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$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
$189,900
Rare land offering on Horns Point Road! One of Dorchester County's most sought after neighborhoods - just outside town limits. Tranquil views over fields to the Choptank River. Partially wooded. Health Dept. approved and ready to go! Plans subject to review by the sellers. Lot #5 can be purchased separately for $98,750.

Horns Point Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$98,750
Rare land offering on Horns Point Road! Build on this individual parcel or purchase it together with neighboring Lot #4 (Tax ID# 07-239823 - 2.04+/- acres) for $189,900. Perfect setting for your custom home design. Inquire today for more details!

Horns Point Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$425,000
6 Beds ⋅ 3 Baths
Welcome to your own private slice of Maryland's Eastern Shore! Nestled on over 8 acres in picturesque East New Market, this one-of-a-kind country estate offers the perfect blend of space, functionality, and rural charm. Originally built in 1974, the home was thoughtfully expanded in 1999 with a spacious Colonial addition, creating an impressive residence featuring 6 generously sized bedrooms and 3 full bathrooms—ideal for large families, multigenerational living, or anyone who appreciates room to spread out. The heart of the home offers multiple living areas, a formal dining room, and abundant natural light, while the attached two-car garage provides everyday convenience. For hobbyists, mechanics, contractors, farmers, or entrepreneurs, the property truly shines with two massive detached workshop/garage buildings. These versatile structures provide exceptional storage, workspace, equipment housing, or the opportunity to operate a home-based business. Step outside and experience everything country living has to offer. More than 7 acres are currently utilized for crop production, making the property ideal for hobby farming, homesteading, horses, or continued agricultural use. Enjoy harvesting fresh peaches, pears, and grapes from your own fruit trees and vines, while the expansive grounds offer endless possibilities for a large vegetable garden, additional orchards, or recreational space. Relax on the welcoming front porch with your morning coffee or entertain family and friends on the rear patio while taking in peaceful views of the surrounding farmland and open skies. Located just minutes from the historic town of East New Market and a short drive to Cambridge, the property provides convenient access to shopping, dining, schools, healthcare, and outdoor recreation, including the Choptank River, Blackwater National Wildlife Refuge, boating, fishing, hunting, and numerous public parks. Commuters will also appreciate easy access to Maryland Routes 14, 16, and 50, connecting you to the Chesapeake Bay, Easton, Salisbury, and Delaware beaches. If you've been searching for acreage, privacy, workshop space, and a spacious home with unlimited potential, 5640 Thompsontown Road delivers a rare opportunity to enjoy the best of Eastern Shore living.

5640 Thompsontown Rd, East New Market

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$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
$299,000
3 Beds ⋅ 2 Baths
Beautifully renovated and move-in ready, this furnished 3-bedroom, 2-full-bath home is nestled in the heart of Sika deer country. The home is in excellent condition and features beautiful hardwood and luxury vinyl plank flooring, central heating and air, mini-splits, a pellet stove, and a detached one-car garage with a finished bonus room above, complete with electric and a mini-split for heating and air. Outside, enjoy a storage shed, fire pit, established orchard with pin oak, apple and persimmon trees, and a deer feeder that conveys. The nearby public boat ramp and marina provide easy access to the Honga River. Whether you're looking for a full-time residence, weekend getaway or hunting retreat, this turnkey property is ready to enjoy. Backs up to a 350+ acre managed Sika deer/farm property. *A new septic system is scheduled to be installed within the next 30-60 days. The existing system is functioning; however, replacement was recommended following a recent inspection, and the seller is moving forward with installation.

2243 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$3,200,000
Looking for a business opportunity, want to expand your business? This exceptional property offers outstanding income and business potential, including opportunities for a private retreat, vacation rental, event or wedding venue, guided hunting and fishing, sporting clay, kayak, water sports experiences and other outdoor recreational offerings. Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$3,200,000
Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$3,200,000
5 Beds ⋅ 6 Baths
Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$129,900
2 Beds ⋅ 1 Baths
Escape to your own private retreat with this 5.02-acre property located just minutes from the renowned Blackwater National Wildlife Refuge. Featuring a 2-bedroom, 1-bath home, this fixer-upper offers an excellent opportunity to renovate, invest, or create the hunting cabin or private retreat you’ve always wanted. Surrounded by some of Maryland’s premier outdoor recreation, the property is ideally situated for hunters and nature enthusiasts. Enjoy outstanding opportunities for sika deer, whitetail deer, and wild turkey hunting, with Blackwater National Wildlife Refuge and thousands of acres of nearby public lands helping make this a destination for wildlife and outdoor adventure. Nearby marinas and public boat ramps provide excellent opportunities for boating, fishing, and crabbing. Whether you���re looking for a weekend getaway, recreational property, or a project with ample potential, this property offers the perfect combination of privacy, acreage, and an exceptional location. Bring your vision and make this Eastern Shore property your own. Property sold as-is.

2439 Asquith Island Rd, Crapo

Listing courtesy of Iron Valley Real Estate Crossroads. Contact: 2403979292
$275,000
3 Beds ⋅ 1 Baths
Escape to the peace and privacy of Maryland's Eastern Shore with this charming ranch-style home situated on 2 acres of land. Offering comfortable one-level living, this well-maintained property features 3 bedrooms, 1 full bath, and a spacious layout designed for everyday living. Inside, you'll find a thoughtfully updated interior with modern touches while maintaining the home's warmth and character. Recent improvements include a newer roof and siding, providing added value and peace of mind. Outside, the oversized detached 2-car garage offers endless possibilities for vehicle storage, hobbies, a workshop, or recreational equipment. The expansive lot provides plenty of room for gardening, outdoor entertaining, pets, and enjoying the surrounding countryside. With no HOA restrictions, ample parking, and room for boats, RVs, trailers, or additional outdoor toys, this property offers the freedom and flexibility many buyers are seeking. Conveniently located near Cambridge and Route 50, you'll enjoy easy access to shopping, dining, healthcare, and all the recreation the Chesapeake Bay region has to offer. Whether you're looking for a full-time residence, a weekend retreat, or a property with space to spread out and enjoy country living, this Eastern Shore gem is ready to welcome you home.

3714 Hicksburg Rd, East New Market

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$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
$415,000
3 Beds ⋅ 3 Baths
Open House Sunday 8/13/26 12-1:30pm NEW PRICE $425,000! MOTIVATED SELLERS! Enjoy this beautiful countryside home situated on over 2 acres, this secluded property is surrounded by mature trees, offering exceptional privacy and a peaceful, natural setting. Tucked back from the road, you’ll immediately appreciate the quiet atmosphere and room to spread out. The main level offers a thoughtful and versatile layout, featuring a half bathroom great for guest, that is right next to the mudroom/laundry room off of the rear door entry. A well thought out open concept formal living room off of the kitchen, a a spacious formal dining room to host gatherings, and a comfortable casual family room ideal for everyday living. The open-concept kitchen equipped with all stainless steel appliances and a large gas range flows seamlessly into the family room that has an option to install a gas fireplace with the existing hookup already in place, creating the perfect space for gathering and entertaining. The kitchen also includes a dedicated dining area and seating space with stools at the counter— ideal for casual meals, morning coffee, or hosting guests. Upstairs, you’ll find three bedrooms, along with two full bathrooms. A loft area on the second level provides flexible additional living space — perfect for a home office, reading area, or secondary lounge. A convenient half bathroom is located on the main level for guests. The primary bedroom walk-in shower was just recently renovated (May 2026) with all new tiling and an added rain-head shower head for a spa feeling. **** Please note the pool, playground set, and deep freezer do not convey with the property**** Enjoy peaceful mornings and relaxing evenings on the inviting front porch, where you can take in the serene surroundings. A separate storage shed (no electric) offers added convenience for lawn equipment, tools, or hobbies. With expansive acreage for room to expand, wooded privacy, and well-appointed living spaces, this property offers the perfect blend of comfort, functionality, and Eastern Shore charm.

6941 Hubbard Rd, Hurlock

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$35,000

5226 Heron Rd, Cambridge

Listing courtesy of Blufin Realty, LLC.. Contact: 2406886645