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Stunning views meet a cosmopolitan outlook.

Westport is often referred to as "New England in tradition, cosmopolitan in outlook," mainly because of its perse architecture and vibrant downtown area, which generates a healthy commercial environment, a feeling of a New England town, and the convenience of modern life.

Consequently, this area is more cosmopolitan than the other northern towns of Wilton and Weston and offers beach-style living. As a result, Westport is also referred to as part of Connecticut's Gold Coast and is home to many thriving business executives, artists, and actors. Westport provides residents and tourists with a wide range of leisure activities and recreational venues.

What to Love

  • Access to the water and beach
  • Quaint downtown area
  • Incredible arts community

Local Lifestyle

If you are looking for a picturesque New England town close to New York City, then Westport is perfect for you. This community offers everything for all ages and interests, with its busy downtown area, striking views, delicious food establishments, charming architecture, flawless coastlines, and high-energy vibes.

Dining, Entertainment, & Shopping

Although Westport is home to endless outdoor activities and fun shopping experiences, it is also often known as a foodie's utopia. Here you will find an endless array of dishes for gatherings, a special date night, and even a quick snack that the whole family will love.

For example, La Plage is a local favorite with outdoor seating by the water. Manna Toast provides customers with vegan breakfast and lunch options, while Kawa Ni is a go-to spot for Japanese cuisine. The Whelk serves inventive seafood plates in cozy surroundings. Allium Eatery features a lovely selection of well-curated French-inspired dishes and many other delicacies that will leave your mouth watering. Bartaco is another fantastic restaurant with a unique menu of sesame ribeye, roasted duck tacos, spicy cucumber salad, spiced chicken verde rice bowls, and much more.

For fun after your fantastic dining experience, check out the area's unique stores, such as Serena and Lily, Terrain, and Bungalow.

The Levitt Pavilion for the Performing Arts is a popular entertainment spot renowned for the Summer Session, the longest-running free outdoor festival in the country.

Things to Do

Westport has no shortage of gorgeous beach scenery, with the sandy shores of Compo Beach, Saugatuck Shores Beach, Old Mill Beach, and Burying Hill Beach within easy reach. Residents enjoy sailing, boating, or walking along the tranquil coastline.

Outside of its shopping and dining opportunities, there are many things to enjoy in this quaint area, including Longshore Community Club. Every Westport resident has access to this incredible club, where they can enjoy golf, tennis, paddle sports, and other water-related activities. There is even an outdoor ice skating rink in the wintertime.

The Saugatuck Rowing & Fitness Club is a popular health club with renowned rowing programs and competitions for all ages, a fitness center, personal training programs, and the Boathouse Restaurant.

Schools

The Westport School District is a top-rated public school district that offers schools to over 5,000 students, with a student-teacher ratio of 11 to 1. Some of the more well-known schools here include:

  • Staples High School, Grades 9-12
  • Bedford Middle School, Grades 6-8
  • Long Lots Elementary School, Grades K-5
Min. Price
Max. Price
Beds
Baths
Sold
6 Florian Court Westport, CT 06880
5 BD / 6 | 1 BA / 7,970 SQ.FT. SOLD: $3,500,000
6 Florian Court,
Westport CT 06880
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55 Sturges Highway Westport, CT 06880
6 BD / 6 | 2 BA / 6,538 SQ.FT. SOLD: $3,500,000
55 Sturges Highway,
Westport CT 06880
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Sold
60 Wilton Road #2C Westport, CT 06880
4 BD / 3 | 1 BA / 3,460 SQ.FT. SOLD: $3,500,000
60 Wilton Road #2C,
Westport CT 06880
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Sold
71 Old Road Westport, CT 06880
6 BD / 5 | 1 BA / 6,300 SQ.FT. SOLD: $3,499,000
71 Old Road,
Westport CT 06880
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Sold
249 Greens Farms Road Westport, CT 06880
7 BD / 6 | 3 BA / 10,104 SQ.FT. SOLD: $3,480,000
249 Greens Farms Road,
Westport CT 06880
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Sold
4 Silver Brook Road Westport, CT 06880
5 BD / 4 | 2 BA / 6,944 SQ.FT. SOLD: $3,475,000
4 Silver Brook Road,
Westport CT 06880
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Sold
3 Bolton Lane Westport, CT 06880
6 BD / 6 | 1 BA / 7,899 SQ.FT. SOLD: $3,470,000
3 Bolton Lane,
Westport CT 06880
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Sold
5 Elwil Drive Westport, CT 06880
5 BD / 5 | 1 BA / 5,887 SQ.FT. SOLD: $3,450,000
5 Elwil Drive,
Westport CT 06880
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Sold
18 Frescenius Road Westport, CT 06880
7 BD / 6 | 2 BA / 6,200 SQ.FT. SOLD: $3,450,000
18 Frescenius Road,
Westport CT 06880
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Sold
2 Twin Falls Lane Westport, CT 06880
5 BD / 6 | 1 BA / 6,789 SQ.FT. SOLD: $3,450,000
2 Twin Falls Lane,
Westport CT 06880
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Sold
6 Fraser Road Westport, CT 06880
5 BD / 3 | 1 BA / 7,420 SQ.FT. SOLD: $3,425,000
6 Fraser Road,
Westport CT 06880
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2 Webb Road Westport, CT 06880
6 BD / 5 | 2 BA / 5,497 SQ.FT. SOLD: $3,400,000
2 Webb Road,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
36 Maple Avenue South Westport, CT 06880
6 BD / 6 | 1 BA / 7,387 SQ.FT. $5,599,000
Open House: Apr 20, 2026, 1:00 PM - 3:00 PM
$5,599,000
36 Maple Avenue South,
Westport CT 06880
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