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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
18 Danbury Avenue Westport, CT 06880
5 BD / 4 | 2 BA / 3,148 SQ.FT. $15,000
$15,000
18 Danbury Avenue,
Westport CT 06880
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For Sale
19 Bluewater Hill Westport, CT 06880
3 BD / 3 BA / 3,066 SQ.FT. $15,000
$15,000
19 Bluewater Hill,
Westport CT 06880
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For Sale
10 Fernwood Road Westport, CT 06880
5 BD / 3 | 1 BA / 4,029 SQ.FT. $13,500
$13,500
10 Fernwood Road,
Westport CT 06880
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For Sale
12 Danbury Avenue Westport, CT 06880
4 BD / 4 | 1 BA / 2,274 SQ.FT. $13,000
$13,000
12 Danbury Avenue,
Westport CT 06880
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For Sale
9 Rowland Place Westport, CT 06880
3 BD / 2 BA / 1,212 SQ.FT. $13,000
$13,000
9 Rowland Place,
Westport CT 06880
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For Sale
18 Bridge Street Westport, CT 06880
5 BD / 4 BA / 2,882 SQ.FT. $12,850
$12,850
18 Bridge Street,
Westport CT 06880
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For Sale
20 Grassy Plains Road #20 Westport, CT 06880
5 BD / 5 | 1 BA / 3,888 SQ.FT. $12,500
$12,500
20 Grassy Plains Road #20,
Westport CT 06880
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For Sale
71 High Point Road Westport, CT 06880
5 BD / 3 | 1 BA / 6,310 SQ.FT. $12,500
$12,500
71 High Point Road,
Westport CT 06880
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For Sale
38 Sturges Commons Westport, CT 06880
5 BD / 3 | 2 BA / 4,743 SQ.FT. $12,000
$12,000
38 Sturges Commons,
Westport CT 06880
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For Sale
17 Ferry Lane Westport, CT 06880
6 BD / 4 BA / 3,800 SQ.FT. $11,000
$11,000
17 Ferry Lane,
Westport CT 06880
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For Sale
208 Bayberry Lane Westport, CT 06880
3 BD / 3 | 1 BA / 3,692 SQ.FT. $10,000
$10,000
208 Bayberry Lane,
Westport CT 06880
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For Sale
14 North Avenue Westport, CT 06880
4 BD / 2 | 1 BA / 3,280 SQ.FT. $10,000
$10,000
14 North Avenue,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
16 Westport Avenue Westport, CT 06880
4 BD / 4 | 1 BA / 3,260 SQ.FT. $7,495,000
Open House: May 14, 2026, 11:00 AM - 2:00 PM
$7,495,000
16 Westport 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
Open House: May 17, 2026, 1:00 PM - 3:00 PM
$4,799,000
11 Wake Robin Road,
Westport CT 06880
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For Sale
32 Webb Road Westport, CT 06880
8 BD / 9 BA / 8,412 SQ.FT. $4,199,000
Open House: May 16, 2026, 12:00 PM - 2:00 PM
$4,199,000
32 Webb Road,
Westport CT 06880
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For Sale
1 Flower Farm Lane Westport, CT 06880
5 BD / 5 | 3 BA / 9,819 SQ.FT. $4,100,000
Open House: May 16, 2026, 11:00 AM - 1:00 PM
$4,100,000
1 Flower Farm Lane,
Westport CT 06880
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For Sale
4 Charcoal Lane Westport, CT 06880
5 BD / 4 | 1 BA / 6,015 SQ.FT. $3,450,000
Open House: May 14, 2026, 10:30 AM - 1:00 PM
$3,450,000
4 Charcoal Lane,
Westport CT 06880
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For Sale
221 Greens Farms Road Westport, CT 06880
5 BD / 5 | 1 BA / 5,789 SQ.FT. $3,350,000
Open House: May 17, 2026, 1:00 PM - 3:00 PM
$3,350,000
221 Greens Farms Road,
Westport CT 06880
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For Sale
21 Dover Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,535 SQ.FT. $2,750,000
Open House: May 23, 2026, 1:00 PM - 3:00 PM
$2,750,000
21 Dover Road,
Westport CT 06880
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For Sale
5 Tanglewood Lane Westport, CT 06880
4 BD / 3 BA / 3,253 SQ.FT. $1,975,000
Open House: May 14, 2026, 11:00 AM - 2:00 PM
$1,975,000
5 Tanglewood Lane,
Westport CT 06880
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For Sale
44 Sniffen Road Westport, CT 06880
3 BD / 2 BA / 2,246 SQ.FT. $1,420,000
Open House: May 14, 2026, 11:00 AM - 1:00 PM
$1,420,000
44 Sniffen Road,
Westport CT 06880
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For Sale
5 Lehn Farm Road Westport, CT 06880
3 BD / 2 BA / 1,352 SQ.FT. $1,399,000
Open House: May 16, 2026, 12:00 PM - 2:00 PM
$1,399,000
5 Lehn Farm Road,
Westport CT 06880
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For Sale
7 Keller Lane Westport, CT 06880
6 BD / 2 | 1 BA / 4,137 SQ.FT. $1,325,000
Open House: May 17, 2026, 1:00 PM - 3:00 PM
$1,325,000
7 Keller Lane,
Westport CT 06880
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For Sale
170 Imperial Avenue Westport, CT 06880
3 BD / 1 | 1 BA / 2,640 SQ.FT. $1,098,000
Open House: May 16, 2026, 12:00 PM - 3:00 PM
$1,098,000
170 Imperial Avenue,
Westport CT 06880
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