$1,486,985Average Value$452Average Price per Sq Ft33Homes 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 67 days on the market compared to the national average of 57 days. The median sale price for homes in Weston, CT over the last 12 months is $1,400,000, up 2% from the median home sale price over the previous 12 months.
Welcome to 181 Georgetown Road, a timeless Weston antique dating back to 1820 that beautifully blends historic character with modern comfort. Rich in period charm and thoughtfully updated for today's lifestyle, this inviting 4/5-bedroom, 3.5-bath residence offers nearly 3,000 square feet of living space set amidst picturesque grounds designed for year-round enjoyment. Inside, original
Nestled on 2.25 breathtaking hilltop acres, this is one of Lower Weston's beautiful building sites. Set in a picturesque, level meadow w/ mature trees, the property offers exceptional privacy on a coveted cul-de-sac just south of Weston Center, near the Historical Society, & minutes from the Merritt Parkway. Whether you choose to renovate the existing home or create the custom estate you've
Welcome to 49 Blue Spruce Circle, a sun-drenched contemporary colonial nestled on two picturesque acres of mature trees and vibrant flowering plants. Boasting 3,297 square feet of versatile living space, this 4-bedroom, 3.1-bath home features a unique, airy layout designed to maximize natural light at every turn. The heart of the home centers around an inviting, open floor plan that flows
A RARE property. The 28- year owners lovingly restored their 18th century antique and expanded it to 6,050 SF of modern comfort on its 4 acres including a 11/4 ac. pond. Albeit, the renovation of the property's antique 1,100 SF, 2 BR continually-rented cottage may be the financial coup for 42% marginal tax bracket (Fed+CT) buyers who assume a 6.25%, 80% ($2,080,000 of 2.6M asking) 30 yr. fixed
Charming two-bedroom cottage set on a beautifully level property, offering a private retreat surrounded by a peaceful, bucolic setting. This home is full of potential-bring your vision and transform it into your perfect escape or year-round residence. Enjoy the ease of convenience of a prime location, just minutes to shopping, dining and major commuting routes. A rare opportunity to create
Welcome to 181 Georgetown Road, a timeless Weston antique dating back to 1820 that beautifully blends historic character with modern comfort. Rich in period charm and thoughtfully updated for today's lifestyle, this inviting 4/5-bedroom, 3.5-bath residence offers nearly 3,000 square feet of living space set amidst picturesque grounds designed for year-round enjoyment. Inside, original
Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with
Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary
A true family home incorporating 12 rooms 6 bedrooms 5 full baths, including a ground floor ensuite InLaw apartment,and 2 bedrooms The Premiere ensuite owners bedroom is on the second floor with a walk in shower and tub.Three other second floor bedrooms with two sitting areas with fire place , 2 bathrooms and an office leading to a second floor sun large family room next to the deck. A second W/D
Welcome to 11 Hunt Lane! This charming Colonial delivers lots of space and flexibility while situated at the end of a tranquil double cul-de-sac in Lower Weston, near the Westport line. Perfect for entertaining, the sun-filled, spacious interior boasts excellent flow. Enter a charming two-story foyer flanked by a living room with fireplace and dining room with wet bar and sliders to a beautiful
Surrounded by nature and complete privacy, this unique home offers a peaceful retreat with exceptional indoor-outdoor living. A large, welcoming entry foyer features tile flooring and a skylight that fills the space with abundant natural light. Hardwood floors and custom windows are found throughout the home.The main level showcases a spacious living room with a wood-burning fireplace and walls
This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With
Tucked away on a coveted lower Weston cul-de-sac, this beautifully renovated colonial offers the rare combination of privacy, style, and resort-inspired living. Thoughtfully updated by the current owner, the home is truly turnkey and ready for its next chapter. Sun-filled interiors showcase sophisticated finishes and an effortless flow for both everyday living and entertaining. The renovated
Nestled on 2.25 breathtaking hilltop acres, this is one of Lower Weston's beautiful building sites. Set in a picturesque, level meadow w/ mature trees, the property offers exceptional privacy on a coveted cul-de-sac just south of Weston Center, near the Historical Society, & minutes from the Merritt Parkway. Whether you choose to renovate the existing home or create the custom estate you've
2026 New Home Construction...Stunning transitional 5-bedroom estate blending classic curb appeal with a clean, modern interior - beautifully sited on 2.35 private acres. This immaculate five-bedroom home offers five ensuite bedrooms (including a luxurious primary suite), exceptional finishes and thoughtful details throughout:Thermador appliances, high-end fixtures, and gorgeous White Oak floors
Property Id: 1735921Available Fall 2026. Furnished Studio (Airbnb Favorite)Now available for direct bookings.Read info & terms in Description below. Beautiful private studio with private entry. Furnished, Airbnb type. Book on airbnb or message with start/end dates. No Phone calls.T E R M S3-month minimum in general.4-month minimum from October/November. No
Property Id: 1332235Location- Weston, CT 06883 Nestled alongside one of Weston’s most picturesque stretches of Newtown Turnpike, this cozy apartment in a New England cottage offers an opportunity to experience small town living. This charming space is tucked along a quiet private road where stone walls line the landscape and large historic homes are separated with plenty of privacy.
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
Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary
This exquisite custom estate on 4.7+/- acres is an incredible opportunity available for lease, and will take your breath away. Set atop one of the highest points in the area, this luxurious retreat blends modern luxury, convenience, privacy and treetop vistas into one irresistible package. Sited to capture the incomparable views, every room and multiple terraces have gorgeous panoramas, with a
Tucked along the water's edge of the Saugatuck River, this enchanting one-bedroom cottage is a true slice of heaven - serene, private, and utterly removed from the everyday. Wake to the soft sound of the river and spend your days surrounded by nature's quiet perfection. The open great room invites you to gather, unwind, and stay a while - anchored by a magnificent stone fireplace that becomes the
Recently renovated from top to bottom, the home features a stunning new kitchen, beautifully updated bathrooms, new flooring, designer lighting, and updated plumbing throughout. The spacious, open layout offers oversized rooms, abundant natural light, and comfortable living spaces designed for both everyday living and entertaining. Move right in and enjoy a fully equipped home complete with
At the End of a Coveted Cul-de-sac in Lower Weston - Welcome to 55 Blueberry Hill! A picture-perfect lifestyle awaits in this thoughtfully reimagined and beautifully appointed country home. This stunning 4-bedroom, 3-full and 2-half bath residence spans over 4,500 sq.ft., offering a gracious layout, gleaming hardwood floors throughout, and timeless architectural details. The custom center-hall
A rare opportunity for lovers of contemporary design-the architect-designed Glass House of Weston is available for rent. This renovated home boasts an open floorplan flooded w/natural light from floor-to-ceiling windows and skylights, offering serene views of its well-maintained natural surroundings, lush foliage, and striking rock outcroppings. The LR features soaring ceilings, mahogany windows,
Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary
Charming retreat in lower Easton nestled on 3+ acres just over the Westport border! This warm & inviting home exudes character and charm with the comforts of modern day amenities such as central AC and generator. Enter through the welcoming screened in porch where you can relax in the morning with your coffee in hand and at night with your favorite drink. Enjoy the sunny great room/art studio and
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