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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 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.

Completely renovated 3 br colonial on private rd in Westport with private gate right off Post Road. New Hardwood fl throughout, New windows, New kitchen/bath with new SS appliances, marble counter tops. 
1st Fl has open floor plan with full nature light, dinning room has sliders to deck on back of house. 
2nd fl has 3 BR / 2 full baths plus one office / nursery room . Master bedroom has full bath and sliders to private deck. 
Lower level is finished with tile floor leading to large 0.44 acre flat backyard ( 0.23 acre backyard in Norwalk , 0.21 acre in Westport)..
House has oilheat, high efficient split air conditions also offer hot/cold air.
Walking distance to train station and minutes to I-95, golf club, beaches and all Westport has to offer!
Property is located in Westport School District. Agent/Owner $799,000 Show

5 Renzulli Road Westport, Connecticut

3 Beds 4 Baths 2,284 SqFt 0.440 Acres

Great opportunity to own in Westport! Fully renovated Hi Ranch with new exterior paint, attached 2 car garage.  New kitchen, baths, hardwood floors, appliances, oil tank, central air. Family room with slider to deck. Finished walk out lower level with full bath. Minutes to Downtown Westport, shopping, restaurants, train station and major highways. Come make this house your home today! See agent to agent remarks on offer submission. $774,900 Active

360 Main Street Westport, Connecticut

3 Beds 3 Baths 2,048 SqFt 0.290 Acres

Unique In-Town Cape!!
Located on a peaceful cul-de-sac just minutes away from downtown Westport this spacious Cape has three levels of living space drenched in natural light.  Perfect for the days of working from home the first floor (front entry level) has a family room that could be used as an office or studio with garage access and a laundry room/utility space. The second level has hardwood floors throughout with two bedrooms, the kitchen with a sliding glass door leading to the backyard, a full bath, and a sizable living room with a wood burning fireplace.  The expansive eat-in kitchen features maple cabinets, stainless steel appliances, and a center island with additional seating.  Tucked away on the third floor there are two very large bedrooms with ample closet space, another full bath, and pull down stairs to the attic for storage. The garage is deep and extends the full depth of the house with even more amazing storage space. The backyard is private, level, landscaped, and fenced in. The neighborhood is family-friendly and within the Coleytown school district. Move-in ready...Welcome to Westport. $749,900 Show

8 Willowbrook Drive Westport, Connecticut

4 Beds 2 Baths 2,328 SqFt 0.130 Acres

OPPORTUNITY KNOCKING! Great level 1.28 acre property in convenient location. Easy access to Merritt, downtown Westport. Build your dream home. House sold AS IS. $725,000 Active

1 Tuck Lane Westport, Connecticut

4 Beds 3 Baths 2,061 SqFt 1.280 Acres