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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
5 Nutmeg Lane Westport, CT 06880
5 BD / 3 | 2 BA / 4,498 SQ.FT. SOLD: $2,311,500
5 Nutmeg Lane,
Westport CT 06880
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Sold
28 Spicer Road Westport, CT 06880
5 BD / 4 | 1 BA / 5,437 SQ.FT. SOLD: $2,310,000
28 Spicer Road,
Westport CT 06880
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Sold
159 Compo Road South Westport, CT 06880
4 BD / 3 | 1 BA / 4,031 SQ.FT. SOLD: $2,302,500
159 Compo Road South,
Westport CT 06880
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Sold
238 Greens Farms Road Westport, CT 06880
6 BD / 5 | 1 BA / 6,394 SQ.FT. SOLD: $2,300,000
238 Greens Farms Road,
Westport CT 06880
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Sold
443 Riverside Avenue Westport, CT 06880
4 BD / 3 BA / 2,943 SQ.FT. SOLD: $2,300,000
443 Riverside Avenue,
Westport CT 06880
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Sold
40 Red Coat Road Westport, CT 06880
4 BD / 3 | 1 BA / 5,955 SQ.FT. SOLD: $2,300,000
40 Red Coat Road,
Westport CT 06880
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41 Richmondville Avenue #310 Westport, CT 06880
2 BD / 2 | 1 BA / 1,630 SQ.FT. SOLD: $2,300,000
41 Richmondville Avenue #310,
Westport CT 06880
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Sold
11 Danbury Avenue Westport, CT 06880
4 BD / 2 BA / 1,606 SQ.FT. SOLD: $2,300,000
11 Danbury Avenue,
Westport CT 06880
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Sold
8 Laurel Road Westport, CT 06880
5 BD / 3 | 1 BA / 4,518 SQ.FT. SOLD: $2,300,000
8 Laurel Road,
Westport CT 06880
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Sold
10 Heathwood Lane Westport, CT 06880
4 BD / 4 | 1 BA / 4,000 SQ.FT. SOLD: $2,290,000
10 Heathwood Lane,
Westport CT 06880
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Sold
7 Mansfield Place Westport, CT 06880
4 BD / 4 BA / 3,270 SQ.FT. SOLD: $2,250,000
7 Mansfield Place,
Westport CT 06880
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Sold
40 Bauer Pl Extension Westport, CT 06880
5 BD / 5 | 1 BA / 5,286 SQ.FT. SOLD: $2,250,000
40 Bauer Pl Extension,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
14 Mayflower Parkway Westport, CT 06880
6 BD / 5 | 3 BA / 10,906 SQ.FT. $5,295,000
Open House: Sep 21, 2025, 2:00 PM - 4:00 PM
$5,295,000
14 Mayflower Parkway,
Westport CT 06880
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For Sale
216 Hillspoint Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,669 SQ.FT. $4,999,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$4,999,000
216 Hillspoint Road,
Westport CT 06880
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For Sale
102 Compo Road South Westport, CT 06880
7 BD / 7 | 1 BA / 6,679 SQ.FT. $4,350,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$4,350,000
102 Compo Road South,
Westport CT 06880
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For Sale
365 Greens Farms Road Westport, CT 06880
6 BD / 4 | 1 BA / 4,420 SQ.FT. $3,800,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$3,800,000
365 Greens Farms Road,
Westport CT 06880
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For Sale
3 Bolton Lane Westport, CT 06880
6 BD / 6 | 1 BA / 7,899 SQ.FT. $3,799,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$3,799,000
3 Bolton Lane,
Westport CT 06880
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For Sale
111 Sturges Highway Westport, CT 06880
5 BD / 6 | 2 BA / 7,359 SQ.FT. $3,750,000
Open House: Sep 20, 2025, 1:00 PM - 3:00 PM
$3,750,000
111 Sturges Highway,
Westport CT 06880
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For Sale
8 Fillow Street Westport, CT 06880
6 BD / 5 | 2 BA / 6,610 SQ.FT. $3,250,000
Open House: Sep 21, 2025, 2:00 PM - 4:00 PM
$3,250,000
8 Fillow Street,
Westport CT 06880
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For Sale
40 Hermit Lane Westport, CT 06880
5 BD / 4 | 2 BA / 4,142 SQ.FT. $2,995,000
Open House: Sep 21, 2025, 2:00 PM - 4:00 PM
$2,995,000
40 Hermit Lane,
Westport CT 06880
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For Sale
158 Compo Road North Westport, CT 06880
6 BD / 6 | 1 BA / 6,351 SQ.FT. $2,900,000
Open House: Sep 20, 2025, 1:00 PM - 3:00 PM
$2,900,000
158 Compo Road North,
Westport CT 06880
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For Sale
20 Old Hill Road Westport, CT 06880
5 BD / 5 | 1 BA / 5,916 SQ.FT. $2,795,000
Open House: Sep 20, 2025, 2:00 PM - 5:00 PM
$2,795,000
20 Old Hill Road,
Westport CT 06880
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For Sale
5 Ridgewood Lane Westport, CT 06880
5 BD / 4 | 1 BA / 4,198 SQ.FT. $2,600,000
Open House: Sep 20, 2025, 12:00 PM - 2:00 PM
$2,600,000
5 Ridgewood Lane,
Westport CT 06880
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For Sale
30 Cavalry Road Westport, CT 06880
4 BD / 3 | 2 BA / 4,013 SQ.FT. $2,592,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$2,592,000
30 Cavalry Road,
Westport CT 06880
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