Westport

Westport has often been chosen by Hollywood to play the part of the picture-perfect suburb, with its pretty estates with rolling lawns and its two quaint downtowns. It’s not just an act though, Westport really is a lovely town, located on the banks of the Long Island Sound and with the Saugatuck River running through its center. By the 1900s, Westport had become the suburb of choice for the creative class, serving as the honeymoon destination for F. Scott and Zelda Fitzgerald, and becoming home to many other artists, including a large group of cartoonists. And of course, Paul Newman and Joanne Woodward lived in Westport for more than 40 years. That bohemian spirit still lives on in Westport, even if it's cloaked in lush respectability and grand, modern farmhouses. But twitch your nose like Bewitched’s Samantha (a longtime fictional Westport resident) and you’ll discover Westport’s magic.

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Living in Fairfield County

Fairfield County is often called Connecticut’s Gold Coast, referring to a string of waterfront towns that glisten in the sun, with hubs of finance interlaced with beach towns and nautical villages—albeit villages with some of the prosperous populations in the country. The station names called off by the train conductors evoke images of ultimate suburbia: Greenwich, Stamford, Darien, Norwalk, and Westport. Residents have long been drawn to Fairfield County because of its proximity to New York City, thanks its many stops on the commuter rail, while offering idyllic country acreage, as well as views and access to the Long Island Sound. Houses here include aristocratic estates, where sailing and horseback riding is still a part of daily life; glass-walled architectural Modernist icons; and solid, historic clapboard Colonials that might have been models for a 19th-century painting.