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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 Berkeley Road Westport, CT 06880
5 BD / 4 | 2 BA / 4,957 SQ.FT. SOLD: $2,800,000
1 Berkeley Road,
Westport CT 06880
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Sold
1 Country Lane Westport, CT 06880
6 BD / 6 | 1 BA / 7,151 SQ.FT. SOLD: $2,800,000
1 Country Lane,
Westport CT 06880
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Sold
2 Bermuda Road Westport, CT 06880
5 BD / 3 | 1 BA / 4,048 SQ.FT. SOLD: $2,800,000
2 Bermuda Road,
Westport CT 06880
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Sold
20 Old Hill Road Westport, CT 06880
5 BD / 5 | 1 BA / 5,916 SQ.FT. SOLD: $2,795,000
20 Old Hill Road,
Westport CT 06880
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Sold
20 Crawford Road Westport, CT 06880
5 BD / 4 | 1 BA / 5,424 SQ.FT. SOLD: $2,780,000
20 Crawford Road,
Westport CT 06880
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Sold
29 Otter Trail Westport, CT 06880
4 BD / 3 | 2 BA / 3,660 SQ.FT. SOLD: $2,780,000
29 Otter Trail,
Westport CT 06880
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Sold
60 Wilton Road #2B Westport, CT 06880
2 BD / 2 | 1 BA / 2,517 SQ.FT. SOLD: $2,775,000
60 Wilton Road #2B,
Westport CT 06880
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15 Sunrise Road Westport, CT 06880
5 BD / 6 | 1 BA / 5,407 SQ.FT. SOLD: $2,769,000
15 Sunrise Road,
Westport CT 06880
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Sold
7 Over Rock Lane Westport, CT 06880
5 BD / 4 BA / 3,311 SQ.FT. SOLD: $2,760,500
7 Over Rock Lane,
Westport CT 06880
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Sold
54 North Avenue Westport, CT 06880
5 BD / 4 | 1 BA / 5,780 SQ.FT. SOLD: $2,750,000
54 North Avenue,
Westport CT 06880
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23 Rayfield Road Westport, CT 06880
5 BD / 5 | 1 BA / 4,605 SQ.FT. SOLD: $2,750,000
23 Rayfield Road,
Westport CT 06880
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Sold
36 Morningside Drive North Westport, CT 06880
5 BD / 5 | 1 BA / 4,577 SQ.FT. SOLD: $2,750,000
36 Morningside Drive North,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
27 Owenoke Park Westport, CT 06880
6 BD / 4 BA / 3,572 SQ.FT. $6,750,000
Open House: Mar 5, 2026, 11:00 AM - 3:00 PM
$6,750,000
27 Owenoke Park,
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: Feb 28, 2026, 1:00 PM - 3:00 PM
$4,400,000
32 Webb Road,
Westport CT 06880
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For Sale
8 Iris Lane Westport, CT 06880
4 BD / 3 BA / 2,959 SQ.FT. $1,499,000
Open House: Feb 26, 2026, 1:00 PM - 3:00 PM
$1,499,000
8 Iris Lane,
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: Feb 25, 2026, 2:00 PM - 4:00 PM
$1,430,000
783 Post Road East #201,
Westport CT 06880
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For Sale
785 Post Road East #102 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,395,000
Open House: Feb 25, 2026, 2:00 PM - 4:00 PM
$1,395,000
785 Post Road East #102,
Westport CT 06880
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