$1,467,637Average Value$438Average Price per Sq Ft18Homes 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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GreatSchools:
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On average, homes in Weston, CT sell after 64 days on the market compared to the national average of 55 days. The median sale price for homes in Weston, CT over the last 12 months is $1,390,000, up 1% from the median home sale price over the previous 12 months.
This restored, 6,100sf, expanded 18th century farmhouse commands a view of its 1.24 acre, brook-fed lake, expansive lawn, raised beds and 400 ft. bleached stone driveway. Those features read: Big Tented Celebration, Fabulous Local Tomatoes. The former NYC chef's kitchen is open to the entertaining areas' 5 rooms that circle around the heartbeat that makes a home feel and taste just right. A
A modern contemporary meets an enchanting treehouse retreat. This beautiful, remodeled sanctuary is tucked away on a private cul-de-sac in Lower Weston. Spanning over 5,400 square feet across 3 levels. The home seamlessly blends bold, sophisticated aesthetics w/ the natural serenity of its 2.61-acre setting. The interior is defined by vaulted ceilings & walls of glass that flood the home w/
CONTEMPORARY RETREAT IN LOWER WESTON. Set on over two private acres in coveted Weston, this timeless Contemporary offers beautifully proportioned, light-filled living spaces designed for both relaxed everyday living and elegant entertaining. A gracious foyer welcomes you into the home, where a dramatic sunken living room with soaring vaulted ceilings and a striking stone fireplace creates an
This restored, 6,100sf, expanded 18th century farmhouse commands a view of its 1.24 acre, brook-fed lake, expansive lawn, raised beds and 400 ft. bleached stone driveway. Those features read: Big Tented Celebration, Fabulous Local Tomatoes. The former NYC chef's kitchen is open to the entertaining areas' 5 rooms that circle around the heartbeat that makes a home feel and taste just right. A
A modern contemporary meets an enchanting treehouse retreat. This beautiful, remodeled sanctuary is tucked away on a private cul-de-sac in Lower Weston. Spanning over 5,400 square feet across 3 levels. The home seamlessly blends bold, sophisticated aesthetics w/ the natural serenity of its 2.61-acre setting. The interior is defined by vaulted ceilings & walls of glass that flood the home w/
Welcome to this sophisticated country Cape blending modern living with charm in Weston's Georgetown area. White picket fences and stepping stones through an arbor welcome you to the front porch of this beautiful home! Set at the end of a quiet cul-de-sac on a level acre with inviting circular driveway, the home's open floor plan creates comfortable flow for everyday living & entertaining. Two
This charming one bedroom and one bath home is tucked between Devil's Den Nature Preserve and the Saugatuck Reservoir conveniently located in North Weston. Sited on a half-acre, this home is serene and in the midst of nature. All measurements approximate. Weston residents are provided the opportunity to purchase parking emblem to access Westport amenities, including beaches and pool.
Lindsey R. MullholandDouglas Elliman of Connecticut
CONTEMPORARY RETREAT IN LOWER WESTON. Set on over two private acres in coveted Weston, this timeless Contemporary offers beautifully proportioned, light-filled living spaces designed for both relaxed everyday living and elegant entertaining. A gracious foyer welcomes you into the home, where a dramatic sunken living room with soaring vaulted ceilings and a striking stone fireplace creates an
Come & be dazzled by this Nantucket inspired water-front country estate! Custom craftmanship is the hallmark throughout this 5BR home. A gracious foyer welcomes you & leads you to sunny living room w/ bay window, large dining room w/ custom built-ins & fireplace.The recently remodeled kitchen is a chef's dream w/ 6 burner Wolf Gas range, 8 ft. granite topped center island, a double sub-zero &
This is very special. INVESTOR'S DREAM !! AN AMAZING OPPORTUNITY IN LOWER WESTON-DIRECT SAUGATUCK RIVER FRONT VIEWS-Beautiful home with separate living spaces featuring living rooms, family rooms, dining areas, newer kitchens & baths, wraparound decks with serene river views and so much more. Beautiful hardwood floors throughout, updated bathrooms and kitchens, newly updated oil tanks and heating
Set along one of Weston's most picturesque and sought-after roads in Lower Weston, this beautifully renovated Colonial farmhouse blends timeless charm with thoughtful modern upgrades on 2.59 level acres. Meticulously maintained and move-in ready, the home offers 4 bedrooms, 3 full baths, and approximately 2,646 square feet, including a finished walk-out lower level with fireplace. The sun-filled
Welcome to your dream home in Weston, CT! This stunning five-bedroom, five-bathroom colonial home is nestled on a private cul-de-sac in one of the most sought-after neighborhoods in Weston. Step into timeless elegance with this beautifully crafted traditional Colonial home, where classic charm meets modern livability. Designed with a seamlessly flowing layout, this residence offers the perfect
Welcome to this recently updated New England retreat with stone walls, a circular gravel driveway, and manicured grounds. Fenced and setback charming 5-bed and 2 full + 2 half baths colonial with sun-filled galleries and rooms. 2 fireplaces, 2-story cathedral ceilings. The modern open-floor kitchen (2025) opens to the dining room, family room, and a large deck. Luxurious MAIN FLOOR primary
Rare oppotunity to purchase a magical 2 acre parcel of land w/ a little slice of frontage on Aspetuck River in coveted Stonybrook Association. Beautiful lot with fabulous views in true lower Weston on Westport border! Stonybrook is a unique enclave of homes in Weston and offers swimming, boating, tennis, zipline, basketball court, playground, picnic benches and more, all for the use of homeowners
Rare opportunity to own a historic 2-acre compound featuring a circa 1770 home (1223 SF), charming 1930s cottage (1048 SF), classic barn, and a rare surviving corn crib. An exceptional property rich in New England history & character! Step into the heart of the 1770 home where centuries-old craftsmanship is on full display. Massive hand-hewn beams stretch across the ceiling, beautifully preserved
Property Id: 987925Down a country lane and sitting on pretty farmland, is this cozy late 50's 2Bdrm-shingled cottage -Easy one level living that includes newly updated kitchen with new,app's, nice tile /counters-and bath- all- freshly painted and move in ready. Enjoy the convenient yet private location, just across the street from popular Bisceglie-Scribner Park, comprised of 53.5 acres
Located on a quiet Cul De Sac in lower Weston,3 bedrooms,2 full and 1 half bath. THe primary bedroom has its own full bath and walk in closet. . Lower level includes the family room and separate office with the half bath. Landscaped level lawn with extensive fencing in the back to keep your pets in and the deer out.Home is a classic raised ranch offering 2100 sq ft of living space.Weston
Stunning Home for Rent on Good Hill Road, Weston, CTWelcome to Good Hill Road, a beautifully appointed residence nestled in the desirable town of Weston, Connecticut. This spacious 4-bedroom, 3-bathroom home offers 3,618 square feet of thoughtfully designed living space, providing the perfect blend of comfort and style for families of all sizes.Key Features:4 Bedrooms:
Beautifully renovated with custom finishes. 4 decks, turf patio, scenic wooded backyard pond feeding into Kettle Creek, 40 yard flat front yard. 3 mi to Merritt Parkway, walk/bike to Schools, Town Center & Library, 7 mi to Compo Beach. First floor office, living room with fireplace, 1/2 bath, open vaulted ceiling kitchen with fireplace opening to front and rear decks. Sunroom leads to above
MOVE-IN READY! This charming CT storybook Cape has been completely redone & is turn key. Located in lower Weston on gorgeous 2.5 acre across from Katherine Ordway Preserve & just minutes to Weston's award winning school campus, town center & downtown Westport. EVERYTHING has been updated including freshly redone hardwood floors, new kitchen & 3 new full baths. The entire house has been freshly
Stunning farmhouse in Weston! - Updated kitchen with white shaker-style cabinets, quartz counters, subway tile backsplash, large island, and stainless steel appliances!! - Light & bright living room with wood-burning fireplace - Sliding door from living room leads to huge back deck! - Large primary bedroom with huge walk-in closet featuring custom shelving system - Updated bathroom features
Beautiful mid century home with walls of glass, elevated ceilings, wrap around deck, and patio. If you love feeling as if the outside is part of your interior world this may be your perfect rental home. Beautiful open floor plan with a fireplace in the living room and dining room, updated granite high end kitchen all open to the wrap around deck. Primary bedroom with en-suite and three additional
Completely renovated ranch, thoughtfully designed and built by a renowned Weston builder for his own residence, offering exceptional quality and craftsmanship throughout. Tucked away on a quiet cul-de-sac in desirable Lower Weston, this home blends privacy with convenience. Designed with everyday living and entertaining in mind, the property offers everything a family could want. Enjoy access to
Charming Restored Antique with River Frontage in Lower Weston. Available for Yearly Rental. 3100 SF of refined living space with 4 beds and 4 full 1 half baths. Enter thru the expansive Foyer with fireplace and half bath Powder Room. The large Living Room/Dining Room with fireplace offers ample space. Library/Den with fireplace, wet bar and built ins. Solarium with sky lights perfect for enjoying
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.
Wonderful, charming historic Farmhouse nestled next to the Aspetuck River, but not too close! Well-appointed eat-in kitchen. Beautiful wide plank Chestnut flooring. Inviting covered porch overlooking a level backyard with views of the river. Just 10 Minutes to Main Street, Westport. Fully equipped with sheets, towels, silverware, etc... bring personal items and groceries and you are all set!
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