$1,472,753Average Value$445Average Price per Sq Ft13Homes For Sale
Small town surrounded by woodlands and countryside
Founded in 1787 and set 58 miles northeast of New York City, Weston is a Connecticut town with community spirit, scenic countryside and a diverse range of single-family homes with acreage. “I raised my family in Weston — I love it,” says Lori Ferber, a Realtor with William Raveis Real Estate who has over 25 years of experience in the area. “It’s such a warm, inviting, caring, amazing town.” Local businesses are set in the town center, along with schools for all ages and key amenities like the Weston Public Library and Weston Senior Center. “We don’t have HomeGoods or Costco — we have land,” Ferber says. “There is a lot of natural beauty — you sit on your backyard porch, and you might see interesting birds and deer.” The area’s small-town ambiance keeps the community tightknit, but neighboring towns, like Wilton and Westport are within 5 miles, and commuting to NYC is common. “You have the best of both worlds — a peaceful quiet neighborhood but everything at your fingertips,” Ferber says.
Sports, hiking and more in Weston
The 50-acre Bisceglie-Scribner Park is the town’s main green space, with Little League fields, pickleball courts and a swimming pond. For 50-plus residents, the Weston Senior Center offers group exercise classes like yoga, pickleball and tai chi. Hikers and birders enjoy the 1,700-acre Devil’s Den Preserve, with over 20 miles of dirt-packed trails and birds like American robins and blue jays. “Devil’s Den is the big place to go hiking,” Ferber says. For golfers, the private Aspetuck Valley Country Club offers an 18-hole course, as well as a pool and pickleball courts for members. For an easy summer trip, Westport beaches are about 8 miles away. “Westport is our sister town,” Ferber says. “Their beaches have playgrounds, skateparks — you can have a beach barbecue.
Local families love the playground at the 50-acre Bisceglie-Scribner Park in Weston.
For hikers, the 1,700-acre Devil’s Den Preserve includes over 20 miles of tree-lined, dirt-packed trails.
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Secluded single-family homes and mansion estates
Set along country roads without sidewalks, Weston’s single-family homes are diverse, but colonials, ranch-styles and cottages from the 18th century through the late 20th century are common. Popular features include covered patios, board-and-batten windows and detached or attached garages. There are also 21st-century mansion estates, some with up to 12,000 square feet of living space. Common features of these larger homes include multi-car garages, wraparound decks and pools. Weston’s homes are often secluded on 2- to 4-acre pastoral lots with mature trees, including oaks and maples. “Also, most houses have septic tanks and private wells,” Ferber says.
Single-family home prices range from $600,000 to $1 million, but larger homes on at least two acres start around $1 million. “Searching for homes is hard because the inventory is low right now,” Ferber says. “People are just waiting for houses to be listed. It’s a seller’s market.”
Single-family homes in Weston are generally a mix of colonials, ranch-styles and cottages from the 18th century through the late 20th century.
21st century homes with pools and multi-car garages are common in Weston.
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Learning and celebrating at town events
Weston’s community calendar is packed year-round with sports programs, classes and celebrations. “For the Memorial Day Fair, there’s a parade along Weston Road,” Ferber says. “Everyone lines up and watches, then goes to the fair at Weston Elementary. It’s adorable.” In October, Weston Founders Day on the Town Green features music, food and historic exhibits and artwork that reflect the town’s 200-plus-year history, along with fun traditions, like the annual town picture. There are events every day at the Weston Senior Center, including art classes, speaking engagements and group trips to NYC. At the Weston Public Library, residents may sign up for clubs like photography, cookbook and sip n’ stitch. For kids, there are summer and fall camps, as well as the Weston Performing Arts Summer Camp.
Small, locally owned shops and restaurants
“We have only one little town center and it makes you think back to the days of Norman Rockwell,” Ferber says. At Weston Shopping Center, Lily’s Weston Market has pantry essentials, deli cuts and fresh produce. “It’s an amazing supermarket with everything you need and very high quality, but it’s not a place where you’re going to get 20 different brands of laundry detergent,” Ferber says. “It’s just a pleasure when you need a half pound of roast beef and you go in, and everyone knows you.” Next door, Lunch Box serves comfort staples like fried chicken, Philly cheesesteaks and pizza. Other businesses here include Minute Men Cleaners and Weston Pharmacy. “If you’re sick, the drug store will deliver to your house,” Ferber says. “CVS or Walgreens would never do that, but that’s the great thing about a small town — they go above and beyond.” Four miles away, there are more shopping and dining options in Wilton, including a Stop & Shop for a wider selection of groceries, Tusk & Cup Fine Coffee for a morning cup and Cactus Rose for an after-dinner drink.
Lunch box in Weston is known for its delicious pizzas and subs.
Locals find fresh produce, deli cuts and pantry staples at Lily’s Weston Market.
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Weston public schools receive high marks from Niche
Weston is part of the Weston School District, rated A overall by Niche, and all the district’s schools are located right in town along School Road. Local kids may start at the B-plus-rated Hurlbutt Elementary, before moving on to Weston Intermediate for third to fifth grade and Weston Middle for sixth to eighth grade — both rated A. The A-plus-rated Weston High offers over two dozen extracurriculars for students, including clubs like crochet, fishing and women in film. “It’s a very gentle thing because these kids have been together since they started school,” Ferber says. “It feels much smaller and intimate. They know each other better.”
Students from Weston begin their education at Hurlbutt Elementary School, rated B-plus by Niche.
Weston Middle School serves students in grades 6th through 8th and is rated A by Niche.
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Getting around from Weston
State Route 53 runs through Weston and merges with state Route 15 about a mile away, which leads 18 miles southeast to Bridgeport, and 58 miles southwest to New York City, an 80- to 120-minute drive during rush hour. Locals are generally car-dependent, but Weston offers a dial-a-ride service for senior and disabled residents; Westport Station is 7 miles away with a commuter rail. “We also have our own volunteer ambulance, which you don’t see many times,” Ferber says. “They get there faster than the paramedics. That’s a wonderful thing to have.” Norwalk Hospital is 9 miles away; Westchester County Airport is 24 miles away, and John F. Kennedy International Airport is 56 miles away.
Written By
Travis Rocha
Photography Contributed By
Jerome Strauss
Video By
Mark Barakat
Interested in learning more about homes in this area?
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On average, homes in Weston, CT sell after 60 days on the market compared to the national average of 54 days. The median sale price for homes in Weston, CT over the last 12 months is $1,399,500, up 2% from the median home sale price over the previous 12 months.
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Designed for flexibility & privacy. Stunningly re-imagined & rebuilt Westport residence offers TWO distinct living levels w/bdrm suites on both floors. Ideal for today's evolving lifestyles. Main-level living is complimented by a private lower-level retreat, perfect for guests, home offices, or extended living needs, all set on beautiful, serene property.Prepare to be wowed by this 4-bedroom, 3
Modern luxury meets historic charm on 5 private acres in lower Weston. Set at the end of a long, tree-lined drive, this reimagined Tudor Revival estate—once the retreat of Godspell creator John-Michael Tebelak—offers exceptional privacy and turnkey living. Renovated and expanded by architect Jack Franzen, the main home features 7 bedrooms, 8 full and 2 half baths, a dramatic two-story
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Quintessential cul-de-sac living in the heart of sought-after Weston small town suburbia with top rated schools. This stately center hall Colonial sits gracefully atop a hill, offering privacy, elevated views, and a peaceful wooded setting complete with a charming treehouse tucked into the surrounding woods. Inside, the home offers the flow today's buyers seek, featuring beautifully updated
Exquisite 1970 Renovated 3 Bedroom House with Renovated Barn and Private Art Museum in Weston, CT Nestled in the heart of Lower Weston, Connecticut, this exceptional 3.25 acre property offers a unique blend of historic charm and modern luxury. Situated on a meticulously landscaped estate, this renovated 3-bedroom house presents an unparalleled opportunity to experience gracious living alongside
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39 Tannery South is the kind of home that makes you exhale the second you walk in. Thoughtfully updated, every space feels intentional, warm, and beautifully designed. An open concept layout flows through a stunning kitchen with custom cabinetry, quartz counters, glass tile backsplash and a generous island made for gathering. The living room features custom barn door sliders that let you create a
This beautifully renovated 4-bedroom Colonial in Lower Weston, Connecticut, exemplifies exceptional craftsmanship and attention to detail throughout. Set on a level, two-acre corner lot, the home offers both privacy and a tranquil setting. The modern kitchen features top-quality finishes and flows seamlessly into the family and dining rooms, overlooking a picturesque backyard. The living room,
On one of Weston's most coveted cul-de-sacs, this custom Colonial offers over 6,200 sq ft across three finished levels plus a full lower level, set on just over two flat private acres. From the moment you step inside, the light is unmistakable, with oversized windows illuminating generous rooms and impressive vertical scale. The professionally appointed kitchen with Thermador double ovens, Viking
27+ acres of serene land along the Aspetuck River spreading between Weston and Fairfield. A rare opportunity to build your dream home and have seclusion while bordering Westport with all modern day conveniences and shopping. Close to Aspetuck Valley Country Club and golf course, The Patterson Club, Camp Aspetuck and the Connecticut Audubon Society. *All parcels sold together. *See attached
This exceptional stone home, blending contemporary design with natural tranquility, sits on 2 private acres in Weston. Expertly engineered & beautifully constructed, the home welcomes you through a dramatic two-story foyer into a sun-filled living room with floor-to-cathedral windows, a custom two-sided fireplace, and sweeping woodland views. Open chef's kitchen features granite countertops,
In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every
Picture perfect story book stone and shingle cape with charming interior stone walls located on historic road in the heart of Lower Weston. Stunning, newly renovated Kitchen with honed marble countertops, island, breakfast bar and wood beams that opens to a lovely Sun Room that would make a fabulous play room, sitting room, or extra office. The Family Room and Dining Room are inviting with the
SHORT TERM FURNISHED WESTON RENTAL Do you love modern homes but the charm of wood beams? This 3/4 bedroom rental home is for you! This architecturally significant home is a wonderful former Westport barn that is now a light-filled modern home. The first floor's two-story open living area has a living room with fireplace, dining room, and kitchen, while also offering a library and full bath.
Set in Fairfield's desirable Aspetuck area, this special property feels like a private retreat, tucked away with stunning views of the Aspetuck River and waterfall in every season. Built by an artist in the 1930s, the home was intentionally designed with expansive windows to capture the surrounding landscape and natural light. The front-to-back living room is filled with light and features
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