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Living in Westport CT

Westport is a unique and flourishing New England community with a cosmopolitan feel and vibrant cultural life, situated just 40 miles outside of New York City and located on the beautiful Long Island Sound. Westport’s transportation options contribute to its vitality, with easy access to Interstate 95, the Merritt Parkway, and two Metro-North stations serving Stamford and Grand Central Terminal.

Westport has approximately 27,000 residents and nine different neighborhoods, each with its own distinctive characteristics and small-town feel. Primarily a single-family home community, the neighborhoods range from modern coastal homes to beachfront properties near Compo Beach and Saugatuck Shores, riverfront properties, historic houses, exclusive neighborhoods, and quaint residences in walkable neighborhoods located near the center of town.

A major draw to Westport for families is its extraordinary education system with five elementary schools, two middle schools, and one of the highest-ranked high schools in the state and nation – Staples High School. Staples high school voted #1 in CT on Niche 2021. Westport is also home to two outstanding K-12 private school options; Greens Farms Academy and Pierrepont School.

Residents of Westport enjoy two downtown areas. Main Street is a lively and walkable downtown with a wide variety of specialty stores, boutique shops, small businesses, and an exciting restaurant scene. In Saugatuck Center, you will find a historic revitalized retail and dining destination.
Westport is one of the top Fairfield County dining destinations with its eclectic mix of dining choices. You can enjoy everything from fine dining to quintessential New England taverns to historic establishments to a variety of outdoor dining experiences. With over 70 dining options and a wide array of acclaimed restaurants to choose from, Westport is a top go-to destination in Fairfield County for dining.

Westport also offers exceptional recreational facilities to promote a healthy lifestyle. There are three public beaches with miles of shoreline, one state beach, two marinas, the Long Shore public golf course, tennis courts, two public pools, a sailing school, and the Westport/Weston YMCA.

Nature lovers have many opportunities to enjoy the outdoors in Westport, including community gardens, weekly farmers market (Westport Farmer’s Market voted top 10 in the Northeast), a variety of beautiful parks and conservation trails as well as the Earthplace Nature Discovery Center, the Wakeman Town Farm Sustainability Center, and Newman Poses Preserve, to name a few.

There are a number of private country club options in town. The Birchwood Country Club has a 9-hole golf course cited among the top 20 in the country which also houses tennis and swimming facilities. For equestrian lovers, there is the Fairfield County Hunt Club, Connecticut’s premier equestrian country club. It is a year-round club on 40 acres of scenic property that includes dining, event venue, clubhouse, stables, indoor riding arena, tennis courts, paddle tennis courts and swimming pool. For those that love the water scene, there is the Saugatuck Rowing and Fitness club, a private rowing club located on the Saugatuck River.

Westport is also home to outstanding cultural and entertainment venues, including the Westport Country Playhouse, Community Theater, Levitt Pavilion for the Performing Arts, Museum of Contemporary Art, the Museum for History and Culture, and the Astronomical Society. The town draws over 12,000 inventors, innovators and creative individuals each year to the largest one-day event called Maker Faire Connecticut — a venue for “makers” to show hobbies, experiments and projects. Other not-to-be-missed annual events include the Memorial Day Parade, The Great Duck Race, the summer concert series at Levitt Pavilion, Yankee Doodle Fair, and the Festival of Fine Arts.

For you entrepreneurs, Westport is a great place to grow and launch a business:

Westport Means Business. Westport is a great place to live, raise a family — and grow and launch a business.
• Westport is #3 in CT Top Business Friendly Towns
• Westport ranked among the Top 500 Cities to Start a Small Business

Westport is ranked an A+ community to live. The town has approximately 9,900 homes and apartments in town covering over 20 square miles. The majority of the homes (86%) are single family 3 and 4 bedrooms. Many of the homes are sited on 1 to 2 acres. The median sale price for a home in Westport in the beginning of 2021 was $1,600,000.

Westport is ranked the #1 small city in the state of CT. You can have it all in Westport. The convenience of living near New York City, enjoy the town character with its culture, arts, a variety of amenities from beach, boating, parks, pools, golf, dining all while maintaining its small-town New England character. To learn more about the housing market and moving to Westport, let’s chat!