$1,453,202Average Value$441Average Price per Sq Ft32Homes 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
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GreatSchools:
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On average, homes in Weston, CT sell after 53 days on the market compared to the national average of 50 days. The median sale price for homes in Weston, CT over the last 12 months is $1,399,500, up 5% from the median home sale price over the previous 12 months.
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Hilltop Luxury with Unmatched Views, Privacy, and Sophistication Perched on a private hilltop, this architecturally designed masterpiece by Paul Harris and built by JD Rogers Development, offers a rare combination of seclusion, elegance & convenience. Just minutes from top-rated schools and the town center, this extraordinary home is a sanctuary where thoughtful design meets timeless comfort.
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Property Id: 1735921WESTON CT. Studio (500 sq. ft.)1 Private BathroomGreat AmenitiesPlease read full ad before inquiring.Available furnished. Long term $2,300/month. Utilities included.Available in September 2025. More details can be provided on unit when inquiring.RENT TERMS:$2,300/m. 9+ month term$2,400/m. 3-8 month termDeposit based on
Move-in before school starts! This stunning 7,000+ sq. ft Georgian colonial has been recently renovated from head to toe! This elegant light-filled residence with its open floor plan boasts 5 spacious ensuite bedrooms, high ceilings, hardwood floors, and several possible office spaces. Its flow is perfect for both entertaining and family life. The chef's eat-in kitchen is a true showstopper:
Property Id: 1332235WESTON, CT- Experience the difference to living in a busy city. Weston CT has so much to offer including tranquility and safety.NOTE: At this time ONLY leasing at the end of summer for a minimum of 8+ monthsApartment is inside a large house, on the 2nd floor. Fully Private entrance. Note, this is not the entire house, it is an apartment in part of the
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