Main Content

Westport - Image

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
125 Hillandale Road Westport, CT 06880
6 BD / 7 | 1 BA / 10,350 SQ.FT. SOLD: $5,200,000
125 Hillandale Road,
Westport CT 06880
Explore
Sold
7 North Ridge Road Westport, CT 06880
6 BD / 6 | 3 BA / 11,774 SQ.FT. SOLD: $5,075,000
7 North Ridge Road,
Westport CT 06880
Explore
Sold
19 High Point Road Westport, CT 06880
5 BD / 6 | 3 BA / 9,280 SQ.FT. SOLD: $5,050,000
19 High Point Road,
Westport CT 06880
Explore
Sold
190 Hillspoint Road Westport, CT 06880
4 BD / 5 BA / 4,333 SQ.FT. SOLD: $5,025,000
190 Hillspoint Road,
Westport CT 06880
Explore
Sold
5 Roosevelt Road Westport, CT 06880
4 BD / 4 | 1 BA / 3,353 SQ.FT. SOLD: $5,005,220
5 Roosevelt Road,
Westport CT 06880
Explore
Sold
39 Maple Avenue South Westport, CT 06880
6 BD / 7 | 1 BA / 8,080 SQ.FT. SOLD: $5,004,000
39 Maple Avenue South,
Westport CT 06880
Explore
Sold
10 Surf Road Westport, CT 06880
4 BD / 4 BA / 5,885 SQ.FT. SOLD: $5,000,000
10 Surf Road,
Westport CT 06880
Explore
Sold
11 Beachside Common Westport, CT 06880
5 BD / 7 | 1 BA / 14,038 SQ.FT. SOLD: $5,000,000
11 Beachside Common,
Westport CT 06880
Explore
Sold
129 Long Lots Road Westport, CT 06880
6 BD / 6 | 2 BA / 7,663 SQ.FT. SOLD: $5,000,000
129 Long Lots Road,
Westport CT 06880
Explore
Sold
31 Woody Lane Westport, CT 06880
6 BD / 7 | 2 BA / 10,390 SQ.FT. SOLD: $5,000,000
31 Woody Lane,
Westport CT 06880
Explore
Sold
4 Ferry Lane East Westport, CT 06880
6 BD / 6 | 2 BA / 6,700 SQ.FT. SOLD: $5,000,000
4 Ferry Lane East,
Westport CT 06880
Explore
Sold
108 Clapboard Hill Road Westport, CT 06880
5 BD / 4 | 1 BA / 5,312 SQ.FT. SOLD: $4,950,000
108 Clapboard Hill Road,
Westport CT 06880
Explore
Min. Price
Max. Price
Beds
Baths
For Sale
24 Compo Parkway Westport, CT 06880
5 BD / 4 | 2 BA / 5,199 SQ.FT. $5,300,000
Open House: Jan 11, 2026, 1:00 PM - 3:00 PM
$5,300,000
24 Compo Parkway,
Westport CT 06880
Explore
For Sale
10 Tierney Lane Westport, CT 06880
5 BD / 4 | 4 BA / 7,400 SQ.FT. $4,899,000
Open House: Jan 10, 2026, 12:00 PM - 2:00 PM
$4,899,000
10 Tierney Lane,
Westport CT 06880
Explore
For Sale
21 Warnock Drive Westport, CT 06880
6 BD / 6 | 3 BA / 9,700 SQ.FT. $4,795,000
Open House: Jan 11, 2026, 1:00 PM - 3:00 PM
$4,795,000
21 Warnock Drive,
Westport CT 06880
Explore
For Sale
26 Morningside Drive South Westport, CT 06880
7 BD / 7 | 1 BA / 9,335 SQ.FT. $4,700,000
Open House: Jan 10, 2026, 12:00 PM - 2:00 PM
$4,700,000
26 Morningside Drive South,
Westport CT 06880
Explore
For Sale
32 Webb Road Westport, CT 06880
8 BD / 9 BA / 8,412 SQ.FT. $4,599,999
Open House: Jan 11, 2026, 1:00 PM - 3:00 PM
$4,599,999
32 Webb Road,
Westport CT 06880
Explore
For Sale
102 Compo Road South Westport, CT 06880
7 BD / 7 | 1 BA / 6,679 SQ.FT. $4,150,000
Open House: Jan 11, 2026, 1:00 PM - 3:00 PM
$4,150,000
102 Compo Road South,
Westport CT 06880
Explore
For Sale
26 Treadwell Avenue Westport, CT 06880
5 BD / 4 | 1 BA / 3,200 SQ.FT. $3,295,000
Open House: Jan 11, 2026, 1:00 PM - 3:00 PM
$3,295,000
26 Treadwell Avenue,
Westport CT 06880
Explore
For Sale
25 Old Road Westport, CT 06880
5 BD / 4 | 1 BA / 6,330 SQ.FT. $2,750,000
Open House: Jan 12, 2026, 1:00 PM - 3:00 PM
$2,750,000
25 Old Road,
Westport CT 06880
Explore
For Sale
123 Greens Farms Road Westport, CT 06880
4 BD / 3 | 2 BA / 5,207 SQ.FT. $2,750,000
Open House: Jan 10, 2026, 11:30 AM - 1:00 PM
$2,750,000
123 Greens Farms Road,
Westport CT 06880
Explore
For Sale
41 Richmondville Avenue #Duplex 2 Westport, CT 06880
2 BD / 2 | 1 BA / 1,760 SQ.FT. $2,495,000
Open House: Jan 10, 2026, 9:30 AM - 10:30 AM
$2,495,000
41 Richmondville Avenue #Duplex 2,
Westport CT 06880
Explore
For Sale
21 Woods Grove Road Westport, CT 06880
4 BD / 3 | 1 BA / 3,237 SQ.FT. $2,300,000
Open House: Jan 11, 2026, 12:00 PM - 2:00 PM
$2,300,000
21 Woods Grove Road,
Westport CT 06880
Explore
For Sale
785 Post Road East #204 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,625,000
Open House: Jan 10, 2026, 1:00 PM - 3:00 PM
$1,625,000
785 Post Road East #204,
Westport CT 06880
Explore

This content is currently unavailable. Please check back later or contact the site's support team for more information.
Sold Listings - Last 30 Days
New Listings - Last 30 Days
Skip to content