37 North Neck Road

Experience the ultimate Vineyard getaway at this extraordinary Chappy waterfront estate. Complete with a 140-foot deepwater dock, five bedroom main house and three bedroom guesthouse, this property offers a rare blend of seclusion, luxury, and recreation. Just minutes from Edgartown village, yet worlds apart in privacy and tranquility.

The main residence is architecturally striking, yet warm and welcoming. Nearly every room enjoys sweeping views of Nantucket Sound, while thoughtful details abound including fir floors, shiplap walls, and a large porch supported by locust posts. Built to the highest standards, the home features five bedrooms, including a spectacular second floor primary suite with panoramic water views. A fully equipped gym including steam shower and sauna are located on the lower level, and the expansive great room with large dining table makes entertaining effortless.

The outdoor spaces are equally captivating. Rolling lawns extend to a private sandy beach, perfect for swimming, paddle boarding, or relaxing from one of two floating platforms at the dock. From here, enjoy a front row seat to yacht regattas and stunning sunsets.  The deepwater dock accommodates vessels with a 6–8 ft draft and includes two moorings.

The guesthouse is privately set apart with its own kitchen, living area, and three comfortable bedrooms, ideal for extended family or guests.

Located across from the Royal and Ancient Chappaquiddick Links for a quick round of golf and just minutes to Downtown Edgartown's shops and restaurants.