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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
For Sale
359 Greens Farms Road Westport, CT 06880
6 BD / 6 | 2 BA / 7,748 SQ.FT. $5,499,000
$5,499,000
359 Greens Farms Road,
Westport CT 06880
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For Sale
4 Sycamore Drive Westport, CT 06880
6 BD / 6 | 2 BA / 8,935 SQ.FT. $5,199,000
Open House: Jul 19, 2026, 1:00 PM - 3:00 PM
$5,199,000
4 Sycamore Drive,
Westport CT 06880
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For Sale
36 Maple Avenue South Westport, CT 06880
6 BD / 6 | 1 BA / 7,387 SQ.FT. $5,199,000
$5,199,000
36 Maple Avenue South,
Westport CT 06880
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For Sale
22 Dawn Drive Westport, CT 06880
4 BD / 4 | 1 BA / 4,000 SQ.FT. $4,995,700
$4,995,700
22 Dawn Drive,
Westport CT 06880
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For Sale
1 Coastal Court Westport, CT 06880
5 BD / 5 | 2 BA / 5,550 SQ.FT. $4,995,000
$4,995,000
1 Coastal Court,
Westport CT 06880
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For Sale
22 Evergreen Avenue Westport, CT 06880
5 BD / 5 BA / 5,103 SQ.FT. $4,850,000
$4,850,000
22 Evergreen Avenue,
Westport CT 06880
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For Sale
11 Wake Robin Road Westport, CT 06880
5 BD / 5 | 1 BA / 7,583 SQ.FT. $4,799,000
$4,799,000
11 Wake Robin Road,
Westport CT 06880
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For Sale
2 Windy Hill Road Westport, CT 06880
6 BD / 6 | 2 BA / 8,185 SQ.FT. $4,795,000
$4,795,000
2 Windy Hill Road,
Westport CT 06880
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For Sale
21 Lockwood Circle Westport, CT 06880
6 BD / 6 | 1 BA / 6,611 SQ.FT. $4,495,000
$4,495,000
21 Lockwood Circle,
Westport CT 06880
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For Sale
159 Easton Road Westport, CT 06880
6 BD / 6 | 2 BA / 8,356 SQ.FT. $4,450,000
Open House: Jul 19, 2026, 1:00 PM - 3:00 PM
$4,450,000
159 Easton Road,
Westport CT 06880
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For Sale
6 Janson Drive Westport, CT 06880
6 BD / 6 | 3 BA / 7,499 SQ.FT. $4,250,000
$4,250,000
6 Janson Drive,
Westport CT 06880
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For Sale
48 Woodside Avenue Westport, CT 06880
6 BD / 5 | 1 BA / 6,244 SQ.FT. $4,100,000
$4,100,000
48 Woodside Avenue,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
2 Half Mile Common Westport, CT 06880
4 BD / 4 | 1 BA / 5,039 SQ.FT. $3,100,000
Open House: Jul 16, 2026, 11:00 AM - 2:00 PM
$3,100,000
2 Half Mile Common,
Westport CT 06880
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For Sale
18 Silver Brook Road Westport, CT 06880
4 BD / 3 | 2 BA / 4,013 SQ.FT. $2,350,000
Open House: Jul 18, 2026, 1:00 PM - 3:00 PM
$2,350,000
18 Silver Brook Road,
Westport CT 06880
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For Sale
4 Sycamore Drive Westport, CT 06880
6 BD / 6 | 2 BA / 8,935 SQ.FT. $5,199,000
Open House: Jul 19, 2026, 1:00 PM - 3:00 PM
$5,199,000
4 Sycamore Drive,
Westport CT 06880
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For Sale
159 Easton Road Westport, CT 06880
6 BD / 6 | 2 BA / 8,356 SQ.FT. $4,450,000
Open House: Jul 19, 2026, 1:00 PM - 3:00 PM
$4,450,000
159 Easton Road,
Westport CT 06880
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For Sale
7 High Gate Road Westport, CT 06880
4 BD / 3 BA / 2,604 SQ.FT. $1,699,000
Open House: Jul 19, 2026, 1:00 PM - 3:00 PM
$1,699,000
7 High Gate Road,
Westport CT 06880
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