Refine Search
Map
Sort by
$339,900
4 Beds ⋅ 3 Baths
Welcome to 105 Mako Drive, where modern style, everyday comfort, and move-in-ready convenience come together. This beautifully renovated home has been updated from top to bottom with careful attention to detail, creating a like-new feel from the moment you step inside. The bright, open floor plan is filled with natural light and features brand-new flooring, fresh interior paint, and stylish finishes throughout. The impressive kitchen offers sleek cabinetry, beautiful countertops, and stainless steel appliances, making it ideal for both daily living and entertaining. Spacious bedrooms provide a comfortable place to relax, while the fully renovated bathrooms feature clean, contemporary finishes with upscale touches. Step outside to enjoy your own private backyard, perfect for quiet evenings or entertaining family and friends. Conveniently located just minutes from downtown Cambridge, local marinas, shopping, and dining, this home offers the ideal combination of convenience and Eastern Shore charm. Simply move in and start enjoying everything this exceptional home has to offer. Schedule your private showing today!

105 Mako Dr, Cambridge

Listing courtesy of ListWithFreedom.com. Contact: 8554564945
$624,000
4 Beds ⋅ 3 Baths
Discover the perfect blend of privacy, comfort, and waterfront living with this exceptional move-in-ready Colonial, nestled on 6.01 scenic acres. Offering 4 bedrooms, 3 full baths, and an abundance of versatile living space, this property is ideal as a full-time residence, weekend retreat, or multigenerational home. Wake up to peaceful water views and enjoy your morning coffee on the expansive rear deck overlooking the tranquil setting. Inside, you'll find a spacious country kitchen, a flexible first-floor bedroom or home office, and inviting living areas designed for both everyday living and entertaining. The property is loaded with sought-after amenities, including a private floating dock for boating, fishing, or kayaking, a detached workshop with electricity, heating, and air conditioning perfect for hobbies or storage, and a separate in-law suite complete with its own sauna, providing an ideal space for guests, extended family, or potential rental opportunities. Additional features include a two-car attached garage, an attractive stone walkway with brick front steps, and the peace and privacy that only a rural waterfront setting can provide. Conveniently located just minutes from Cambridge's shopping, restaurants, and schools, while also offering easy access to nearby beaches and major metropolitan areas, this is a rare opportunity to own an affordable waterfront property with acreage, privacy, and exceptional versatility.

5214 David Greene Rd, Cambridge

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$309,000
3 Beds ⋅ 2 Baths
Welcome to 3548 Chateau Dr. in East New Market! This well-maintained property offers the perfect blend of comfort, functionality, and additional living space. Major upgrades were completed in 2018, providing peace of mind and modern appeal. The property features an oversized detached two-car garage with a studio apartment above—ideal for guests, extended family, a home office, or potential rental income. Enjoy the privacy of the fully fenced backyard, complete with a storage shed for all your outdoor equipment and tools. Don't miss this versatile property with plenty of space and endless possibilities! Buyer to verify permitted uses of the studio apartment with local zoning requirements.

3548 Chateau Dr, East New Market

Listing courtesy of Century 21 Harbor Realty. Contact: 4105482100
$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. This home is in excellent condition, features include 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, an 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. Deer feeder conveys.

2243 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$299,000
3 Beds ⋅ 2 Baths
Brand New Construction! Offered at 299,000! Welcome to this beautifully crafted new construction Modern Farmhouse by the reputable local builder, "Lomaxx Custom Homes!" This move-in BRAND NEW construction home ready 3-bedroom, 2-bath ranch offers 1,292± square feet of thoughtfully designed living space with quality craftsmanship and stylish finishes throughout. The open-concept floor plan features luxury vinyl plank flooring, a spacious living room with a vaulted ceiling, exposed beam, and a cozy electric fireplace with mantle, creating a warm and inviting gathering space. The well-appointed kitchen is designed for both everyday living and entertaining, showcasing quartz countertops, a center island with two pendant lights, high-quality cabinetry, stainless steel appliances, and ample cabinet space. The private primary suite includes a walk-in shower and generous closet space, while the second full bath features a convenient tub/shower combination for family or guests. A rear entry provides easy access to the backyard, where the home backs to mature woods, offering a peaceful setting and added privacy. Additional highlights include an attached front-entry garage, public water and sewer, central electric heating and air conditioning, and a **one-year builder's home warranty** for added peace of mind. Ideally located just minutes from downtown Cambridge, shopping, dining, parks, the waterfront, and major commuter routes, this exceptional home combines modern comfort, quality construction, and everyday convenience. Don't miss your opportunity to own a brand-new home built with pride by Lomaxx Custom Homes! You don't want to miss out on this beautiful home!

1617 Stone Boundary Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$569,000
4 Beds ⋅ 4 Baths
Built in 2025, this popular Dune model overlooks the golf course and enjoys sweeping fairway views and western sunsets. Offering 4 bedroms and 3.5 baths with first floor primary suite, the thoughtfully designed floor plan is ideal for everyday living and entertaining. The main level features a spacious great room, dining area gourmet kitchen and the first-floor primary suite with a large walk-in closet. A screened porch with a fireplace extends the living space and provides a comfortable place to relax or entertain. Upstairs are three additional bedrooms, a bonus room and an expansive covered deck with panoramic golf course views, the perfect place to enjoy morning coffee or take in the sunset. Located in Tides at River Marsh, adjacent to the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina, this home offers the convenience of nearby dining, golf, shopping and scenic walking paths. Community amenities continue to expand with a pool, clubhouse and pickleball courts slated to open soon.

2711 Marsh Elder Dr, Cambridge

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$329,900
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
$324,900
2 Beds ⋅ 3 Baths
Welcome to 329 Shipyard Drive, a spacious townhome in one of Cambridge's most convenient waterfront communities. Offering over 2,400 square feet of living space, this home features an open, functional floor plan with generous room sizes, abundant natural light, and plenty of space for everyday living or weekend getaways. The main living area flows nicely into the kitchen and dining space, making it easy to entertain family and friends. Upstairs, you'll find comfortable bedrooms, including a spacious primary suite with its own private bath and ample closet space. Located in a gated, water-oriented community, residents enjoy access to a community pool and the convenience of being just minutes from downtown Cambridge's restaurants, shops, marina, and waterfront parks. Whether you're looking for a full-time residence, a low-maintenance second home, or an investment opportunity, this property offers the perfect combination of space, location, and easy living on Maryland's Eastern Shore.

329 Shipyard Dr, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$590,000
3 Beds ⋅ 2 Baths
A very nice manufactory home on the water, with great fishing and crabbing off the dock. A very nice home with great views of the Chesapeake Bay. It has a fire pit and a large yard for family games. There is a large deck for watchings sunsets. All the furniture is included. There is 2 car garage with electric, with remote for garage. You will need purchase Flood Insurance.

1230 Horse Point Rd, Fishing Creek

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$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
$349,990
3 Beds ⋅ 3 Baths
Welcome to Tides at River Marsh, an exceptional community adjacent to the renowned River Marsh Golf Club and Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina along the scenic Choptank River. Residents enjoy resort-style amenities, including a clubhouse, swimming pool, and walking and biking trails, with convenient access to historic downtown Cambridge's waterfront dining, shopping, museums, and marinas. Annapolis, Easton, and Ocean City are all within easy reach. This move-in ready villa offers 3 bedrooms, 2.5 bathrooms, and a 2-car garage. The gourmet kitchen is beautifully appointed with quartz countertops, a designer tile backsplash, stainless steel appliances, double wall ovens, and a vented range hood. Wide-plank flooring flows throughout the main living areas, complementing the open-concept design. Relax year-round on the screened porch or entertain on the paver patio while enjoying peaceful open-space views and added backyard privacy. Experience low-maintenance living with luxury finishes in one of Maryland's premier Eastern Shore communities.

2129 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$389,900
3 Beds ⋅ 2 Baths
NEW PRICE! Enjoy space, privacy, and modern efficiency on a premium 1.03-acre country lot! This stunning 2025-built home is 100% completed and ready for its very first owners. Step inside to a bright, open-concept layout anchored by a kitchen featuring sleek granite countertops. Built for comfort and lower utility bills, this home comes equipped with an energy-efficient heat pump and an on-demand tankless hot water heater. Enjoy peaceful Eastern Shore living—complete with an attached garage, ample driveway parking, and a sprawling backyard—easy drive to Easton, Seaford and Cambridge. Unbeatable value and zero wait time to build!

6706 Jayar Way, Hurlock

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$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
$375,000
4 Beds ⋅ 3 Baths
Welcome to 300 Shepard Avenue in the desirable Shepherd Village community of Cambridge, Maryland! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of modern style, comfort, and functionality. Step inside to an inviting open-concept floor plan featuring luxury vinyl plank flooring, abundant natural light, and a spacious living area designed for everyday living and entertaining. The gourmet kitchen boasts granite countertops, stainless steel appliances, ample cabinet space, a center island, and a bright dining area overlooking the backyard. Upstairs, you’ll find a generous primary suite with a private bath and walk-in closet, along with three additional bedrooms that provide plenty of space for family, guests, or a home office. Outside, enjoy a backyard perfect for entertaining, relaxing, or creating your own outdoor oasis. The attached two-car garage and spacious driveway provide ample parking and storage. Conveniently located just minutes from downtown Cambridge, shopping, restaurants, waterfront attractions, parks, schools, and Route 50, this move-in-ready home offers modern living in one of the Eastern Shore’s growing communities. Don’t miss your opportunity to make this beautiful home yours—schedule your private tour today!

300 Shepherd Ave, Cambridge

Listing courtesy of Fairfax Realty Premier. Contact: 3014399500
$359,990
3 Beds ⋅ 4 Baths
Located in Lennar’s premier waterfront community of Tides at River Marsh on Maryland’s scenic Eastern Shore, this move-in ready luxury 4-level end-unit townhome offers the perfect blend of coastal living and modern convenience. Nestled in Cambridge adjacent to the Hyatt Regency Chesapeake Bay Resort, residents enjoy resort-style amenities including a clubhouse, swimming pool, walking and biking trails, tennis and pickleball courts, and access to a nearby marina. Surrounded by championship golf, boating, nature trails, and wildlife preserves, the community is also just minutes from downtown Cambridge’s shops, restaurants, and waterfront attractions, with convenient access to Annapolis and Delaware beaches. This beautifully designed home features a 2-car garage, 3 bedrooms, 3 full baths, and 1 half bath, luxury vinyl plank flooring, a spacious kitchen with a large quartz island, stainless steel appliances, and stylish cabinetry. The finished walk-out lower level provides additional living space with direct outdoor access, while the expansive 4th-level loft offers flexible living space and opens to a private rooftop deck, perfect for relaxing or entertaining. Agents must accompany buyers on their first visit.

2198 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$249,990
3 Beds ⋅ 3 Baths
Lennar’s Tides at River Marsh is a premier resort-style community on Maryland’s scenic Eastern Shore in Cambridge, surrounded by the natural beauty of the Choptank River and the acclaimed River Marsh Golf Club. Residents enjoy a relaxed waterfront lifestyle with exceptional amenities, including a clubhouse, swimming pool, walking and biking trails, tennis and pickleball courts, and nearby marina access. Conveniently located adjacent to the Hyatt Regency Chesapeake Bay Resort and just minutes from downtown Cambridge, Blackwater National Wildlife Refuge, and Route 50, the community offers easy access to shopping, dining, recreation, Annapolis, and Ocean City. This move-in ready luxury end-unit townhome features a 2-car garage, 3 bedrooms, 2 full baths, and 1 half bath. The gourmet kitchen showcases stainless steel appliances, quartz countertops, a decorative backsplash, and wide-plank flooring throughout the main living areas. The spacious owner’s suite includes upgraded tile in the bath, while the finished walkout lower level provides additional living and entertaining space. Enjoy private wooded views from this desirable homesite. Photos are for illustrative purposes only. Agent must accompany first visit.

2185 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$324,950
4 Beds ⋅ 2 Baths
Step through the front door and be instantly transported to a bygone era. This beautifully maintained, turnkey 1895 home welcomes you with a grand two-story staircase, timeless architectural details, and the warmth of a residence that has been cherished for generations. The main level offers an inviting and effortless flow. From the elegant entry hall, you’ll move seamlessly into the comfortable living room, formal dining room, and spacious family room. Newly painted hardwood floors, abundant natural light, and oversized windows create a bright, welcoming atmosphere throughout. The charming kitchen blends historic character with modern convenience, featuring brand-new appliances and direct access to a full bathroom with newly added flooring and separate laundry room with back door exit to the yard. This renovated home boasts a new roof, new HVAC, furnace, condenser and air supply duct work. Ascend the stunning staircase to the second floor, where you’ll find three inviting bedrooms and a full bath with charming ball and claw tub. The third floor offers a private fourth bedroom—ideal as a guest suite, home office, artist’s studio, or peaceful retreat. Throughout the home, original features showcase the craftsmanship of a bygone era, including stained-glass accents, original fireplace mantels, hardwood flooring, and thoughtfully preserved architectural details rarely found in today’s homes. Outside, the fenced backyard is both functional and versatile, offering off-street parking, a detached climate-controlled garage, and an additional storage shed for tools, hobbies, or gardening equipment. Perfectly situated just a short stroll across Cambridge’s iconic drawbridge, this home places you moments from downtown’s charming shops, restaurants, churches, banks, and post office. Commuters and travelers alike will appreciate the convenient access to Easton, Salisbury, Maryland’s Eastern Shore and Delaware beaches, Annapolis, BWI Airport, and Washington, D.C. More than just a house, this is a rare opportunity to own a piece of history—a place where timeless character, modern comfort, and future memories come together. This home is ready for the next family story.

415 Maryland Ave, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$325,000
4 Beds ⋅ 3 Baths
KEEP MORE CASH AT CLOSING! Up to $10K Seller Credit + One-Hour Open House THIS IS THE OPPORTUNITY YOU HAVE BEEN WATCHING FOR. This home is now PRICED TO SELL AT $325,000, and the seller is adding a $10,000 SELLER CREDIT the buyer can put to work wherever it helps most: toward CLOSING COSTS, PREPAID ESCROWS, or a TEMPORARY OR PERMANENT RATE BUYDOWN to lower the monthly payment, in any combination the buyer's loan program allows. TRANSLATION: LESS CASH TO BRING TO CLOSING and a MONTHLY PAYMENT BUILT TO FIT THE BUDGET, on a property already priced aggressively for today's market. THE SELLER IS MOTIVATED, FULLY READY TO CLOSE, and is calling for HIGHEST AND BEST OFFERS. Bring your strongest terms and a clean, well qualified buyer, and let's meet at the settlement table. Nestled in the charming Blackwater Landing community, this stunning Colonial-style home, built in 2022, offers a perfect blend of modern comfort and timeless elegance. With 2,431 square feet of thoughtfully designed living space, this residence is ready to welcome you home. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas, creating an ideal space for both relaxation and entertaining. The abundance of natural light, enhanced by recessed lighting, highlights the luxurious vinyl plank flooring and plush carpeting throughout. The eat-in kitchen is a chef's dream, featuring ENERGY EFFICIENT appliances, including a refrigerator, freezer, dishwasher, microwave, and electric oven/range, ensuring energy efficiency without compromising on style. The home boasts a spacious walk-in closet, providing ample storage for your wardrobe and personal belongings. Convenience is key with a laundry area located on the upper floor, complete with a washer and dryer, making laundry day a breeze. Safety and security are paramount, with smoke detectors, a security system, and carbon monoxide detectors thoughtfully installed for peace of mind. Outside, the property is equally impressive. The 0.23-acre lot features well-maintained sidewalks and street lights, enhancing the neighborhood's charm and safety. The attached front-entry garage, complete with a garage door opener, offers easy access and additional storage space, while the asphalt driveway provides ample parking for guests. This home is not just a place to live; it's a sanctuary where comfort meets convenience. With its excellent condition and modern amenities, it's ready for you to create lasting memories. Don't miss the opportunity to make this beautiful home your own in the desirable Blackwater Landing community. Experience the perfect blend of style, comfort, and functionality in a space that truly feels like home. Images are licensed real estate marketing materials and are virtually staged.

1672 Terrapin Cir, Cambridge

Listing courtesy of KC Realty Group. Contact: info.kcrealtygroup@gmail.com
$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
$315,000
4 Beds ⋅ 3 Baths
Welcome to Blackwater Landing! Built in 2023, this move-in ready 4-bedroom, 2.5-bath home offers the perfect blend of modern style and everyday comfort. The open-concept layout features a spacious living area and an eat-in kitchen complete with granite countertops, stainless steel appliances, and a peninsula island—ideal for entertaining or daily living. Upstairs, the owner’s suite offers a walk-in closet and private bath, while three additional bedrooms and a conveniently located second-floor laundry room provide plenty of space and functionality. A two-car garage adds extra storage and convenience. Located just minutes from downtown Cambridge, shopping, dining, and Route 50, this home is ready for its next owner.

1625 Terrapin Cir, Cambridge

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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
$179,900
2 Beds ⋅ 2 Baths
New price reduction! This charming 2-bedroom, 2-bathroom, top floor unit in the desirable Deep Harbour gated community offers a blend of comfort and convenience. Enjoy access to the community pool, Cambridge Creek and many local amenities such as shopping, dining, and recreational activities. Available for purchase or lease.

900 Marshy Cv Unit #401, Cambridge

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

$370,990
4 Beds ⋅ 4 Baths
Enjoy stunning golf course views from the backyard of this beautifully designed two-story villa featuring a spacious paver patio and attached two-car garage. Designed for comfortable main-level living, the home offers a luxurious first-floor owner’s suite and an open-concept layout perfect for everyday living and entertaining. The gourmet kitchen flows seamlessly into the dining area and expansive Great Room, creating a bright and inviting gathering space. Upstairs, an open loft overlooks the Great Room and provides additional flexible living space. Three secondary bedrooms surround the loft, including a second owner’s suite—ideal for multi-generational living, extended guests, or added privacy. The additional bedrooms offer plenty of room for family, visitors, a home office, or hobby space. Combining elegant finishes, thoughtful design, and picturesque golf course views, this exceptional home delivers both comfort and versatility.

2125 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$395,000
4 Beds ⋅ 3 Baths
Built just one year ago and barely lived in, this spacious 4-bedroom, 2.5-bath home in Longboat Estates offers modern comfort and an unbeatable Eastern Shore lifestyle. The open-concept floor plan features luxury vinyl plank flooring, a beautifully appointed kitchen with granite countertops, stainless steel appliances, and a large center island, all flowing into a bright family room with a gas fireplace. Upstairs, the spacious primary suite includes a walk-in closet and private en-suite bath with dual vanities and an oversized tiled shower. An attached two-car garage, generous living spaces, and a private backyard backing to trees complete the package. Enjoy access to community amenities including a pool, boat ramp, and dock. Conveniently located just minutes from downtown Cambridge, waterfront dining, marinas, the Choptank River, Blackwater National Wildlife Refuge, and the Harriet Tubman Underground Railroad Visitor Center. Enjoy the benefits of nearly new construction without the wait!

178 Regulator Dr N, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$359,990
4 Beds ⋅ 3 Baths
Enjoy stunning golf course views from this brand-new construction villa featuring a desirable main-level owner’s suite and a low-maintenance lifestyle. Thoughtfully designed, this two-story home offers an open-concept layout with soaring ceilings, a gourmet kitchen, spacious family room, versatile flex space, and a luxurious primary suite on the first floor. Upstairs, a central loft provides additional living space and is surrounded by three secondary bedrooms, along with an unfinished storage area for added convenience. Outdoor living is equally impressive with a screened porch and private paver patio overlooking the golf course—perfect for relaxing or entertaining while taking in the scenic views.

2131 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$294,900
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
$305,000
3 Beds ⋅ 4 Baths
Beautiful End-Unit Townhome Loaded with Upgrades – Move-In Ready! Welcome home to this stunning 3-bedroom, 2.5-bath end-unit townhome located in the desirable gated community of Deep Harbour. Offering modern upgrades and spacious living across three levels, this home combines comfort, style, and convenience. The first floor features wood flooring, a large recreation room or home office, complete with a convenient half bath and access to the attached one-car garage. On the second level, you'll also find wood flooring throughout with an open and inviting floor plan featuring a spacious kitchen with Corian countertops, upgraded cabinetry, stainless steel appliances, and a dining area with access to a generous 10' x 20' deck—perfect for entertaining or relaxing outdoors. The large living room provides ample space for gathering, while the stylish shiplap accent wall in the half bath adds a touch of charm. Enjoy the amazing cross breeze when the windows are open. The third level features a spacious primary suite with a tray ceiling, walk-in closet, and an elegant en-suite bath offering a double vanity and a large tiled walk-in shower. Two additional bedrooms and a full bath complete this level. Residents of Deep Harbour enjoy gated community amenities, including a community pool, marina, and scenic jogging and walking paths. Conveniently located near downtown entertainment, dining, shopping, and grocery stores, you'll have everything you need just minutes from your doorstep. Don't miss the opportunity to own this beautifully maintained townhome in one of the area's most desirable waterfront communities. Schedule your private showing today! Tenant occupied -available for ownership on or after August 17, 2027

301 Shipyard Dr Unit #59, Cambridge

Listing courtesy of Keller Williams Select Realtors of Cambridge. Contact: 4102711265
$449,900
4 Beds ⋅ 3 Baths
Experience the best of Eastern Shore living at 419 Osprey Circle, a spacious and beautifully appointed home offering over 3,400 square feet of thoughtfully designed living space in one of Cambridge's most desirable neighborhoods. Combining generous room sizes, flexible living areas, and an exceptional location just minutes from the waterfront, this home delivers the perfect blend of comfort, convenience, and lifestyle. Step inside to discover a dramatic two-story family room filled with natural light that serves as the heart of the home. The open and inviting floor plan offers plenty of space for both everyday living and entertaining, while a dedicated main-level office or den provides the perfect setting for remote work, studying, or a private retreat. The upper level is highlighted by an impressive luxury primary suite designed to be your own private sanctuary. This expansive retreat features a large bedroom, a separate sitting area, a stunning fully renovated spa-inspired bathroom, and a custom walk-in closet that offers both beauty and exceptional storage. Also located upstairs is a spacious loft or den overlooking the two-story family room below, creating additional living space that could easily be converted into a fourth bedroom if desired. Outside, the property offers a generous yard with plenty of room to relax, entertain, garden, or simply enjoy the peaceful surroundings. Located just minutes from historic downtown Cambridge and the scenic shores of the Choptank River, residents enjoy easy access to waterfront dining, marinas, parks, shopping, and year-round outdoor recreation. Cambridge has become one of Maryland's most sought-after waterfront communities, known for its vibrant downtown, rich maritime heritage, boating, fishing, kayaking, paddleboarding, and proximity to the renowned Blackwater National Wildlife Refuge. The area is also home to the internationally recognized IRONMAN Maryland and Eagleman 70.3 triathlons, which attract athletes and visitors from around the world each year. These iconic events showcase Cambridge's stunning waterfront setting, scenic country roads, and active outdoor lifestyle, adding to the energy and appeal of this unique community. Whether you're enjoying a day on the water, exploring local restaurants and shops, or simply relaxing in your spacious home, 419 Osprey Circle offers an opportunity to embrace the lifestyle that makes Maryland's Eastern Shore such a special place to live. Conveniently located within easy reach of Annapolis, the Delaware and Maryland beaches, and the Washington-Baltimore metropolitan area, this exceptional property is ready to welcome you home.

419 Osprey Cir, Cambridge

Listing courtesy of RLAH @properties. 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