$1,544,976Average Value$459Average Price per Sq Ft37Homes 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?
Reach out to
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an experienced agent in this area.
GreatSchools:
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On average, homes in Weston, CT sell after 66 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 $1,405,000, 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 over 3 breathtaking acres with over 500 feet of frontage on the west branch of the Saugatuck River, this exceptional property offers the perfect blend of privacy, outdoor living and natural beauty. Surrounded by mature trees and lush lawns, the setting is nothing short of spectacular--truly one of the most beautiful in Weston. The spacious home is thoughtfully designed with an open
An exceptional example of mid-century modern architecture, this sophisticated 4-bedroom retreat on a cul-de-sac in Weston was designed by renowned Westport architect Larry Michaels & is defined by clean lines, dramatic proportions and an extraordinary connection to nature. Designed to bring the outdoors in, the home unfolds around walls of glass & expansive high windows that draw natural light
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
The Oasis at Richmond Hill is a rare mid-century modern retreat nestled at the end of a quiet cul-de-sac in Weston. Set on 2 acres of landscaped grounds bordered by towering spruce, elms, and rhododendrons, this 1956 residence offers a seamless blend of architecture and nature. Inspired by the Harvard Five, its design features clean lines, warm materials, and walls of glass that frame the
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
Bring your creativity and vision to make this distinctive home your own. Ideally situated in lower Weston, just 1 mile from the award-winning Weston schools and minutes, this contemporary style home is set on 2.23 private acres with a heated pool. The flexible, open floor plan features dramatic walls of glass that bring the outdoors in and showcase the beautiful surroundings year-round. The home
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
Welcome to this spacious 4-bedroom, 3-bath Colonial offering 2,700+ square feet of versatile living space in Lower Weston. Set on 2.3 private wooded acres, the home features a flexible floor plan with generous living areas, a finished lower level, and a bright four-season room that provides additional year-round living space. The main level has the convenience of first-floor laundry along with an
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
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
Just 1/2 mile from the Westport border on a prestigious Weston cul de sac sits this beautiful, spacious 4 bedroom family colonial. Expansive kitchen gleams with stainless steel appliances and opens to family room with fireplace. Rounding out the ample first floor is a large living room with a second fireplace, cozy dining room, and spacious sun room that opens to the large deck and lovely
**A Sun-Filled Weston Retreat with Exceptional Space, Style & Spectacular Grounds** Welcome to 81 Trails End Road, an impressive 12-room, 6-bedroom, 5-bath residence where exceptional natural light, beautifully designed living spaces and magnificent level grounds create a truly special place to come home. Oversized triple-pane Andersen windows capture sunlight throughout the day, filling
Property Id: 1332235 (Available Nov/Dec for minimum 90 days or more) (Book direct or on the popular sites) Enjoy a large relaxing apartment in a cottage style house with modern living amenities. On 2nd floor wi th it's own entry door and 1,400 square feet of living space. Full details below. -All furniture included (only rented furnished) -2 large bedrooms
Property Id: 1332235 (Available Nov/Dec for minimum 90 days or more) (Book direct or on the popular sites) Enjoy a large relaxing apartment in a cottage style house with modern living amenities. On 2nd floor wi th it's own entry door and 1,400 square feet of living space. Full details below. -All furniture included (only rented furnished) -2 large bedrooms
Property Id: 1735921 (Available December 2026 for minimum 90 days or more) This is a top rated "Airbnb Favorite" in the area. This studio has all you need for a relaxing stay. It's a 500 sq ft. space w/kitchen, bartop, desk, and more. This is setup for a single occupant. -All furniture included -Private bathroom -Washer/Dryer -Fully equipped kitchen
Property Id: 1735921 (Available December 2026 for minimum 90 days or more) This is a top rated "Airbnb Favorite" in the area. This studio has all you need for a relaxing stay. It's a 500 sq ft. space w/kitchen, bartop, desk, and more. This is setup for a single occupant. -All furniture included -Private bathroom -Washer/Dryer -Fully equipped kitchen
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
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
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,
Welcome to 24 N Calvin Rd, an exceptional residence set in the prestigious enclave of Weston, where timeless elegance meets serene New England beauty. Perfectly positioned on a private, picturesque setting, this distinguished home offers a rare combination of sophistication, comfort, and refined living. Thoughtfully designed with attention to detail, the home features expansive, light-filled
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
Nestled on over 3 breathtaking acres with over 500 feet of frontage on the west branch of the Saugatuck River, this exceptional property offers the perfect blend of privacy, outdoor living and natural beauty. Surrounded by mature trees and lush lawns, the setting is nothing short of spectacular--truly one of the most beautiful in Weston. The spacious home is thoughtfully designed with an open
Experience the elegance and tranquility of this exquisite two-bedroom cottage nestled within a picturesque lakeside estate. Bathed in natural light, this like-new home radiates charm and luxury. Revel in the open floor plan with granite kitchen counters and newer appliances, while the spacious bedrooms offer a haven of comfort. Discover quality finishes, high ceilings, and gorgeous hardwood
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