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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
1 Angora Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,628 SQ.FT. SOLD: $2,650,000
1 Angora Road,
Westport CT 06880
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Sold
79 Riverside Avenue Westport, CT 06880
3 BD / 3 | 1 BA / 1,841 SQ.FT. SOLD: $2,650,000
79 Riverside Avenue,
Westport CT 06880
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Sold
24 Ferry Lane East Westport, CT 06880
BD / BA / 1 SQ.FT. SOLD: $2,650,000
24 Ferry Lane East,
Westport CT 06880
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Sold
38 Pequot Trail Westport, CT 06880
6 BD / 4 | 1 BA / 5,009 SQ.FT. SOLD: $2,650,000
38 Pequot Trail,
Westport CT 06880
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Sold
11 Harbor Road Westport, CT 06880
4 BD / 4 BA / 3,566 SQ.FT. SOLD: $2,650,000
11 Harbor Road,
Westport CT 06880
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11 Old Hill Road Westport, CT 06880
4 BD / 4 | 1 BA / 3,935 SQ.FT. SOLD: $2,645,000
11 Old Hill Road,
Westport CT 06880
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Sold
10 Wakenor Road Westport, CT 06880
5 BD / 5 | 1 BA / 5,008 SQ.FT. SOLD: $2,630,000
10 Wakenor Road,
Westport CT 06880
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19A Darbrook Road Westport, CT 06880
6 BD / 6 | 2 BA / 7,354 SQ.FT. SOLD: $2,625,000
19A Darbrook Road,
Westport CT 06880
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39 Cross Highway Westport, CT 06880
4 BD / 4 | 1 BA / 3,876 SQ.FT. SOLD: $2,609,500
39 Cross Highway,
Westport CT 06880
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Sold
7 Fermily Lane Westport, CT 06880
7 BD / 5 | 1 BA / 4,826 SQ.FT. SOLD: $2,600,108
7 Fermily Lane,
Westport CT 06880
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Sold
123 Greens Farms Road Westport, CT 06880
4 BD / 3 | 2 BA / 5,207 SQ.FT. SOLD: $2,600,000
123 Greens Farms Road,
Westport CT 06880
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2 Fairport Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,288 SQ.FT. SOLD: $2,600,000
2 Fairport Road,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
8 Loretta Court Westport, CT 06880
6 BD / 6 | 3 BA / 9,576 SQ.FT. $6,895,000
Open House: Jul 18, 2026, 11:00 AM - 1:00 PM
$6,895,000
8 Loretta Court,
Westport CT 06880
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For Sale
2 Half Mile Common Westport, CT 06880
4 BD / 4 | 1 BA / 5,039 SQ.FT. $3,100,000
Open House: Jul 18, 2026, 11:00 AM - 1:00 PM
$3,100,000
2 Half Mile Common,
Westport CT 06880
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For Sale
240 North Avenue Westport, CT 06880
4 BD / 4 | 1 BA / 3,778 SQ.FT. $3,499,000
Open House: Jul 18, 2026, 12:00 PM - 2:00 PM
$3,499,000
240 North Avenue,
Westport CT 06880
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For Sale
107 Roseville Road Westport, CT 06880
3 BD / 2 | 1 BA / 1,572 SQ.FT. $1,199,000
Open House: Jul 18, 2026, 12:00 PM - 3:00 PM
$1,199,000
107 Roseville Road,
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: Jul 18, 2026, 1:00 PM - 3:00 PM
$11,995,000
14 Owenoke Park,
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
11 Bellaire Drive Westport, CT 06880
4 BD / 3 | 1 BA / 3,946 SQ.FT. $13,000
Open House: Jul 18, 2026, 1:00 PM - 3:00 PM
$13,000
11 Bellaire Drive,
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 18, 2026, 2:00 PM - 4:00 PM
$1,699,000
7 High Gate 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
Open House: Jul 19, 2026, 12:00 PM - 2:00 PM
$4,495,000
21 Lockwood Circle,
Westport CT 06880
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For Sale
5 Lehn Farm Road Westport, CT 06880
3 BD / 2 BA / 1,352 SQ.FT. $1,299,000
Open House: Jul 19, 2026, 12:00 PM - 2:00 PM
$1,299,000
5 Lehn Farm Road,
Westport CT 06880
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For Sale
13 Edgemarth Hill Road Westport, CT 06880
7 BD / 7 | 1 BA / 8,700 SQ.FT. $5,999,999
Open House: Jul 19, 2026, 1:00 PM - 3:00 PM
$5,999,999
13 Edgemarth Hill 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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