Windward Key Homes with Pool

Windward Key Homes with Pool

Welcome to Windward Key, an enchanting subdivision nestled in the picturesque Chesapeake Beach, Maryland. This delightful community offers a perfect blend of coastal charm and modern living, making it an ideal destination for families, retirees, and anyone looking to embrace the serene lifestyle of the Chesapeake Bay.

Windward Key is renowned for its beautifully designed homes, many of which feature inviting pools, providing residents with a refreshing oasis to enjoy during the warm summer months. Imagine sipping your morning coffee poolside, or hosting lively weekend barbecues with friends and family, all while basking in the sun’s warm embrace. These homes are not just residences; they are a lifestyle choice that emphasizes relaxation and leisure.

The subdivision is conveniently located near the stunning beaches of the Chesapeake Bay, offering easy access to a variety of water activities such as boating, fishing, and kayaking. Windward Key is also in close proximity to local parks, hiking trails, and community amenities, ensuring that residents can enjoy the great outdoors year-round. The vibrant local community is filled with charming shops, delicious dining options, and engaging events, providing a perfect blend of relaxation and entertainment.

Whether you’re seeking a permanent residence or a seasonal getaway, Windward Key presents an exceptional opportunity to experience coastal living at its finest. With homes that boast pools and a community that embraces the beauty of nature, Windward Key is more than just a place to live; it’s a place to thrive. Come discover your dream home in this idyllic subdivision today!

Newest Windward Key Homes with Pool

$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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