Located along Connecticut's Gold Coast just 48 miles from New York City, Westport offers a coastal lifestyle with access to Long Island Sound beaches and an established arts scene. The Westport Country Playhouse anchors the town's cultural offerings, while downtown features independent shops and restaurants. The average rent of $2,930 reflects the town's premium housing market.

Westport's neighborhoods each have distinct characteristics. Saugatuck, near the southwestern train station, features walkable streets lined with local businesses. Greens Farms, the town's oldest neighborhood, maintains its historic character and has its own train station. Compo provides waterfront living opportunities, while Westport Village centers around Post Road and Main Street, where shops and restaurants line the Saugatuck River.

Two Metro-North Railroad stations serve Westport, with trains reaching Manhattan in approximately one hour. Interstate 95 and the Merritt Parkway provide driving routes to surrounding areas, while local buses connect neighborhoods. The town hosts numerous financial services and professional firms, including Bridgewater Associates. Westport's public schools consistently rank among Connecticut's top districts.