Westport Connecticut
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Area Description

Westport has established itself as a suburban, commuter town, providing residents easy access to New York and other major cities in Connecticut. The town's natural beauty appeals to affluent city workers who move to the more affluent neighborhoods, while it's outstanding school system educates their children. It became something of a cultural haven in the 1920's, and that vibe lasts to this day, with excellent arts and cultural facilities.

Area Highlights

The Neighbors

Families, affluent, very well-educated, commuters, executives, management, financial workers, scientists and technical service workers.


House prices above state average, average sales numbers, bigger homes, suburban neighborhoods.


Quiet, residential, strong sense of community, local events.

You'll Love

The town’s history, coastal location, school system, proximity to New York, numerous parks and open spaces.

Perfect For

Commuting, raising a family, culture, arts, entertainment, exercising.

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Explore houses in Westport, a historical and cultural town located on Long Island Sound.

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Around the Area

Westport Connecticut, like much of New England, was settled by colonists in the 17th century, and was the scene of several battles during the revolutionary war. After its incorporation as a town in 1835, Westport became a prosperous agricultural community, but after blight destroyed much of the farm lands, mills and factories became the dominant industry.

During the 20th century, artists, authors and musicians moved to Westport to escape the commercial pressures of New York, leading to Westport becoming something of a cultural haven. When, in the 1950s, baby boomers and city workers discovered its cultural heritage, Westport became more of a commuter town, and the population grew rapidly.

During the early decades of the 20th century, several artists, writers and musicians moved to Westport to the escape the pressures of big city life; perhaps the most famous was F. Scott Fitzgerald. This cultural influence helped make the Westport Country Playhouse earn the description “one of the country’s most respected summer theaters.”

Compo Beach, on Long Island Sound, is listed on the National Register of Historic Places. The Westport town government owns Cockenoe Island, which is home to several bird rookeries and allows limited camping overnight during the summer months. The Westport parks department oversees a variety of parks which are ideal for picnics, exercise and recreation, hiking and biking and some even feature beaches.

Westport’s excellent school system has contributed to the rapid growth of new families moving to the area over recent decades. The only high school in the town was listed as one of the best 1,000 schools in the nation; the same year saw the completion of a near $80 million renovation, which saw Staples High School named the best high school in Connecticut in 2011. The local school district also has two middle schools - which, in 2011, ranked numbers 1 and 2 in the state - and five elementary schools.



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