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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
Sold
12 Meeker Road Westport, CT 06880
5 BD / 4 | 2 BA / 6,748 SQ.FT. SOLD: $2,590,000
12 Meeker Road,
Westport CT 06880
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Sold
4 The Fenway Westport, CT 06880
6 BD / 4 | 1 BA / 5,083 SQ.FT. SOLD: $2,581,433
4 The Fenway,
Westport CT 06880
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Sold
4 Compo Hill Avenue Westport, CT 06880
3 BD / 4 BA / 3,150 SQ.FT. SOLD: $2,575,000
4 Compo Hill Avenue,
Westport CT 06880
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Sold
8 Dexter Road Westport, CT 06880
5 BD / 4 | 2 BA / 5,349 SQ.FT. SOLD: $2,560,000
8 Dexter Road,
Westport CT 06880
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Sold
58 North Avenue Westport, CT 06880
6 BD / 5 | 1 BA / 4,210 SQ.FT. SOLD: $2,553,000
58 North Avenue,
Westport CT 06880
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Sold
7 McMahon Lane Westport, CT 06880
4 BD / 3 | 1 BA / 5,644 SQ.FT. SOLD: $2,550,000
7 McMahon Lane,
Westport CT 06880
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Sold
30 Sniffen Road Westport, CT 06880
5 BD / 5 | 1 BA / 5,450 SQ.FT. SOLD: $2,550,000
30 Sniffen Road,
Westport CT 06880
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Sold
56 Charcoal Hill Road Westport, CT 06880
5 BD / 3 BA / 3,072 SQ.FT. SOLD: $2,535,000
56 Charcoal Hill Road,
Westport CT 06880
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Sold
38 Berndale Drive Westport, CT 06880
6 BD / 4 BA / 5,284 SQ.FT. SOLD: $2,525,000
38 Berndale Drive,
Westport CT 06880
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38 Tamarac Road Westport, CT 06880
5 BD / 4 | 1 BA / 2,976 SQ.FT. SOLD: $2,500,000
38 Tamarac Road,
Westport CT 06880
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48 Cavalry Road Westport, CT 06880
4 BD / 4 BA / 4,190 SQ.FT. SOLD: $2,500,000
48 Cavalry Road,
Westport CT 06880
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3 Turtleback Lane Westport, CT 06880
4 BD / 4 | 1 BA / 4,542 SQ.FT. SOLD: $2,500,000
3 Turtleback Lane,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
5 Tanglewood Lane Westport, CT 06880
4 BD / 3 BA / 3,253 SQ.FT. $1,975,000
Open House: May 31, 2026, 12:00 PM - 2:00 PM
$1,975,000
5 Tanglewood Lane,
Westport CT 06880
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For Sale
25 Old Road Westport, CT 06880
5 BD / 4 | 1 BA / 6,330 SQ.FT. $2,200,000
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$2,200,000
25 Old Road,
Westport CT 06880
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For Sale
159 Easton Road Old Westport Turnpike Westport, CT 06880
6 BD / 6 | 2 BA / 8,356 SQ.FT. $4,450,000
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$4,450,000
159 Easton Road Old Westport Turnpike,
Westport CT 06880
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For Sale
8 Loretta Court Westport, CT 06880
6 BD / 6 | 3 BA / 9,576 SQ.FT. $7,500,000
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$7,500,000
8 Loretta Court,
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
Open House: May 31, 2026, 1:00 PM - 3:00 PM
$4,495,000
21 Lockwood Circle,
Westport CT 06880
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For Sale
40 Richmondville Avenue Westport, CT 06880
6 BD / 5 | 1 BA / 3,700 SQ.FT. $2,495,000
Open House: May 31, 2026, 12:00 PM - 2:00 PM
$2,495,000
40 Richmondville Avenue,
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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For Sale
21 Covlee Drive Westport, CT 06880
4 BD / 4 | 1 BA / 4,444 SQ.FT. $6,875,000
Open House: May 31, 2026, 2:00 PM - 4:00 PM
$6,875,000
21 Covlee Drive,
Westport CT 06880
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For Sale
14 Owenoke Park Westport, CT 06880
5 BD / 5 | 2 BA / 6,050 SQ.FT. $11,995,000
Open House: May 31, 2026, 1:30 PM - 3:30 PM
$11,995,000
14 Owenoke Park,
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 31, 2026, 1:00 PM - 3:00 PM
$4,799,000
11 Wake Robin Road,
Westport CT 06880
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For Sale
21 Dover Road Westport, CT 06880
5 BD / 4 | 1 BA / 6,356 SQ.FT. $2,750,000
Open House: May 31, 2026, 1:00 PM - 4:00 PM
$2,750,000
21 Dover Road,
Westport CT 06880
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For Sale
299 Saugatuck Avenue Westport, CT 06880
4 BD / 4 | 2 BA / 5,627 SQ.FT. $2,799,000
Open House: May 31, 2026, 2:00 PM - 4:00 PM
$2,799,000
299 Saugatuck Avenue,
Westport CT 06880
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