Martha's Vineyard, Massachusetts, USA

Living in Martha's Vineyard

Iyna Bort Caruso

Some second-home communities mirror real life. They serve up a familiar lifestyle. The only difference is the surroundings. But off the Massachusetts coast, Martha’s Vineyard is a second-home luxury real estate community transplanted in time.

Martha’s Vineyard is New England’s largest resort island, located seven miles off the mainland or about a 45-minute ferry ride away. Its year-round population of 20,000 swells to five times the size with seasonal visitors hankering for a toehold in the sand. The Martha's Vineyard luxury home area is composed of six villages: the “up-island” communities of Chilmark, West Tisbury and Aquinnah, which tend to be more rural and private, and the more populous “down-island” enclaves of Oak Bluffs, Tisbury and Edgartown. Despite its popularity, the Vineyard remains authentic. High profilers come here to lay low. It is still a region of farm stands, country roads and Victorian gingerbread cottages. Barron listed the Vineyard among the top second-home locations in America.