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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
3 Eno Lane Westport, CT 06880
4 BD / 5 | 1 BA / 7,091 SQ.FT. SOLD: $2,999,000
3 Eno Lane,
Westport CT 06880
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Sold
216 Hillspoint Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,669 SQ.FT. SOLD: $2,995,000
216 Hillspoint Road,
Westport CT 06880
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Sold
195 Hillspoint Road Westport, CT 06880
3 BD / 2 | 1 BA / 2,549 SQ.FT. SOLD: $2,981,000
195 Hillspoint Road,
Westport CT 06880
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Sold
56 Roseville Road Westport, CT 06880
5 BD / 6 | 1 BA / 6,857 SQ.FT. SOLD: $2,975,000
56 Roseville Road,
Westport CT 06880
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Sold
16 Juniper Road Westport, CT 06880
4 BD / 4 | 1 BA / 3,933 SQ.FT. SOLD: $2,965,000
16 Juniper Road,
Westport CT 06880
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Sold
22 Marion Road Westport, CT 06880
6 BD / 4 | 2 BA / 6,416 SQ.FT. SOLD: $2,950,000
22 Marion Road,
Westport CT 06880
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Sold
21 Long Lots Lane Westport, CT 06880
6 BD / 6 | 1 BA / 6,148 SQ.FT. SOLD: $2,950,000
21 Long Lots Lane,
Westport CT 06880
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Sold
28 Cavalry Road Westport, CT 06880
5 BD / 5 | 1 BA / 4,690 SQ.FT. SOLD: $2,950,000
28 Cavalry Road,
Westport CT 06880
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Sold
72 Coleytown Road Westport, CT 06880
4 BD / 4 | 2 BA / 5,450 SQ.FT. SOLD: $2,942,500
72 Coleytown Road,
Westport CT 06880
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Sold
60 Wilton Road Westport, CT 06880
2 BD / 2 | 1 BA / 2,517 SQ.FT. SOLD: $2,925,000
60 Wilton Road,
Westport CT 06880
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Sold
5 River Lane Westport, CT 06880
5 BD / 4 | 2 BA / 4,636 SQ.FT. SOLD: $2,900,000
5 River Lane,
Westport CT 06880
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2 Fairport Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,288 SQ.FT. SOLD: $2,893,000
2 Fairport Road,
Westport CT 06880
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Min. Price
Max. Price
Beds
Baths
For Sale
19 Mortar Rock Road Westport, CT 06880
6 BD / 6 | 2 BA / 8,190 SQ.FT. $4,899,000
Open House: Apr 19, 2026, 2:00 PM - 4:00 PM
$4,899,000
19 Mortar Rock Road,
Westport CT 06880
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For Sale
91 Turkey Hill Road South Westport, CT 06880
5 BD / 4 | 2 BA / 8,192 SQ.FT. $3,395,000
Open House: Apr 18, 2026, 12:00 PM - 3:00 PM
$3,395,000
91 Turkey Hill Road South,
Westport CT 06880
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For Sale
13 Highland Road Westport, CT 06880
4 BD / 3 BA / 2,170 SQ.FT. $1,369,000
Open House: Apr 16, 2026, 11:00 AM - 2:00 PM
$1,369,000
13 Highland Road,
Westport CT 06880
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For Sale
7 Rowland Place Westport, CT 06880
2 BD / 1 BA / 948 SQ.FT. $1,125,000
Open House: Apr 18, 2026, 11:00 AM - 2:00 PM
$1,125,000
7 Rowland Place,
Westport CT 06880
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