Westport

Welcome to Westport

A quaint New England town located on Connecticut’s Gold Coast, Westport sits along the Long Island Sound and the Saugatuck River, approximately 50 miles from New York City. Westport is known for its strong sense of community, with its schools regularly ranked by national publications as among the best in the country. A suburban setting, lively downtown area, and easy access to nature make Westport an idyllic New England town.

Nearby Neighborhoods

Norwalk, Weston, Wilton, Fairfield

Nearby Transportation

Metro-North Railroad Stations (Green’s Farms, Westport); Interstate 95; U.S. 1; Merritt Parkway

Explore Westport

Homes of Westport Connecticut (1)
Homes of Westport Connecticut (2)
Homes of Westport Connecticut (3)
Homes of Westport Connecticut (4)
Homes of Westport Connecticut (5)

Homes

Traditional New England colonials, historical farmhouses, Nantucket shingle-style homes, and modern houses can all be found in Westport. Its housing stock is diverse in architecture and time period, offering a variety of high-quality housing for residents.

Listings in the Area

16 Sue Terrace, Westport, Connecticut - 4 Bedrooms  
3 Bathrooms  
9 Rooms - Previous PhotoNext Photo1 of 26
16 Sue Terrace
$12,500 MO.
Westport
4 BR  |  3 BA  |  9 RM
Cheryl Cusa  (203) 221-0666
Helen R. Cusa  (203-221-0666
33 Grassy Plains Road, Westport, Connecticut - 4 Bedrooms  
4.5 Bathrooms  
11 Rooms - Previous PhotoNext Photo1 of 40
33 Grassy Plains Road
$2,250,000
Westport
4 BR  |  4.5 BA  |  11 RM
Anshu Chawla  (203) 221-0666
7 Fairview Drive, Westport, Connecticut - 4 Bedrooms  
2.5 Bathrooms  
9 Rooms - Previous PhotoNext Photo1 of 35
7 Fairview Drive
$1,649,000
Westport
4 BR  |  2.5 BA  |  9 RM
Mary Kate Klemish-Boehm  (203) 221-0666
230 Saugatuck Avenue Apt 20, Westport, Connecticut - 2 Bedrooms  
2.5 Bathrooms  
4 Rooms - Previous PhotoNext Photo1 of 32
230 Saugatuck Avenue, APT 20
$849,000
Westport
2 BR  |  2.5 BA  |  4 RM
Mary Kate Klemish-Boehm  (203) 221-0666
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Westport has a wide array of different styles of homes and architecture that work together beautifully. There are many classic New England homes built in the 1800s as well as modern and authentic farm-style homes.
- Kathleen Lawton Gibbon, Real Estate Agent

love the mix of old and new, large and small. We have old farmhouses, beautiful Nantucket shingle-style homes, and more modern homes as well. Compo Beach and Saugatuck Shores have really changed since I moved here in 2003. The tiny little beach cottages have turned into beautiful year-round homes.
- Adrienne Durkin, Real Estate Agent

The Lifestyle

A strong sense of community distinguishes the town of Westport, whose residents are often involved with local schools, organizations, and government. Given Westport’s suburban feel and world-class cultural offerings, community members enjoy a slower-paced lifestyle without sacrificing the arts, dining, and cultural attractions of larger cities.

Church Lane
Church Lane
Home to many restaurants and shops
Westport's Main Street
Westport's Main Street

The residents of Westport create a strong sense of community, with many active in local politics, the schools, and community service. I believe that is in large part why Westport schools are often ranked number one in the state of Connecticut.
- Kathleen Lawton Gibbon, Real Estate Agent

Longshore Club Park
Longshore Club Park
168 acres of parks and recreation spaces, as well as a golf course

Outdoors

There is no shortage of outdoor activities for Westport residents. Sitting along the Long Island Sound and Saugatuck River, the town offers great boating, watersports, trails, and public gardens. Highlights include Sherwood Island State Park, Compo Beach, Longshore Club Park, and Earthplace.

Compo Beach is spectacular! Not just the beach itself, but the playground, and the summer nights where friends gather for dinners and beautiful sunsets.
- Adrienne Durkin, Real Estate Agent

An amenity unique to Westport is absolutely Longshore Club Park, a former country club purchased by the town in 1960. It offers an 18-hole golf course (discounted rates for Westport residents), a restaurant (La Plage), a swimming pool, and so much more.
- Adrienne Durkin, Real Estate Agent

Cultural Attractions / Landmarks

With an agricultural past and more recent artistic history, Westport boasts natural and man-made landmarks such as Sherwood Island State Park. Longshore Club Park, Westport Playhouse, MoCA Westport, and the Levitt Pavilion.

Levitt Pavilion
Levitt Pavilion
The Levitt Pavilion offers concerts all summer...and most of them are free!” – Adrienne Durkin
Westport Playhouse
Westport Playhouse
'The Westport Playhouse was created in 1931 and offers great plays for all ages.” – Adrienne Durkin

The Westport Country Playhouse is in a beautiful complex fronted by barn vernacular but underpinned by the technologically exceptional. The seasonal programs are always considered among the best of the best small live performances from around the country.
- Mark Gilrain, Real Estate Agent

The Levitt Pavilion offers wonderful shows and concerts for both adults and children.
- Kathleen Lawton Gibbon, Real Estate Agent

The Westport Museum of Contemporary Art (Westport MoCA) is on wooded grounds on the edge of town. The exhibits and programs are hosted in a historic stone home which was also a former broadcast studio.
- Mark Gilrain, Real Estate Agent

I love all of the amenities that Westport offers. From the beaches to the arts to shops and restaurants, its a very cultural town.
- Mary Kate Klemish-Boehm, Real Estate Agent

Finalmente Trattoria
Finalmente Trattoria
Cozy, family-owned Italian spot offering fresh Italian fare.
Harvest
Harvest
This wine bar and restaurant dishes up “farm-to-fork” food, supporting local farms in the process.
Kawa Ni
Kawa Ni
Enjoy sake, inventive cocktails, and Japanese and Pan-Asian plates here.
La Plage
La Plage
This waterfront seafood restaurant and oyster bar is located inside of The Inn at Longshore and serves up local coastal cuisine in a casual, relaxing atmosphere.
Little Barn
Little Barn
Rustic casual American fare served in a barn-like building
Sherwood Diner
Sherwood Diner
Offering old-school diner fare since 1977
The Cottage
The Cottage
Recently debuted restaurant spotlighting American cooking and inspired by global cultures
The Whelk
The Whelk
'The Whelk on the Saugatuck River promenade is alight with windows and views. It offers parties of whatever size amazing shellfish selections, and entrees and small plates that amaze.” – Mark Gilrain
Walrus Alley
Walrus Alley
Serving up Southern-style fare and barbecue

Dining

Westport’s food scene rivals that of much larger cities, with an array of world-class restaurants that offer fresh coastal cuisine, farm-fresh produce, and innovative seasonal menus. Local favorites include La Plage inside The Inn at Longshore, Bar Taco, The Whelk, and Finalmente Trattoria.

What can I say about the Westport food scene? It has to be seen to be believed. There’s a huge foodie’s list of destination restaurants and the options for food markets and farmers markets are every bit as incredible as well.
- Mark Gilrain, Real Estate Agent

Bar Taco is a family favorite with high-quality food and a fun atmosphere with scenic views of downtown Westport and the Saugatuck River.
- Kathleen Lawton Gibbon, Real Estate Agent

Nightlife

The social town of Westport’s nightlife consists of lively bar settings, concerts at Levitt Pavilion, and shows at Westport Playhouse. Church Lane, which is closed to cars during the mild-weather months, often offers live music, while institutions like the Spotted Horse Tavern provides a great atmosphere indoors.

Black Duck Cafe
Black Duck Cafe
Housed in a mid-1800s barge, Black Duck Cafe is a tavern that also serves fresh seafood
Spotted Horse Tavern
Spotted Horse Tavern
A New American tavern housed in the historic Sherwood House (circa 1808) with a great brunch, full bar, and a creative spin on comfort food classics.

They closed Church Lane to cars for as long as the weather is mild enough. There is often live music, and it feels like Europe!
- Adrienne Durkin, Real Estate Agent

For nightlife, it is a social town: dining, the playhouse, concerts at the pavilion, and spots for drinks are all part of the scene.mark
- Mark Gilrain, Real Estate Agent

Post Road
Post Road
Post Road is the epitome of Westport’s shopping scene, featuring a large number of stores like Brandy Melville, Madewell, Lululemon, Coach, and a four-story Anthropologie.
Terrain
Terrain
Visit Terrain for plants, home accessories, and gifts. There’s also a great cafe under the trellis of plants.
Terrain, interior
Terrain, interior

Shopping

Westport is a premier shopping destination for upscale retail stores and unique speciality stores, with tens of thousands of square feet of retail space added to Downtown Westport in recent years. Main Street is home to an array of shopping options, including fashionable boutiques and home goods stores. Post Road is the epitome of Westport’s shopping scene, featuring a large number of luxury stores like Brandy Melville, Madewell, Lululemon, Coach, and a four-story Anthropologie.

Spend an afternoon sauntering along Main Street on the north stretch of the Saugatuck River. National on-trend fashion stores fill the blocks, or you can shop for designer home goods, books, athletic gear, and children’s brands. Tens of thousands of square feet of retail space has been added throughout the walkable center of downtown in the last five years. With sidewalk cafes always hopping, it’s destination number one.
- Mark Gilrain, Real Estate Agent

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