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Shelter Island, N.Y.

Average household income: $102,386

Shelter Island is that 12-square-mile land mass between the North and South Forks of Long Island, in the Long Island Sound. The population multiples in the summer, and tourists have vacationed in the summer cottages of Shelter Island Heights since the late 1800s. Notable residents include fashion commentator Simon Doonan, actress Julie Kavner and the author Robert Lipsyte.

H. Gruber | Flickr