Refine Search
Map
Sort by
$1,495,000
7 Beds ⋅ 5 Baths
McNeil Pointe is a unique, coveted, 2-mile long peninsula of luxury homes. Nestled within the serene enclave of McKeil Pointe, this exquisite 7-bedroom, 5.5-bathroom farmhouse-style residence offers an unparalleled blend of luxury and comfort, set against a backdrop of lush landscapes and tranquil water features. Spanning approximately 5000+/- square feet, this home is a true sanctuary, designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior, where you will find custom, hand-cut walnut floors throughout the open first floor and 2nd floor common areas. The heart of the home is the gourmet kitchen, featuring upgraded countertops, a large island, and top-of-the-line stainless steel appliances, including a six-burner stove and double ovens. The adjoining great room, complete with a cozy gas fireplace, creates an ideal space for gatherings, while the breakfast area invites leisurely mornings with views of the beautifully landscaped surroundings and water. Retreat to the primary suite, a luxurious haven with a bay front window that floods the space with natural light. The en-suite bathroom boasts a jetted tub, walk-in shower, and dual vanities, providing a spa-like experience at home. Each additional bedroom is generously sized, ensuring comfort for all. The exterior consists of 120' of deep, wraparound covered porches, with exposed rafters, beaded ceilings, a standing seam metal roof and stamped stone floors for all-season enjoyment. The remaining exterior of the property is equally impressive, featuring extensive hardscaping, multiple outdoor living spaces including a waterside deck, perfect for alfresco dining or simply soaking in the serene views. The heated in-ground pool offers a refreshing escape on warm days, while the private dock on Fishing Creek provides direct access to water activities such as kayaking, fishing, and swimming. Set on a sprawling 5.7-acre lot, the property is partly wooded and beautifully landscaped, offering privacy and tranquility. The gentle sounds of the nearby pond and the picturesque river views enhance the peaceful ambiance, making this home a true retreat from the hustle and bustle of everyday life. With ample parking, including a gravel driveway accommodating up to four vehicles, and security features, this residence combines luxury with practicality. Experience the exclusive lifestyle that this remarkable property offers, where every detail has been thoughtfully curated for your enjoyment and comfort. Additional features include, but are not limited to 3 zone central air. colonial and solid louvered doors throughout, 6 bedrooms with direct water views, and the 3rd Floor boasts a large Rec room, full bath and two bedrooms with four wide dormers.

5207 Brooks Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$899,999
4 Beds ⋅ 3 Baths
Cambridge - waterfront paradise on Jenkins Creek, offering direct, easy access to the Choptank River! Nestled on a private lot with a peaceful, country feel, this charming home combines serene Eastern Shore living with the convenience of being just minutes from downtown Cambridge. Step inside to bright, sunlit interiors featuring soaring cathedral ceilings and rich hardwood floors. Cozy up on cool winter evenings by the fireplace/ woodstove, or unwind in the spacious main-floor primary suite, complete with a walk-in closet, updated bath with a walk-in shower, and direct access to the deck through large sliding doors framing picturesque water views. Upstairs, you'll find two additional bedrooms, a full bath, a versatile bonus room or potential fourth bedroom, and generous extra space ideal for storage or future expansion. Outdoor living is truly exceptional, featuring two private decks, a welcoming front porch, and a wonderful screened porch perfect for relaxing or entertaining. The rip-rapped shoreline includes a private dock equipped with water and electricity—ready for your boating and fishing adventures. Complete with an attached oversized garage, this captivating coastal retreat has so much to love!

2503 Legacy Ct, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to Crump Point, an extraordinary renovated waterfront sanctuary nestled on approximately 5± private acres overlooking the tranquil waters of Church Creek. Offering exceptional privacy and captivating panoramic views, this remarkable property captures the essence of Eastern Shore waterfront living. Thoughtfully designed to embrace its breathtaking surroundings, the 3-bedroom, 2.5-bath residence offers stunning water views from nearly every room. The main level is anchored by a spacious gourmet kitchen featuring an oversized island, creating the perfect space for entertaining or gathering with family while enjoying the picturesque waterfront backdrop. All new stainless steel appliances throughout. The first-floor primary suite provides a private retreat complete with serene waters views, waterside deck, walk-in closet, walk-in shower, and oval soaking tub. Outdoor living is equally impressive with a spacious waterfront deck, screened waterside porch, and an upper-level waterside deck—ideal for morning coffee, evening sunsets, or simply taking in the ever-changing beauty of Church Creek. A private pier offers direct access to the water for boating, kayaking, fishing, and crabbing, while the beautifully landscaped grounds provide ample room to enjoy the peaceful surroundings. Additional features include a circular driveway, attached two-car garage, first-floor split-unit heating and cooling, and second-floor central air with baseboard heat. Whether you’re seeking a full-time residence or a weekend waterfront escape, Crump Point offers a rare opportunity to own an exceptional Eastern Shore property where privacy, natural beauty, and timeless waterfront living come together in perfect harmony.

1619 Perseus Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$424,900
3 Beds ⋅ 3 Baths
One of a kind 31+ acre farmette with established trails, open fields, ponds and Farm Creek water frontage, offering excellent Sika deer, goose and duck hunting and endless opportunities to enjoy the outdoors. The property includes a well-maintained 3 bedroom, 2 3/4 bath home with a conditioned crawl space, 3 stall barn, fenced pastures, pole barn and shop/shed. The perfect blend of recreation, hobby farming and peaceful country living for the hunter and nature enthusiast alike.

2562 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$624,000
4 Beds ⋅ 3 Baths
Discover the perfect blend of privacy, comfort, and waterfront living with this exceptional move-in-ready Colonial, nestled on 6.01 scenic acres. Offering 4 bedrooms, 3 full baths, and an abundance of versatile living space, this property is ideal as a full-time residence, weekend retreat, or multigenerational home. Wake up to peaceful water views and enjoy your morning coffee on the expansive rear deck overlooking the tranquil setting. Inside, you'll find a spacious country kitchen, a flexible first-floor bedroom or home office, and inviting living areas designed for both everyday living and entertaining. The property is loaded with sought-after amenities, including a private floating dock for boating, fishing, or kayaking, a detached workshop with electricity, heating, and air conditioning perfect for hobbies or storage, and a separate in-law suite complete with its own sauna, providing an ideal space for guests, extended family, or potential rental opportunities. Additional features include a two-car attached garage, an attractive stone walkway with brick front steps, and the peace and privacy that only a rural waterfront setting can provide. Conveniently located just minutes from Cambridge's shopping, restaurants, and schools, while also offering easy access to nearby beaches and major metropolitan areas, this is a rare opportunity to own an affordable waterfront property with acreage, privacy, and exceptional versatility.

5214 David Greene Rd, Cambridge

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$50,000
Build your dream home on this scenic 3.53-acre wooded lot in the exclusive Heron Harbor community, nestled along Webbs Creek, which feeds into the Choptank River. Surrounded by water and nature, this peaceful setting offers access to a community pier on navigable water—perfect for kayaking, boating, and enjoying fresh Eastern Shore crabs. HOA fees include dock maintenance and BIP septic hook-up access. With easy access to downtown Cambridge, shopping, restaurants, and more, you’ll enjoy the perfect balance of convenience and seclusion. Embrace the best of Eastern Shore living in this quiet, water-oriented community.

5229 Heron Rd, Cambridge

Listing courtesy of Northrop Realty. Contact: (302) 539-0800
$82,000
3 Beds ⋅ 2 Baths
Welcome to an exceptional opportunity in Cambridge! Whether you’re a first-time homebuyer, downsizing, or looking to relocate to the area, this charming property offers affordability, comfort, and convenience in one package. Featuring 3 bedrooms and 2 full bathrooms, this well-maintained home offers a functional layout with comfortable living spaces and plenty of natural light. The spacious living area flows into the kitchen and dining space, creating an inviting atmosphere for everyday living or entertaining. Outside, you’ll enjoy a manageable yard with room to garden, relax, or personalize to your liking. Conveniently located just minutes from downtown Cambridge, you’ll have easy access to local restaurants, shopping, the waterfront, parks, and the vibrant Chesapeake Bay lifestyle. Commuters will appreciate the quick access to Route 50, making travel to Easton, Salisbury and the Maryland and Delaware beaches a breeze. Don’t miss your chance to own an affordable home on Maryland’s beautiful Eastern Shore—schedule your private showing today! * Buyer must receive approval through Southside Landing office.

2631 Rebecca Ln, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$167,900
Great opportunity to own nearly 8 acres featuring some of the highest and driest ground in Toddville. Located in sought after Sika deer country, this property offers a peaceful rural setting with hunting opportunities, abundant wildlife, and a creek running through the property. The land features a great combination of woods, newly planted pines and natural habitat, creating an ideal setting for Sika deer, wildlife and outdoor recreation. Property features a brand new complete 4 chamber septic system (never used), adding value and future potential, existing well. Also conveying is a 27 ft camper with bump out, providing a great setup for a hunting retreat or weekend getaway. The older home on the property is in need of repairs, including a new roof and is being sold as-is, bring your vision to renovate and bring back to life or tear down and build your own home. Enjoy the privacy, open space and natural beauty of Dorchester County with fishing, boating, public boat ramps and marinas close by.

2551 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$849,500
3 Beds ⋅ 3 Baths
Price adjustment! Charming custom Cape Cod built by R. Lucas on Church Creek with 150'+/- bulkheaded shoreline, 17K lb. lift and boat ramp perfect for launching kayaks, canoes, etc. The home offers spacious living areas boasting custom built-ins and woodburning fireplace. Just off the family room is access to a hallway with staircase to large unfinished space over the two car garage. Porch to the rear of the house situated to enjoy the tranquil water views. Roof new in 2026 along with other recent upgrades.

4712 Steamboat Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$998,500
4 Beds ⋅ 4 Baths
Exceptional waterfront estate in Dorchester County offers sweeping panoramic views of Church Creek with direct access to the Chesapeake Bay . Also located in the highly sought after Cambridge South Dorchester School District . Featuring over 470 feet of protected shoreline , a private dock with 4 feet of water depth, and a boat lift , this property is a rare opportunity for true waterfront living . The 3400 square foot , two and a half story home is thoughtfully designed to capture stunning water views from every angle . In side you will find four spacious bedrooms , including a grand primary suite , along with two full baths and a half bath on the upper level. The main floor is ideal for both everyday living and entertaining . offering a large waterfront dining room , a cozy water view den , and an expansive living room with a wood burning fireplace . The modern kitchen is beautifully updated and includes a pantry and a covered side porch. A unique extended screened porch off the dining room provides the perfect setting to relax and take in the serene views of Church Creek. Upstairs, the luxurious master suite features walk in closets, and the master bathroom showcases a vintage inspired clawfoot tub , a standout feature for those drawn to a modern farmhouse aesthetic , along side a walk in shower. Step out onto your private deck from the master bedroom to enjoy breathtaking sunsets over the water. Two additional bedrooms share a well appointed bathroom , spacious laundry room includes a new washer and dryer . The third floor offers flexible space with two large rooms , ideal for additional bedrooms , a home office , office gym, or media room . Additional features include multiple outbuildings : a two car garage, a kennel with three bays ready for future fencing , and a separate structure perfect for storage of a office. The property spans three lots totaling 3.395 acres of land , accessed by a long privately owned driveway that ensures ultimate privacy . This truly remarkable waterfront retreat where privacy, natural beauty, and expansive water views come together , an opportunity that must be experienced to be fully appreciated

4928 Gregory Rd, Cambridge

Listing courtesy of Stafford-Stafford Real Estate. Contact: 4103107755
$650,000
4 Beds ⋅ 3 Baths
MAJOR PRICE REDUCTION! A rare opportunity to own a private waterfront retreat that not only offers an exceptional Eastern Shore lifestyle, but also a proven income-producing investment — with over $46,000 in rental payouts over the past two years and an active upcoming reservation calendar, the next owner can enjoy immediate revenue while still reserving time for personal use. Escape the pace of city life and discover your own secluded waterfront sanctuary on St. John's Creek, nestled among 3.5 picturesque acres. Conveniently located within an easy drive of Baltimore, Washington, D.C., and Northern Virginia, this peaceful retreat is surrounded by the natural beauty of Maryland's Eastern Shore, where bald eagles, osprey, herons, ducks, geese, sika deer, and other wildlife are part of everyday life. The charming cottage is filled with warmth and character, offering a welcoming living room with a mantle and pellet stove, a cozy kitchen and dining area, a versatile first-floor bedroom, laundry room with daybed, and a full bath. Upstairs, a spacious bedroom with a half bath and wood stove creates a peaceful, storybook-like retreat. The brick-floored screened porch overlooks St. John's Creek and the private pier, providing the perfect setting for morning coffee, evening cocktails, or simply watching boats and wildlife pass by. Designed for gathering family and friends, the thoughtfully crafted carriage house (guest house/second dwelling) significantly expands the property's versatility. It features a spacious bunk room with six bunk beds, an oversized second-floor bedroom accommodating two queen beds, plus a main level with kitchen, dining area, living room, and full bath. An attached two-car barn-style garage provides additional storage and functionality. Between the cottage and carriage house, the property comfortably sleeps up to 15 overnight guests. Offered fully furnished and completely turnkey, the property is ready to enjoy from day one. Relax around the waterside fire pit, launch kayaks and paddleboards from your private pier, or dine just minutes away at the popular Boats & Hose Restaurant. Due to the property's active vacation rental schedule, showing availability is limited — a comprehensive virtual tour will be available soon, allowing prospective buyers to experience the property while private showings are accommodated around existing guest reservations. Whether you're looking for a private waterfront getaway, a full-time residence, or an investment with established income potential, this property offers the flexibility to do it all. This is a rare opportunity to purchase a turnkey waterfront property with immediate income already in place.

4004 Robinson Neck Rd, Taylors Island

Listing courtesy of Sharon Real Estate P.C.. Contact:

$169,900
Hunters Haven! The perfect blend of recreation and opportunity with this 16-acre hunting property. Featuring a versatile large agricultural field, a blank canvas to make it your own, strategically plant food plots or the back right corner is an ideal location for a future impoundment to attract and sustain wildlife. This property has a little bit of everything for outdoor enthusiasts, offering excellent hunting for sika deer, whitetail deer, waterfowl, and turkeys along with some pond fishing. The diverse habitat and open field create ideal conditions for both seasoned hunters and those looking to establish a private retreat. An older mobile home currently sits on the property and is considered a tear-down, but it provides a valuable head start with existing infrastructure. Electric service is active, and there is an existing septic system on site (condition unknown), offering potential for future building or campsite development. Whether you're looking to create your own hunting getaway, invest in recreational land, or develop a rural homestead, this property offers a unique opportunity with plenty of potential.

2839 Lakesville Crapo Rd, Church Creek

Listing courtesy of Taylor Properties. Contact:

$169,900
1 Beds ⋅ 1 Baths
Hunters Haven! The perfect blend of recreation and opportunity with this 16-acre hunting property with 2 ponds. Featuring a versatile large agricultural field, a blank canvas to make it your own, strategically plant food plots or the back right corner is an ideal location for a future impoundment to attract and sustain wildlife. This property has a little bit of everything for outdoor enthusiasts, offering excellent hunting for sika deer, whitetail deer, waterfowl, and turkeys along with some pond fishing. The diverse habitat and open field create ideal conditions for both seasoned hunters and those looking to establish a private retreat. An older mobile home currently sits on the property and is considered a tear-down, but it provides a valuable head start with existing infrastructure. Electric service is active, and there is an existing septic system on site (condition unknown), offering potential for future building or campsite development. Whether you're looking to create your own hunting getaway, invest in recreational land, or develop a rural homestead, this property offers a unique opportunity with plenty of potential.

2839 Lakesville Crapo Rd, Church Creek

Listing courtesy of Taylor Properties. Contact:

$378,000
102.4 Acres of prime waterfowl hunting. Property is 2 parcels. Parcel 4 is 35 Acres and Parcel 5 is 67.4 Acres. Parcel 5 was subdivided in January of 2026 and was originally 131 Acres.

Griffith Neck Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$59,950
Price Improvement — Beautiful Homesite Near the Water in Ferry Farms Take advantage of a rare opportunity to own this 2.20± acre homesite in the sought-after Ferry Farms community. Located just a short walk from the water and the community pier, this property offers a peaceful, private setting bordered by wooded, community-owned open space. The natural surroundings create a tranquil retreat with a scenic, tree-lined backdrop perfect for relaxing and enjoying the outdoors. Whether you’re planning a full-time residence or a weekend escape, this property offers the ideal setting to build your custom home near the water while still enjoying privacy and the beauty of nature. Buyer Notice: Buyers are encouraged to contact the Maryland Department of the Environment (MDE) and Dorchester County Planning & Zoning to confirm all building requirements, including wetlands or Critical Area considerations, possible restrictions, and connection requirements for the community B.I.P. system. Plat, covenants, and restrictions are available in the document section.

814 Cody Dr Unit #LOT 17, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000