From 1652, when Nathaniel Sylvester, a sugar merchant from Barbados, acquired sole title to Shelter Island and became its first white residents to 1730, when it became a town, the island developed slowly. By mid-century some 900 islanders farmed and made fertilizer from the mossbunker herring. The northwest corner of the island, eventually the Heights, was bought up in the early 19th century by Frederick Chase, who named his domain Prospect.
In 1871 a group of 24 Brooklyn clergymen and laymen, incorporated as the Shelter Island Grove and Camp Meeting Association of the Methodist Episcopal Church, purchased the Chase acres on the condition that the two factories converting mossbunker herring to fertilizer be removed. After 8 years the camp meetings were moved to Jamesport. Today the Shelter Island Heights Property Owners Association is committed to preserving the distinctive character of the community, its historic buildings and its physical environment.
But from the beginning the Heights was conceived as a community with parks, open spaces, a hotel, and lots for private residences. Between 1872 and 1880 about 70 cottages were constructed; by the late 1880s another 30 were added; by 1890 the current layout was defined.
The second wave of development (after 1880) saw larger houses in a variety of styles: Stick, Queen Anne, and Colonial Revival. They feature elaborate embellishments on porches and a sense of fantasy that is derived from a combination of clapboard siding, bands of scalloped shingles, and elaborate, cut-work balustrades and carved friezes.
Equally significant is the manner in which the planners exploited the natural configuration of the site. The 300 or so acres rise gradually from the shore to reach the impressive (for Long Island) height of 150 feet above sea level. The Heights is bounded by water on three sides, making a view of the sound and bays available from many vantage points. All the original roads are laid out in a series of sweeping curves that descend in a broad scallop pattern to the water’s edge.