Vineyard Haven

Vineyard Haven is the Island’s working harbor and its year-round front door — the Steamship Authority runs here every day of the year, and that shapes the town. Main Street stays open through the winter, with a bookshop, a hardware store and a grocery rather than a season’s worth of boutiques. Homes for sale run from village houses within walking distance of the ferry to properties on West Chop, where the bluff looks north across Vineyard Sound, and around Lake Tashmoo. Buyers who mean to live here rather than visit tend to look in Vineyard Haven first: the shortest trip off-Island, the most year-round neighbours, and the least seasonal swing of the six towns.