Windward Key Homes with Traditional Style

Windward Key Homes with Traditional Style

Welcome to Windward Key, a charming subdivision nestled in the picturesque town of Chesapeake Beach, Maryland. This delightful community offers a serene escape from the hustle and bustle of city life, all while being conveniently located along the stunning shores of the Chesapeake Bay. With its rich history and vibrant local culture, Chesapeake Beach is the perfect backdrop for those seeking a peaceful yet engaging lifestyle.

Windward Key is known for its beautiful traditional-style homes, which exude timeless elegance and warmth. These residences feature classic architectural elements, such as inviting front porches, gabled roofs, and carefully crafted details that create a sense of community and belonging. Each home is designed with comfort and functionality in mind, making it an ideal choice for families, retirees, or anyone looking to enjoy the best of coastal living.

Residents of Windward Key benefit from easy access to a variety of recreational activities, including boating, fishing, and hiking in nearby parks. The community is also just a stone’s throw away from charming local shops, delicious dining options, and family-friendly attractions, ensuring there’s always something to explore.

As you stroll through the tree-lined streets of Windward Key, you’ll feel the warmth of a welcoming neighborhood where neighbors become friends. Whether you’re sipping your morning coffee on your porch or enjoying a sunset stroll along the bay, life in Windward Key is a beautiful blend of relaxation and adventure. Discover your dream home in this enchanting subdivision and embrace the idyllic lifestyle that awaits you in Chesapeake Beach!

Newest Windward Key Homes with Traditional Style

$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:

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