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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 Crooked Mile Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,710 SQ.FT. SOLD: $2,375,000
1 Crooked Mile Road,
Westport CT 06880
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8 Twin Circle Drive Westport, CT 06880
4 BD / 3 BA / 3,692 SQ.FT. SOLD: $2,375,000
8 Twin Circle Drive,
Westport CT 06880
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20 Bauer Place Westport, CT 06880
5 BD / 5 | 1 BA / 4,941 SQ.FT. SOLD: $2,375,000
20 Bauer Place,
Westport CT 06880
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44 Charcoal Hill Road Westport, CT 06880
4 BD / 3 | 1 BA / 3,900 SQ.FT. SOLD: $2,365,000
44 Charcoal Hill Road,
Westport CT 06880
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41 Richmondville Avenue #Penthouse Westport, CT 06880
2 BD / 2 BA / 1,630 SQ.FT. SOLD: $2,365,000
41 Richmondville Avenue #Penthouse,
Westport CT 06880
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12 Iron Gate Hill Westport, CT 06880
5 BD / 4 BA / 4,667 SQ.FT. SOLD: $2,362,500
12 Iron Gate Hill,
Westport CT 06880
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14 Sandy Hill Terrace Westport, CT 06880
5 BD / 4 | 1 BA / 5,084 SQ.FT. SOLD: $2,360,000
14 Sandy Hill Terrace,
Westport CT 06880
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222 Compo Road South Westport, CT 06880
4 BD / 4 | 1 BA / 4,449 SQ.FT. SOLD: $2,360,000
222 Compo Road South,
Westport CT 06880
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8 Sandhopper Trail Westport, CT 06880
4 BD / 2 | 1 BA / 5,055 SQ.FT. SOLD: $2,350,000
8 Sandhopper Trail,
Westport CT 06880
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11 Dogwood Lane Westport, CT 06880
4 BD / 3 BA / 3,156 SQ.FT. SOLD: $2,337,500
11 Dogwood Lane,
Westport CT 06880
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23 Bulkley Avenue North Westport, CT 06880
6 BD / 5 | 1 BA / 5,282 SQ.FT. SOLD: $2,333,000
23 Bulkley Avenue North,
Westport CT 06880
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17 Bridge Street Westport, CT 06880
5 BD / 4 | 1 BA / 4,620 SQ.FT. SOLD: $2,330,789
17 Bridge Street,
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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