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$419,999
2 Beds 2 Baths
Coming Soon! Great opportunity to own affordable waterfront on the Honga River. This private, one-level 2 bedroom, 2 full bath home is move-in ready and offers the opportunity to add your own personal updates. Enjoy a rip-rapped shoreline, a private pier, protected boat basin and spectacular sunrises and sunsets. Boat, fish, crab, kayak or simply relax from your own backyard. Bring your golf cart and enjoy the Hoopers Island lifestyle, just minutes from Old Salty's Restaurant and the Hoopers Island General Store. Coming Soon! Great opportunity to own affordable waterfront on the Honga River. The property also includes the recreational lot across the street. Two (2) sheds convey.

1211 Flowers Rd, Fishing Creek

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

$599,000
3 Beds 2 Baths
Escape to the unspoiled beauty of Hoopers Island, where peaceful waterfront living and world-class fishing, crabbing, and boating are part of everyday life. Situated on a beautifully landscaped 1.06-acre corner lot, this charming 3-bedroom, 2-bath home offers the ideal Eastern Shore retreat with generous indoor and outdoor spaces designed for gathering with family and friends. The heart of the home is a beautifully appointed kitchen featuring granite countertops, abundant cabinetry with under-cabinet lighting, a center island, double wall ovens, cooktop, wet bar, and custom wood ceilings. Original pocket doors, warm wood accents, and pellet stoves add timeless character throughout, while the spacious sunroom with stone hearth creates a cozy place to unwind year-round. A private hot tub room, large covered porch, rear deck, fenced yard, and mature shade trees complete the inviting outdoor setting. Upstairs offers three bedrooms, a full bath, and a loft that comfortably accommodates additional guests, making this an ideal full-time residence or weekend getaway. Two storage sheds provide ample space for boating and outdoor equipment. Included in the sale is a rare additional 0.13-acre Commercial Maritime waterfront parcel featuring a 100-foot pier with approximately 5 feet of water depth, multiple boat slips, and endless opportunities to enjoy the Chesapeake Bay lifestyle. Whether your passion is offshore fishing, crabbing, kayaking, or simply watching the sunset over the water, this property is ready for your next adventure. Located just minutes from local favorites including Old Salty's Restaurant, Hoopers Island General Store, and Madhouse Oysters, this exceptional offering combines authentic Eastern Shore charm with the waterfront lifestyle so many dream of—but few ever find.

2404 and 2407 Hoopers Island Rd, Fishing Creek

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

$279,000
2 Beds 2 Baths
Seller is offering a $10,000 contribution toward buyer closing costs with an acceptable offer! Step inside this charming, move-in ready 2 bedroom, 2 full bath home situated on nearly 1 acre on Hoopers Island. This spacious, beautifully renovated home features new central HVAC, remodeled kitchen and baths, new flooring and modern upgrades throughout. The large deep lot offers plenty of room for outdoor living, gardens, boat storage and more. Perfect as a full-time residence, weekend retreat or vacation rental. Bring your bikes, golf cart, kayaks and fishing gear and experience the Hoopers Island lifestyle. Enjoy crabbing, boating, fishing, beautiful sunrises and sunsets and all the charm this waterfront community has to offer, a great place to call home!

2527 Old House Point Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$8,950,000
24 Beds 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971

$319,700
BACK ON THE MARKET WITH IMPROVED PRICE-THIS IS THE LOCATION!!!! ***********************PUBLIC SEWER IS ON THIS PROPERTY************************************* If you’ve been searching for the perfect canvas to build your Delmarva masterpiece, look no further. This rare offering features over 1.5 acres of low-maintenance waterfront land on the Little Choptank River, comprised of two cleared, level lots ready for your own personal dream. One of the most significant hurdles to waterfront building has already been cleared for you. This property 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

$284,999
3 Beds 2 Baths
Historic District charm meets everyday convenience at 113 Willis Street. This adorable circa-1916 Victorian sits just down the street from the Choptank River and close to the heart of downtown Cambridge, where you can enjoy local restaurants, shops, parks, marinas, waterfront events, and the character that makes this Eastern Shore town so special. Inside, this three-bedroom home blends classic early 20th-century charm with practical updates, including newer windows, roof, siding, drywall, electrical wiring, and central air, an uncommon and valuable bonus in many historic homes. The welcoming wraparound porch gives the home instant curb appeal, while the fully fenced yard, alley access, off-street parking, and garage/workshop add everyday functionality that is hard to find in this setting. Whether you need storage, hobby space, tools, bikes, or a spot for weekend projects, the garage/workshop gives you flexibility beyond the main house. Cute, comfortable, updated, and full of Cambridge character, this home offers historic charm, modern comfort, and downtown convenience all in one very lovable package.

113 Willis St, Cambridge

Listing courtesy of Keller Williams Flagship. Contact:

$475,000
1 Beds 1 Baths
Exceptional waterfront opportunity with gorgeous water views, deep water access, and extensive boating amenities in a welcoming, waterfront neighborhood known for its friendly and laid-back atmosphere. This fully ADA-compliant 1-bedroom home features a thoughtfully renovated full bath with roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. Relax on the enclosed porch overlooking the water or head outside to the impressive pier offering approximately 6’ MLW, a lookout platform, and four boat lifts including two 1,500lb jet ski lifts, an 8,000lb lift, and a 20,000lb lift installed in 2022—an incredible setup for boating, fishing, and enjoying life on the water. Additional improvements include a new 50-year architectural shingle roof with transferable warranty installed in 2023 and a new well in 2024, plus public sewer service. Wheelchair ramp and lift convey. Detached garage/workshop with concrete floors and newer electric panel offers excellent storage and workspace potential, plumbing in workshop is currently disconnected- but could be hooked up by the new owner. There is an additional storage shed near the pier perfect for kayaks, fishing gear, and outdoor equipment. Bring your personal touches and bring this home to life! Property is being sold as-is. Appointment required for all showings.

5023 Russell Rd, Woolford

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

$629,900
2 Beds 2 Baths
Enjoy breathtaking Honga River and Chesapeake Bay views from this exceptional waterfront property featuring a long private pier with multiple slips and two boat lifts. This well-maintained 2 bedroom, 2 full bath home offers comfortable coastal living with a riprapped shoreline, spacious yard and endless opportunities for boating, fishing, crabbing and embracing the Hoopers Island lifestyle. The expansive waterfront deck offers the perfect place to relax, entertain and enjoy cookouts with family and friends while taking in the panoramic waterfront views. Stunning sunrise and sunsets create the ideal setting for a full-time residence, weekend getaway, a peaceful waterfront retreat. Bring your golf cart and bicycles and enjoy nearby local favorites including Old Salty’s Restaurant and Hooper’s Island General Store. Conveniently located within walking distance to a local marina and public boat ramp.

1709 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$249,900
2 Beds 3 Baths
***PRICE IMPROVEMENT*** Nestled in the charming Riverview Townhouse Condominiums, this lovely brick end-unit townhome offers distant views of the Choptank River, Cambridge Yacht Basin, and the Choptank Lighthouse. Recently updated throughout, this home features a new HVAC (2025), windows (2023), recent water heater, fresh paint, luxury vinyl plank flooring, updated lighting, and ceiling fans. Blending modern updates with timeless Colonial style, this warm and inviting home truly feels like home. Step inside to an open floor plan connecting the living and dining areas, perfect for everyday living and entertaining. The bright and airy kitchen features double windows, recent appliances, new granite countertops, freshly painted cabinetry, and updated lighting. Upstairs, both spacious bedrooms offer private en-suite bathrooms with tub/shower combinations, updated vanities, mirrors, and lighting. A stacked washer and dryer add everyday convenience. Enjoy peaceful water views and maintenance-free living with lawn care and trash service included. Best of all, the location is unbeatable — just two blocks from downtown Cambridge restaurants, shops, the art center, marina, and the Ironman finish line. Whether you are searching for a primary residence, weekend getaway, or Airbnb investment opportunity, this property checks every box. The only problem… you may never want to leave!

600-3 Water St, Cambridge

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

$1,085,000
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

$695,000
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

$189,900
4 Beds 2 Baths
Welcome to 1603 Steamboat Wharf Rd in Hoopersville, MD—an inviting home set within a peaceful, water-oriented community where everyday living feels like a retreat. Surrounded by scenic views and the natural beauty of the Eastern Shore, this property offers a lifestyle centered around the water, whether it’s sunsets over the water or quiet evenings outdoors. Inside, the home offers approximately 2,000 +/- square feet with 4 bedrooms and a flexible bonus space that can serve as a 5th bedroom, home office, or guest area. The layout provides comfortable living spaces with room to gather, unwind, and entertain.Recent updates, including new flooring and appliances, complement the home’s welcoming feel while allowing you to settle in with ease. If you’re looking for a home that offers more than just a place to live—one that delivers a relaxed, waterfront lifestyle—this is a must-see.

1603 Steamboat Wharf, Fishing Creek

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$1,035,000
5 Beds 5 Baths
MAJOR PRICE IMPROVEMENT of $165K since first listed- HURRY to claim this unmatched waterfront oasis- Set on just shy of 4.5 private acres at the end of a quiet dead-end road, this stunning property boasts over 2,700 square feet, five bedrooms, and an incredible 1,000 feet of water frontage—creating a rare combination of space, privacy, and panoramic views of coveted Little Choptank River. Designed and built by an architect for their own personal retreat, this one-of-a-kind coastal waterfront sanctuary blends thoughtful design with the natural beauty distinct to the Eastern Shore. Enjoy effortless waterfront living with your own private pier featuring 3’ mean low water, a protected lagoon, and endless opportunities for boating, jet ski'ing, crabbing/fishing, kayaking, and exploring nature abound. Surrounded by wildlife and untouched beauty, this is the kind of setting that feels worlds away—yet you’re just minutes from the charm, dining, and shops of downtown Cambridge. And the opportunities don’t stop there!!--NO HOA and strong Airbnb potential make this not only a dream retreat, but a smart investment just in time for summer.

1307 Broadview Dr, Cambridge

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242

$2,295,000
4 Beds 4 Baths
Set on a 2.38 acre peninsula with 1,100 feet of waterfrontage, 1301 Broadview Drive is a thoughtfully crafted waterfront retreat defined by exceptional materials, timeless detail, and water views from every room. The exterior pairs stone and cedar shingles with copper lanterns and bluestone hardscaping for a classic Eastern Shore look, while inside, custom millwork, mahogany accents, brass floor registers, and a refined mix of designer fixtures and finishes create a warm and elevated feel throughout. The main level is designed for both everyday living and effortless entertaining, centered around an open gourmet kitchen with Shaw fireclay sinks, Waterworks fixtures, marble counters and backsplash, a mahogany island, and a fully integrated appliance suite. A beautifully finished butler’s pantry, breakfast area with custom bench seating, and great room with custom built ins and a gas fireplace with marble surround add both style and function. A dining room, library or office with built ins, powder room, mudroom, and laundry room complete the main level, while the covered deck provides the perfect place to take in the sunset. Upstairs, the private spaces are equally inviting, highlighted by a serene primary suite with a large walk-in closet, private deck, and a spacious marble bath with soaking tub and custom shower. Additional bedrooms offer custom closets, designer lighting, and beautifully finished baths, while a gym and rear upper deck add to the home’s comfort and flexibility. Outside, sweeping views stretch across the Chesapeake Bay, Little Choptank River, and Fishing Creek, with a waterside pool (as-Is) , pier with lift, boat ramp, and detached storage garage completing this exceptional property. Modern conveniences including Nest climate control, security cameras, fiber wiring in most rooms, and smartphone-controlled dimmers add ease to a home where craftsmanship, comfort, and waterfront living come together beautifully.

1301 Broadview Dr, Cambridge

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com

$849,500
3 Beds 2 Baths
Improved Pricing! Was $875,000 now $849,500. Major Interior Renovations completed in 2022 (see attachment for full list). This beautifully updated and meticulously maintained, 3-bedroom, 2-bath home offers over 2,300 square feet of bright living space designed to capture the beauty of waterfront living. Panoramic water views greet you from nearly every room, with the living room highlighting breathtaking vistas of Fishing Creek. Two spacious living areas, each with a cozy fireplace, make relaxing or entertaining effortless year-round. The open gourmet kitchen features custom finishes, modern updates, and a built-in wine cooler—perfect for gathering with family and friends. The primary suite includes a private bath, while the open floor plan provides both functionality and seamless flow. Major systems have already been taken care of for you—roof replaced in 2018, HVAC replaced in 2022, and new thermostats installed in 2024—so you can move in with confidence. A new sprinkler system, plus all French gutter drains installed in 2025 and an improved Dry-Zone encapsulated crawl space further enhance efficiency and long-term protection. For added reassurance, the home includes transferable flood insurance and annual Dry-Zone, HVAC and pest control inspection contracts. Home is connected to public sewer, helping to simplify ownership from day one. Ideally located just a short distance from historic Cambridge, the Hyatt Regency Chesapeake Bay Golf Resort, and within easy reach of Easton, Oxford, and St. Michaels, you’ll also enjoy close proximity to Blackwater Wildlife Refuge—perfect for exploring nature, spotting eagles’ nests, or enjoying canoeing, biking, and hiking trails.

1318 Bell Ln, Woolford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$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:

$349,900
3 Beds 2 Baths
WOW! Seller is motivated and has drastically reduced. Act now while there is plenty of summer left. Chesapeake sunsets and Honga River sunrises. Watermen heading out at dawn. Ospreys, heron, and egrets hunting their dinner. A short walk to crabs harvested that very morning. Everything that makes the Eastern Shore unique -- the Bay, windswept marshes, seafood, its deeply rooted history -- in a magical place where time slows down so you can catch up. Check out the former Airbnb " Hoopers Island Victorian" listing to find out what makes the house and island so special, from the past visitor's reviews. 🏡 The House Cross a breathtaking causeway and you are smack dab in the middle of an island that measures 1/3 of a mile across. this Chesapeake Bay to the west, Honga River to the east, tidal marsh to the north, and a marina to the south. You are surrounded by water and can see it from every room in the house. A spacious Victorian filled with historic details, high ceilings and original hardwood floors. Windows everywhere, all designed to bring in natural light and bay breezes, 3 bedrooms (comfortably sleeps 8), 1.5 baths, all new appliances. 1.4 acres, privacy, outdoor shower, grazing deer and resident Osprey family. Air-conditioning, high-speed internet, 2 fridges. 🔑 Lock and Load All you have to do is move in. Seller has completed extensive renovations. Includes most furniture and lighting, including dining table and chairs, living room couch and chairs, 5 beds, bureaus, TV and 2 refrigerators. Hammock chairs, porch furniture, fishing poles, crab nets and appliances. 🌾 The Island Two miles off Maryland’s Eastern Shore and 45 minutes from historic Cambridge lies Hoopers Island—one of the last inhabited islands in the Chesapeake Bay. Stretching ten miles and made up of three barrier islands, it’s home to pelicans, ospreys, great blue herons, egrets, cormorants, ibis, and only about 500 year‑round residents. Outdoors, the lifestyle truly comes alive--summer firepits under the stars, crisp fall evenings along the shoreline, and kayak adventures just moments way (kayaks included). Each season brings its own rhythm from sun-soaked summer days to the deeply restorative autumn season. 📍 The Region Close to Easton, St. Michaels, and Oxford. Blackwater National Wildlife Refuge offers hiking paths and 17 miles of water trails and a wide variety of local wildlife and scenic views. The Harriet Tubman Museum. a 10-minute drive to Old Salty's Restaurant, an Eastern Shore institution. A 10-minute walk to the freshest crabmeat and steamed crabs. Day trips to Ocean City or Rehoboth Beach, or carve out a half day visit to St Michaels, Oxford or Easton/

1606 Steamboat Wharf Rd, Fishing Creek

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

$448,500
4 Beds 4 Baths
Back on the market! Due to no fault of the Seller's, you have another chance to make this your home! Welcome to resort-style living at the prestigious Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina in Cambridge, Maryland. This beautifully maintained townhome offers the perfect blend of comfort, convenience, and Eastern Shore charm, located within one of the region’s most sought-after waterfront resort communities along the Choptank River. This 4 Bedroom 3.5 Bathroom home features tasteful upgrades throughout, including maple cabinetry in the kitchen and bathrooms, granite countertops, crown molding, and quality finishes that add warmth and sophistication to the living spaces. Enjoy a balcony on the front of the home offering views of the Choptank River-perfect for morning coffee or evening sunsets. The rear of the home offers three outdoor living spaces, ideal for entertaining, relaxing, or enjoying the peaceful resort surroundings Enjoy a relaxed coastal lifestyle just moments from the award-winning River Marsh Golf Club, marina, spa, waterfront pools, and dining. Whether you’re searching for a primary residence or weekend retreat this property places you in the heart of resort living. Golf, pool, and certain resort amenities may require membership or additional fees.

2830 Persimmon Pl Unit #A5, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$499,900
3 Beds 3 Baths
Stunning waterfront views of the Choptank await you at 7 Hatsawap Rd, Cambridge, MD 21613! Imagine unwinding on your multi-level deck soaking in breathtaking sunsets and peaceful water views. This beautifully updated home features three bedrooms and two-and-a-half baths with great Air B&B potential. A welcoming foyer with marble flooring opens to wood floors that extend throughout most of the home. The updated kitchen offers quartz countertops, newer appliances, a convenient breakfast bar, and separate breakfast area. A formal living room with a cozy fireplace, separate dining area, and large family room provide versatile spaces for both everyday living and entertaining. The second floor primary suite is a private retreat featuring a vaulted ceiling, walk-in closet, balcony access with water views, and a charming retro-inspired primary bath full of character. Situated on a desirable corner lot just minutes from the community dock with water access, this property also offers paved parking for added convenience. Close to historic downtown Cambridge, shopping, restaurants, and more! No town taxes and not located in a flood zone.

7 Hatsawap Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$235,000
2 Beds 2 Baths
Experience affordable waterfront living without compromising on lifestyle in this beautifully updated top-floor penthouse. From your private balcony, enjoy peaceful long-water views stretching toward the Choptank River and front-row seats to the Fourth of July fireworks over the water. Offering 1,493 square feet of thoughtfully updated living space, this 2-bedroom, 2-bath residence features new luxury vinyl plank flooring throughout, upgraded lighting, elegant chair rail detailing, and a spacious open layout designed for comfortable everyday living. The modern kitchen has been refreshed with all-new stainless steel appliances, while the full-size stacked washer and dryer add everyday convenience. The generous primary suite includes a spa-inspired bath with dual vanities, a walk-in shower, and timeless white marble flooring. Located within the secure, gated Deep Harbour waterfront community, residents enjoy elevator access, front-door intercom entry, an assigned indoor garage parking space, and the added benefit of a rare private storage unit. Deep Harbour offers an exceptional waterfront lifestyle with a community marina, piers, kayak launch, scenic walking paths, swimming pool, bathhouse, picnic areas, and beautifully maintained grounds along Cambridge Creek. Just moments from historic downtown Cambridge, you'll enjoy locally owned restaurants, shops, marinas, festivals, and the exciting Cambridge Harbor redevelopment on the Choptank River, bringing new waterfront dining, entertainment, and recreational amenities. Perfectly positioned for commuters and weekend travelers alike, Cambridge offers convenient access to Annapolis, Easton, Salisbury, Ocean City, and the broader Chesapeake Bay region—making it easy to enjoy coastal living while staying connected to work and recreation. Whether you're looking for a full-time residence, weekend retreat, or low-maintenance waterfront home, this penthouse delivers exceptional value, security, and an enviable Eastern Shore lifestyle. 𝗣𝗿𝗼𝗽𝗲𝗿𝘁𝘆 𝗛𝗶𝗴𝗵𝗹𝗶𝗴𝗵𝘁𝘀 • Top-floor penthouse with long water views toward the Choptank River • 1,493 sq. ft. | 2 Bedrooms | 2 Full Baths • Private balcony with water views and Fourth of July fireworks • New luxury vinyl plank flooring throughout • All-new stainless steel kitchen appliances • Full-size stacked washer & dryer • Spacious primary suite with dual vanities, walk-in shower & marble flooring • Upgraded lighting fixtures and chair rail detailing • Assigned indoor garage parking space • Rare private storage unit • Secure gated building with front-door intercom • Two elevators serving all residential floors • Waterfront community with marina, piers & kayak launch • Swimming pool, bathhouse, picnic areas & waterfront walking paths • Minutes to historic downtown Cambridge • Near the exciting Choptank Harbor waterfront redevelopment • Easy access to Easton, Annapolis, Salisbury, Ocean City & the Chesapeake Bay • Affordable, low-maintenance waterfront living on Maryland's Eastern Shore

700 Cattail Cv Unit #412, Cambridge

Listing courtesy of Kinetic Realty, Inc.. Contact: (443) 222-0010

$8,950,000
24 Beds 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971

$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