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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
4 Deepwood Lane Westport, CT 06880
6 BD / 5 | 1 BA / 6,935 SQ.FT. SOLD: $3,350,000
4 Deepwood Lane,
Westport CT 06880
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147 Cross Highway Westport, CT 06880
5 BD / 4 | 2 BA / 6,190 SQ.FT. SOLD: $3,327,000
147 Cross Highway,
Westport CT 06880
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Sold
60 Wilton Road #Penthouse Westport, CT 06880
2 BD / 2 | 1 BA / 2,437 SQ.FT. SOLD: $3,325,000
60 Wilton Road #Penthouse,
Westport CT 06880
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Sold
6 Sharp Turn Road Westport, CT 06880
6 BD / 4 | 1 BA / 5,661 SQ.FT. SOLD: $3,310,000
6 Sharp Turn Road,
Westport CT 06880
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Sold
232 Bayberry Lane Westport, CT 06880
5 BD / 4 | 1 BA / 5,432 SQ.FT. SOLD: $3,300,000
232 Bayberry Lane,
Westport CT 06880
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99 Hillspoint Road Westport, CT 06880
5 BD / 4 | 2 BA / 6,027 SQ.FT. SOLD: $3,300,000
99 Hillspoint Road,
Westport CT 06880
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17 Greenbrier Road Westport, CT 06880
4 BD / 4 BA / 4,360 SQ.FT. SOLD: $3,275,000
17 Greenbrier Road,
Westport CT 06880
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3 Old Hill Farms Road Westport, CT 06880
5 BD / 5 | 3 BA / 8,008 SQ.FT. SOLD: $3,275,000
3 Old Hill Farms Road,
Westport CT 06880
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16 Burr School Road Westport, CT 06880
5 BD / 4 | 1 BA / 5,056 SQ.FT. SOLD: $3,250,000
16 Burr School Road,
Westport CT 06880
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Sold
3 Hickory Hill Road Westport, CT 06880
5 BD / 4 | 1 BA / 5,059 SQ.FT. SOLD: $3,250,000
3 Hickory Hill Road,
Westport CT 06880
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249 Sturges Highway Westport, CT 06880
5 BD / 5 | 4 BA / 8,639 SQ.FT. SOLD: $3,250,000
249 Sturges Highway,
Westport CT 06880
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27 Old Hill Farms Road Westport, CT 06880
5 BD / 3 | 1 BA / 4,298 SQ.FT. SOLD: $3,250,000
27 Old Hill Farms Road,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
783 Post Road East #204 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,575,000
Open House: Jun 17, 2026, 4:00 PM - 6:00 PM
$1,575,000
783 Post Road East #204,
Westport CT 06880
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For Sale
781 Post Road East #102 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,460,000
Open House: Jun 17, 2026, 4:00 PM - 6:00 PM
$1,460,000
781 Post Road East #102,
Westport CT 06880
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For Sale
8 Loretta Court Westport, CT 06880
6 BD / 6 | 3 BA / 9,576 SQ.FT. $6,895,000
Open House: Jun 18, 2026, 11:00 AM - 1:00 PM
$6,895,000
8 Loretta Court,
Westport CT 06880
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For Sale
22 Sturges Commons Westport, CT 06880
5 BD / 6 | 2 BA / 4,911 SQ.FT. $3,295,000
Open House: Jun 18, 2026, 11:00 AM - 1:00 PM
$3,295,000
22 Sturges Commons,
Westport CT 06880
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For Sale
71 High Point Road Westport, CT 06880
5 BD / 3 | 1 BA / 6,310 SQ.FT. $1,995,000
Open House: Jun 18, 2026, 11:00 AM - 1:30 PM
$1,995,000
71 High Point Road,
Westport CT 06880
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For Sale
7 Short Street Westport, CT 06880
4 BD / 3 | 1 BA / 3,241 SQ.FT. $2,800,000
Open House: Jun 18, 2026, 11:00 AM - 2:00 PM
$2,800,000
7 Short Street,
Westport CT 06880
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For Sale
53 Clinton Avenue Westport, CT 06880
5 BD / 5 | 1 BA / 7,055 SQ.FT. $2,650,000
Open House: Jun 18, 2026, 11:00 AM - 2:00 PM
$2,650,000
53 Clinton Avenue,
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: Jun 18, 2026, 11:00 AM - 2:00 PM
$1,699,000
7 High Gate Road,
Westport CT 06880
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For Sale
1 Twin Oaks Lane Westport, CT 06880
5 BD / 5 | 1 BA / 9,421 SQ.FT. $5,500,000
Open House: Jun 20, 2026, 11:00 AM - 1:00 PM
$5,500,000
1 Twin Oaks Lane,
Westport CT 06880
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For Sale
143 North Avenue Westport, CT 06880
3 BD / 3 BA / 2,192 SQ.FT. $1,699,000
Open House: Jun 20, 2026, 12:00 PM - 3:00 PM
$1,699,000
143 North Avenue,
Westport CT 06880
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For Sale
159 Easton Road Westport, CT 06880
6 BD / 6 | 2 BA / 8,356 SQ.FT. $4,450,000
Open House: Jun 21, 2026, 1:00 PM - 3:00 PM
$4,450,000
159 Easton Road,
Westport CT 06880
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