Georgetown, CT

Set in the wooded hills of Fairfield County, Georgetown is a charming historic village sitting right at the crossroads where Wilton, Redding, Weston, and Ridgefield meet. Home to around 1,800 people, the village originally developed around the 19th-century Gilbert and Bennett wire mill and still preserves a distinct, antique character. Quiet residential streets branch off the main roads, lined with well-kept historic homes, local shops, and neighborhood restaurants.

ATTRPedro Xing / CC0

For prospective homebuyers, Georgetown has an interesting quirk: because the village straddles multiple borders, your property taxes, municipal services, and school district depend on which side of the town line your house falls on. Despite those administrative boundaries, residents share a tight-knit community anchored by the walkable village center, a dedicated local fire department, and easy driving routes into the surrounding commuter hubs.