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.