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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
11 Old Mill Road Westport, CT 06880
1 BD / 1 BA / 580 SQ.FT. $7,500
$7,500
11 Old Mill Road,
Westport CT 06880
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For Sale
61 Hillandale Road Westport, CT 06880
3 BD / 1 | 1 BA / 1,724 SQ.FT. $7,500
$7,500
61 Hillandale Road,
Westport CT 06880
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For Sale
23 Turkey Hill Road North Westport, CT 06880
3 BD / 2 | 1 BA / 1,940 SQ.FT. $7,000
$7,000
23 Turkey Hill Road North,
Westport CT 06880
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For Sale
5 Church Lane #410 Westport, CT 06880
2 BD / 2 BA / 1,184 SQ.FT. $6,750
$6,750
5 Church Lane #410,
Westport CT 06880
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For Sale
310 Main Street Westport, CT 06880
3 BD / 2 | 1 BA / 2,029 SQ.FT. $6,700
$6,700
310 Main Street,
Westport CT 06880
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For Sale
17-B Long Lots Road Westport, CT 06880
3 BD / 3 BA / 1,456 SQ.FT. $6,500
$6,500
17-B Long Lots Road,
Westport CT 06880
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For Sale
5 Guyer Road Westport, CT 06880
3 BD / 1 | 1 BA / 1,556 SQ.FT. $6,000
$6,000
5 Guyer Road,
Westport CT 06880
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For Sale
19 Hickory Drive Westport, CT 06880
3 BD / 2 BA / 1,073 SQ.FT. $5,500
$5,500
19 Hickory Drive,
Westport CT 06880
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For Sale
63 Kings Highway North Westport, CT 06880
4 BD / 1 | 1 BA / 1,494 SQ.FT. $5,500
$5,500
63 Kings Highway North,
Westport CT 06880
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For Sale
2 Scofield Place Westport, CT 06880
2 BD / 1 BA / 938 SQ.FT. $5,250
$5,250
2 Scofield Place,
Westport CT 06880
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For Sale
7 Colony Road #A Westport, CT 06880
2 BD / 1 BA / 883 SQ.FT. $4,990
Open House: Aug 30, 2026, 1:00 PM - 4:00 PM
$4,990
7 Colony Road #A,
Westport CT 06880
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For Sale
3 Wild Rose Road Westport, CT 06880
3 BD / 2 BA / 1,064 SQ.FT. $4,700
$4,700
3 Wild Rose Road,
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. $1,850,000
Open House: Aug 29, 2026, 1:00 AM - 4:00 PM
$1,850,000
5 Aspetuck Lane,
Westport CT 06880
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For Sale
2 Charcoal Lane Westport, CT 06880
3 BD / 3 BA / 3,810 SQ.FT. $2,000,000
Open House: Aug 29, 2026, 11:00 AM - 1:00 PM
$2,000,000
2 Charcoal Lane,
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: Aug 29, 2026, 12:00 PM - 2:00 PM
$6,895,000
8 Loretta Court,
Westport CT 06880
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For Sale
2 Drumlin Road Westport, CT 06880
4 BD / 3 BA / 2,528 SQ.FT. $15,000
Open House: Aug 29, 2026, 12:00 PM - 2:00 PM
$15,000
2 Drumlin Road,
Westport CT 06880
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For Sale
16 Rockyfield Road Westport, CT 06880
5 BD / 4 | 3 BA / 7,652 SQ.FT. $4,250,000
Open House: Aug 29, 2026, 12:00 PM - 3:00 PM
$4,250,000
16 Rockyfield Road,
Westport CT 06880
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For Sale
14 Owenoke Park Westport, CT 06880
5 BD / 5 | 2 BA / 6,050 SQ.FT. $11,995,000
Open House: Aug 30, 2026, 1:00 PM - 3:00 PM
$11,995,000
14 Owenoke Park,
Westport CT 06880
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For Sale
13 Edgemarth Hill Road Westport, CT 06880
7 BD / 7 | 1 BA / 8,700 SQ.FT. $5,999,999
Open House: Aug 30, 2026, 1:00 PM - 3:00 PM
$5,999,999
13 Edgemarth Hill Road,
Westport CT 06880
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For Sale
8 Pleasant Valley Lane Westport, CT 06880
7 BD / 7 | 2 BA / 8,762 SQ.FT. $5,650,000
Open House: Aug 30, 2026, 1:00 PM - 3:00 PM
$5,650,000
8 Pleasant Valley Lane,
Westport CT 06880
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For Sale
4 Bradley Street Westport, CT 06880
5 BD / 4 BA / 3,255 SQ.FT. $2,997,000
Open House: Aug 30, 2026, 1:00 PM - 3:00 PM
$2,997,000
4 Bradley Street,
Westport CT 06880
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For Sale
15 Hyatt Lane Westport, CT 06880
3 BD / 2 BA / 1,512 SQ.FT. $905,000
Open House: Aug 30, 2026, 1:00 PM - 3:00 PM
$905,000
15 Hyatt Lane,
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: Aug 30, 2026, 1:00 PM - 4:00 PM
$4,450,000
159 Easton Road,
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: Aug 30, 2026, 1:00 PM - 4:00 PM
$1,399,000
4 Half Mile Common,
Westport CT 06880
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