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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
310 Main Street Westport, CT 06880
3 BD / 2 | 1 BA / 1,437 SQ.FT. $1,299,000
Open House: Nov 23, 2025, 12:00 PM - 2:00 PM
$1,299,000
310 Main Street,
Westport CT 06880
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For Sale
220 Lansdowne #220 Westport, CT 06880
2 BD / 2 | 1 BA / 2,050 SQ.FT. $1,200,000
$1,200,000
220 Lansdowne #220,
Westport CT 06880
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For Sale
483 Main Street Westport, CT 06880
3 BD / 2 BA / 1,450 SQ.FT. $1,199,000
$1,199,000
483 Main Street,
Westport CT 06880
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For Sale
14 Northfield Drive Westport, CT 06880
3 BD / 2 BA / 1,813 SQ.FT. $1,169,000
$1,169,000
14 Northfield Drive,
Westport CT 06880
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For Sale
785 Post Road East #304 Westport, CT 06880
1 BD / 1 BA / 1,020 SQ.FT. $1,150,000
Open House: Nov 22, 2025, 1:00 PM - 3:00 PM
$1,150,000
785 Post Road East #304,
Westport CT 06880
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For Sale
21 Wright Street Westport, CT 06880
3 BD / 2 | 1 BA / 1,507 SQ.FT. $995,000
Open House: Nov 22, 2025, 1:00 PM - 3:00 PM
$995,000
21 Wright Street,
Westport CT 06880
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For Sale
68 Center Street Westport, CT 06880
4 BD / 2 | 1 BA / 2,044 SQ.FT. $925,000
Open House: Nov 23, 2025, 2:00 PM - 4:00 PM
$925,000
68 Center Street,
Westport CT 06880
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For Sale
489 Main Street Westport, CT 06880
BD / BA / 0.38 SQ.FT. $900,000
$900,000
489 Main Street,
Westport CT 06880
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For Sale
489 Main Street Westport, CT 06880
5 BD / 4 BA / 2,192 SQ.FT. $900,000
$900,000
489 Main Street,
Westport CT 06880
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For Sale
23 Bridge Street Westport, CT 06880
4 BD / 3 BA / 3,054 SQ.FT. $899,000
$899,000
23 Bridge Street,
Westport CT 06880
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For Sale
28 Crescent Park Road Westport, CT 06880
3 BD / 2 BA / 1,152 SQ.FT. $649,000
$649,000
28 Crescent Park Road,
Westport CT 06880
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For Sale
9 Crescent Park Road Westport, CT 06880
3 BD / 1 | 1 BA / 920 SQ.FT. $599,000
$599,000
9 Crescent Park Road,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
10 Tierney Lane Westport, CT 06880
5 BD / 4 | 4 BA / 7,400 SQ.FT. $4,899,000
Open House: Nov 22, 2025, 1:00 PM - 3:00 PM
$4,899,000
10 Tierney Lane,
Westport CT 06880
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For Sale
26 Morningside Drive South Westport, CT 06880
7 BD / 7 | 1 BA / 9,035 SQ.FT. $4,895,000
Open House: Nov 23, 2025, 12:00 PM - 2:00 PM
$4,895,000
26 Morningside Drive South,
Westport CT 06880
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For Sale
32 Webb Road Westport, CT 06880
8 BD / 9 BA / 8,412 SQ.FT. $4,700,000
Open House: Nov 23, 2025, 1:00 PM - 3:00 PM
$4,700,000
32 Webb Road,
Westport CT 06880
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For Sale
221 Greens Farms Road Westport, CT 06880
5 BD / 6 | 1 BA / 5,789 SQ.FT. $3,500,000
Open House: Nov 23, 2025, 12:00 PM - 2:00 PM
$3,500,000
221 Greens Farms Road,
Westport CT 06880
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For Sale
3 Nassau Road Westport, CT 06880
5 BD / 4 BA / 3,486 SQ.FT. $2,995,000
Open House: Nov 22, 2025, 2:00 PM - 4:00 PM
$2,995,000
3 Nassau Road,
Westport CT 06880
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For Sale
19A Darbrook Road Westport, CT 06880
6 BD / 6 | 2 BA / 7,354 SQ.FT. $2,850,000
Open House: Nov 23, 2025, 11:00 AM - 1:00 PM
$2,850,000
19A Darbrook Road,
Westport CT 06880
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For Sale
26 Hitchcock Road Westport, CT 06880
5 BD / 3 | 2 BA / 4,549 SQ.FT. $2,639,000
Open House: Nov 23, 2025, 1:00 PM - 3:00 PM
$2,639,000
26 Hitchcock Road,
Westport CT 06880
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For Sale
30 Cavalry Road Westport, CT 06880
4 BD / 3 | 2 BA / 4,013 SQ.FT. $2,474,000
Open House: Nov 23, 2025, 1:00 PM - 3:00 PM
$2,474,000
30 Cavalry Road,
Westport CT 06880
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For Sale
24 Warnock Drive Westport, CT 06880
3 BD / 2 | 1 BA / 2,844 SQ.FT. $1,999,000
Open House: Nov 23, 2025, 1:00 PM - 3:00 PM
$1,999,000
24 Warnock Drive,
Westport CT 06880
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For Sale
15 Cross Highway Westport, CT 06880
4 BD / 3 | 1 BA / 3,716 SQ.FT. $1,995,000
Open House: Nov 22, 2025, 1:00 PM - 3:00 PM
$1,995,000
15 Cross Highway,
Westport CT 06880
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For Sale
5 Willow Walk Westport, CT 06880
4 BD / 2 | 1 BA / 4,237 SQ.FT. $1,899,000
Open House: Nov 22, 2025, 1:00 PM - 3:00 PM
$1,899,000
5 Willow Walk,
Westport CT 06880
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For Sale
785 Post Road East #104 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,585,000
Open House: Nov 22, 2025, 1:00 PM - 3:00 PM
$1,585,000
785 Post Road East #104,
Westport CT 06880
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