14 Cow Bay Road, Edgartown

Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion, the property remains just minutes from the charm and sophistication of downtown Edgartown. The six-bedroom main residence is a masterclass in timeless design and effortless elegance. Grand yet inviting, the home offers beautifully proportioned living and dining spaces, a thoughtfully designed chef’s kitchen and a sweeping screened porch, all oriented to capture wonderful views across the pool and out to Vineyard Sound. Every room is infused with natural light and a sense of understated luxury. The grounds are nothing short of spectacular, a curated landscape of mature plantings, expansive stone terraces, and romantic pergolas draped in cascading wisteria. At the heart of the property, a stunning pool and lounge area create a private resort-like setting, ideal for both intimate relaxation and sophisticated, large-scale entertaining. A separate carriage/guest house with full amenities offers flexible accommodations for guests or staff. This is more than a home; it is a rare and irreplaceable offering, a legacy property in one of the island’s most coveted coastal settings.