30 Water Gate Road, Vineyard Haven

Set privately in one of Vineyard Haven’s most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and ready access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for both gathering and quiet retreat, with an effortless indoor-outdoor flow that embraces the surrounding landscape. Bedrooms are thoughtfully positioned on opposite wings of the home, with three on one side and two—along with a striking office—on the other. The primary suite is exceptionally private, overlooking neighboring lawns, gardens, and the conservation land.

The main living room is warm and inviting, anchored by a massive wood-burning fireplace and complemented by beautiful hardwood floors. A chef’s kitchen connects seamlessly to both indoor and outdoor living areas, ideal for entertaining. An attached two-car garage adds convenience.

The grounds feature a wide-open lawn bordered by a classic stone wall, mature plantings, and established garden beds, including a fenced vegetable garden. A post-and-beam barn/boathouse offers flexible space for storage, recreation, or workshop use. Ownership includes access to neighborhood tennis courts and a dock on Lake Tashmoo, making it easy to enjoy morning paddles, sunset swims, and the best of Vineyard coastal living. A property of this scale, setting, and heritage rarely comes to market—an opportunity to carry forward a truly special family estate that combines an “up-island” feel with the convenience of nearby shops and restaurants.

First Floor

Two wings of the house - one with the kitchen, laundry, a large living room with fireplace, and the primary suite and the second with a living room with cathedral ceiling, two full bathrooms, a den and the office on the end.

Second Floor

Two sections upstairs - one with two bedrooms and a full bathroom and the second with a landing and a spacious bedroom.

Basement

Unfinished basement for storage. Part crawl space.

Parking

Peastone Driveway

Other Buildings

Barn for storage/rec space/workshop.