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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
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19 Old Hill Farms Road Westport, CT 06880
5 BD / 5 | 1 BA / 7,595 SQ.FT. SOLD: $6,250,000
19 Old Hill Farms Road,
Westport CT 06880
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54 Compo Mill Cove Westport, CT 06880
4 BD / 4 | 1 BA / 5,606 SQ.FT. SOLD: $6,125,000
54 Compo Mill Cove,
Westport CT 06880
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2 Charcoal Hill Common Westport, CT 06880
6 BD / 7 | 1 BA / 7,200 SQ.FT. SOLD: $6,100,000
2 Charcoal Hill Common,
Westport CT 06880
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8 Bradley Street Westport, CT 06880
5 BD / 5 | 2 BA / 4,532 SQ.FT. SOLD: $5,750,000
8 Bradley Street,
Westport CT 06880
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2 Hidden Hill Road Westport, CT 06880
7 BD / 8 | 1 BA / 10,061 SQ.FT. SOLD: $5,750,000
2 Hidden Hill Road,
Westport CT 06880
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119 Compo Road South Westport, CT 06880
7 BD / 7 | 3 BA / 8,500 SQ.FT. SOLD: $5,700,000
119 Compo Road South,
Westport CT 06880
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17 Moss Ledge Road Westport, CT 06880
6 BD / 6 | 1 BA / 9,220 SQ.FT. SOLD: $5,650,000
17 Moss Ledge Road,
Westport CT 06880
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29 Sturges Commons Westport, CT 06880
6 BD / 7 | 2 BA / 8,817 SQ.FT. SOLD: $5,575,000
29 Sturges Commons,
Westport CT 06880
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27 Narrow Rocks Road Westport, CT 06880
7 BD / 8 | 2 BA / 9,500 SQ.FT. SOLD: $5,550,000
27 Narrow Rocks Road,
Westport CT 06880
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10 Greenwood Lane Westport, CT 06880
6 BD / 6 | 2 BA / 8,972 SQ.FT. SOLD: $5,541,153
10 Greenwood Lane,
Westport CT 06880
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25 Soundview Drive Westport, CT 06880
4 BD / 4 | 1 BA / 3,492 SQ.FT. SOLD: $5,540,000
25 Soundview Drive,
Westport CT 06880
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83 Red Coat Road Westport, CT 06880
6 BD / 6 | 2 BA / 6,400 SQ.FT. SOLD: $5,516,360
83 Red Coat Road,
Westport CT 06880
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Max. Price
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For Sale
195 Hillspoint Road Westport, CT 06880
3 BD / 2 | 1 BA / 2,549 SQ.FT. $2,499,000
Open House: Sep 20, 2025, 1:00 PM - 3:00 PM
$2,499,000
195 Hillspoint Road,
Westport CT 06880
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For Sale
56 Charcoal Hill Road Westport, CT 06880
5 BD / 3 BA / 3,072 SQ.FT. $2,495,000
Open House: Sep 20, 2025, 12:00 PM - 2:00 PM
$2,495,000
56 Charcoal Hill Road,
Westport CT 06880
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For Sale
171 Compo Road South Westport, CT 06880
4 BD / 3 | 2 BA / 3,800 SQ.FT. $2,495,000
Open House: Sep 21, 2025, 12:00 PM - 3:00 PM
$2,495,000
171 Compo Road South,
Westport CT 06880
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For Sale
61 Edgewater Commons Lane Westport, CT 06880
4 BD / 3 | 1 BA / 3,397 SQ.FT. $2,259,000
Open House: Sep 21, 2025, 2:30 PM - 4:30 PM
$2,259,000
61 Edgewater Commons Lane,
Westport CT 06880
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For Sale
60 Sylvan Road North Westport, CT 06880
4 BD / 3 | 1 BA / 3,430 SQ.FT. $2,199,000
Open House: Sep 20, 2025, 1:00 PM - 3:00 PM
$2,199,000
60 Sylvan Road North,
Westport CT 06880
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For Sale
17 Clover Lane Westport, CT 06880
5 BD / 3 | 1 BA / 3,000 SQ.FT. $2,195,000
Open House: Sep 21, 2025, 12:00 PM - 2:00 PM
$2,195,000
17 Clover Lane,
Westport CT 06880
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For Sale
785 Post Road East #303 Westport, CT 06880
3 BD / 2 BA / 1,600 SQ.FT. $1,750,000
Open House: Sep 20, 2025, 11:00 AM - 2:00 PM
$1,750,000
785 Post Road East #303,
Westport CT 06880
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For Sale
785 Post Road East #104 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,585,000
Open House: Sep 20, 2025, 11:00 AM - 2:00 PM
$1,585,000
785 Post Road East #104,
Westport CT 06880
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For Sale
785 Post Road East #201 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,545,000
Open House: Sep 20, 2025, 11:00 AM - 2:00 PM
$1,545,000
785 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. $1,495,000
Open House: Sep 20, 2025, 11:00 AM - 2:00 PM
$1,495,000
785 Post Road East #102,
Westport CT 06880
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For Sale
785 Post Road East #301 Westport, CT 06880
2 BD / 2 | 1 BA / 1,300 SQ.FT. $1,450,000
Open House: Sep 20, 2025, 11:00 AM - 2:00 PM
$1,450,000
785 Post Road East #301,
Westport CT 06880
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For Sale
785 Post Road East #203 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,390,000
Open House: Sep 20, 2025, 11:00 AM - 2:00 PM
$1,390,000
785 Post Road East #203,
Westport CT 06880
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