Cambridge Homes with Pool

Cambridge Homes with Pool

Welcome to Cambridge, Maryland – a hidden gem nestled in Dorchester County, where history meets modern living along the picturesque banks of the Choptank River. Known for its charming waterfront views and rich cultural heritage, Cambridge offers a unique blend of small-town warmth and vibrant community spirit. With its historic downtown filled with boutique shops, art galleries, and delightful eateries, residents enjoy a lifestyle that is both relaxed and engaging.

One of the standout features of this lovely city is its abundance of outdoor recreational opportunities. From the serene landscapes of the Blackwater National Wildlife Refuge to the scenic trails of the Cambridge Creek, nature enthusiasts will find endless ways to explore and appreciate the beauty of the Eastern Shore.

For those seeking a home that combines comfort with luxury, Cambridge boasts a selection of stunning properties that come equipped with private pools. Imagine basking in the sun on a warm summer day, enjoying a refreshing dip in your own backyard oasis, or hosting unforgettable gatherings with family and friends around the poolside. These homes not only provide a perfect retreat for relaxation but also elevate your lifestyle with the ultimate in outdoor entertainment.

Whether you are a first-time homebuyer or looking to upgrade your living space, Cambridge offers a diverse range of homes with pools that cater to every taste and budget. Experience the charm of this remarkable city while enjoying the luxury of your own private escape. Discover your dream home in Cambridge today, where every day feels like a vacation!

Newest Cambridge Homes with Pool

4 Beds ⋅ 4 Baths

Beautifully positioned backing to the golf course, this move-in ready luxury 4-level end-unit townhome is located in Lennar's premier waterfront community of Tides at River Marsh on Maryland's scenic Eastern Shore. Offering 3 bedrooms, 3 full baths, 1 half bath, and a 2-car garage, this home features 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 fourth-level loft opens to a private rooftop deck, perfect for relaxing or entertaining. 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, championship golf, and nearby marina access. Conveniently located just minutes from downtown Cambridge's shopping, dining, and waterfront attractions, with easy access to Annapolis and Delaware beaches.

2206 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

2 Beds ⋅ 2 Baths

Experience the best of Eastern Shore living in this beautifully appointed, fully furnished condo located in a gated waterfront community. This turnkey home offers 2 spacious bedrooms, 2 full bathrooms, and 1,610 square feet of thoughtfully designed living space. Designer furnishings throughout create an elegant, move-in-ready retreat, making it perfect as a full-time residence, weekend retreat or investment. Enjoy the relaxed waterfront lifestyle with the comfort, security, and amenities of this exceptional community.

700 Cattail Cove Unit #411, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

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

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:

3 Beds ⋅ 3 Baths

Move right into this beautiful home in Cambridge’s historic district! It features a fully updated kitchen and baths, a new HVAC system, and a picture-perfect front porch. The attic and crawlspace have been improved for optimum energy efficiency. For a fun, modern twist, head up the cool spiral staircase to a fully finished third-floor space. Outside, enjoy a fantastic backyard with raised garden beds already in place, a storage shed, and alleyway access. Off-street parking. Love the look? The owner will even consider parting with some of the furnishings!

109 Willis St, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

2 Beds ⋅ 2 Baths

Welcome to Penthouse #302 at Oakley Beach, one of Cambridge’s most desirable waterfront condominium communities. Perched on the top floor, this beautifully appointed 2-bedroom, 2-bath residence offers breathtaking panoramic views of the Choptank River and the convenience of low-maintenance waterfront living. Inside, you'll find an open and inviting floor plan featuring 9-foot ceilings, gleaming hardwood floors, and a well-appointed kitchen with granite countertops, quality cabinetry, and ample workspace. The spacious living area is accented by a cozy gas fireplace and opens directly to a covered balcony where you can relax and take in the stunning river vistas. A rare and highly desirable bonus, the sale includes a deeded boat slip, providing direct access to the Choptank River and making it easy to enjoy boating, fishing, and waterfront adventures right from your community. Located within Cambridge’s Historic District, Oakley Beach is just minutes from downtown shops, restaurants, galleries, and waterfront attractions. This thoughtfully designed penthouse is ideal as a full-time residence, weekend retreat, or vacation getaway. With only 24 residences spread across four elevator-served buildings, residents enjoy a peaceful and private setting along with exceptional community amenities, including a swimming pool, common pier, beautifully maintained grounds, and abundant guest parking. If spectacular water views, upscale finishes, and turnkey living are what you're seeking, Penthouse #302 at Oakley Beach deserves your attention.

3 Oakley St, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800

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:

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:

4 Beds ⋅ 3 Baths

From the inviting front porch, upgraded stone-accented exterior, to the to the fully fenced backyard, this beautifully maintained 4BR/2.5BA is ready to impress. Natural light fills the open living spaces, highlighted by a cozy gas fireplace and a stylish kitchen featuring granite countertops, stainless steel appliances, a pantry, and a center island perfect for gathering. The main level also offers a private office, or an additional welcome area, while upstairs you’ll find four spacious bedrooms, convenient second-floor laundry, and a generous primary suite with a walk-in closet and dual-sink vanity. Solar panels provide added efficiency, and community amenities including a pool and docks offer the perfect setting for enjoying the Eastern Shore lifestyle. Simply unpack and start enjoying everything this beautiful home and amenity-rich community have to offer.

502 Regulator Dr S, Cambridge

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

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:

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:

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

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