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$299,000
3 Beds ⋅ 3 Baths
Welcome to this charming farmette featuring a 3 bedroom, 2 3/4 bath home that has been elevated and features a conditioned crawl space, includes a 3-stall barn, pole barn and shop/shed. Situated on over 8.5 acres, this property offers open fields, established pastures with fencing, a pond and wooded areas, creating the perfect blend of recreation, hobby farming and peaceful country living for the nature enthusiast and hunters alike. Enjoy Sika deer and waterfowl hunting right in your own backyard, with endless opportunities to enjoy the outdoors. Nearby marinas and public boat ramps provide convenient access for boating, fishing and crabbing.

2562 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$199,000
One of a kind nearly 22+/- acre recreational property offering an exceptional setting for the outdoor enthusiast. Partially wooded with established trails, open fields and Farm Creek water frontage, the property offers excellent opportunities for Sika deer, goose and duck hunting. Nearby marinas and public boat ramps provide convenient access for boating, fishing and crabbing. Whether you're looking for a private hunting retreat or simply a place to enjoy the Eastern Shore outdoors, this unique property offers endless recreational opportunities. This property is accessible from Toddville Road, providing easy, private access.

Sika Deer & Waterfowl Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,690,000
A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,690,000
7 Beds ⋅ 3 Baths
A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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
$699,000
4 Beds ⋅ 3 Baths
This custom-built 4 bedroom home on over 3.5 acres in Heron Harbor perfectly blends elegance and luxury with coastal charm and comfort! With a private community pier and dock on Fishing Creek, homes like this are seldom available but this 2019 Charles " Wiggs" Brohawn custom dream home can be yours for under $700K! The floor plan is designed for both sophistication and livability...access formal living and office space with crown molding and 9'+ ceilings from the foyer, relax with family and friends in the open kitchen and great room at the back of the main level with a gas fireplace and screened rear porch. The gourmet Kitchen features quartz countertops, a 5 burner gas cooktop, double wall oven, large island, and stainless appliances. A large Butler's Pantry with wet bar and wine storage provides additional storage beyond the extensive custom cabinetry. In addition to the island seating, enjoy meals in the bright and sunny dining space. Enjoy the rear screened porch with ceiling fan during three seasons and the inviting gas fireplace in the expansive great room during the winter months. At the top of the stairs, guests can enjoy a large flex-space to the right while the private bedrooms are accessed to the left. The spacious primary bedroom has 2 walk-in closets and a luxurious en-suite bathroom with an oversized tile walk-in shower with seat and multiple shower head as well as dual vanities. A large central atrium connects the primary to the 3 additional large bedrooms, laundry room, and bathroom with dual vanities and tub-shower along with pull-down attic access. In addition to the stunning interior, enjoy the charm of the welcoming front porch, the convenience of an oversized 2 car garage, and the beauty & privacy of the wooded 3.73 acres. Come see all that this property and community have to offer at our Open House on 9/12! Home is owner-occupied so please don't access property/driveway without an approved showing appointment; all buyers and their agents to complete due diligence regarding property taxes, zoning, measurements school, HOA, insurance, and other property information. Schedule your tour today!

5230 Heron Rd, Cambridge

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$665,000
2 Beds ⋅ 1 Baths
Welcome to Fishing Creek, where Chesapeake Bay waterfront living takes center stage. This beautifully renovated coastal retreat offers approximately 138 feet of water frontage, extensive riprap shoreline protection and incredible views in nearly every direction. Step outside and enjoy an impressive 155-foot private pier with boat lift, jet ski lift, electric, lighting and plumbing, creating the perfect setup for boating, fishing, crabbing and everything the Eastern Shore lifestyle has to offer. Inside, the home has been thoughtfully transformed with an updated kitchen and appliances, renovated tile bathroom, updated flooring, recessed lighting, a gorgeous 200+ sq. ft. sunroom surrounded by windows and water views. Wake up to sunrise over the harbor, unwind with sunsets over the Chesapeake, and enjoy the water from nearly every room. The investment into this property goes far beyond what you can see. Major improvements include a new septic field, extensive riprap shoreline stabilization, upgraded pier infrastructure with boat lift, jet ski lift, updated dock, electric on dock and plumbing, a custom Amish built two-story bunkhouse with insulation, flooring and electric, a 200-amp electrical upgrade, renovated bathroom, new kitchen appliances, waterfront hardscape patio, exterior improvements and a new well pump and many more. These are the big-ticket improvements that deliver true peace of mind. Peaceful, private and built to enjoy the Chesapeake, this is more than a waterfront home. It’s your own Eastern Shore escape.

2530 Hoopers Island Rd, Fishing Creek

Listing courtesy of Keller Williams Flagship. Contact:

$649,000
4 Beds ⋅ 3 Baths
Experience the charm of waterfront living with breathtaking sunrise views over Madison Bay. Set on 2.2 acres, this beautifully maintained 4 bedroom, 3 bath home offers approximately 800 feet of rip-rapped shoreline, a private deep-water pier with multiple slips, the perfect blend of comfort and outdoor recreation. The home features a beautifully renovated kitchen with custom cabinetry, quartz countertops, GE Café appliances, brand-new Bosch high-efficiency inverter heat pumps, new luxury vinyl plank flooring and a large waterfront deck perfect for entertaining or simply relaxing while taking in the scenic water views. Additional features include an attached two-car garage, detached garage/storage building, private deep well and county sewer. Enjoy boating, fishing, kayaking, biking and running right outside your door. Located near Blackwater National Wildlife Refuge and public hunting lands, this property is ideal for outdoor enthusiasts and nature lovers. Conveniently located near the Madison public boat ramp, volunteer fire company and just 15 minutes from Route 50 and Cambridge, with shopping, restaurants and Emily's Produce nearby. Whether you are looking for a full-time residence or private waterfront retreat, this property offers the very best of Maryland's Eastern Shore lifestyle. This property would also work very well as an Airbnb. Motivated sellers, offers are welcome.

4825 Madison Canning House Rd, Madison

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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
$799,900
4 Beds ⋅ 3 Baths
Experience the natural beauty and tranquility of Maryland's Eastern Shore from this exceptional waterfront retreat in Dorchester County. Tucked away at the end of a private street on Brooks Creek, this remarkable property boasts over 180 degrees of breathtaking water views from its spectacular lot. Designed for boating enthusiasts, the waterfront features approximately 120 feet of pier with multiple boat lifts, a bulk headed shoreline, a private boat ramp, a small sandy beach, and expansive lawn surrounded by mature landscaping. This charming 4-bedroom, 3-bath home has been thoughtfully designed to capture panoramic water views from virtually every room. The updated kitchen features granite countertops, stainless steel appliances, and ample workspace, while hardwood flooring flows throughout the main living areas. The open floor plan seamlessly connects the spacious dining area and living room, creating an inviting setting for everyday living and entertaining. Three generously sized bedrooms are located on the main level. The impressive family room is the heart of the home, showcasing a gas fireplace, built-in bar, and walls of windows that frame the ever-changing waterfront scenery. Upstairs, the private primary suite is a true sanctuary, featuring soaring cathedral ceilings and dramatic floor-to-ceiling windows that provide sweeping panoramic water views from both the sleeping and sitting areas. A second gas fireplace creates a cozy atmosphere, while the luxurious en-suite bath offers a garden tub, walk-in shower, and spacious walk-in closet. Outdoor living is equally exceptional. Relax on the expansive screened porch while enjoying spectacular sunsets and the abundant wildlife and waterfowl that call Brooks Creek home. An oversized concrete patio provides additional space for entertaining, and two storage sheds—including one equipped with two refrigerators—offer excellent convenience for boating, fishing, and gatherings. Dual driveways provide ample parking for multiple vehicles, boats, and trailers. From your private pier, enjoy easy access by boat to Tilghman Island, St. Michaels, and many of the Mid-Shore's most charming waterfront towns, where you'll find renowned restaurants, marinas, boutique shopping, and endless opportunities to experience the best of Eastern Shore living. Whether you're seeking a full-time residence, weekend escape, or the ultimate waterfront lifestyle, this rare Brooks Creek property offers an extraordinary combination of privacy, recreation, and unforgettable views.

803 Seabreeze Rd, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 520-2707
$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
$439,900
3 Beds ⋅ 2 Baths
Whether you're dreaming of a peaceful country lifestyle or ready to bring your horses home, this picturesque farmette on nearly 5.5 acres is ready for you. The property is already set up with established pastures, a barn featuring four stalls and a feed room and plenty of space for horses and other animals. The updated 3 bedroom, 2 full bath farmhouse blends modern updates with timeless charm and features newer mini-split heating and cooling systems, a cozy pellet stove and a convenient first-floor primary bedroom. A detached two car garage includes a 1 bedroom, 1 bath apartment above, ideal for guests, extended family, rental income, or a private home office.

5125 Rhodesdale Rd, Rhodesdale

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
$320,000
3 Beds ⋅ 2 Baths
$10,000 Price Reduction – Rare Chesapeake Bay Waterfront Opportunity! Waterfront homes under $325,000 are becoming increasingly difficult to find, making this well-maintained island retreat an exceptional value. Enjoy sweeping western views across the Chesapeake Bay, spectacular sunsets, and the peaceful waterfront lifestyle you've been dreaming of. Ideal as a full-time residence, weekend getaway, or a short-term rental investment. The home features an updated kitchen with a center island, gas range, coffee bar, and luxury vinyl plank flooring. Flexible living spaces include a first-floor bedroom and office/playroom, an updated bath, a spacious family room, and a private second-floor owner's suite. Additional highlights include ductless mini-split heating and cooling, hot water baseboard heat, high-speed internet availability, rip-rapped shoreline, and a BAT septic system installed in 2019. A county-owned public boat ramp is just down the street beside a privately owned marina where slips may be available for rent (buyer to verify). A brand-new survey and legal description are available upon request. With a $10,000 price reduction, this is one of the best opportunities to own Chesapeake Bay waterfront without the premium price tag.

1814 Hoopersville Rd, Fishing Creek

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

$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
$297,000
The most significant hurdle to building on waterfront is permitting for permit septic. This property already has PUBLIC SEWER. This rare offering is 1.8 acres on two combined deeded waterfront parcels situated on the quiet and serine Little Choptank River. Build your dream home or invest. 1609 comes with a current tidewater buffer setback variance (BOA Case #2109), allowing for the construction of a dwelling inside the typical 100-foot setback. Most importantly, this variance does not expire and transfers directly to the new owner, providing a unique "plug and play" opportunity that is nearly impossible to find. Call me today to learn more.

1609 Heliport Rd, Woolford

Listing courtesy of Keller Williams Realty Delmarva. Contact: (410) 524-6400
$895,000
4 Beds ⋅ 3 Baths
Welcome to 6011 Sunnyside Court...a true destination! This waterfront sanctuary has been completely refreshed with fabulous interior paint and a brand new 30 year roof! It is complimented by a sparkling saltwater pool and wide-open views of the Warwick River -your own resort! Moreover, this property provides great supplemental income for the astute investor. Enjoy the river-front complex when time allows yet rent "the resort" easily while you are otherwise engaged. This listing is unique in that it is sited on land that provides great views of the river which makes it a very popular airbnb property yet no flood insurance is required. It was designed with generously-sized rooms, a beautiful pool side leisure area and ample gardens. In sum, it is a splendidly built, upscale oasis in East New Market. The house is perfectly sited on a spacious 1.2 acre parcel in which to enjoy all seasons. This stylish hide-a-way has it all. Five bedrooms, upscale finishes and room to play. The first floor is fantastic with a wide open floor plan, 2 full bedrooms, a powder room, covered porch and views galore! A gracious living room has French doors overlooking and leading to the pool area. A modern white kitchen has island seating, tons of counterspace and opens to a large dining space with river and pool views. The sunroom has walls of windows and steps to an inviting patio area. The second floor is upscale with room for friends and family. A private primary suite has wonderful views, a stylish bath and great closet space. Two additional bedrooms and bath and laundry complete this light-filled floor. The third floor has great potential with a soaring ceiling and large windows promising future fun! The waterfront pool, inviting patios, riverfront dock and green gardens await your arrival. The saltwater pool is surrounded by a wrought iron fence, secure, yet allows views from all points. The patio has room for games and lounging. Garden areas and game playing lawns are ready for fun. An uncovered pergola and a top of the line dock is ready for your toys and boats. Parking for everyone and the best view in East New Market can be yours! Restaurants and shopping are close by too.

6011 Sunnyside Ct, East New Market

Listing courtesy of Compass. Contact: (410) 429-7425
$59,999
Nice high elevation building lot on Hoopers Island. Well and septic already in place, includes a newer 4-chamber septic system. Drain fields to be completed once house plans are approved. Great opportunity to build your dream home and enjoy the Hoopers Island lifestyle.

2820 Hoopers Island Rd, Church Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$450,000
1 Beds ⋅ 1 Baths
Exceptional opportunity to create your own Eastern Shore waterfront retreat with approximately 6' MLW—a standout feature for sailing enthusiasts and boaters seeking dependable deep-water access. Set in a welcoming waterfront community with a relaxed, laid-back atmosphere, this property offers beautiful water views and an impressive collection of boating amenities, making it an ideal home base for exploring the Chesapeake Bay and surrounding waterways. The private pier is the centerpiece of the property, offering approximately 6 feet of mean low water, a lookout platform, and four boat lifts—including two 1,500-lb jet ski lifts, an 8,000-lb lift, and a 20,000-lb lift installed in 2022. Whether your passion is sailing, power boating, fishing, crabbing, kayaking, or simply spending your days by the water, the infrastructure is already in place to embrace the waterfront lifestyle. The 1-bedroom home is fully ADA-compliant and offers an enclosed waterside porch perfect for relaxing and taking in the view. The renovated full bath features a roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. A wheelchair ramp and lift also convey. Recent improvements include a 50-year architectural shingle roof installed in 2023 with transferable warranty and a new well installed in 2024, along with the convenience of public sewer service. A detached garage/workshop with concrete floors and a newer electrical panel provides excellent space for storage, hobbies, or boating equipment. Plumbing in the workshop is currently disconnected but could be reconnected by the new owner. An additional waterside storage shed near the pier is ideal for kayaks, fishing gear, and outdoor equipment. Bring your vision and make this waterfront property your own. With deep water, substantial boating infrastructure, and beautiful views, this is a unique opportunity to establish a Chesapeake Bay getaway tailored to the way you want to enjoy the water. Property is being sold as-is. Appointment required for all showings.

5023 Russell Rd, Woolford

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

$684,900
4 Beds ⋅ 2 Baths
Enjoy waterfront living in this updated 4 bedroom, 2 bath waterfront home with stunning sunrise and sunset views over the Honga River and Chesapeake Bay. Bright and inviting with comfortable living spaces, cathedral ceilings, this home is ideal as a full-time residence, weekend retreat or airbnb investment. The property features a large pole barn with electric and heating & air, shed, large deck and spacious outdoor landing with fire pit overlooking breathtaking Chesapeake Bay views. Located just across from a marina and public boat ramp, you’ll have easy access to boating, fishing and crabbing. Newer well and septic plus a fully riprapped shoreline. Bring your golf cart, kayaks and bikes and enjoy all that Hoopers Island has to offer. Nearby favorites include Old Salty’s Restaurant and Hooper’s Island General Store.

1750 Hoopersville, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$99,900
3 Beds ⋅ 1 Baths
Affordable 3 Bedroom, 1 Bathroom home conveniently located in Toddville and includes the vacant land parcel across the street (Parcel 164). Previously rented as a hunting lodge, good for overnights, a casual retreat or full time living. Located across from Elijah’s General Store and near public boat ramps, Blackwater national wildlife refuge and marinas. Enjoy fishing, crabbing, hunting, biking, and boating.

2703 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,350,000
4 Beds ⋅ 5 Baths
A Private Waterfront Estate Where the World Falls Quiet—and Time Slows to Your Pace... There are homes that offer space. And there are homes that offer escape. At 5419 Ragged Point Road, you leave more than traffic behind—you leave noise, urgency, and compromise. Just a comfortable drive from Washington, D.C., Baltimore, and Ocean City, this contemporary waterfront estate gives you something rare: true privacy without isolation. Set on nearly 12 acres, with an extraordinary 1,500 feet of frontage along the quiet waters of Brooks Creek, this is not simply a home. It is a front-row seat to nature—uninterrupted, unhurried, and entirely your own. Inside, the house speaks in the language of craftsmanship. Four bedrooms. Two full and three half baths. Built in 2007 with a discipline you can feel in every line and finish. And unlike most properties of this caliber, it is offered fully furnished—each piece chosen to complement the home, not merely fill it. The kitchen is not designed to impress—it simply does. Precision appliances from Wolf, Sub-Zero, and Bosch. Everything exactly where it should be, whether you are preparing a quiet dinner for two or hosting a weekend that stretches late into the evening. The primary suite offers a different kind of luxury—the kind that restores you. A deep soaking tub. A separate shower. Silence when you want it. Space when you need it. But it is outside where this property earns its distinction. Step onto one of several balconies or decks, and the view does the work for you. Water in every direction. Light changes by the hour. Mornings that begin with stillness and sunrise and end with beauty that seem almost staged. A private pier extends your living space into the creek, complete with water, electric, and a 12,000 lb boat lift. For boaters, it is effortless. For fishermen, irresistible. For hunters, the presence of a duck blind and abundant wildlife turns the land itself into an asset few properties can claim. And yet, for all its features, the real value of this home is harder to measure. It is the moment you realize you have nowhere else to be. The quiet conversation lasts longer because it can. The feeling—rare, and increasingly valuable—that you have found a place that gives more than it takes. If you’ve been waiting for a property that offers not just waterfront, but a way of living that feels deliberate, private, and complete—this is it. Come see it for yourself. You’ll know very quickly whether it’s simply a beautiful home… or the one you’ve been looking for.

5419 Ragged Point Rd, Cambridge

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

$349,950
3 Beds ⋅ 2 Baths
****PRICE IMPROVEMENT****** Coastal Charm & Exceptional Space! This thoughtfully designed Cape Cod blends classic Eastern Shore charm with a relaxed coastal feel and an inviting, open layout. The spacious kitchen flows seamlessly into the dining and living areas, creating a warm and welcoming space for everyday living and entertaining. One of the true highlights is the expansive 36’ x 10’ screened front porch, the perfect spot to unwind while enjoying refreshing Bay breezes, beautiful sunrises, and spectacular Eastern Shore sunsets. The main-level primary bedroom offers convenient one-floor living, while the upper level features two generously sized bedrooms, each with abundant closet space. For those needing serious storage or workspace, the oversized 3-car garage measures approximately 36’ x 35’ and offers exceptional versatility. One bay features an impressive 18’ garage door, providing ample room for an RV, boat, workshop, or all your favorite watersport toys. A separate 2-car section provides plenty of additional room for vehicles and storage. Ideally located just a short distance from Old Salty’s Restaurant and Hoopers Island General Store, this property offers the perfect combination of peaceful coastal living and convenient access to local favorites. Whether you're looking for a full-time residence, weekend escape, or your own Eastern Shore retreat, this charming Cape Cod offers a wonderful opportunity to embrace the relaxed pace and natural beauty of coastal living. Solar Run Solar panels are leased; Buyer to assume the solar lease, subject to transfer approval. Current lease balance as of April 2026 is $27,969. – Monthly payment is $201.87 the amount goes up 2.9% annually in April, and the monthly electric bill is $13.00. No transfer fee but there is a $250.00 credit check fee.

2576 Hoopers Island Rd, Fishing Creek

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$699,900
7 Beds ⋅ 3 Baths
THE ORIGINAL HOME OF "CAPTAIN JOHNNIE" BUILT IN 1920 AND TOTALLY RESTORED. EXPANSIVE WATER-VIEWS WITH 300 FEET OF RIP RAP/BULK HEADING. PERFECT FOR YEAR ROUND LIVING, WEEKLY VACATION RENTAL OR VACATION HOME . BEAUTIFUL HARDWOOD FLOORS, FULLY EQUIPPED EAT IN KITCHEN, HUGE FAMILY/GREAT ROOM WITH WALL MOUNTED TV . HOME IS FULLY FURNISHED AND EXCEPTIONALLY EQUIPPED - EVERYTHING EXCEPT POOL/CARD TALBE CONVEYS. DIRECT TV AND HUGHES INTERNET. NIT-RED SEPTIC SYSTEM, HAS BEEN A SUCCESSFUL VACATION RENTAL - CAN PROVIDE DOCUMENTATION. LARGE OUTBUILDING HOUSING BIKES,CANOES AND KAYAKS THAT ALL CONVEY FABULOUS ON LINE ARTICLE AND PICTURES OF HOOPERS ISLAND AND LOCATION "ONLYINYOURSTATE - MARYLAND - MOST SCENIC DRIVE MD

1632 Steamboat Wharf Rd S, Fishing Creek

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937