Chappy Waterfront Estate | Private Beach & Dock

Escape to Chappaquiddick at this private waterfront estate with five bedrooms in the main house and a three-bedroom guesthouse. Enjoy sweeping Nantucket Sound views, a private sandy beach, and a 140-foot deepwater dock for boating and paddleboarding. Spacious indoor and outdoor living areas, a gym with sauna, and a prime location near Edgartown make this the perfect getaway for family and friends. The space Waterfront compound with main house and separate guesthouse on Chappaquidick Island, offering privacy and panoramic Nantucket Sound views from nearly every room. Main House Open layout with warm fir floors and shiplap walls; expansive great room with fireplace and dining area; 5 bedrooms (2 on first floor, 3 on second including primary king suite); finished lower level with gym, steam shower, and sauna; large wrap-around porch flowing to rolling lawns. Guesthouse Independent with own kitchen and living area; 3 bedrooms for added separation. Outdoor Spaces Gentle lawns to a private sandy beach and a deepwater dock; seamless indoor-outdoor flow with water vistas dominating. Ideal serene retreat for groups up to 16 Guest access Access instructions are provided once a booking is made Other things to note EXCLUSIVE WATERFRONT RETREAT on Chappaquiddick Island * Sweeping panoramic views of Nantucket Sound from nearly every room. Front-row seat to yacht regattas and breathtaking sunsets. * Private sandy beach with direct access to calm waters – perfect for swimming, paddleboarding, kayaking, or relaxing shoreside. * 140-foot deepwater dock (accommodates boats with 6–8 ft draft) plus two moorings and two floating platforms. Bring your boat! * Across the road from the historic Royal & Ancient Chappaquiddick Links – step out for a round on this charming 9-hole hidden gem. * Secluded privacy yet just minutes by car to vibrant downtown Edgartown for fine dining, boutique shopping, and island attractions. * Spacious compound: Main house + separate guesthouse (total 8 bedrooms, 6 bathrooms) sleeps up to 16 comfortably. Ideal for large families or groups. * Main House Highlights – Architecturally striking with warm fir floors and shiplap walls; expansive great room with fireplace; gourmet kitchen; central AC; private gym with steam shower and sauna; ping pong table; smart TVs; washer/dryer. * Guesthouse Perks – Own full kitchen and living area for added privacy; perfect for extended family or guests. * Outdoor Bliss – Rolling lawns to the water; large porch with outdoor dining and furniture; outdoor shower. Linens provided. * Ultimate Martha’s Vineyard escape blending tranquility, recreation, and refined coastal luxury. Paradise on Chappy!