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
For Sale
90 Main Street #4 Westport, CT 06880
1 BD / 1 BA / 671 SQ.FT. $3,900
$3,900
90 Main Street #4,
Westport CT 06880
Explore
For Sale
25 Oakview Circle Westport, CT 06880
2 BD / 2 BA / 960 SQ.FT. $3,500
$3,500
25 Oakview Circle,
Westport CT 06880
Explore
For Sale
56 Richmondville Avenue Westport, CT 06880
2 BD / 1 BA / 800 SQ.FT. $3,250
$3,250
56 Richmondville Avenue,
Westport CT 06880
Explore
For Sale
148 Imperial Avenue #1 Westport, CT 06880
2 BD / 1 BA / 1,286 SQ.FT. $3,200
$3,200
148 Imperial Avenue #1,
Westport CT 06880
Explore
For Sale
1 Sylvan Lane #C Westport, CT 06880
1 BD / 1 BA / 1,025 SQ.FT. $3,100
$3,100
1 Sylvan Lane #C,
Westport CT 06880
Explore
For Sale
10 Wild Rose Road Westport, CT 06880
1 BD / 1 BA / 2,819 SQ.FT. $2,650
$2,650
10 Wild Rose Road,
Westport CT 06880
Explore
For Sale
1835 Post Road East #3B Westport, CT 06880
1 BD / 1 BA / 850 SQ.FT. $2,500
$2,500
1835 Post Road East #3B,
Westport CT 06880
Explore
For Sale
11 Rockyfield Road Westport, CT 06880
0 BD / 1 BA / 260 SQ.FT. $1,500
$1,500
11 Rockyfield Road,
Westport CT 06880
Explore
Min. Price
Max. Price
Beds
Baths
For Sale
1 Driftwood Point Road Westport, CT 06880
3 BD / 3 | 1 BA / 3,231 SQ.FT. $7,489,000
Open House: Oct 17, 2026, 11:00 AM - 1:00 PM
$7,489,000
1 Driftwood Point Road,
Westport CT 06880
Explore
For Sale
4 Turkey Hill Lane Westport, CT 06880
5 BD / 4 | 1 BA / 5,318 SQ.FT. $3,295,000
Open House: Oct 17, 2026, 11:00 AM - 1:00 PM
$3,295,000
4 Turkey Hill Lane,
Westport CT 06880
Explore
For Sale
2 Drumlin Road Westport, CT 06880
4 BD / 3 BA / 2,315 SQ.FT. $1,895,000
Open House: Oct 17, 2026, 11:00 AM - 1:00 PM
$1,895,000
2 Drumlin Road,
Westport CT 06880
Explore
For Sale
280 Main Street Westport, CT 06880
3 BD / 2 | 1 BA / 1,936 SQ.FT. $1,199,000
Open House: Oct 17, 2026, 11:00 AM - 1:00 PM
$1,199,000
280 Main Street,
Westport CT 06880
Explore
For Sale
2 Drumlin Road Westport, CT 06880
4 BD / 3 BA / 2,315 SQ.FT. $12,000
Open House: Oct 17, 2026, 11:00 AM - 1:00 PM
$12,000
2 Drumlin Road,
Westport CT 06880
Explore
For Sale
124 Harvest Commons #124 Westport, CT 06880
2 BD / 3 | 1 BA / 2,141 SQ.FT. $1,325,000
Open House: Oct 17, 2026, 12:00 PM - 1:30 PM
$1,325,000
124 Harvest Commons #124,
Westport CT 06880
Explore
For Sale
142 Easton Road Westport, CT 06880
5 BD / 6 BA / 7,192 SQ.FT. $2,950,000
Open House: Oct 17, 2026, 12:00 PM - 2:00 PM
$2,950,000
142 Easton Road,
Westport CT 06880
Explore
For Sale
14 High Point Road Westport, CT 06880
5 BD / 5 | 1 BA / 6,094 SQ.FT. $2,999,999
Open House: Oct 17, 2026, 1:00 PM - 3:00 PM
$2,999,999
14 High Point Road,
Westport CT 06880
Explore
For Sale
4 Bradley Street Westport, CT 06880
5 BD / 4 BA / 3,255 SQ.FT. $2,885,000
Open House: Oct 17, 2026, 1:00 PM - 3:00 PM
$2,885,000
4 Bradley Street,
Westport CT 06880
Explore
For Sale
4 Lookout Lane Westport, CT 06880
4 BD / 3 | 1 BA / 2,301 SQ.FT. $1,699,000
Open House: Oct 17, 2026, 1:00 PM - 4:00 PM
$1,699,000
4 Lookout Lane,
Westport CT 06880
Explore
For Sale
233 Hillspoint Road Westport, CT 06880
4 BD / 4 | 1 BA / 3,624 SQ.FT. $6,975,000
Open House: Oct 18, 2026, 11:00 AM - 2:00 PM
$6,975,000
233 Hillspoint Road,
Westport CT 06880
Explore
For Sale
1 Twin Oaks Lane Westport, CT 06880
5 BD / 6 | 1 BA / 8,521 SQ.FT. $4,550,000
Open House: Oct 18, 2026, 12:00 PM - 2:00 PM
$4,550,000
1 Twin Oaks Lane,
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