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
56 Charcoal Hill Road Westport, CT 06880
5 BD / 3 BA / 3,072 SQ.FT. SOLD: $2,535,000
56 Charcoal Hill Road,
Westport CT 06880
Explore
Sold
38 Berndale Drive Westport, CT 06880
6 BD / 4 BA / 5,284 SQ.FT. SOLD: $2,525,000
38 Berndale Drive,
Westport CT 06880
Explore
Sold
10 Maple Avenue North Westport, CT 06880
5 BD / 5 | 2 BA / 5,676 SQ.FT. SOLD: $2,525,000
10 Maple Avenue North,
Westport CT 06880
Explore
Sold
38 Tamarac Road Westport, CT 06880
5 BD / 4 | 1 BA / 2,976 SQ.FT. SOLD: $2,500,000
38 Tamarac Road,
Westport CT 06880
Explore
Sold
48 Cavalry Road Westport, CT 06880
4 BD / 4 BA / 4,190 SQ.FT. SOLD: $2,500,000
48 Cavalry Road,
Westport CT 06880
Explore
Sold
3 Turtleback Lane Westport, CT 06880
4 BD / 4 | 1 BA / 4,542 SQ.FT. SOLD: $2,500,000
3 Turtleback Lane,
Westport CT 06880
Explore
Sold
6 Elmwood Road Westport, CT 06880
5 BD / 3 | 1 BA / 5,000 SQ.FT. SOLD: $2,500,000
6 Elmwood Road,
Westport CT 06880
Explore
Sold
6 Marion Road Westport, CT 06880
5 BD / 4 | 1 BA / 4,622 SQ.FT. SOLD: $2,499,000
6 Marion Road,
Westport CT 06880
Explore
Sold
7 Buena Vista Drive Westport, CT 06880
4 BD / 2 | 1 BA / 1,838 SQ.FT. SOLD: $2,495,000
7 Buena Vista Drive,
Westport CT 06880
Explore
Sold
5 Ridgewood Lane Westport, CT 06880
5 BD / 4 | 1 BA / 4,198 SQ.FT. SOLD: $2,492,500
5 Ridgewood Lane,
Westport CT 06880
Explore
Sold
20 Church Street South Westport, CT 06880
6 BD / 5 | 1 BA / 4,725 SQ.FT. SOLD: $2,475,000
20 Church Street South,
Westport CT 06880
Explore
Sold
7 West Parish Road Westport, CT 06880
5 BD / 4 | 2 BA / 4,942 SQ.FT. SOLD: $2,465,000
7 West Parish Road,
Westport CT 06880
Explore
Min. Price
Max. Price
Beds
Baths
For Sale
27 Owenoke Park Westport, CT 06880
6 BD / 4 BA / 3,572 SQ.FT. $6,750,000
Open House: Mar 5, 2026, 11:00 AM - 3:00 PM
$6,750,000
27 Owenoke Park,
Westport CT 06880
Explore
For Sale
32 Webb Road Westport, CT 06880
8 BD / 9 BA / 8,412 SQ.FT. $4,400,000
Open House: Feb 28, 2026, 1:00 PM - 3:00 PM
$4,400,000
32 Webb Road,
Westport CT 06880
Explore
For Sale
13 Rockyfield Road Westport, CT 06880
5 BD / 5 | 2 BA / 7,409 SQ.FT. $4,299,000
Open House: Mar 1, 2026, 1:00 PM - 4:00 PM
$4,299,000
13 Rockyfield Road,
Westport CT 06880
Explore
For Sale
8 Iris Lane Westport, CT 06880
4 BD / 3 BA / 2,959 SQ.FT. $1,499,000
Open House: Feb 26, 2026, 1:00 PM - 3:00 PM
$1,499,000
8 Iris Lane,
Westport CT 06880
Explore
For Sale
783 Post Road East #201 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,430,000
Open House: Feb 25, 2026, 2:00 PM - 4:00 PM
$1,430,000
783 Post Road East #201,
Westport CT 06880
Explore
For Sale
785 Post Road East #102 Westport, CT 06880
2 BD / 2 | 1 BA / 1,416 SQ.FT. $1,395,000
Open House: Feb 25, 2026, 2:00 PM - 4:00 PM
$1,395,000
785 Post Road East #102,
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