Welcome to Westport
If coastal living has always been your dream, then put the quintessential New England town of Westport on your real estate map.
Westport was first settled in the 1600s. The town prospered as an agricultural community, distinguishing itself during the Civil War as the nation’s leading onion producer. Westport is now considered one of the gems of Connecticut’s gold coast. And today, some of America’s best oysters come from local waters. Meanwhile it has diversified, earning fame as both “The Marketing Capital of the U.S.,” and home to the country’s largest hedge fund.
Long known as an artists’ colony, Westport has held strong to its cultural past. The Westport Country Playhouse and Levitt Pavilion offer outstanding performances, drawing nationally known actors and entertainers. Joanne Woodward, Michael Bolton and Anne Hathaway are the latest in a long line of famous residents – stretching back to F. Scott Fitzgerald, Elizabeth Taylor and Jason Robards, drawn here by Westport’s creative vibe. Westport is also known for its strong public education. There are five elementary schools, two middle schools and Staples High School, which for decades has been rated as one of the best in the nation.
Westport’s downtown is a charming, thriving and constantly evolving hub. It’s filled with an eclectic mix of unique boutiques and international retailers. Saugatuck – just two miles from Main Street – is another dynamic retail, restaurant and residential destination. Westport is just 45 miles from New York City, via I-95 or the Merritt Parkway. Two train stations serve Metro-North’s New Haven line, at both Westport and Greens Farms station.
Explore the neighborhoods Westport has to offer
below and reach out to learn more.
Compo Beach
For generations, Westporters have enjoyed Compo Beach’s good life, with friends and family. Favorite features include basketball, volleyball and pickleball courts; a skate park, and an intriguing and innovative playground constructed from all-natural materials.
Compo’s Ned Dimes Marina was completely renovated a few years ago. Its modern concrete dock system is typically found only in private marinas and yacht clubs. Nearby dry racks hold kayaks, windsurfers and small sailboats.
Westporters love to barbecue and host clambakes at one of the dozens of grills on Compo’s South Beach. Located just steps from the town’s iconic cannons that commemorate the 1777 British landing, part of a march to burn an arsenal in Danbury, followed by the historic Battle of Compo Hill. It is a favorite spot to watch spectacular sunsets and enjoy views with family and friends.
Compo truly comes alive for the July 4th fireworks (held, traditionally, a day or two earlier). Over 10,000 folks arrive early, for a day of picnics, parades and pyrotechnics shot from a barge anchored just offshore. There are house parties up and down Soundview Drive, and huge gatherings across the road on the sand. Soundview, the main road, forms the backbone of the funky little beach neighborhood.
In 1920, F. Scott Fitzgerald lived a quarter mile from the beach, on South Compo Road. He wrote his novel “The Beautiful and the Damned,” and gazed across open land toward Long Island Sound – views that later influenced “The Great Gatsby.” Fitzgerald’s house still stands, at the corner of Longshore Club Park.
Longshore – owned since 1960 by the town of Westport – is a true gem. Its 200-plus acres include an 18-hole golf course, tennis and paddle courts, two swimming pools, a marina and an outdoor ice skating rink. The Longshore Sailing School offers lessons and rentals (including kayaks, canoes and paddleboards). The Inn at Longshore is a favorite site for weddings, while La Plage at Longshore is a popular spot for waterfront dining.
Downtown
Westport’s downtown has a bit of everything: a river, charm, plenty of restaurants, an exciting mix of national retailers and unique mom-and-pop shops, an innovative library, intriguing activities, and plenty of buzz.
Located on the banks of the Saugatuck River with an actual Main Street a few yards away, “downtown” is both a place and a state of mind. It includes the Post Road, and Church Lane; featuring the new retail/residential Bedford Square complex, and the area just across the bridge, boasting with even more art galleries, restaurants, activities and shopping experiences.
The Westport Downtown Merchants Association sponsors a year-long calendar of events. From horse-drawn carriage rides at Christmas to a mid-summer art show with painters, sculptors and photographers from across the Northeast, there is truly something for everyone here.
Shopping downtown includes a mixture of boutiques and brand name shops including Barnes and Noble, Anthropologie, Patagonia, Urban Outfitters, Serena & Lily, WEST, Great Stuff, Marine Layer and more.
Dining favorites downtown include The Spotted Horse, Pink Sumo, The Cottage, Amis, GG & Joe’s, Bar Taco, Arezzo, and more.
Best of all: the parking is free!
Greens Farms
In 1648, five farmers from Fairfield staked out this area as prime real estate. Lured by rich pasturelands and plentiful brooks and streams, the men struck a deal with the Wallops Indian tribe living there, and settled along the waterfront. Their investment proved wise. The settlement prospered and grew, eventually taking the name of one of the founding farmers: John Green. Proximity to Long Island Sound, and distinction as the oldest residential section of Westport have contributed to Greens Farms’ reputation as a promised land for suburban settlers.
The Westport public school system consistently ranks in the top five percent in the state. Meanwhile, Greens Farms Academy provides a traditional private school experience. Founded in 1925, it encompasses 26 acres on the former Beachside Avenue estate of the Bedford family. An elegant stone house, with commanding views of Long Island Sound, serves today as Greens Farms Academy’s main building.
Burying Hill is the hidden jewel of Westport’s beaches. Off the beaten track at the end of a sweeping turn on Beachside Avenue, its name comes from its former role: a burial place used by settlers until about 1725. Some of the best fly-fishing can be had when the full moon causes sand eel hatches. Sunset views are incredible to watch here too.
Around the corner from Burying Hill Beach, looking like a Norman Rockwell painting, is the Greens Farms train station. There is ample parking (fees apply). Shuttle bus service is also available.
The Greens Farms neighborhood also encompasses Turkey Hill Road. Martha Stewart got her start in the pristine colonial (which she spent 20 years renovating). She filmed her television show in her antique barn, and threw memorable parties for her friends and family. Turkey Hill joins Morningside Drive, Clapboard Hill and Devon Road as some of Westport’s most exclusive addresses.
There’s also Beachside Avenue. Homes here fetch up to $25 million. Phil Donohue and Marlo Thomas reassembled one of the great properties of early Westport, purchasing three contiguous lots comprising nearly eight acres. From the Gold Coast of Beachside Avenue to the pastoral meadows of Nyala Farm, where cows grazed just a few years ago, Greens Farms has changed little over the years.
The five farmers from Fairfield who in 1648 first singled out the area as prime real estate were visionaries. Nearly four centuries later, residents are attracted by the same rich, desirable land and waterfront living the original settlers coveted.
Long Lots
A bit of old Westport lives north of the Post Road, in between Fairfield and Southport. The neighborhood is framed by the 40-acre Fairfield County Hunt Club, a beloved staple in Westport.
Founded nearly 100 years ago for equestrians and polo players, and with notable members over the years like Martha Stewart, Paul Newman, Frank Deford, Robert Ludlum and Harry Reasoner, it’s still a spot for horse shows and polo matches.
There’s much more about the neighborhood that draws in families from all around the world. The Hunt Club consists of two swimming pools, both tennis and paddle courts, a formal dining room, a casual grill room, plus a 60-by-120 foot skating rink. Meanwhile, six barns and several indoor and outdoor rings maintain the historic riding tradition.
Don’t be surprised to see horses being ridden on the roads near the Hunt Club. It is truly a sight to see!
The Long Lots neighborhood derives its name from the original “long lots,” drawn for farmers in the 1600s. At the time, they reached all the way north to Weston. Much of that history still remains in the area, including the oldest house still standing in Westport. It was built in 1690 on (yes) Long Lots Road.
Saugatuck
Saugatuck is an Indian word meaning “mouth of the river.” There is no better way to enjoy Westport’s charming character and seaside lifestyle than by exploring this historic yet always evolving enclave. The Saugatuck River defines this area. It was originally Westport’s commercial center, with easy water and rail access to New York, Boston and points far beyond. For many decades it was a close-knit Italian neighborhood filled with churches, triple-decker homes, and family-owned stores and businesses.
Today, a renaissance has brought funky stores, many new restaurants, an ice cream shop, a paddleboard rental and 20 apartments to its walkable, vibrant streets. Of course, the arrival and departure of trains still defines Saugatuck’s rhythms. The railroad station provides frequent access to New York, Boston and points beyond. Just 47 miles from Grand Central Terminal, the Westport commute is convenient for commuters and day trippers.
Some of Westport’s best dining can also be found here. Viva Zapata has been a landmark watering hole for decades. Longtime favorites such as the Black Duck (featured on “Diners, Drive-Ins and Dives”), Tarantino’s, Tutti’s and Dunville’s join newcomers like The Whelk, Kawa Ni, Rainbow Thai, Bistro du Soleil and Parker Mansion in making Saugatuck a destination for food lovers of all cuisines.
Saugatuck offers waterfront living at its best. Stony Point winds down to the river, from the railroad station. Handsome Nantucket-style homes by Michael Greenberg, Peter Cadoux and other noted builders gracefully command the landscape, along Saugatuck Avenue on the way to Saugatuck Shores. That’s the Cape Cod-style community anchored by Harbor Road and an impressive lagoon. A narrow arched bridge welcomes residents and visitors to this tight-knit, family neighborhood. Quaint beach cottages and contemporary homes with deep-water docks set the stage for an active, maritime lifestyle.
Sailing has always been an integral part of Westport. Prominently situated at the head of the river is Cedar Point Yacht Club. Its sailing program is renowned in New England. Wednesday night competitive races are a summer highlight. Nearby, Saugatuck Harbor Yacht Club offers cruising, fishing and racing, plus year-round entertainment and a special interest schedule for members.
Rowing enthusiasts of all ages are also drawn to the Saugatuck Rowing Club, on the river near the heart of Saugatuck. The modern facility – with a first-class fitness center, public restaurant and killer views – turns out some of the top rowers in the country. The youth program is particularly well regarded, with college coaches vying to give scholarships to SRC boys and girls.
Coleytown
Coleytown is another historic residential neighborhood. Tucked away in the northern part of town, and bisected by the Merritt Parkway, the area is named after the Coley family.
They farmed the land in that specific area of town for over 200 years. There was once a thriving village here that included a small green, a schoolhouse, shoemaker, blacksmith, yarn manufacturer, horse stables and five of the Coley homes.
There’s no commerce in Coleytown today; just handsome homes, a school, fire station, and the infamous Newman-Poses Preserve. The 39-acre tract features woodlands, wetlands, open fields, stands of old white pine, and a trail beside the Aspetuck River.
And yes, it’s named for that Newman. The nature preserve is the only public memorial approved by the family of the late Paul Newman as a way to honor the actor, philanthropist, and longtime Coleytown resident. Recalling how much they all enjoyed hiking and swimming on the land behind their home, the family donated eight of those acres to the town back in 2008.
Old Hill
One of Westport’s oldest settlements, Old Hill has changed little from colonial days. Here, some of the town’s most historic homes grace tree-lined streets. Two cemeteries honor 18th-century patriots, who trained for battle on a grassy field nearby. They had good reason: In 1777 the British marched to Danbury on Wilton Road, which forms the neighborhood’s eastern border.
Old Hill is also where you’ll find Earthplace. Founded in 1958 in the woods off Stony Brook Road, the hands-on nature center includes a natural history museum (with a live Birds of Prey exhibit, and indoor Animal Hall), and a state-licensed preschool.
A variety of habitats thrive in over 70 acres of open space. Several miles of walking trails are open to the public (some are suitable for wheelchairs and strollers).
Earthplace is home to Harbor Watch, the renowned water quality research program here in town. A wide range of educational programs and volunteer opportunities draw children, teenagers and adults to this environmental gem right here in town.
The newest attraction in Old Hill is the Wadsworth Arboretum. The 12-acre sanctuary adjacent to Earthplace is a quiet haven filled with beautiful trees, flowers and a variety of hiking trails. Designated as open space in perpetuity, the arboretum is managed by the tree warden as well as the Westport Tree Board.