Oak Bluffs

Oak Bluffs is the liveliest of the six towns and the easiest to walk. Its Campground holds more than three hundred gingerbread cottages — carpenter Gothic, painted in colours no other town would permit — set in circles around the Tabernacle. Ocean Park fronts the water with a bandstand at its centre, and Circuit Avenue carries most of the Island’s restaurants and evening life. Homes for sale range from cottages standing a few feet apart in the Campground to shingled houses on the East Chop bluff with Nantucket Sound in front of them. Oak Bluffs is the most affordable of the down-Island towns to buy into, has the strongest year-round rental demand, and has a ferry terminal in the middle of it.