 Chapel Rd, Easton

Listing courtesy of The Land Group. Contact:

Selling Office: The Land Group.

$1,450,000

Waterfront Retreat in Cooke’s Hope – Perfectly positioned along Easton’s sought-after Oxford Road corridor, this custom waterfront home in Cooke’s Hope offers timeless design and a relaxed Eastern Shore lifestyle just minutes from downtown Easton. Designed by Pam Gardner, the home features 3 bedrooms, 2.5 baths and an open floor plan filled with natural light and beautiful water views. A dramatic two-story foyer leads to the vaulted waterfront living room with skylights and wood floors, creating an inviting setting for everyday living and entertaining. The waterside primary suite offers a private retreat with a fireplace and spa-inspired bath featuring a steam shower and soaking tub. The kitchen is designed for both everyday living and entertaining with granite countertops, bar seating and casual dining space. A private den with built-ins and fireplace offers a comfortable office or reading retreat, while the light-filled cupola room provides flexible space for a studio, lounge or creative escape. A separate bedroom wing ensures privacy for family or guests while a detached one-bedroom guest apartment offers additional accommodations. Outdoor living includes a screened porch and waterside deck overlooking the tranquil setting. A two-car garage provides excellent storage for vehicles and waterfront gear. The leased boat slip with water and electric at the community pier (available 2026) offers easy access to the surrounding waterways. A rare opportunity to enjoy waterfront living just minutes from Easton, Oxford and St. Michaels!

Waterfront Retreat in Cooke’s Hope – Perfectly positioned along Easton’s sought-after Oxford Road corridor, this custom waterfront home in Cooke’s Hope offers timeless design and a relaxed Eastern Shore lifestyle just minutes from downtown Easton. Designed by Pam Gardner, the home features 3 bedrooms, 2.5 baths and an open floor plan filled with natural light and beautiful water views. A dramatic two-story foyer leads to the vaulted waterfront living room with skylights and wood floors, creating an inviting setting for everyday living and entertaining. The waterside primary suite offers a private retreat with a fireplace and spa-inspired bath featuring a steam shower and soaking tub. The kitchen is designed for both everyday living and entertaining with granite countertops, bar seating and casual dining space. A private den with built-ins and fireplace offers a comfortable office or reading retreat, while the light-filled cupola room provides flexible space for a studio, lounge or creative escape. A separate bedroom wing ensures privacy for family or guests while a detached one-bedroom guest apartment offers additional accommodations. Outdoor living includes a screened porch and waterside deck overlooking the tranquil setting. A two-car garage provides excellent storage for vehicles and waterfront gear. The leased boat slip with water and electric at the community pier (available 2026) offers easy access to the surrounding waterways. A rare opportunity to enjoy waterfront living just minutes from Easton, Oxford and St. Michaels!

6780 Cookes Hope Rd, Easton

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

Selling Office: Monument Sotheby's International Realty.

$1,400,000

Welcome to this enchanting waterfront retreat, beautifully sited on 6.2 acres overlooking Old House Cove with scenic passage out to San Domingo Creek. Designed in a coastal style and offering 3,340 sq. ft., this 4-bedroom, 2.5-bath residence blends timeless comfort with the natural beauty of the Eastern Shore. A charming front porch sets the tone, leading into sunlit living spaces with soaring vaulted ceilings and gleaming American Cherry hardwood floors. The main-level primary suite is a serene haven with a private sitting area and spa-like bath. Upstairs, a loft lounge overlooks the living room and connects to three additional bedrooms and a shared hall bath. The gourmet kitchen, outfitted with premium appliances, flows seamlessly into the dining area, living room with cozy gas fireplace, and waterside sunroom that opens to a deck with sweeping views. A private office, versatile bonus room, and attached 2-car garage add convenience and flexibility. Outdoors, the private pier( with electricity and water) offers two slips and electric lift, inviting endless days on the water, while mature trees, lush landscaping, and native flora frame this idyllic setting. Countless updates further enhance this exceptional St. Michaels offering and a recent survey shows room for pool.

4 Beds ⋅ 3 Baths

Welcome to this enchanting waterfront retreat, beautifully sited on 6.2 acres overlooking Old House Cove with scenic passage out to San Domingo Creek. Designed in a coastal style and offering 3,340 sq. ft., this 4-bedroom, 2.5-bath residence blends timeless comfort with the natural beauty of the Eastern Shore. A charming front porch sets the tone, leading into sunlit living spaces with soaring vaulted ceilings and gleaming American Cherry hardwood floors. The main-level primary suite is a serene haven with a private sitting area and spa-like bath. Upstairs, a loft lounge overlooks the living room and connects to three additional bedrooms and a shared hall bath. The gourmet kitchen, outfitted with premium appliances, flows seamlessly into the dining area, living room with cozy gas fireplace, and waterside sunroom that opens to a deck with sweeping views. A private office, versatile bonus room, and attached 2-car garage add convenience and flexibility. Outdoors, the private pier( with electricity and water) offers two slips and electric lift, inviting endless days on the water, while mature trees, lush landscaping, and native flora frame this idyllic setting. Countless updates further enhance this exceptional St. Michaels offering and a recent survey shows room for pool.

8095 Church Neck Rd, Saint Michaels

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

Selling Office: Coldwell Banker Realty.

$1,395,000

121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.

121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.

121 W Chestnut, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: