Shelter Island, NY

Shelter Island Heights sits on the northern tip of Shelter Island, serving as the first welcoming sight for anyone taking the ferry over from Greenport. Home to about 1,600 year-round residents, the neighborhood has the feel of a historic coastal village, known for its colorful Victorian gingerbread cottages tucked along hilly, tree-lined lanes overlooking Dering Harbor. While summer brings seasonal visitors, the area maintains a peaceful, tight-knit atmosphere throughout the rest of the year.

ATTRNatecation / CC BY-SA 4.0

Everyday living in the Heights is convenient and relaxed, with local bakeries, small markets, and the ferry landing all within easy walking distance. Local children attend the Shelter Island School District, which educates students from kindergarten through twelfth grade in a single community school. It gives residents a quiet, scenic island retreat that still enjoys straightforward connections to both the North and South Forks of Long Island.