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Westport - Image

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
14 Burr School Road Westport, CT 06880
6 BD / 7 | 2 BA / 7,888 SQ.FT. $6,785,000
$6,785,000
14 Burr School Road,
Westport CT 06880
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For Sale
5 Baldwin Place Westport, CT 06880
6 BD / 5 | 3 BA / 9,062 SQ.FT. $6,495,000
$6,495,000
5 Baldwin Place,
Westport CT 06880
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For Sale
28 Ferry Lane East Westport, CT 06880
5 BD / 6 | 3 BA / 8,466 SQ.FT. $6,250,000
$6,250,000
28 Ferry Lane East,
Westport CT 06880
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For Sale
46 Compo Mill Cove Westport, CT 06880
4 BD / 4 | 2 BA / 5,567 SQ.FT. $5,995,000
$5,995,000
46 Compo Mill Cove,
Westport CT 06880
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For Sale
10 Mary Jane Lane Westport, CT 06880
6 BD / 6 | 1 BA / 6,900 SQ.FT. $5,990,000
$5,990,000
10 Mary Jane Lane,
Westport CT 06880
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For Sale
21 Sturges Commons Westport, CT 06880
6 BD / 6 | 3 BA / 10,521 SQ.FT. $5,980,000
$5,980,000
21 Sturges Commons,
Westport CT 06880
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For Sale
3 Stony Point West Westport, CT 06880
6 BD / 7 | 2 BA / 6,561 SQ.FT. $5,925,000
$5,925,000
3 Stony Point West,
Westport CT 06880
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For Sale
8 Pleasant Valley Lane Westport, CT 06880
7 BD / 7 | 2 BA / 8,762 SQ.FT. $5,650,000
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$5,650,000
8 Pleasant Valley Lane,
Westport CT 06880
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For Sale
5 West Branch Road Westport, CT 06880
6 BD / 7 | 2 BA / 9,394 SQ.FT. $5,599,000
$5,599,000
5 West Branch Road,
Westport CT 06880
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For Sale
80 Compo Road North Westport, CT 06880
4 BD / 3 | 2 BA / 7,105 SQ.FT. $5,549,000
$5,549,000
80 Compo Road North,
Westport CT 06880
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For Sale
1 Twin Oaks Lane Westport, CT 06880
5 BD / 5 | 1 BA / 9,421 SQ.FT. $5,500,000
Open House: May 31, 2026, 12:00 PM - 3:00 PM
$5,500,000
1 Twin Oaks Lane,
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
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$5,199,000
36 Maple Avenue South,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
19 East Horseshoe Lane Westport, CT 06880
5 BD / 4 | 1 BA / 5,476 SQ.FT. $3,190,000
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$3,190,000
19 East Horseshoe Lane,
Westport CT 06880
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For Sale
2 Charcoal Lane Westport, CT 06880
3 BD / 3 BA / 3,810 SQ.FT. $2,198,000
Open House: May 31, 2026, 1:00 PM - 4:00 PM
$2,198,000
2 Charcoal Lane,
Westport CT 06880
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For Sale
4 Baywood Lane Westport, CT 06880
5 BD / 2 | 1 BA / 2,166 SQ.FT. $1,600,000
Open House: May 31, 2026, 12:00 PM - 2:00 PM
$1,600,000
4 Baywood Lane,
Westport CT 06880
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For Sale
1 Twin Oaks Lane Westport, CT 06880
5 BD / 5 | 1 BA / 9,421 SQ.FT. $5,500,000
Open House: May 31, 2026, 12:00 PM - 3:00 PM
$5,500,000
1 Twin Oaks Lane,
Westport CT 06880
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For Sale
3080 Sturges Highway Westport, CT 06880
5 BD / 5 | 2 BA / 7,317 SQ.FT. $2,999,000
Open House: May 31, 2026, 2:00 PM - 4:00 PM
$2,999,000
3080 Sturges Highway,
Westport CT 06880
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For Sale
16 Westport Avenue Westport, CT 06880
4 BD / 4 | 1 BA / 3,260 SQ.FT. $6,995,000
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$6,995,000
16 Westport Avenue,
Westport CT 06880
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For Sale
8 Pleasant Valley Lane Westport, CT 06880
7 BD / 7 | 2 BA / 8,762 SQ.FT. $5,650,000
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$5,650,000
8 Pleasant Valley Lane,
Westport CT 06880
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For Sale
4 Cardinal Lane Westport, CT 06880
4 BD / 3 | 1 BA / 4,651 SQ.FT. $2,250,000
Open House: May 31, 2026, 12:00 PM - 3:00 PM
$2,250,000
4 Cardinal Lane,
Westport CT 06880
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For Sale
253 Riverside Avenue #101 Westport, CT 06880
2 BD / 3 BA / 1,300 SQ.FT. $10,500
Open House: May 31, 2026, 2:00 PM - 4:00 PM
$10,500
253 Riverside Avenue #101,
Westport CT 06880
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For Sale
253 Riverside Avenue #201 Westport, CT 06880
2 BD / 3 BA / 1,300 SQ.FT. $11,500
Open House: May 31, 2026, 2:00 PM - 4:00 PM
$11,500
253 Riverside Avenue #201,
Westport CT 06880
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For Sale
253 Riverside Avenue #102 Westport, CT 06880
2 BD / 3 BA / 1,300 SQ.FT. $10,500
Open House: May 31, 2026, 2:00 PM - 4:00 PM
$10,500
253 Riverside Avenue #102,
Westport CT 06880
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For Sale
253 Riverside Avenue #202 Westport, CT 06880
2 BD / 3 BA / 1,200 SQ.FT. $11,500
Open House: May 31, 2026, 2:00 PM - 4:00 PM
$11,500
253 Riverside Avenue #202,
Westport CT 06880
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