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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
32 Edgewater Hillside Westport, CT 06880
3 BD / 3 | 1 BA / 3,236 SQ.FT. SOLD: $4,400,000
32 Edgewater Hillside,
Westport CT 06880
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20 Bermuda Road Westport, CT 06880
5 BD / 4 | 1 BA / 6,632 SQ.FT. SOLD: $4,400,000
20 Bermuda Road,
Westport CT 06880
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8 Shadbush Lane Westport, CT 06880
7 BD / 8 | 2 BA / 9,514 SQ.FT. SOLD: $4,400,000
8 Shadbush Lane,
Westport CT 06880
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Sold
61 High Point Road Westport, CT 06880
6 BD / 6 | 3 BA / 8,277 SQ.FT. SOLD: $4,395,000
61 High Point Road,
Westport CT 06880
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Sold
26 Morningside Drive South Westport, CT 06880
7 BD / 7 | 1 BA / 9,335 SQ.FT. SOLD: $4,350,000
26 Morningside Drive South,
Westport CT 06880
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Sold
5 Marc Lane Westport, CT 06880
4 BD / 4 | 1 BA / 5,550 SQ.FT. SOLD: $4,310,811
5 Marc Lane,
Westport CT 06880
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Sold
Undisclosed Westport, CT 06880
6 BD / 6 | 2 BA / 5,127 SQ.FT. SOLD: $4,300,000
Undisclosed,
Westport CT 06880
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1 Sleepy Hollow Road Westport, CT 06880
5 BD / 6 | 1 BA / 7,853 SQ.FT. SOLD: $4,300,000
1 Sleepy Hollow Road,
Westport CT 06880
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Sold
6 Pan Handle Lane Westport, CT 06880
5 BD / 7 | 2 BA / 10,471 SQ.FT. SOLD: $4,300,000
6 Pan Handle Lane,
Westport CT 06880
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Sold
86 Old Road Westport, CT 06880
6 BD / 5 | 1 BA / 7,468 SQ.FT. SOLD: $4,275,000
86 Old Road,
Westport CT 06880
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Sold
21 Lockwood Circle Westport, CT 06880
6 BD / 6 | 1 BA / 6,611 SQ.FT. SOLD: $4,265,000
21 Lockwood Circle,
Westport CT 06880
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5 High Point Road Westport, CT 06880
5 BD / 5 | 2 BA / 8,835 SQ.FT. SOLD: $4,250,000
5 High Point Road,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
300 Greens Farms Road Westport, CT 06880
4 BD / 2 BA / 2,186 SQ.FT. $8,700
Open House: Oct 29, 2026, 11:00 AM - 2:00 PM
$8,700
300 Greens Farms Road,
Westport CT 06880
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For Sale
7 Marsh Road Westport, CT 06880
3 BD / 3 BA / 2,091 SQ.FT. $2,049,000
Open House: Oct 31, 2026, 11:00 AM - 1:00 PM
$2,049,000
7 Marsh Road,
Westport CT 06880
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For Sale
14 Great Marsh Road Westport, CT 06880
4 BD / 3 | 1 BA / 3,987 SQ.FT. $5,500,000
Open House: Oct 31, 2026, 12:00 PM - 2:00 PM
$5,500,000
14 Great Marsh Road,
Westport CT 06880
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For Sale
3 Allen Lane Westport, CT 06880
3 BD / 2 | 1 BA / 1,400 SQ.FT. $1,350,000
Open House: Oct 31, 2026, 12:00 PM - 2:00 PM
$1,350,000
3 Allen Lane,
Westport CT 06880
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For Sale
1 Driftwood Point Road Westport, CT 06880
3 BD / 3 | 1 BA / 3,231 SQ.FT. $6,789,000
Open House: Oct 31, 2026, 1:00 PM - 3:00 PM
$6,789,000
1 Driftwood Point Road,
Westport CT 06880
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For Sale
217 Wilton Road Westport, CT 06880
6 BD / 5 | 2 BA / 5,696 SQ.FT. $3,950,000
Open House: Oct 31, 2026, 1:00 PM - 3:00 PM
$3,950,000
217 Wilton Road,
Westport CT 06880
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For Sale
17 Greenbrier Road Westport, CT 06880
4 BD / 4 BA / 4,360 SQ.FT. $3,450,000
Open House: Oct 31, 2026, 1:00 PM - 3:00 PM
$3,450,000
17 Greenbrier Road,
Westport CT 06880
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For Sale
61 Washington Avenue Westport, CT 06880
BD / BA / 0.41 SQ.FT. $1,100,000
Open House: Nov 1, 2026, 12:00 PM - 2:00 PM
$1,100,000
61 Washington Avenue,
Westport CT 06880
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For Sale
61 Washington Avenue Westport, CT 06880
3 BD / 1 BA / 1,044 SQ.FT. $1,100,000
Open House: Nov 1, 2026, 12:00 PM - 2:00 PM
$1,100,000
61 Washington Avenue,
Westport CT 06880
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For Sale
1 Sunrise Road #B Westport, CT 06880
2 BD / 2 | 1 BA / 1,202 SQ.FT. $995,000
Open House: Nov 1, 2026, 12:00 PM - 2:00 PM
$995,000
1 Sunrise Road #B,
Westport CT 06880
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For Sale
124 Harvest Commons #124 Westport, CT 06880
2 BD / 3 | 1 BA / 2,141 SQ.FT. $1,325,000
Open House: Nov 1, 2026, 12:30 PM - 2:00 PM
$1,325,000
124 Harvest Commons #124,
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: Nov 1, 2026, 1:00 PM - 3:00 PM
$5,650,000
8 Pleasant Valley Lane,
Westport CT 06880
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