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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
56 Roseville Road Westport, CT 06880
5 BD / 6 | 1 BA / 6,857 SQ.FT. SOLD: $3,550,000
56 Roseville Road,
Westport CT 06880
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2A Whippoorwill Lane Westport, CT 06880
6 BD / 6 | 2 BA / 8,558 SQ.FT. SOLD: $3,525,719
2A Whippoorwill Lane,
Westport CT 06880
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Sold
123 Cross Highway Westport, CT 06880
5 BD / 5 | 1 BA / 7,048 SQ.FT. SOLD: $3,500,000
123 Cross Highway,
Westport CT 06880
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150 Hillspoint Road Westport, CT 06880
4 BD / 4 BA / 3,759 SQ.FT. SOLD: $3,500,000
150 Hillspoint Road,
Westport CT 06880
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Sold
6 Florian Court Westport, CT 06880
5 BD / 6 | 1 BA / 7,970 SQ.FT. SOLD: $3,500,000
6 Florian Court,
Westport CT 06880
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13 Terhune Drive Westport, CT 06880
6 BD / 5 | 1 BA / 6,010 SQ.FT. SOLD: $3,499,999
13 Terhune Drive,
Westport CT 06880
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42 Spriteview Avenue Westport, CT 06880
3 BD / 3 | 1 BA / 4,033 SQ.FT. SOLD: $3,499,000
42 Spriteview Avenue,
Westport CT 06880
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71 Old Road Westport, CT 06880
6 BD / 5 | 1 BA / 6,300 SQ.FT. SOLD: $3,499,000
71 Old Road,
Westport CT 06880
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249 Greens Farms Road Westport, CT 06880
7 BD / 6 | 3 BA / 10,104 SQ.FT. SOLD: $3,480,000
249 Greens Farms Road,
Westport CT 06880
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4 Silver Brook Road Westport, CT 06880
5 BD / 4 | 2 BA / 6,944 SQ.FT. SOLD: $3,475,000
4 Silver Brook Road,
Westport CT 06880
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3 Bolton Lane Westport, CT 06880
6 BD / 6 | 1 BA / 7,899 SQ.FT. SOLD: $3,470,000
3 Bolton Lane,
Westport CT 06880
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5 Elwil Drive Westport, CT 06880
5 BD / 5 | 1 BA / 5,887 SQ.FT. SOLD: $3,450,000
5 Elwil Drive,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
5 Aspetuck Lane Westport, CT 06880
6 BD / 2 | 2 BA / 3,240 SQ.FT. $1,650,000
Open House: Sep 5, 2026, 1:00 PM - 4:00 PM
$1,650,000
5 Aspetuck Lane,
Westport CT 06880
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For Sale
4 Half Mile Common Westport, CT 06880
4 BD / 2 BA / 1,834 SQ.FT. $1,399,000
Open House: Sep 5, 2026, 1:00 PM - 4:00 PM
$1,399,000
4 Half Mile Common,
Westport CT 06880
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For Sale
4 Crawford Road Westport, CT 06880
5 BD / 3 | 1 BA / 4,471 SQ.FT. $2,595,000
Open House: Sep 5, 2026, 2:00 PM - 4:00 PM
$2,595,000
4 Crawford Road,
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: Sep 5, 2026, 2:30 PM - 4:30 PM
$6,895,000
8 Loretta Court,
Westport CT 06880
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For Sale
16 Westport Avenue Westport, CT 06880
4 BD / 4 | 1 BA / 3,260 SQ.FT. $6,495,000
Open House: Sep 6, 2026, 11:00 AM - 1:00 PM
$6,495,000
16 Westport Avenue,
Westport CT 06880
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For Sale
2 Windy Hill Road Westport, CT 06880
6 BD / 6 | 2 BA / 8,185 SQ.FT. $4,600,000
Open House: Sep 6, 2026, 1:00 PM - 3:00 PM
$4,600,000
2 Windy Hill Road,
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: Sep 6, 2026, 1:00 PM - 4:00 PM
$4,450,000
159 Easton Road,
Westport CT 06880
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