Chesapeake Beach Homes with Pool

Chesapeake Beach Homes with Pool

Welcome to Chesapeake Beach, Maryland—an enchanting coastal gem nestled in Calvert County, where the serene beauty of the Chesapeake Bay meets the charm of small-town living. This picturesque town is renowned for its stunning waterfront views, rich maritime history, and a vibrant community that welcomes newcomers with open arms. Whether you're strolling along the sandy shores, enjoying fresh seafood at local eateries, or exploring the scenic trails, Chesapeake Beach offers a lifestyle that's as refreshing as a gentle sea breeze.

For those seeking a home that combines comfort with leisure, Chesapeake Beach boasts an impressive selection of properties with pools. Imagine stepping into your backyard oasis, where you can unwind in the cool water after a long day or host unforgettable summer gatherings with family and friends. Homes with pools in this area are not just a luxury; they are a lifestyle choice that enhances your living experience.

With its close-knit community, excellent schools, and a variety of recreational activities, Chesapeake Beach is perfect for families, retirees, and anyone looking to enjoy a slower pace of life. The town's proximity to Washington D.C. and Annapolis also makes it an ideal location for commuters who want to retreat to a tranquil environment after a busy workday.

Explore the diverse range of homes with pools in Chesapeake Beach and discover your perfect sanctuary by the bay. Let the soothing sounds of the water and the warmth of the sun create the backdrop for your new life in this charming coastal community. Your dream home awaits!

Newest Chesapeake Beach Homes with Pool

$659,900
4 Beds ⋅ 3 Baths
Welcome home to this stunning property in the highly sought‑after Lake Karylbrook community, offering a serene, private setting on over 3 acres. This immaculate, professionally designed 4‑level home features 4 finished levels, nearly 3500 sqft of finished living space, 4 bedrooms, 2.5 baths, and a welcoming front porch, a spacious deck perfect for outdoor enjoyment. Step outside and enjoy summer to the fullest with your own inground pool—perfect for relaxing or entertaining. Inside, the open and airy layout is enhanced by beautiful hardwood floors, abundant natural light, chic recessed lighting, and a charming wood‑burning fireplace. The updated gourmet kitchen is sure to impress with granite countertops and stainless-steel appliances. The finished basement provides exceptional additional living space, including a large family room with a bar and a separate rec room/man cave on the lower level. This home blends comfort, elegance, and modern updates in a peaceful, desirable neighborhood. A must‑see property. Eligible for USDA 0% down Financing!!

3611 Karen Dr, Chesapeake Beach

Listing courtesy of RE/MAX Advantage Realty. Contact:

$719,900
5 Beds ⋅ 4 Baths
Price reduction and One year home warranty included!!!! Welcome to 4416 Snowy Egret Court, a stunning 5-bedroom, 3 full bath, 1 half bath home located at the end of a quiet cul-de-sac in the highly desirable Breezy Point Estates community of Chesapeake Beach. Just one mile from the Chesapeake Bay, residents enjoy beach passes and private water access all year, offering the perfect blend of coastal living and everyday convenience. This beautifully maintained home is packed with upgrades and designed for both comfortable living and entertaining. Major improvements include a new roof and expansive deck installed in 2021, new vinyl plank flooring throughout the entire home, a whole-house water softener system, updated well plumbing with a new pressure tank, and fresh paint throughout. The bright and inviting kitchen features classic white cabinetry, stainless steel appliances, generous counter space, and an open layout that flows seamlessly into the main living areas. Spacious rooms throughout the home provide flexibility for family living, guests, home offices, or hobby spaces. Step outside and discover your own private backyard retreat. The saltwater pool is perfect for cooling off on warm summer days, while the large deck offers plenty of space for grilling, entertaining, or simply relaxing and enjoying the peaceful setting. Nestled in one of Chesapeake Beach's most sought-after neighborhoods, this home offers the rare combination of community amenities, water privileges, modern updates, and exceptional outdoor living. With beach access and passes, Chesapeake Bay privileges, and a prime cul-de-sac location, 4416 Snowy Egret Court is the perfect place to enjoy the Maryland waterfront lifestyle.

4416 Snowy Egret Ct, Chesapeake Beach

Listing courtesy of Deep Roots Real Estate. Contact: 4439676687
$759,900
3 Beds ⋅ 5 Baths
Discover coastal living at its finest at 8048 Windward Key Dr, Chesapeake Beach! This "as-is" gem offers breathtaking views of the canal and the iconic Chesapeake Bay, placing you right in the heart of everything this charming waterfront town has to offer. Located just steps away from the renowned Rod 'N' Reel Resort, you'll enjoy the convenience of walking to local restaurants, marina boat storage, and more. Whether you're an avid boater or simply love the water, this property has you covered with on-site boat slips (not deeded). Picture yourself savoring every sunrise and sunset from your private decks or hosting friends and family as you take in the dazzling Chesapeake Beach fireworks right from the comfort of your home. It’s a lifestyle of relaxation, natural beauty, and endless opportunity. With so much more to discover, this is your chance to own a slice of paradise. Don't wait—this coastal retreat won't last long!

8048 Windward Key Dr, Chesapeake Beach

Listing courtesy of Compass. Contact: (410) 429-7425
$749,900
4 Beds ⋅ 5 Baths
COASTAL LUXURY MEETS EVERYDAY VACATION LIVING in Windward Key on the Chesapeake Bay. Experience the ultimate waterfront lifestyle in this four-level townhome nestled in the sought-after Windward Key community in the heart of Chesapeake Beach. Whether you are searching for a full-time residence or the perfect weekend retreat, this exceptional home offers resort-style living with water views and upscale amenities throughout. Designed for both comfort and entertaining, the home features 4 bedrooms, 4 full baths, and 1 half bath across four spacious levels filled with natural light. The main living level showcases a well-appointed kitchen, dining area, and expansive great room with a cozy gas fireplace — all enhanced by water views and an open, airy feel. The upper level hosts the primary suite along with two additional bedrooms, while vaulted ceilings create an inviting sense of space and elegance. The top level offers exceptional flexibility with its own full bath, wet bar, and private deck, ideal for a home office, guest suite, lounge, or entertainment space overlooking the Bay. The entry level provides additional finished living space with a full bath, perfect for guests, recreation, fitness, or flex living. Direct access to the attached one-car garage adds convenience and functionality. Outdoor living is elevated with multiple decks on every level, creating seamless indoor-outdoor enjoyment and endless opportunities to relax and take in the coastal setting. Residents of Windward Key enjoy exclusive amenities including a waterfront pool overlooking the Chesapeake Bay and a private beach. Located within walking distance to restaurants, shops, parks, boardwalks, marinas, nature trails, and local entertainment, this is Chesapeake coastal living at its finest.

8076 Windward Key Dr, Chesapeake Beach

Listing courtesy of RE/MAX Realty Group. Contact:

$774,900
4 Beds ⋅ 5 Baths
MAJOR PRICE IMPROVEMENT. Experience an elevated waterfront lifestyle in the coveted Windward Key community, ideally positioned along the shores of the Chesapeake Bay in the heart of Chesapeake Beach. This exceptional four-level townhome blends refined design with water views, offering 3 bedrooms, 4 full baths, and 1 half bath across thoughtfully designed living spaces. Sunlight pours through expansive windows, illuminating rich cherry hardwood floors that flow throughout the main and upper levels. The main living level is designed for both elegant entertaining and everyday comfort, featuring a spacious great room with a gas fireplace, an inviting dining area, and a well-appointed gourmet kitchen with stainless steel appliances, pantry, and wine refrigerator. Step onto the private deck to take in tranquil bay and fishing creek views—perfect for morning coffee or evening gatherings. The lower level offers a versatile recreation space with a full bath and dedicated laundry room, ideal for guests or extended living, with seamless access from the attached garage. From here, step outside to your deck and connect directly to the waterfront walkway, embracing the true essence of coastal living. Upstairs, the primary suite serves as a luxurious retreat, complete with a custom closet system, additional storage, and a spa-inspired bath featuring a jetted soaking tub and separate shower. A private deck off the suite captures breathtaking water views, creating a serene escape. This level also includes an additional bedroom and full bath. The top level provides exceptional flexibility, offering a private suite with full bath and walk-in closet—perfect as a fourth bedroom, executive office, or fitness studio—opening to yet another deck with sweeping, unobstructed views of the bay. An attached garage, additional storage, and private driveway ensure convenience, while Windward Key residents enjoy exclusive amenities including a pool and private beach. Just moments from and walking distance to local dining, shopping, marinas, water sports, and the Chesapeake Beach Water Park, this home also offers easy access to Washington DC, Annapolis, Joint Base Andrews, and Northern Virginia. Live where you play—and indulge in the luxury of waterfront living every day.

8054 Windward Key Drive, Chesapeake Beach

Listing courtesy of RE/MAX Realty Group. Contact:

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