Dering Harbor, NY

Tucked onto the quiet northern shore of Shelter Island, Dering Harbor is New York's smallest incorporated village, home to around 50 year-round residents. Originally established as a tranquil 19th-century summer retreat, this pocket-sized community offers unmatched privacy and classic coastal charm. Life here revolves around the water, with picturesque views of the bay and easy access to the nearby ferry heading over to Greenport on Long Island's North Fork. While daily essentials, schools, and community services are shared across the wider island, Dering Harbor remains a peaceful, secluded haven for anyone seeking true waterfront tranquility.