Westport sits along the western shoreline of Connecticut’s Gold Coast, where the Saugatuck River meets Long Island Sound. About 50 miles northeast of Manhattan, it has long attracted New York commuters, creatives, and families looking for a coastal suburb with real substance. The town has a walkable Main Street, two Metro-North stations, highly ranked schools, and miles of waterfront. It feels like a small town with the cultural depth and dining scene of somewhere much larger.
Two commercial hubs anchor daily life: the Main Street downtown corridor and the revitalized Saugatuck Center near the river. Both are stocked with independent shops, restaurants, and cafes. The population is roughly 27,000, and the community skews affluent, with a strong presence of finance professionals, entrepreneurs, and creatives. Westport consistently ranks as one of the most desirable places to live in the Northeast, and for good reason.
Two Metro-North stations with express trains reaching Grand Central in about 70 minutes
Top-rated public schools, anchored by Staples High School (one of the highest-ranked in Connecticut)
Sandy beaches, including Compo Beach, Burying Hill Beach, and Sherwood Island State Park
A thriving arts scene with Westport Country Playhouse, MoCA Westport, and Levitt Pavilion
Walkable downtown with locally owned boutiques, national brands, and a standout restaurant lineup
Strong community programming, from the Westport Farmers Market to Yankee Doodle Fair
Access to I-95 and the Merritt Parkway for easy highway travel throughout the region
Westport’s housing stock runs the full spectrum: antique colonials, mid-century ranches, updated Cape Cods, grand shingle-style estates, and modern new construction. Lot sizes range from compact quarter-acre plots near the beach to two-acre spreads in the northern part of town. Homes closer to the water tend to sit on smaller lots but command a premium for proximity and views. Farther north, you’ll find larger parcels with more privacy and a rural feel.
The town is made up of over a dozen recognized neighborhoods, each with its own character. Here’s a snapshot of the most well-known:
Compo Beach: Steps from Long Island Sound. Formerly seasonal bungalows, now mostly year-round homes on smaller lots. Residents walk to the beach, Longshore Club Park, and waterfront dining at La Plage. Schools: Greens Farms Elementary, Bedford Middle School.
Saugatuck / Saugatuck Shores: A coastal enclave along the river and harbor. Waterfront properties, deep-water docks, yacht clubs, and a private beach for Saugatuck Shores residents. The area also includes Saugatuck Island, which sits beyond a one-lane bridge and feels especially secluded. Schools: Saugatuck Elementary, Bedford Middle School.
Greens Farms: A southern neighborhood with historic homes, rolling landscapes, and its own Metro-North station. Greens Farms Academy (a private K-12 school) is located here. Quiet, residential, and close to the water. Schools: Greens Farms Elementary, Bedford Middle School.
Old Hill: Wooded and peaceful, bordered by the Saugatuck River. Walking distance to downtown and the train. Home to Earthplace Nature Center and Birchwood Country Club. Part of the Kings Highway North Historic District. One of Westport’s most sought-after addresses. Schools: Kings Highway Elementary, Coleytown Middle School.
Coleytown: The most northern and rural part of town. Two-acre zoning, stone walls, winding roads, and large estates behind gated driveways. Country living with full access to everything Westport offers. Schools: Coleytown Elementary, Coleytown Middle School.
Long Lots: A residential area west of downtown with a range of home styles and lot sizes. Includes the newer Hunt Club sub-neighborhood near the Fairfield border. Schools: Long Lots Elementary, Bedford Middle School.
Downtown / Westport Village: Walkable neighborhood near Main Street with a variety of building styles, including condos, townhomes, and single-family homes. Ideal for buyers who want to be in the center of it all.
Local Tip: Westport has two distinct commercial areas. Main Street downtown is the primary shopping and dining hub, while Saugatuck Center (near the train station) offers riverside dining, galleries, and summer concerts. Buyers who want walkability to both should look at neighborhoods like Old Hill, Saugatuck, or Downtown.
New construction is active across town, particularly in Compo Beach and Saugatuck Shores, where older cottages are being replaced with larger shingle-style homes. There’s a growing value gap between fully renovated or newly built homes and older properties that need work. Condition, location, and lot characteristics are the biggest factors driving value.
Westport’s restaurant scene punches well above its weight for a town this size. Here’s a taste:
Oko: Japanese cuisine set along the Saugatuck River, led by Chef Brian Lewis, sourcing from local farms and Tokyo’s famed Tsukiji fish market
Kawa Ni: Inventive Japanese small plates, sake, and cocktails in a casual, shareable setting
Gabriele’s of Westport: Elegant Italian steakhouse known for high-quality meat, seafood, and great people-watching
NÔMADE: Modern Mediterranean fare in a Marrakech-inspired space with a lively bar scene
The Whelk: Market-driven seafood on the river with private nooks and locally sourced ingredients
Rive Bistro: Classic French fare with scenic river views
The Cottage: A local favorite with a rotating, globally inspired menu and inventive cocktails
Terrain Café: Greenhouse-style eatery serving brunch, lunch, and dinner with a seasonal, locally inspired menu
For quick bites and morning fuel, The Granola Bar (started by two Westport moms) is a go-to for coffee, salads, and specialty lunches. Jack’s Coffee serves ethically sourced organic brews and baked goods. Maman offers Parisian-style pastries and coffee, while Aux Délices provides French-inspired sandwiches, salads, and prepared meals. Fatto A Mano Bakery specializes in naturally leavened sourdough and traditional Italian pastries, and Kneads is a bakery-cafe-mill with fresh breads and an all-day menu.
For casual family dining, BarTaco and Spotted Horse Tavern are reliable picks. And the Sherwood Diner has been serving generous portions of classic American comfort food for years.
Local Tip: La Plage at Longshore is open to everyone (not just club members). In summer, the patio bar and outdoor seating on the water are the place to be.
Main Street and the surrounding blocks offer a strong retail lineup. National brands like J.Crew, Lululemon, Theory, Anthropologie, Vuori, Vince, and Madewell sit alongside local independents. Mitchells of Westport, a sprawling family-owned boutique, has been a town institution for decades, carrying designer apparel, accessories, and jewelry with exceptional personal service.
Home design is well represented with Serena & Lily, Pottery Barn, West Elm, Design Within Reach, and boutiques like Astele, Bel Mondo, Bungalow, and Millie Rae’s. Kerri Rosenthal offers vibrant home décor, artwork, clothes, fabric, and wallpaper. For jewelry, Lux Bond & Green, JL Rocks, Middlemarch, and Tiffany & Co. are all in town.
And then there’s Terrain. With its greenhouse atrium, live moss wall, and seasonal garden installations, it’s as much experience as store. The on-site café is a destination in its own right, and they host curated events year-round.
Westport keeps a full calendar:
Levitt Pavilion: Free outdoor concerts and performances all summer long
Westport Country Playhouse: Professional theater productions year-round
MoCA Westport: Contemporary visual arts exhibitions and summer art camps
Yankee Doodle Fair: Annual carnival hosted by the Westport Woman’s Club with rides, games, and food
LobsterFest: A Rotary Club fundraiser featuring live music, local cuisine, and fresh lobster
Sidewalk Sales: Summer outdoor shopping events on Main Street with food trucks, live music, and pop-up bars
Westport Farmers Market: Fresh, local, seasonal produce and goods
Summer Music on Church Lane: Outdoor live music with food and socializing
4th of July at Compo Beach: Fireworks, music, and community celebration sponsored by Melissa and Doug
Compo Beach is the town’s marquee beach: 29 acres of sandy shoreline with a boardwalk, pavilion, volleyball courts, a wooden playscape, and a concession stand. Burying Hill Beach and Old Mill Beach round out the public beach options.
Sherwood Island State Park, Connecticut’s first state park, features open lawns, picnic areas, swimming, marsh areas, an observation platform, nature trails, and educational programs. Earthplace, a nature discovery center, provides trails for outdoor exploration and educational programs on local wildlife. Wakeman Town Farm offers hands-on programming for adults and kids.
Longshore Club Park is a public facility for residents with an 18-hole golf course (ranked among the best in Connecticut), La Plage restaurant, the P.A.L. skating rink, three swimming pools, nine Har-Tru tennis courts, two platform tennis courts, a pavilion, picnic areas, a marina, and a sailing school.
Birchwood Country Club is a private club with a nine-hole golf course (cited among the top ten in the U.S.), seven Har-Tru tennis courts, two lighted platform tennis courts, an Olympic-sized pool, and event dining. The Fairfield County Hunt Club sits on 40 acres and includes stables, an indoor equestrian arena, tennis courts, and a swimming pool.
Local Tip: The Clubhouse Westport offers upscale multi-sport simulators (virtual golf on world-famous courses and more) plus a seasonal rooftop bar. The Wonder is a modern indoor play space designed for younger children.
Westport has two Metro-North stations on the New Haven Line: the main Westport station (locally called Saugatuck) and Greens Farms. Express trains from the Westport station reach Grand Central Terminal in about 70 minutes. Local trains take roughly 90 minutes. Both stations have commuter parking (permits available, with a waitlist for monthly spots; daily parking available on a first-come basis).
By car, Manhattan is about 50 miles away via I-95 or the Merritt Parkway. Without traffic, the drive takes about 75 to 80 minutes, though rush-hour commuters should plan for longer. The highway access also makes it easy to reach other Fairfield County towns, Stamford, and the airports.
Westport’s public school system is a major draw for families. Staples High School consistently ranks among the top public high schools in Connecticut. The district includes five elementary schools, two middle schools, and one high school:
Coleytown Elementary (K–5)
Kings Highway Elementary (K–5)
Long Lots Elementary (K–5)
Saugatuck Elementary (K–5)
Greens Farms Elementary (K–5)
Bedford Middle School (6–8)
Coleytown Middle School (6–8)
Staples High School (9–12)
Private school options include:
Greens Farms Academy (Pre-K–12)
Pierrepont School (K–12)
One River School (K–12, art and design focused)
Cindy Raney & Team is the elite, boutique real estate team in Fairfield County. They are extremely well versed in the industry, having sold over half a billion dollars in luxury real estate. Cindy’s team is particularly focused on the client experience, helping them throughout the home buying or selling process to ensure that their experience with the team is exceptional.
