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$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:

$650,000
3 Beds ⋅ 3 Baths
This Extremely well maintained Property has so much to offer. Starting with 2 lots 519 & 521 together for 6.18 ac. The Solar Panels provide a large percentage of Electric with most months electric bills costing not much more than $35.00. The 3 BR w oversized closet space 2 1/2 Baths , Full laundry room, storage. A walk up stairs to the attic that is fully floored and has a exhaust fan. The immaculate 3 car garage has a 4th door in the back, electric, cement floors and work benches with tons of storage. Included is the Hustler 72" Zero Turn Mower. Out building #2 48x16 cement floor, electric. Out building #3 is 32x48 with a 16x48 addition. One with a 14' overhead door and the other with a standard door both are equipped with electric and cement floors and are all in Immaculate Condition. Their is a BIP (Bermed Infiltration Pond) located on the property and the tax fee is $250.00 annually per lot. Enjoy the Fresh Seafood specialties just steps away at the Boats & Hose Restaurant. Visit the Camp Ground on Bay Shore Rd. and Crabbing & fishing steps away several feet away at the Taylors Is. Bridge. Lots of Wildlife seen here. Hurry take a look.

Taylors Island

Listing courtesy of Brenton Realty Group. Contact: 4104794663
$299,000
3 Beds ⋅ 1 Baths
Welcome to 2517 Old House Point Rd, one of the cutest homes in Fishing Creek. Sitting on elevated ground this three bedroom, one bathroom home has water views from the front and back yard. Large garage you could keep a boat or kayaks and bikes with loft and lean to. Quiet area with relaxing feeling.

2517 Old House Point Rd, Fishing Creek

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$325,000
3 Beds ⋅ 2 Baths
This comfortable circa 1908 home has undergone a significant interior renovation including new paint, luxury vinyl plank floors, new baths and kitchen, new appliances and ceiling fans. High efficiency heat pumps await the new Buyer. The original exterior architectural details including original wood clapboard siding have been restored and maintained. The Property is located in a Cambridge's Historic District and is very convenient to downtown Cambridge shops and restaurants, the Choptank Rive, parks and waterfront events. The early 20th Century 3 bedroom - 2 bath dwelling offers historic charm and modern amenities and awaits your purchase. Enjoy your front open porch!

207 Willis St, Cambridge

Listing courtesy of Eastern Shore Properties, ESP Inc.. Contact:

$199,000
3 Beds ⋅ 1 Baths
Eastern Shore Living with Room to Breathe! Whether you're looking for your first home or the perfect place to simplify and enjoy life, this charming 3-bedroom, 1-bath home offers comfort, convenience, and nearly an acre of land in the peaceful community of Madison. Boating and fishing enthusiasts will love being just minutes from a public boat ramp and marina, while still enjoying easy access to town and everyday amenities. The property features an attached two-car garage, a 12' x 12' storage shed on a concrete pad, and the added peace of mind that comes with a new HVAC system and updated well and septic systems. With plenty of outdoor space for gardening, pets, hobbies, or simply relaxing, this property offers the ideal blend of country charm and Eastern Shore lifestyle. Affordable, move-in ready, and close to the water—don't miss this opportunity!

4658 White Marsh Rd, Madison

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$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 investment property, 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:

$295,000
3 Beds ⋅ 1 Baths
Escape to the peace and privacy of Maryland's Eastern Shore with this charming ranch-style home situated on approximately 2 acres. 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
$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
$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:

$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
$1,399,999
5 Beds ⋅ 3 Baths
Endless westerly vistas stretch across Madison Bay, delivering breathtaking sunsets that feel like a private showing each and every evening. This is more than a home—it’s a waterfront sanctuary designed for those who expect their lifestyle to be as elevated as their surroundings. Welcome to Saltmarsh, an extraordinary 8.5-acre estate where luxury, privacy, and coastal beauty converge. With 5 bedrooms (plus a bonus room that could be considered a 6th) and 3 full bathrooms, this property effortlessly transitions between an exceptional full-time residence and the ultimate weekend retreat for unforgettable gatherings with friends and family. Spanning over 5,000 square feet, the home is thoughtfully designed to maximize both space and scenery, with walls of windows that flood the interior with natural light and showcase those sweeping bay views from nearly every room. The main level is nothing short of an entertainer’s masterpiece—an open-concept layout anchored by a stunning great room, seamlessly flowing into a chef’s gourmet kitchen and sun-drenched sunroom on one side, while the opposite wing reveals a full-scale game room complete with a pool table and custom bar built for hosting on any scale. Step outside and the experience only gets better. Multiple expansive decks offer the perfect setting for everything from quiet mornings to lively evenings, all framed by panoramic water views. At the private dock, every detail has been accounted for—featuring water and electric, two jet ski lifts, and a 10,000-pound boat lift—creating a true waterfront playground. The oversized 3-bay garage provides ample space for all your water toys, equipment, and more—because a property like this is meant to be enjoyed without compromise. Offered fully furnished, Saltmarsh is completely turnkey—allowing you to step right into an effortless, elevated coastal lifestyle from day one. This is not just a home—it’s a statement.

4808 Saltmarsh Rd, Madison

Listing courtesy of Coldwell Banker Realty. Contact: 4105246111
$650,000
4 Beds ⋅ 3 Baths
MAJOR PRICE REDUCTION! A rare opportunity to own a private waterfront retreat that not only offers an exceptional Eastern Shore lifestyle, but also a proven income-producing investment — with over $46,000 in rental payouts over the past two years and an active upcoming reservation calendar, the next owner can enjoy immediate revenue while still reserving time for personal use. Escape the pace of city life and discover your own secluded waterfront sanctuary on St. John's Creek, nestled among 3.5 picturesque acres. Conveniently located within an easy drive of Baltimore, Washington, D.C., and Northern Virginia, this peaceful retreat is surrounded by the natural beauty of Maryland's Eastern Shore, where bald eagles, osprey, herons, ducks, geese, sika deer, and other wildlife are part of everyday life. The charming cottage is filled with warmth and character, offering a welcoming living room with a mantle and pellet stove, a cozy kitchen and dining area, a versatile first-floor bedroom, laundry room with daybed, and a full bath. Upstairs, a spacious bedroom with a half bath and wood stove creates a peaceful, storybook-like retreat. The brick-floored screened porch overlooks St. John's Creek and the private pier, providing the perfect setting for morning coffee, evening cocktails, or simply watching boats and wildlife pass by. Designed for gathering family and friends, the thoughtfully crafted carriage house (guest house/second dwelling) significantly expands the property's versatility. It features a spacious bunk room with six bunk beds, an oversized second-floor bedroom accommodating two queen beds, plus a main level with kitchen, dining area, living room, and full bath. An attached two-car barn-style garage provides additional storage and functionality. Between the cottage and carriage house, the property comfortably sleeps up to 15 overnight guests. Offered fully furnished and completely turnkey, the property is ready to enjoy from day one. Relax around the waterside fire pit, launch kayaks and paddleboards from your private pier, or dine just minutes away at the popular Boats & Hose Restaurant. Due to the property's active vacation rental schedule, showing availability is limited — a comprehensive virtual tour will be available soon, allowing prospective buyers to experience the property while private showings are accommodated around existing guest reservations. Whether you're looking for a private waterfront getaway, a full-time residence, or an investment with established income potential, this property offers the flexibility to do it all. This is a rare opportunity to purchase a turnkey waterfront property with immediate income already in place.

4004 Robinson Neck Rd, Taylors Island

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

$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
$339,900
3 Beds ⋅ 2 Baths
*Sellers will need 30-90 days OR less to find their home of choice. Nestled on 1.89 acres of mostly cleared flat land, this move in ready 3 bed, 2 bath home offers a perfect blend of privacy, comfort and natural beauty. Surrounded by woods, the property provides a peaceful year around retreat but close enough to local restaurants, shops and activities. Spacious open concept living area with a cozy fireplace that flows into a large fully equipped kitchen. This home features 3 beds, 2 full baths and huge heated/air conditioned 12x36 sun room over looking the scenic back yard. A new roof, HVAC system, fresh new carpet and hardwood flooring makes this home a true gem. Outside you will find a 2 car carport along with a detached heated garage. Enjoy the outdoor life that Cambridge offers including fishing, boating, parks and playgrounds!

5622 Ross Neck Rd, Cambridge

Listing courtesy of Samson Properties. Contact: 4433437660
$200,000
Old Maryland National Bank Building will make a great office building or can be used for a Community Center, or used for other uses! There a large parking lot across the street that is included(107 Main Street).

100 Broad St, Hurlock

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$850,000
2 Beds ⋅ 2 Baths
Stunning Custom-Built Coastal Home with Private Beach! This one-of-a-kind coastal home represents over three years of meticulous planning and construction, designed for maximum durability, energy efficiency, and minimal maintenance. No detail has been overlooked in this custom build, which showcases a thoughtful blend of modern features and antique charm. Structural Features: Oversized footers with rebar for a solid foundation Extra-deep 12-inch stone driveway with Typar fabric for durability New culvert pipe at the entrance and concrete-filled block walls, tying everything together for added strength and protection. Flood gates at grade level to safeguard against water entry Block-constructed interior stair tower to ensure no water enters the living space Premium framing using Number 1 Select Southern Yellow Pine, with 9-foot walls and 2x12 floor joists for a rock-solid structure. Truss roof system with hurricane clips, blanket insulation, and metal roofing to prevent sweating Garage & Exterior: 12-inch stone base and 6-inch, 5000 PSI concrete garage floor Fully insulated, stainless steel garage doors Tyvek wrap on the exterior, with reflective 3/8” fan-fold insulation for added energy efficiency PVC trim with a hidden plug system for a clean look Cedar panel siding rated for 130 mph winds Low-maintenance, commercial-grade fiberglass decking with a structural steel frame, hot-dip galvanized for durability Aluminum handrails, powder-coated white for a sleek, coastal design Interior Features & Custom Details: Unique antique accents, including a bronze ship bell mounted on an antique column in the stairwell Spanish-American War fireback backsplash and a historic cast-iron fireplace from Washington, DC Early Bombay-style dresser vanity in the master bathroom with a matching mirror, stained to complement the home’s coastal color palette Handrail leading to the basement crafted from a traditional oar to enhance the coastal theme All wood used is top-tier, including number one clear pressure-treated decking and stainless steel screws for long-lasting performance Energy Efficiency & Sustainability: Air-sealed prior to insulation, with spray foam insulation in walls, floors, band boards, and attic (R-30 in floors, R-60 in the attic) HVAC and attic areas also receive spray foam for maximum efficiency Baffles installed at eaves for optimal airflow, reducing energy costs Electric bills averaging just $100 per month Fire sprinkler system with a discreetly located tank and pump for safety Gourmet Kitchen & Bathrooms: Custom oak kitchen cabinets, painted to match the tongue-and-groove ceiling High-end, 36-inch stainless steel gas stove and energy-efficient appliances Premium Fantasy Brown marble countertops (two grades above granite), sourced from a single slab Arabesque tile backsplash to complete the kitchen design All bathrooms feature white subway tile, with a master bath receiving marble accents and a guest bathroom enhanced with green sea glass accents Both bathrooms include rain showerheads and hand showers for easy cleaning Interior Finishes: Nickel gap walls throughout the kitchen, living room, and hallway, and tongue-and-groove ceilings throughout Solid wood doors with frosted glass inserts and crystal knobs for an elegant touch Stained oak stair treads and handrails, complemented by luxury glue-down commercial plank flooring Thoughtful design focused on safety, efficiency, and low maintenance This home was built with care, incorporating over 40 years of experience and a passion for creating a space that is both functional and beautiful. Perfectly designed to withstand the elements and deliver comfort and style, this is a rare opportunity to own a property that blends the best of modern living with historic charm. Contact us today to schedule your private tour and see firsthand the unmatched craftsmanship and attention to detail that went into this extraordinary home! Be sure to visit the drone and virtual tours of the home

1826 Hoopersville, Fishing Creek

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$275,000
Cambridge - looking for office or commercial space? 103 Cedar may be your place! 960 +/- square ft. building located on one of Cambridge's most traveled roads. Single story with easy access and parking.

103 Cedar St, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545