$378,901Average Value$260Average Price per Sq Ft1Home For Sale
Picturesque country living by the foothills of the Berkshire Mountains
First settled in 1732, the rural town of Winchester retains its historic look and feel. This forested expanse at the base of the Berkshire Mountains is speckled with Colonial Revivals and Craftsman-inspired homes that range from cozy cabins to extravagant lake houses. Some homeowners come for summer vacations, while others stay to raise their children and grandchildren. “There’s a large cross-section of people who come here, so each smaller community is like a little world unto itself,” says Tom McGowan, a realtor and historic home specialist at Elyse Harney Real Estate.
Majestic countryside residences in Winchester
The vast majority of people who live in Winchester own their homes, and those homes have continued to appreciate in value since 2019. Currently, most houses fall into the $225,000 to $750,000 range. However, a lakefront property with a private dock can sell for $900,000 or more. Architectural styles range from charming Cape Cods, cottages and bungalows to Colonial Revival and ranch-styles with second-story overhangs. Though home ages tend to skew half a century or older, most are outfitted with granite countertops and updated appliances. They are often spread acres apart along country roads and obscured by thick tree lines.
A Colonial Revival home with detached garages and solar panels in Winchester.
A Colonial Revival home in Winchester.
A ranch-inspired, large bungalow with a beautiful porch in Winchester.
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Lakes, state parks and mountain views in Winchester
The valley is home to several state parks, such as Platt Hill Scenic Reserve. The main trail loop branches off into many uncharted paths, which makes the park intriguing for hikers or foragers looking for adventure on a road less traveled by. Winchester is also filled with creeks, ponds and lakes, the largest being the three-mile-long Highland Lake. “There are always a bunch of people canoeing, fishing, all sorts of stuff. And the topography here is fabulous: almost anywhere you go in Winchester, you can see the mountains close by,” McGowan says.
Highland Lake is a freshwater lake located in Winchester known for its scenic beauty.
Platt Hill State Park is a 159-acre public recreation space in Winchester.
Norbrook Farm Brewery is a great place to spend a day enjoying trails, frisbee golf and beer.
Resha Beach is a local beach on the shores of Highland lake.
Hole one on Norbrook's frisbee golf course.
Highland Lake offers opportunities for boating, fishing, swimming, kayaking, and paddleboarding.
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Explore Winchester's sister city, Winsted.
A unique and artistic shopping experience in Winsted
Winchester is deeply intertwined with its sister city of Winsted, which serves as a hub of art and commerce. It contains tons of restaurants, antique shops and artist organizations like the American Mural Project, all of which collectively employ about half the town’s population. Farmers Markets and holiday parades are often held on Main Street, bringing together the entire surrounding community. However, Winchester itself is not without its own unique local businesses. Norbrook Farm Brewery offers a wide selection of beers in an outdoor, family-style environment complete with fire pits and a disc golf course. The Colbrook Store is a combination deli and general store where folks drop in for an easygoing lunch.
Top-rated public schools in Winchester
Children in Winchester start their education at Colbrook Consolidated School for kindergarten through sixth grade, then go to Northwestern Regional Middle School for seventh and eighth, and then Northwestern Regional High School for ninth through twelfth. All three schools are ranked among the top 10 public schools in Litchfield County, with Colbrook Consolidated and Northwestern Regional High taking the number one and two spots, respectively. One factor is class size, where the student-to-teacher ratio is usually 10:1 or less. Another is overall test scoring. Across the board, the pipeline fosters proficiencies in reading and math that far exceed national averages.
Colbrook Consolidated School focuses on providing a comprehensive educational experience.
Batcheller Elementary School serves area Winchester residents.
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Navigating into central Connecticut
Public transportation is not readily available in Winchester, so it is a heavily car-dependent area. Though the town may feel remote, it’s a 15-minute drive north to the small town of Colbrook and 10 minutes east to Winsted. Route 8 and Route 44 are quickly accessible for those commuting to Hartford or elsewhere in central Connecticut.
Written By
Sian Syring
Photography Contributed By
Brandon Schulman
Video By
Daniel Willingham
Interested in learning more about homes in this area?
Reach out to
Jim Treanor Jr,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Winchester, CT sell after 39 days on the market compared to the national average of 52 days. The median sale price for homes in Winchester, CT over the last 12 months is $375,000, up 58% from the median home sale price over the previous 12 months.
Two parcels for the price of one! Discover this beautifully maintained split-level ranch at 111 Old North Road in Winchester, offered together with the adjoining already-subdivided 2.5-acre buildable lot at 113 Old North Road. Enjoy the home as-is or explore the endless possibilities-build an in-law house, sell the lot, or develop it as an investment. Inside, the home features a unique layout
Discover effortless living in this inviting home at the sought-after Clockmaker's Hill community. The thoughtfully designed open floor plan creates seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining room, perfect for hosting friends and family. The sun-drenched kitchen features a convenient breakfast bar for casual dining and morning coffee. The
Introducing Sandy Brook Cottage. Perched gently near the banks of the meandering Sandy Brook, this c.1800 home exudes quiet charm and understated elegance. Set on over 3 picturesque acres in the hidden gem of Colebrook. It is a true country escape. One that offers privacy, character, and an effortless connection to nature. Winding stone walls trace the contours of the rolling landscape, creating
Discover the potential in this raised ranch located in beautiful Winsted, CT! Featuring 3 bedrooms and 1.5 bathrooms, this home offers a functional layout and a great opportunity to bring your vision to life. An attached two-car garage adds everyday convenience and plenty of storage. Set on a nice lot, the property is close to town amenities, schools, and outdoor recreation that make Winsted
End Unit Ranch-Style Condo - Winchester. Discover privacy and convenience in this well-maintained one-level end unit nestled in the foothills of the Berkshire Mountains. Offering an open-concept layout, this ranch-style condo features a spacious living room, dining area, kitchen, large bedroom, full bathroom with in-unit laundry, & excellent closet space. While the condo would benefit from
Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39
By far the best place to live in Winsted, Connecticut. Turn of the century construction, every unit overlooks the beautiful Still River, our 700-1000 square-foot one and two bedroom interiors are bright and charming and feature exposed wood beams, 10-foot ceilings, oversized industrial windows, and exposed brick walls. We deliver nature at your door. Our community amenities include same-floor
Sweet home in a Country Setting, this two bedroom ranch style home offers Hard Wood Floors, large eat-in kitchen and a convenient heated mud room that might be used as a office. Bonus is the open large yard for you to enjoy.
At Gilbert Clock Apartments , our designer-inspired amenities set us apart from the competition. We pride ourselves on providing top-quality apartments outfitted with the everyday amenities you expect as well as luxury amenities to delight your senses and enhance your modern life. Indulge your culinary instincts in your state-of-the-art kitchen, furnished with Beautiful and energy-efficient
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