27. Rye, New York (Average Household Income: $297,011)

Rye is located north of New York City and rather close to the border of Connecticut. There are two particularly historic landmarks within Rye: the Boston Post Road Historic District and Playland Amusement Park.

It’s characterized by a significant quantity of rock, marshes, and wetlands, which makes the town both desirably scenic and also challenging for developers. This could explain why it’s so expensive to live there.