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.
Listed by Gerrett Conover of Landvest MV

Property Details of 14 Cow Bay Road, Sengy

Property Details

Interior Features

Based on information submitted to LINKMV as of May 14, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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