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$144,900
4 Beds ⋅ 2 Baths
Discover a prime investment opportunity with this charming 4-bedroom, 2-bathroom bungalow, built in 1940 and boasting 1,725 sq. ft. of potential. Set on a generous 0.69-acre lot, this detached home offers ample space for expansion or outdoor enhancements, making it ideal for future development or rental income. The property features a cozy fireplace, adding character and warmth, while the expansive lot provides room for outdoor activities or additional structures. With no HOA fees, investors can maximize their returns without added costs. Located in a tranquil area, this home is perfect for those seeking a peaceful retreat while remaining accessible to local amenities. The combination of its classic architecture and spacious grounds presents a unique opportunity for both short-term and long-term rental strategies. Unlock the potential of this property and capitalize on the growing demand for residential rentals in the area. Don't miss out on this investment gem!

5314 Suburban Dr, Cambridge

Listing courtesy of Worthington Realty Group, LLC. Contact: 8558494663
$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
$399,000
5 Beds ⋅ 4 Baths
Welcome to 16 Buena Vista Avenue! This very spacious 5 bedroom, 3.5 bath brick rancher is situated on an attractive corner lot in the sought-after, quiet Algonquin neighborhood, within walking distance of Sandy Hill Elementary School. The home offers generous living spaces, a brick fireplace and lots of natural light. A large detached outbuilding features an oversized two-car garage with a spacious bonus recreation room, offering excellent space for entertaining, hobbies and additional storage. Conveniently located near the waterfront, with a nearby marina offering boat slips for rent, as well as shopping, dining, and easy access to Route 50.

16 Buena Vista Ave, Cambridge

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$425,000
3 Beds ⋅ 3 Baths
Enjoy efficient one-level living in a private, peaceful setting on a quiet cul-de-sac. This spacious home features an open floor plan, a beautiful stone fireplace, 3 bedrooms, and 3½ baths. Freshly painted throughout, the home also offers dual tankless water heaters for added efficiency. You are able control the system to adjust the water temperature in both bathrooms and the kitchen The 3-car garage includes fixed stairs leading to a finished bonus space above, complete with a full bath, heating, and air conditioning—perfect for a home office ,or a guest suite. Outside, enjoy a deck, a separate workshop with electricity, and a concrete driveway.An automatic timed irrigation system will keep your lawn and landscaping beautiful.A wonderful combination of comfort, space, privacy, and versatility!

5605 Bayberry Way, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$849,900
3 Beds ⋅ 2 Baths
Trade Traffic for Tides — Your Waterfront Island Escape Awaits! From the moment you cross the bridge onto Hooper's Island, something changes. A sense of peace settles in. Life slows down. The water sets the schedule, neighbors wave as they pass, and the pace becomes simpler, sweeter, and slower—in the very best way. This beautifully remodeled 3-bedroom, 2-full-bath waterfront home is being offered fully furnished and is already an established, highly successful 5-star Airbnb, renting for $430 per night. Whether you're looking for a personal island retreat, an investment property, or the best of both worlds, this home is ready to enjoy from day one. The entire home has been remodeled from the ground up, so nothing in the home is older than 5 years old- appliances, roof, well, mechanicals -you name it!! Imagine looking out your window and seeing crab boats, dolphins playing in the bay, and cruise ships and container vessels making their way across the horizon. A rear wall of floor-to-ceiling glass doors provides panoramic bay views, bringing the water into nearly every room. Cooking becomes relaxing because the views are amazing, even from the kitchen! Wake in the primary suite, open the blinds with a remote control, and take in the water views from the comfort of your bed. Freshly painted and featuring brand-new flooring throughout, the home combines comfortable coastal living with thoughtful modern updates. The crawl space had spray foam insulation, vapor barrier, and a new sump pump installed in 2026. The home is ADA accessible with a ramp to enter from the side, walk-in showers, wrap around Trex decking, and even paved sidewalks with railings leading the whole way to the dock. Smart technology integrated into so many aspects of the property! Access an app to control the thermostat, garage door, RING cameras, and even view the contents of your fridge so you can remember what you need to get at the grocery store! And then there's the waterfront. A private dock, built just two years ago, is ready for your next adventure and includes a 10,000-pound boat lift. Spend your days kayaking, swimming, boating, jet skiing, fishing, or crabbing—or simply sit by the water and watch island life unfold. Search the shoreline for sea glass and seashells, launch the kayak, or cast a line and see what the day brings. On this island, you won't need your car. Leave it parked and explore by foot, bike, or golf cart. Hooper's Island has a general store stocked with everyday essentials, from fishing tackle to ice cream, and Old Salty's, the island's only restaurant, serves wonderful fresh seafood alongside a laid-back tiki bar. Fun fact about Hooper's Island: Before it started as a culinary legend, it all started on this island in 1914 when Augustus E. Phillips opened the A.E. Phillips & Son packing plant. In 1956, faced with a surplus of crabs, Augustus' son and his wife opened a small 'shack' in Ocean City, MD... and we all know how that exploded with popularity! The original processing plant is still part of the company, and when operational, continues to process blue crabs and soft-shell crabs for regional locations.

1210 Horse Point Rd, Fishing Creek

Listing courtesy of Contigo Real Estate. Contact: 7172694566
$789,000
3 Beds ⋅ 2 Baths
Welcome to 4820 Madison Canning House Road! Enjoy picturesque park-like acres of land while simultaneously viewing the beautiful Madison Bay. This elevated house sited on 5.09 acres has it all! Gorgeous water views complete with total peace and tranquility! Designed for ease of use and laid back water living this house bespeaks comfort and airiness. Conveniently located just 15 minutes from downtown Cambridge and a little over an hour from Ocean City, the property is ideally located. The amenities are many as evidenced by a walk through. 3 Bedrooms, 2 baths and many open airy spaces for dining and living areas. A second floor loft with a private deck access completes the fabulous layout! For those inclined to collect toys or hunting/fishing gear, this house has the most awesome lower level I have ever seen! 4 bays open to beautifully finished floors and walls.

4820 Madison Canning House Rd, Madison

Listing courtesy of Compass. Contact: (410) 429-7425
$389,000
2 Beds ⋅ 4 Baths
Welcome home to this beautifully refreshed 3-bedroom, 2.5-bath townhouse offering the perfect blend of comfort, style, and coastal charm. Freshly painted throughout, this spacious home is move-in ready and designed for easy living. Enjoy your morning coffee or unwind in the evening on one of two private balconies, where you can soak in the peaceful surroundings and embrace the waterfront lifestyle. Just moments from the water, this home offers the relaxing atmosphere of a vacation retreat every day. Close to downtown Cambridge with all the restaurants and street festivals, and only an hour from the beach in Ocean City.! Additional highlights include an attached garage, generous living spaces, and access to a community pool, and walking trails, making it easy to enjoy sunny afternoons without leaving the neighborhood. Whether you're looking for a full-time residence, a weekend getaway, or an investment opportunity, this townhouse delivers the feeling of a year-round vacation in a desirable location. Don't miss your chance to own a home where every day feels like a getaway.

214 Tidewater Dr Unit #214, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$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
$339,000
4 Beds ⋅ 1 Baths
Experience the timeless charm of Maryland's Eastern Shore at 4707 Steamboat Road in the peaceful community of Woolford MD. Just steps from the shores of beautiful Church Creek, this beautifully updated traditional farmhouse offers picturesque water views from the screened front porch and the perfect blend of classic Eastern Shore character and modern comfort. Inside, you'll find a bright, open-concept living and dining area that flows effortlessly into a spacious gourmet kitchen featuring updated cabinetry, a gas range, and upgraded flooring. Original hardwood floors throughout the foyer and first-floor bedrooms preserve the home's timeless appeal, while the generously sized rooms showcase the craftsmanship and charm of a bygone era. Extensive recent improvements make this home truly move-in ready. Recent updates include updated double-pane windows for improved energy efficiency, a new refrigerator (2024), new washer and dryer (2025), a new well pump, an owned water treatment system, energy-efficient mini-split heating and cooling systems, luxury vinyl plank flooring upstairs and downstairs, and a new electrical panel—all completed to provide comfort and peace of mind for the next owner. Step outside and enjoy everything this property has to offer. Sip your morning coffee on the rear deck overlooking the spacious backyard, or unwind on the screened front porch while taking in peaceful views of Church Creek. The large lot offers plenty of room to expand, garden, or build a future garage, while the well-maintained folk barn provides abundant storage and adds authentic character to this charming Eastern Shore setting. Whether you're searching for a full-time residence, a peaceful weekend retreat, or a place to enjoy the slower pace of living, 4707 Steamboat Road offers a rare opportunity to own a beautifully updated farmhouse in one of Dorchester County's most scenic locations. As an added bonus, additional equipment and personal property will convey with an acceptable offer.

4707 Steamboat Rd, Woolford

Listing courtesy of Keller Williams Realty. Contact: 3028467839
$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
$297,900
3 Beds ⋅ 1 Baths
Welcome to 603 Roslyn Ave., a charming, tastefully renovated bungalow featuring 3 bedrooms, 1 bath, and a detached 1-car garage. Recent updates include a new roof and windows. The property offers spacious back and side yards and is conveniently located near shopping, restaurants, the boat ramp, and the Choptank River. Make it your weekend getaway, full-time residence, or place of business. Zoned C-2, the property offers many commercial-use possibilities, including retail and service businesses such as general stores, bakeries, pharmacies, clothing shops, and repair services; professional offices for financial, legal, medical, dental, or administrative use; entertainment and recreation uses such as indoor amusement centers, fitness studios, and indoor recreation facilities; food and drink establishments such as restaurants, cafes, and taverns; and limited residential uses, including single-family, multi-family, and mixed-use units, such as apartments a

603 Roslyn Ave, Cambridge

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: (800) 383-3535
$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
$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
$1,375,000
4 Beds ⋅ 5 Baths
End each day with sweeping sunsets over Madison Bay from this exceptional waterfront compound offering 268 feet of protected, rip-rapped shoreline and 1.12 acres of privacy, ideally positioned with a coveted east-west orientation. A private pier equipped with a boat lift and personal watercraft lift enhances the property’s appeal, delivering immediate access to the water and an effortless boating lifestyle. Designed by renowned architect Burhsar Pathare, the impeccably crafted residence spans over 5,000 square feet across three finished levels, featuring 4 bedrooms and 4.5 baths, all thoughtfully positioned to capture unobstructed water views. Beautiful flooring flows throughout, complementing clean architectural lines and high-end finishes. The entry level welcomes you with a large living space highlighted by high ceilings and an abundance of windows that frame stunning water views. A beautiful, full-service bar—complete with sink, dishwasher, and high-end finishes—creates the perfect setting for entertaining. This level also features a spacious laundry and utility area along with a convenient half bath, and provides direct access to the backyard and waterfront setting for seamless indoor-outdoor living. Take the stairs or the elevator to access the upper levels of the home. The main level is truly striking, showcasing soaring 40-foot ceilings and a dramatic wall of glass capturing panoramic bay views. The open-concept design seamlessly integrates the kitchen, dining, and living areas, anchored by a stone fireplace. The gourmet kitchen features a spacious eat-in area and opens to a full-length wraparound deck overlooking the water—ideal for gatherings of any size. The main-level primary suite offers private deck access and a spa-like bath, with an additional full bath also located on this level. Upstairs, a loft overlooks the main living space, along with three generously sized bedrooms, including two ensuite bedrooms with private baths—each bedroom also features its own private deck overlooking the water, offering a peaceful retreat with breathtaking views. The third secondary bedroom features the added convenience of direct elevator access within the room itself. Outdoor living is equally impressive with multiple decking areas and a beautifully designed paver patio featuring a fire pit and sitting walls—all oriented to take full advantage of the waterfront setting. The property is fully fenced, enhancing both privacy and functionality. A gated entrance with electronic access further enhances privacy and security, while an oversized two-car attached garage provides ample convenience and storage. The property is serviced by public sewer and a private well. The residence is offered as a truly turnkey opportunity, conveying with the majority of its high-quality furnishings for an effortless, move-in-ready experience (select artwork and personal items excluded). The adjoining property at 1250 Old Madison Road is also available for purchase (MDDO2012114), featuring a charming 2-bedroom, 2-bath cottage with additional living space and expansive water views—ideal as a guest house or income-producing rental. An exceptional opportunity to fully embrace the waterfront lifestyle—where every day feels like a retreat and lasting memories are made. Mortgage savings may be available for buyers of this listing.

1252 Old Madison Rd, Madison

Listing courtesy of Redfin Corp. Contact: 3016586186
$289,900
4 Beds ⋅ 2 Baths
Priced to move! Welcome home to this charming, move-in-ready retreat packed with updates and space to enjoy indoor and outdoor living. Recent improvements include a new roof, siding, dual HVAC systems for efficient comfort upstairs and down, and more! This well-maintained 4-bedroom, 2-bath split-foyer sits on a generous corner lot of over half an acre, offering the rare bonus of no city taxes while still enjoying public water and sewer. Step outside to an elevated deck perfect for entertaining, along with expansive front and rear yards ideal for relaxing, playing, or hosting gatherings. Inside, you’ll find two spacious family rooms—one on each level—providing flexibility for living, working, or entertaining. Garden and outdoor enthusiasts will love the included raised beds, drip-irrigation system, and two storage sheds, making it easy to cultivate your own seasonal oasis. Nestled in a peaceful setting just outside city limits, this home offers the best of both worlds: quiet living with convenient access to downtown Cambridge, nearby parks, and boat ramps. With its inviting curb appeal and thoughtful updates throughout, this property is ready to welcome you home!

9 Merryweather Dr, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$1,999,750
3 Beds ⋅ 3 Baths
Waterfront Farm - Located along the shores of Marshy Hope Creek, this 113.14-acre farm, with an additional 1.322+/- acre adjoining lot, offers a rare blend of productive farmland, natural beauty, and thoughtfully maintained improvements. Approximately 52.6 acres are tillable and farmed for small grain, offering excellent agricultural opportunity. The remaining acreage comprises mature, open woodlands with cleared paths, suitable for nature walks and ATVs, that gently slope from the homesite down to the water’s edge. The meticulously maintained, single-story 3,270 sq ft home features one-story living. Cathedral ceilings, expansive living spaces, and an inviting layout designed for both comfort and entertaining. The home features three bedrooms and two-and-a-half bathrooms with a functional layout designed for both privacy and everyday living. Radiant floor heating provides consistent warmth throughout the home, reflecting the quality construction and ongoing care of the property. The home is set up for self-sufficiency with an outdoor wood boiler surrounded by a forest full of fuel. Maintained inside and out, the home is move-in ready and offers a rare combination of size, condition, and single-level design. Equestrian and farm amenities include a pole building with two horse stall doors, as well as an additional open shed for equipment or storage, and a water hydrant. Subdivisions are available with soils favorable for obtaining perc permits to create your own family compound. Whether you are seeking a working farm, recreational retreat, horse property, or private waterfront estate, this remarkable property is a great investment opportunity.

5113 River Rd, Hurlock

Listing courtesy of National Land Realty, LLC. Contact: 4434128971
$1,997,500
3 Beds ⋅ 3 Baths
Waterfront Farm - Located along the shores of Marshy Hope Creek, this 113.14-acre farm, with an additional 1.322+/- acre adjoining lot, offers a rare blend of productive farmland, natural beauty, and thoughtfully maintained improvements. Approximately 52.6 acres are tillable and farmed for small grain, offering excellent agricultural opportunity. The remaining acreage comprises mature, open woodlands with cleared paths, suitable for nature walks and ATVs, that gently slope from the homesite down to the water’s edge. The meticulously maintained, single-story 3,270 sq ft home features one-story living. Cathedral ceilings, expansive living spaces, and an inviting layout designed for both comfort and entertaining. The home features three bedrooms and two-and-a-half bathrooms with a functional layout designed for both privacy and everyday living. Radiant floor heating provides consistent warmth throughout the home, reflecting the quality construction and ongoing care of the property. The home is set up for self-sufficiency with an outdoor wood boiler surrounded by a forest full of fuel. Maintained inside and out, the home is move-in ready and offers a rare combination of size, condition, and single-level design. Equestrian and farm amenities include a pole building with two horse stall doors, as well as an additional open shed for equipment or storage, and a water hydrant. Subdivisions are available with soils favorable for obtaining perc permits to create your own family compound. Whether you are seeking a working farm, recreational retreat, horse property, or private waterfront estate, this remarkable property is a great investment opportunity.

5113 River Rd, Hurlock

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

$325,000
3 Beds ⋅ 1 Baths
Cozy all brick Colonial in highly sought out historic West End. Glenburn Ave is one of Cambridge's most beautiful historic streets. The home is located on a corner lot just 2 blocks from the Choptank River, parks and boat ramp. It is walking distance to downtown shops, restaurants, churches, schools, banks and the YMCA. This 1,408 st. ft. home has 1 bedroom, gally kitchen, dining room, laundry and large living room on the first level. The second level has beautiful hard wood floors, 1 full bath, 2 large bedrooms with pull down stairs for attic access. The full bath has large linen closet and ceramic tile. 2 car garage with workshop and wood burning fireplace. The yard is inviting and beautifully landscaped. The home has been lovingly cared for and well maintained through-out the years. It has been only family owned for generations. A must see!!

314 Glenburn Ave, Cambridge

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

4928 Gregory Rd, Cambridge

Listing courtesy of Stafford-Stafford Real Estate. Contact: 4103107755
$450,000
5 Beds ⋅ 3 Baths
***Sellers have found home of choice and are ready to entertain your offer!***Grand and beautifully updated, this circa‑1900 residence offers timeless architectural charm on 1.67 acres of land just moments from downtown and the waterfront. A welcoming wrap‑around porch with ceiling fans, sets the tone, perfect for relaxing and entertaining. The expansive grounds-fenced on three sides-include a spacious three story barn/garage, offering exceptional versatility and opportunity. Enjoy the lovely flagstone patio with fire pit and charming gazebo—ideal for outdoor gatherings and peaceful retreats. Step inside where historic character blends seamlessly with thoughtful updates, preserving the elegance of a bygone era while offering modern comfort and functionality. Generous living spaces, high ceilings, and period details reflect the home’s original craftsmanship, enhanced by tasteful improvements throughout. The generously sized first floor primary suite includes the ideal space for adding an en suite bath, offering flexibility to tailor the home to modern living. Climb the grand staircase to the second level with four spacious bedrooms and a full bath. The third level of the home includes a full bath, with space that could accommodate a sixth bedroom with minimal work. Rarely does a property of this size, stature, and amenity become available so close to shops, dining, and waterfront attractions. A truly special opportunity to own a distinctive piece of history in a prime location.

1311 Race St, Cambridge

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

$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
$289,000
3 Beds ⋅ 4 Baths
Your Eastern Shore dream home WITH A DEEDED MARINA SLIP awaits and is priced to sell in the gated community of Deep Harbour in historic Cambridge, Maryland! This large end unit located just steps from the community pool complex features over 2,400 sq ft of sunlit living space with high ceilings, custom window treatments, a large owner's suite, and ample free parking across from your private driveway and garage! A BRAND NEW HVAC SYSTEM WAS JUST INSTALLED FEB. 2026 - and this new $15K system includes a 10 year manufacturer warranty! This meticulously maintained former model home is owned by the original owners. The spacious living area on the second level is bathed in sunlight from the many large windows and a bay window bump-out. Ceramic tile flooring lines the sunroom and eat-in kitchen with island, stainless steel appliances, and large pantry. Updated wide plank LVP flooring completes the living room with multiple seating areas for entertaining or relaxing, a half bath and closet for storage. The top floor has 3 bedrooms with recently installed carpet and 2 full bathrooms connected by a hallway with LVP flooring and a linen closet. Decorating options are endless in the owner's suite that includes a sitting area with large windows adorned with custom window treatments including blackout blinds, a walk-in closet, and a bathroom with double sinks, a soaking tub, and a walk-in shower. Recently installed berber carpet lines the wide stairways leading from the hardwood flooring greeting you at the entry in the foyer. The first floor features a half bath and a den/guest room along with an exercise room/office with slider to the back patio and community pool, as well as the laundry and utility closets, and access to the large garage with storage area and brackets for your paddelboard and bikes. It's a quick walk or ride to the marina and riverwalk where you have private access to your own deeded boat slip (Slip #3) with association-provided water and electric where you can dock boats up to 33 feet in length. So in addition to enjoying all of the Deep Harbour community amenities, local Cambridge shops and restaurants, and nearby parks and beaches, you can enjoy boating on the Choptank and Chesapeake from your own slip! Whether you're looking for a relaxing vacation home, a homebase for coastal adventures from the Bay to the Ocean, or a poolside escape, you'll have ample free time to enjoy it all with no lawn maintenance and security features like an in-house sprinkler system, alarm system , and fire hydrant right out front all within the gated community. Homes with deeded boat slips aren't often available so visit 322 Shipyard and Slip 3 at the marina today! Monthly water and sewer is a flat rate of $73.20; the $431 association fees represent monthly cost for townhome and $151.00 represent monthly fees for marina slip; see list for additional inclusions; a capital contribution fee may apply; your agent can share information on amenities, HOA/Condo fees, and deferred water/sewer payments from disclosures. All measurements listed are estimated by CubiCasa; buyer and their agent to confirm all measurements, fees, association requirements, tax and school information.

322 Shipyard Dr Unit #82, Cambridge

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$349,900
4 Beds ⋅ 2 Baths
Don't miss this oppurtunity at affordable living at its best, SOLAR ARRAY INCLUDED $13.00 per month electric bill and an in-law suite that can be rented to offset your mortgage! Charming 2019 Remodeled Home with Scenic Fishing Creek Views and Private In-Law Suite Discover tranquility in this beautifully remodeled home in 2019, ideally located with breathtaking Fishing Creek water views. Perfect for nature enthusiasts, anglers, and hunters, this property is nestled in one of the East Coast’s most sought-after outdoor destinations, just minutes from the famed Blackwater National Wildlife Refuge and a short two-hour drive from Washington, D.C. Property Highlights: Versatile Outbuildings: The property features three additional structures, including a large barn with a fully-equipped in-law suite and two spacious sheds, offering ample storage or hobby space. Prime Fishing & Boating Access: Experience some of the region’s best fishing just steps away, with convenient boat storage at the neighboring marina. Local Charm at Your Doorstep: Take a leisurely stroll to Hooper’s Island General Store or dine at the iconic Old Salty’s Restaurant, renowned for its fresh seafood and authentic island charm. Energy Efficiency: A solar array helps drastically reduce or eliminate electric bills, offering eco-friendly and cost-efficient living. A Nature Lover’s Paradise: Surrounded by top-tier fishing, hunting, and wildlife, this home is a serene retreat from the bustle of city life, yet close to all essential amenities. Whether you’re looking for a peaceful weekend escape or a year-round residence, this property combines comfort, adventure, and local charm. Don’t miss your chance to own a piece of Maryland’s hidden paradise!

2826 Hoopers Island Rd, Church Creek

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