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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
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
55 Kings Highway North Westport, CT 06880
3 BD / 2 BA / 1,719 SQ.FT. $10,000
$10,000
55 Kings Highway North,
Westport CT 06880
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For Sale
59 Crescent Road Westport, CT 06880
4 BD / 3 | 1 BA / 4,508 SQ.FT. $9,800
$9,800
59 Crescent Road,
Westport CT 06880
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For Sale
8 Bayberry Ridge Road Westport, CT 06880
3 BD / 3 | 1 BA / 3,315 SQ.FT. $9,500
$9,500
8 Bayberry Ridge Road,
Westport CT 06880
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For Sale
8 Bauer Place Westport, CT 06880
4 BD / 4 BA / 2,599 SQ.FT. $9,000
$9,000
8 Bauer Place,
Westport CT 06880
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For Sale
2 Rockyfield Road Westport, CT 06880
3 BD / 2 | 1 BA / 2,401 SQ.FT. $8,750
$8,750
2 Rockyfield Road,
Westport CT 06880
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For Sale
12 Signal Lane Westport, CT 06880
4 BD / 3 BA / 3,157 SQ.FT. $8,400
$8,400
12 Signal Lane,
Westport CT 06880
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For Sale
32 Regents Park #32 Westport, CT 06880
3 BD / 3 | 1 BA / 3,349 SQ.FT. $8,000
$8,000
32 Regents Park #32,
Westport CT 06880
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For Sale
5 Tall Trees Drive Westport, CT 06880
5 BD / 2 | 1 BA / 2,729 SQ.FT. $8,000
$8,000
5 Tall Trees Drive,
Westport CT 06880
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For Sale
18 Hales Road Westport, CT 06880
4 BD / 2 | 1 BA / 1,542 SQ.FT. $7,500
$7,500
18 Hales Road,
Westport CT 06880
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For Sale
11 Beechwood Lane Westport, CT 06880
4 BD / 2 | 1 BA / 1,886 SQ.FT. $6,200
$6,200
11 Beechwood Lane,
Westport CT 06880
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For Sale
174A Post Road West Westport, CT 06880
4 BD / 3 | 1 BA / 3,678 SQ.FT. $5,950
$5,950
174A Post Road West,
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. $7,500,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$7,500,000
8 Loretta Court,
Westport CT 06880
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For Sale
3 Stony Point Road West Westport, CT 06880
6 BD / 7 | 2 BA / 6,561 SQ.FT. $5,925,000
Open House: Apr 12, 2026, 1:00 AM - 3:00 PM
$5,925,000
3 Stony Point Road West,
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. $5,599,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$5,599,000
36 Maple Avenue South,
Westport CT 06880
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For Sale
21 Lockwood Circle Westport, CT 06880
6 BD / 6 | 1 BA / 6,611 SQ.FT. $4,750,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$4,750,000
21 Lockwood Circle,
Westport CT 06880
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For Sale
32 Webb Road Westport, CT 06880
8 BD / 9 BA / 8,412 SQ.FT. $4,400,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$4,400,000
32 Webb Road,
Westport CT 06880
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For Sale
13 Rockyfield Road Westport, CT 06880
5 BD / 5 | 2 BA / 7,409 SQ.FT. $3,990,000
Open House: Apr 12, 2026, 2:00 PM - 4:00 PM
$3,990,000
13 Rockyfield Road,
Westport CT 06880
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For Sale
114 Cross Highway Westport, CT 06880
5 BD / 4 | 1 BA / 4,179 SQ.FT. $2,700,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$2,700,000
114 Cross Highway,
Westport CT 06880
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For Sale
1 Angora Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,628 SQ.FT. $2,699,000
Open House: Apr 12, 2026, 1:00 PM - 4:00 PM
$2,699,000
1 Angora Road,
Westport CT 06880
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For Sale
9 Marsh Road Westport, CT 06880
4 BD / 3 BA / 2,959 SQ.FT. $2,425,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$2,425,000
9 Marsh Road,
Westport CT 06880
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For Sale
32 Berndale Drive Westport, CT 06880
5 BD / 4 BA / 3,328 SQ.FT. $2,095,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$2,095,000
32 Berndale Drive,
Westport CT 06880
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For Sale
52 Partrick Road Westport, CT 06880
5 BD / 5 | 1 BA / 3,045 SQ.FT. $1,699,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$1,699,000
52 Partrick Road,
Westport CT 06880
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For Sale
783 Post Road East #201 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,430,000
Open House: Apr 12, 2026, 1:00 PM - 3:00 PM
$1,430,000
783 Post Road East #201,
Westport CT 06880
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