Westport

 

Westport is a small coastal community along the western shoreline of Connecticut’s Gold Coast. In this scenic suburb, you will find the charm of small-town living mixed with upscale culture. Much of Westport's prominence is due to its blend of the arts, fine dining, luxury shopping, lifestyle, and proximity to New York City. It has become a prime destination for commuters working in NYC and people relocating to Connecticut.

 

Unlike most small communities, Westport's business community is robust. Between international companies like Bridgewater Associates and family-owned businesses like Mitchell’s of Westport, Westport’s business community is rich in history. The Westport Association and Westport Chamber of Commerce were formed to foster economic development in the area.

 

Westport is home to various beautiful neighborhoods, including Saugatuck/Saugatuck Shores, Greens Farms, Old Hill, Coleytown, Compo Beach, Long Lots, and Downtown Westport. Westport real estate is selling very quickly. Contact Cindy Raney & Team of Connecticut real estate agents and realtors to find townhomes, houses, land, luxury property, and beach homes for sale in Westport, CT.

• Vibrant and charming downtown
• Top-rated schools
• Affluent neighborhoods with luxury homes
• Beautiful parks and beaches
• Less than 50 miles to New York City
• Modern conveniences of city life
• Local farmers markets
• Steeped in art and culture

Westport’s affluent residents live in stunning homes, enjoy exquisite dining, and contribute to a booming economy. The community is known for its excellent schools and beaches and is a great place for people of all ages to live, learn, work, and play. Spend a week in Westport, and you will notice its relaxed atmosphere, small-town feel, and charming downtown area. The community has beautiful outdoor spaces to explore, including state parks and nature preserves. It is one of the most desirable places to live, with a bevy of award-winning schools, a thriving arts community, and a wealth of history. 

 

 

 

New York City's first coffee house to exclusively serve ethically sourced, organic, shade-grown coffee. Baked goods and the best cold brew

 

 

 

Beautiful greenhouse-style eatery with indoor and outdoor seating. Enjoy dining, then stay for shopping!

 

 

 

Westport’s country club for residents has a hotel and waterfront restaurant, La Plage, which is open to anyone.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Gabriele’s of Westport is an elegant Italian steakhouse known for high-quality meat, fresh seafood and great people-watching. NÔMADE is a beautifully decorated Marrakech-style restaurant offering modern Mediterranean fare, and a lively bar scene. The Cottage is a cherished local spot, offering a rotating menu of globally inspired dishes and inventive cocktails. And for tapas, don’t miss Basso.

 

La Plage brings coastal refinement to the water’s edge with its elegant dining room—but in the summer, the patio bar and outdoor seating steal the show. For casual family dining, head to BarTaco or Spotted Horse Tavern.

 

The Whelk, set on the river, is known for its market-driven seafood menu, stylish ambiance, private nooks, and locally sourced ingredients. For classic French fare with scenic river views, Rive Bistro delivers in both flavor and setting.

 

Set along the Saugatuck River, Oko is one of the area’s top destinations for Japanese cuisine. Chef Brian Lewis blends global technique with local flavor, sourcing ingredients from rural Connecticut, upstate New York, and even Tokyo’s famed Tsukiji fish market.

 

 

When it comes to breakfast and lunch spots, do not miss The Granola Bar. Created by two Westport moms, this popular eatery offers coffee, baked goods, salads, and specialty lunch items. Another favorite is Old Mill Grocery & Deli, which serves coffee, breakfast, salads, sandwiches, burgers, hot dogs, pizza, snacks, and ice cream, located steps from Compo Beach.

 

For a taste of Parisian charm, Maman (formerly Miss London’s Bakery) offers a beautiful setting for coffee and pastries, while Aux Délices provides authentic French-inspired sandwiches and salads, perfect for a light lunch. They also stock fridges full of prepared meals, ideal for last-minute dinners on busy nights.

 

Fatto A Mano Bakery specializes in naturally leavened sourdough bread, focaccia, and traditional Italian pastries, making it a go-to for artisanal baked goods. Kneads is a bakery, cafe, and mill offering fresh breads, pastries, and an all-day menu with items like bread pudding french toast and unique sandwiches.

 

The Blondinit delivers an authentic Israeli culinary experience, blending modern and traditional flavors—from salatim like labneh with warm pita to shakshuka and classic schnitzel. For something more nostalgic, the Sherwood Diner—a longtime local favorite—serves generous portions of classic American comfort food, including hearty breakfasts, stacks of pancakes, diner-style burgers, and full dinner plates.

 

Westport offers an exceptional shopping experience, blending nationally loved brands with distinctive local boutiques. Along and around Main Street, you’ll find well-known retailers like J.Crew, Vince, Lululemon, Theory, Anthropologie, Vuori, and Madewell, all offering the convenience of in-person browsing with elevated style.

 

For high-end fashion paired with personalized service, Mitchells of Westport remains a town institution. Nearby, Fred Boutique offers dresses, blouses, outerwear, and more trendy women’s clothing.

 

Home design enthusiasts will appreciate the abundance of décor destinations. Shops like Serena & Lily, Pottery Barn, West Elm, and Design Within Reach provide a range of well-known options for furnishing a home with style. For designer lighting and unique pieces, boutiques like Astele offer high-end finishes with an editorial touch.

 

Other standout home decor boutiques include Bel Mondo, a popular furniture and home décor store with a calming atmosphere and expert designers; Bungalow, a quaint downtown boutique that offers unique antique décor, jewelry, furniture, and home accessories; and Millie Rae’s, which combines home furnishings with women’s apparel and accessories in a charming, coastal-chic setting.

 

Another well-loved option is Kerri Rosenthal, a fresh, vibrant boutique that offers luxury home décor, artwork, clothes, fabric, and wallpaper. 

 

For jewelry, check out Lux Bond & Green, JL Rocks, Middlemarch, and Tiffany & Co. And then there’s Terrain—a destination in itself. With its greenhouse atrium, live moss wall, and seasonal garden installations, it’s a feast for the senses. The on-site café serves brunch, lunch, and dinner with a seasonal, locally inspired menu (don’t miss the signature “potted bread”). Terrain also hosts curated events throughout the year, making it a favorite for both locals and visitors alike.

 

The Westport Downtown Association hosts summer outdoor shopping days in Westport with Sidewalk Sales for locals to walk around Main Street and view sales from shops and boutiques. The event also features local food trucks, live music, and a pop-up bar. The annual LobsterFest is a Rotary Club event that helps support humanitarian projects and features live music, local cuisine, and fresh lobster. The Westport Dog Festival is a fun event that offers competitive obstacle courses, a police K9 show, vendors, food trucks, dog licensing, and more. Enjoy the Westport Farmers Market for fresh, local, healthy seasonal food. And don’t miss the beloved Levitt Pavilion, which has music and entertainment throughout the summer.

 

The community has an annual 4th of July fireworks show sponsored by Melissa and Doug at Compo Beach, with other fun activities like music and local cuisine. For some outdoor time, Sherwood Island is a state park in Westport that features open lawns, picnic areas, swimming, marsh areas, an observation platform, nature trails, and a nature center with educational programs. Birchwood Country Club is a private club that offers dining with event spaces and outdoor facilities. Members enjoy access to seven Har-Tru tennis courts, two lighted platform tennis courts, an Olympic-sized swimming pool, and a nine-hole golf course cited among the top ten in the U.S. 

 

For indoor entertainment, The Clubhouse Westport provides an upscale, multi-sport simulator experience, allowing you to play virtual golf on world-renowned courses or engage in other digital sports. There’s also a seasonal rooftop bar. For a creative outing, MoCa (Museum of Contemporary Art Westport) showcases thought-provoking contemporary art exhibitions and offers summer art camps for children. Earthplace, a nature discovery center, provides trails for outdoor exploration and educational programs focused on local wildlife and environmental stewardship. For younger children, The Wonder is a modern, imaginative indoor play space designed for creative play and exploration. 

 

In terms of events, summers in Westport are enlivened by the annual Yankee Doodle Fair, hosted by the Westport Woman's Club. This fair offers carnival rides, games, food, and entertainment, and the lively Summer Music on Church Lane series, where local musicians perform outdoors, creating a festive atmosphere for dining and socializing.

 

For theater, head to the Westport Country Playhouse and enjoy productions from playwrights, actors, directors, and designers of all backgrounds. 

 

Longshore is a public facility available to residents. It hosts a world of fantastic amenities, including Longshore Golf Course, an 18-hole layout ranked #7 by Northeast Golf Magazine among the “Best Places to Play” in Connecticut. Longshore also includes La Plage, a premium dining and wedding reception venue along the water, the P.A.L. skating rink, three swimming pools, nine Har-Tru tennis courts, two platform tennis courts, Longshore Pavilion, picnic areas, E.R. Strait Marina, and Longshore Sailing School.

 

The Fairfield County Hunt Club is located on 40 acres of scenic property and includes stables, an indoor equestrian arena, tennis courts, and a swimming pool.

 

Wakeman Town Farm is a fun place to visit and offers programming for adults and kids.

 

And for salons, we recommend bird. and SALON dada. Both destinations bring an artistic flair to Westport’s beauty industry, with stylists who reimagine self-expression through a full suite of services (including haircuts, styling, color services, treatments, makeup, and hair extensions).

 

The Westport Public Schools offer a highly rated public education system to the Westport community. There are also many quality private college preparatory schools in the area.

 

Public schools:

 

• Coleytown Elementary School, grades K–5
• Kingshighway Elementary School, grades K–5
• Long Lots Elementary School, K–5
• Saugatuck Elementary, K-5
• Greens Farms Elementary, K-5
• Bedford Middle School, grades 6–8
• Coleytown Middle School, grades 6–8
• Staples High School, grades 9–12

Private schools:

 

• Pierrepont School, grades K–12
• Green Farms Academy, grades pre-K–12
• One River School, grades K–12 (art and design school)