Locals mostly know Madison as a quintessential laid-back beach town with a best-kept-secret feel. But word has gotten out: The community is drawing more and more second-home owners from neighboring metropolises. And although the majority of houses here are Colonial and Cape-style, averaging just below $500,000, the spectacular cedar-shingled waterfront homes—tucked among the hydrangeas of Middle Beach Road and Middle Beach West, and dotting the small streets off Liberty Road—go for millions.
"Often, buyers start out as summer folks," says native Kirsten Adams, who returned five years ago after a stint in San Francisco, "but then they fall in love with the town and realize that Madison is a wonderful place to live year-round. My husband and I made the decision to come back for family and a simpler way of life. It's a great town."
Left: Beautiful homes facing Long Island Sound