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4480 Bachelors Point Rd, Oxford
$1,945,000
Your Custom Dream Waterfront Home Awaits! This rare, build-ready lot offers a blank canvas for you to craft your perfect Eastern Shore estate with spectacular, panoramic views! The 2.9 acre waterfront lot in the Bachelor Pt section of Oxford offers 180 degree panoramic views stretching across the majestic Choptank River. Enjoy the peace of mind of a recently installed rip-rap shoreline over an estimated 569 feet of protected waterfront, providing long-term erosion protection and maintaining your valuable waterfront. The property also includes a new dock setup, featuring a heavy-duty 16,000 lb boat lift and two additional lifts perfect for jet skis. The lot is located within Oxford town limits, offering the advantage of access to public water and sewer hook-ups. Final approval has been given from the Oxford Planning Board for the building plans the current owner proposed providing a massive head start on your construction timeline. Those plans can be included in the sale of the lot and while you may modify them to suit your taste, having approved plans means the property is truly "build-ready." Simply choose your builder and start constructing your dream!

4480 Bachelors Point Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

9450 Canvasback Way, St Michaels
$1,895,000
5 Beds ⋅ 6 Baths
Discover the epitome of luxury living in this stunning Colonial home nestled in the desirable Martingham community. This exquisite residence has been freshly painted and boasts 5 spacious bedrooms and 5.5 totally updated bathrooms. The primary bath has an expansive steam shower, soaker tub and heated floors for those chilly mornings. The heart of the home features a spacious gourmet kitchen equipped with stainless steel appliances, including a Kitchen Aid refrigerator, Wolf double oven, Wolf 5 burner gas cooktop and Wolf dishwasher. Major renovations completed in 2026 include new roof with exposed copper valleys, copper gutters, windows and doors on the back of the house of the 1st floor have been replaced, new air handler on the 3rd floor, attic vent foam insulation, crawlspace has been encapsulated with sump pump and dehumidifier, irrigation and landscaping all have elevated this property to new heights, ensuring modern amenities while preserving its classic charm. Enjoy the ambience of two brick fireplaces, the convenience of an upper-floor laundry, and the tranquility of newly finished hardwood flooring throughout. The expansive private 2.34-acre lot faces the 14th hole of The Links at Perry Cabin picturesque golf course, offering a serene backdrop for outdoor gatherings. Step outside to your personal oasis, complete with a saltwater gunite pool, perfect for summer relaxation. The community enhances your lifestyle with well-maintained common areas and a waterfront picnic area for homeowners. This home is not just a residence; it's a lifestyle. There is nothing left to do but move your furniture in. Don't miss your chance to own this exceptional property!

9450 Canvasback Way, St Michaels

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

7696 Ocean Gtwy, Easton
$1,795,000
Two RT 50 parcels located in Easton on sought after O.C. bound side at corner of Rt 50 and Dutchman s Lane. Office on property in good condition but sold as-is. Zoned General Commercial with all utilities available at site.

7696 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

402 Brookletts Ave, Easton
$1,750,000
Unique parcel of ground in Easton. Sale does NOT include cell tower which will be sold separately. It is in the PRD District but is zoned BC by the Town of Easton with residential as a permitted use. Survey available. The property is not in the Town Historic District. Feel free to ride on the property but no access until January.

402 Brookletts Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

7871 Avon Ct, Easton
$1,695,000
3 Beds ⋅ 3 Baths
Refined waterfront offering on Maryland’s Eastern Shore, 7871 Avon Court has been completely transformed into a sophisticated modern farmhouse blending timeless design and convenience. Thoughtfully renovated to a like-new standard, the residence offers approximately 2,000 square feet with 3 bedrooms, 2.5 baths and a private office/flex space. Dramatic vaulted living spaces, wide-plank flooring, custom finishes and a beautifully reimagined kitchen create interiors that feel both elevated and inviting. Expansive windows frame views of the Tred Avon River from nearly every room, seamlessly connecting the home to its exceptional waterfront setting. Set on a high-bank waterfront site with approximately 360± feet of shoreline and 3± feet MLW, the property is ideally suited for boating, kayaking, paddleboarding and waterfront entertaining. Private pier, sandy beach, mature trees and expansive lawn create a rare park-like setting just minutes from downtown Easton and within easy reach of Washington, Northern Virginia, Philadelphia and surrounding Mid-Atlantic destinations. A compelling waterfront retreat offering privacy, style and effortless Eastern Shore living. Room for pool subject approvals.

7871 Avon Ct, Easton

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

9180 Saint Michaels, Saint Michaels
$1,685,000
5 Beds ⋅ 5 Baths
UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

9180 Saint Michaels, Saint Michaels

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

6385 Canterbury Dr, Easton
$1,595,000
4 Beds ⋅ 4 Baths
Nestled in the prestigious Canterbury subdivision, this exquisite Cape Cod home offers a harmonious blend of luxury and comfort. Spanning over 4,600 square feet, the interior boasts elegant wood floors and an inviting layout, featuring a spacious kitchen with upgraded countertops and a six-burner stove, perfect for culinary enthusiasts. The dining area and cozy built-ins create an ideal setting for gatherings, while the three fireplaces, adorned with charming mantels, add warmth and sophistication. Retreat to the primary suite, complete with a luxurious bath, or enjoy the convenience of an entry-level bedroom. The thoughtful design includes a laundry chute for effortless living. Outside, the expansive 2.44-acre lot is beautifully landscaped, providing a serene backdrop for relaxation. With an attached two-car garage and a commitment to quality, this home embodies an exclusive lifestyle, inviting you to create cherished memories in a space that truly feels like home.

6385 Canterbury Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

503 Cynwood Dr Unit 1, Easton
$1,550,000
Great Investment Opportunity – This 5500+/- sq ft Commercial Condo has a long term Lease with a well-established Tenant. Zoned Commercial, ideal for Medical or related Business. Excellent condition, great visibility and plenty of parking.

503 Cynwood Dr Unit 1, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

31720 Ayres Dr, Trappe
$1,500,000
4 Beds ⋅ 3 Baths
A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact:

8305 Ocean Gtwy, Easton
$1,495,000
Prime commercial location at the corner of Route 50 and Matthewstown Road, offering excellent visibility and convenient access from both roadways. Situated on approximately 0.66 acres, the property is currently operating as a restaurant and features ample on-site parking to accommodate customers and staff. The prominent corner location and dual ingress/egress provide added convenience and accessibility, making this an attractive opportunity for investors or owner-users seeking a strategically positioned commercial property. Investors will appreciate the long-term tenant who would like to stay. Lease is also flexible for seller if buyer is an end-user.

8305 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Bar Neck Rd, Tilghman
$1,495,000
Very rare opportunity to buy 36+/- acres with stunning views of the Chesapeake Bay. Approximately 2,100 feet of rip-rapped shoreline. Property is slated for county sewer. Conservation Easement applies but property is approved for a large main residence and a 4 bedroom detached guest house up to 1,500 sf.

Bar Neck Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

Dover Road, Easton
$1,475,000
29 ± Acres | Easton, Maryland | Development Opportunity. Exceptional 29 ± acre development opportunity located along Maryland Route 331 Dover Rd in Easton, Maryland, directly bordering the Town of Easton limits and the Waylands subdivision. This tract of land offers excellent visibility and a strategic location with significant future development potential. Located within Priority Area 3 of Easton’s Comprehensive Growth Plan Map, the property presents an attractive opportunity for R10A zoning or higher-density residential/community development project, subject to applicable approvals and zoning requirements. The parcel is currently in row crop production, offering an immediate agricultural use while positioning the property for potential future development. Its proximity to established residential development, Town of Easton services, and major transportation routes makes this a compelling opportunity for developers, investors, and land planners.

Dover Road, Easton

Listing courtesy of Meredith Fine Properties. Contact:

21525 Island Club Rd, Tilghman
$1,465,000
3 Beds ⋅ 2 Baths
Turn-key waterfront home with spectacular views from every room. The entire house has been taken down to the studs: exterior and interior walls reframed; shed dormers installed; glass doors and windows placed in every wall; renovated kitchen with quartz countertops, semi-custom cabinets, new appliances, a Butler's Pantry, two new staircases, all new plumbing, electric, HVAC, built-ins, hardi-plank siding, Azek trim, composite decking, custom garage doors -- the list goes on. "Tilghman on Chesapeake" has coveted amenities including a clubhouse and outdoor pool on the water, piers, boat-slips, and sweeping views of the watermen departing at sun-rise. Restaurants and daily amenities are nearby including groceries, liquor, a deli and the best cup of coffee on the Eastern Shore served at the Country Store. Spectacular views, and laid-back community charm, is the timeless appeal that makes Tilghman Island so special. The home can convey furnished if desired.

21525 Island Club Rd, Tilghman

Listing courtesy of Sell Your Home Services. Contact:

104 Mulberry St, Saint Michaels
$1,399,000
3 Beds ⋅ 3 Baths
This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! Come by boat or by car. ACCESS BY APPT ONLY, surveillance cameras.

104 Mulberry St, Saint Michaels

Listing courtesy of RE/MAX One. Contact:

104 Myrtle St, Oxford
$1,399,000
3 Beds ⋅ 3 Baths
Major Price Improvement! Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for enjoying life on the water. Fabulous gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 + feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Sold As Is

104 Myrtle St, Oxford

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

7582 Leadenham Cove Rd, Bozman
$1,350,000
3 Beds ⋅ 3 Baths
Waterfront coastal cottage living at its finest. Come see what makes this 3-bedroom, 2.5-bathroom retreat feel like a secluded getaway, approximately 10 minutes from downtown St. Michaels and two hours from the DC, and Baltimore areas. Set on 16.45 peaceful acres on Leadenham Creek, this property offers southwestern exposure and over 900 feet of shoreline. Sit back and enjoy evening sunset views from the newly installed dock (2025). Two sheds on the property, provide additional storage capability. Step inside to find a cozy, open-concept layout. The kitchen flows directly into a breakfast nook/dining area with built-in seating and an adjoining living room with a wood-burning fireplace, all with waterfront views. On the main level, you’ll find a primary bedroom suite with a full bathroom and access to a bright, private sunroom. A spiral staircase leads to two additional bedrooms. Additional updates include a new HVAC system (2022) and a new roof (2021). Privacy, waterfront, and acreage, all within a short drive of the restaurants, shops, museums, and activities St. Michaels has to offer.

7582 Leadenham Cove Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

28658 Hope Cir, Easton
$1,325,000
4 Beds ⋅ 5 Baths
Located in the desirable Cooke’s Hope community, this spacious home offers approximately 4,966 square feet of finished living space with 4 bedrooms and 4½ baths. Primary suites on both the first and second floors provide flexibility, while two additional bedrooms and a spacious landing complete the upper level. All four bedrooms feature private baths. Recently refinished hardwood floors and tile extend throughout the home. The kitchen, dining room, and living room flow together to create generous spaces for everyday living and entertaining. The kitchen features granite countertops, a center island, stainless steel appliances, abundant cabinetry, an adjoining pantry, and a wet bar. The living room includes a gas fireplace and opens to the rear screened porch. Upper and lower front porches give the home its distinctive presence, while the rear screened porch overlooks a private in-ground gunite pool with a waterfall feature. A spacious stone terrace, mature landscaping, a fully fenced backyard, and adjoining open space create a peaceful and private outdoor setting. Additional features include a main-level laundry room, an attached two-car garage with a finished storage or bonus room above, and a recently encapsulated crawlspace with French drains, sump pumps, and a dehumidifier. Cooke’s Hope amenities include a community dock, canoe storage and launch, walking and exercise trails, tennis and pickleball courts, a private community mailroom, and a fitness center. Convenient to downtown Easton while offering a quiet, established neighborhood setting. Effective August 2026, The Homeowners Association has approached those owners in Cooke’s Hope with property backing to open space along Hope Circle to offer additional lands in the form of a perpetual easement that may be purchased and used for additional private open space, yard, garden and the area may be fenced. Contact listing agent for additional information.

28658 Hope Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

28751 Emanuel St, Easton
$1,295,000
3 Beds ⋅ 4 Baths
Beautifully maintained 3–4 bedroom home set on lovely park-like grounds in the sought after community of Cooke’s Hope. From the welcoming foyer, the home opens to formal living and dining rooms, followed by an inviting great room with cathedral ceiling, fireplace and wet bar. The spacious kitchen offers an abundance of cabinetry, stainless steel appliances, breakfast bar and a cozy breakfast nook overlooking the beautifully landscaped rear yard. Hardwood floors, crown molding and recessed lighting add warmth and character throughout. The first floor primary suite offers a walk-in closet and spacious bath with separate soaking tub. Upstairs, two additional ensuite bedrooms along with a separate office and family/bonus room with a private balcony. Tons of attic storage. Outdoor living is easy here, with a screened and wraparound porch overlooking the mature landscaping and private rear yard with gazebo. Cooke’s Hope offers an exceptional array of amenities, including scenic walking trails, ponds, tennis and pickleball courts, fitness room, community gathering spaces and a waterfront dock with slips and kayak storage. It is a community that offers both an active lifestyle and a sense of space and privacy. A special property in a highly desirable setting, offering one level living with plenty of additional space for family, guests and hobbies.Close to downtown Historic Easton, YMCA, shopping, museums and grocery stores. Please note: Sellers require a mid-April 2027 settlement. A rent-back agreement will be required if an earlier settlement is requested.

28751 Emanuel St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

8410 Bozman Neavitt Rd, Bozman
$1,289,000
4 Beds ⋅ 3 Baths

8410 Bozman Neavitt Rd, Bozman

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

8710 Cummings Rd, Wittman
$1,285,000
3 Beds ⋅ 3 Baths
Well maintained one level living on Cummings Creek. 3 BR's, 2.5 baths, DR, kitchen, waterside living room, 2 car garage, oversized screen porch. Beautiful Westerly sunset views. Pier has a boat lift, water and electric. 4 MLW with an option to extend the pier 50' to get over 5 MLW. Plenty of room to expand the footprint or add a pool. Professional Photos to Come.

8710 Cummings Rd, Wittman

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

202 E Chestnut St, Saint Michaels
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butler’s pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler’s pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

202 E Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

115 W, Oxford
$1,250,000
3 Beds ⋅ 4 Baths
A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.

115 W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Unionville Road, Easton
$1,250,000
Presenting 47+ acres of stunning land just minutes from Easton, perfectly positioned at the intersection of Unionville Road and Miles River Road, extending along Anchorage Road. This expansive property is currently leased for farming and hunting, offering both income potential and recreational opportunities. While it has not been perc tested, the property holds potential for multiple lots, subject to required approvals. A rare investment opportunity with endless possibilities in a highly desirable location. Please note the photos with the house and barn are AI generated. There are no buildings on this property.

Unionville Road, Easton

Listing courtesy of Meredith Fine Properties. Contact:

Ocean Gateway, Easton
$1,250,000
Final section of Lakelands subdivision! Previously approved for up to 48 lots, road cut thru, some water & sewer installed. PUD approved by Town in 2010. See agent for plats, engineering and current status. Unique opportunity! Wetlands needs to be updated with possible additional land becoming available. Road needs completion. Some Capital fees already paid. Water lines partially installed along with sewer lines. Water lines needs upgrading for sprinklers.

Ocean Gateway, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Ocean Gateway, Easton
$1,250,000
Final section of Lakelands subdivision! Previously approved for up to 48 lots, road cut thru, some water & sewer installed. PUD approved by Town in 2010. See agent for plats, engineering and current status. Unique opportunity! Wetlands needs to be updated with possible additional land becoming available. Road needs completion. Some Capital fees already paid. Water lines partially installed along with sewer lines. Water lines needs upgrading for sprinklers.

Ocean Gateway, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

28641 Hope Cir, Easton
$1,195,000
4 Beds ⋅ 4 Baths
Welcome home to 28641 Hope Circle, an elegant 4BR/3.5BA Federal-style residence nestled in the highly sought after Village section of Cooke’s Hope. Spanning 4,772 sq ft of meticulously maintained living space, this property blends timeless Eastern Shore charm with modern luxury. The thoughtful layout offers unmatched flexibility, featuring dual primary suites with one on the main level and one on the upper level, making it perfect for multi-generational living or an exceptional guest arrangement. The upper primary suite serves as a true sanctuary boasting a luxury bath and a private outdoor deck overlooking the serene surroundings. A welcoming foyer leads to formal dining room (currently being used as a living room) with custom wainscoting, and a private home office/study complete with high-end built-in cabinetry. The heart of the home flows into a sunlit breakfast area, a bright laundry room, and a spacious mudroom with custom coat and shoe organizational shelving. From there, a second staircase leads to an incredible, fully equipped media/theater room featuring reclining stadium seating, a movie projector, and an integrated screen. Expanding the living space even further, a fully finished, heated and air-conditioned third-floor bonus room provides endless possibilities for a yoga studio, playroom, gym, or hobby shop. Outside your door, enjoy the prestigious Cooke’s Hope lifestyle, which offers miles of scenic walking trails, a fitness center, tennis courts, a kayak launch, and the community’s signature pastures home to resident Belted Galloway cows, all while being just minutes from historic downtown Easton’s premiers dining and shopping.

28641 Hope Cir, Easton

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

5480 Windward Dr, Tilghman
$1,195,000
4 Beds ⋅ 3 Baths
Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.

5480 Windward Dr, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

28711 Hope Cir, Easton
$1,195,000
4 Beds ⋅ 4 Baths
Approximately 4400 square feet +/- , 3 Level, newly updated, 4 bedroom, Federal style home on a quiet circle. Newer kitchen and first floor owner's en suite, new sun room and finished third floor office/bedroom. Second floor includes two spacious bedrooms, two baths (both en suite); plus, large bonus/storage room which could easily be converted to a 5th bedroom or in-law suite. Perfect for entertaining- the open floor plan with pass-through, double fireplace between the kitchen and great room connects to an enclosed private sun room leading to a fenced-in, paved patio surrounded by wonderful and private garden with new irrigation system allowing for luxurious indoor/outdoor living. Located on other side of the residence in back is an additional fenced-in private garden. The main level laundry and mud rooms connect to the oversized, two car garage. Very large butler's pantry and wet bar off the kitchen. Light-filled windows with plantation shutters and venetian blinds through-out. This bright and sunny home blends elegance, luxury, and everyday comfort. This home allows for exceptional privacy in a close-knit, water access community. Please inquire about the many other Cooke's Hope amenities.

28711 Hope Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

28708 Springfield Dr, Easton
$1,149,900
3 Beds ⋅ 3 Baths
Located on a large corner lot in the Springfield section of Cooke’s Hope, this approximately 3,000-square-foot home offers spacious living areas, an updated main-level primary suite, and a gunite in-ground pool. Wood flooring extends throughout most of the main level, including the living room, with vaulted ceilings and a gas fireplace flanked by built-in bookcases. The living room also provides direct access to the back patio. The dining room features a second gas fireplace, while the kitchen is equipped with stainless steel appliances, a gas cooktop, and double wall ovens. The main-level primary suite is highlighted by a beautifully updated bath with intricate tile flooring, a freestanding tub, tiled shower, and walk-in closet, along with direct access to the back deck. An updated powder room features modern tile finishes. Outside, the privacy-fenced backyard offers an in-ground pool, brick patio, and deck, creating generous space for outdoor living and entertaining. An attached two-car garage provides additional parking and storage. Set within the larger-lot Springfield section of Cooke’s Hope, the property also enjoys access to the community’s extensive amenities, including walking trails, ponds, tennis and pickleball courts, fitness center, community gathering spaces, and community dock, all just outside of Easton.

28708 Springfield Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

no property photo
$1,149,000
1.46 acre commercial lot fronting US Rt. 50 in Easton Commons. Finished street with utilities to site. Zoned CL. Perfect for restaurant and other retail uses. AADT of 35,000

9043 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

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