16. Old Greenwich, Connecticut (Average Household Income: $321,377)

Old Greenwich, Connecticut has long been considered a haven for a number of big-wig Wall Street executives. As a matter of fact, Bernie Madoff’s wife, Ruth, is one of the town’s most notable residents.

In several write-ups about Old Greenwich, authors describe it as a town of huge houses that manages to maintain a seemingly small-town vibe. It shares a view of Long Island Sound with the next town on this list.