$378,240Average Value$259Average Price per Sq Ft1Home For Sale
Winchester has rural charm and mountain views in the Litchfield Hills
Winchester is a leafy town in the Litchfield Hills, a rural region whose rolling hills stretch across Connecticut’s northwestern corner. Known as the Gateway to the Berkshire Mountains, it offers a scenic foothill location with access to outdoor recreation. “The topography here is fabulous; almost anywhere you go in Winchester, you can see the mountains close by,” says Thomas McGowan, a Realtor and historic home specialist with Elyse Harney Real Estate who has over 20 years of experience. The 445-acre Highland Lake is one of Winchester’s most popular attractions, drawing year-round and seasonal residents seeking tranquil lakefront living. Winchester is also home to the city of Winsted, which serves as a downtown area with shops, restaurants and a growing arts scene. “There’s a large cross-section of people who come here, so each smaller community is like a little world unto itself,” McGowan says.
Lakefront homes on Highland Lake offer premium waterfront living.
Victorian and Colonial Revival homes add character to Winsted neighborhoods.
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Year-round recreation at Highland Lake, state parks and the Berkshires
Highland Lake features two public beaches and a boat launch. “There are always a bunch of people canoeing, fishing, all sorts of stuff,” McGowan says. The Marina at Highland Lake offers boat rentals and seasonal slips for storing boats or jet skis. Winchester Lake and Park Pond provide quieter spots for boating and freshwater fishing. These areas are busiest in summer, when camps like Camp Wah-Nee and Greenwood Trails bring kids to town.
Hikers and birdwatchers can explore Platt Hill State Park, a 159-acre reserve with unmarked nature trails. Winchester is also within 5 miles of Burr Pond, Sunnybrook and Stillwater Pond State Parks. The Sue Grossmann Still River Greenway offers a paved path for walking, running and biking, with plans to extend it to Willow and Rowley Streets in Winsted, where there is a skatepark, athletic fields and a playground. Green Woods Country Club has a 10-hole golf course that's open to the public; the course is one of only three 10-hole courses in the United States. Winter sports enthusiasts can head north to the Berkshire Mountains, home to spots like Ski Butternut.
Highland Lake is a freshwater lake located in Winchester known for its scenic beauty.
Burr Pond and Sunnybrook State Parks are minutes from Winchester.
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Residents can pick historic homes, rural retreats or lakefront builds
Winchester offers a wide range of housing options and styles. Some of its oldest homes are in Winchester Center, a historic village with New England-style farmhouses and saltbox-style homes from the 18th century. About 70% of residents live in Winsted, where tree-lined streets feature Cape Cod and raised ranch-style homes, along with 19th-century Victorian and Colonial Revival builds. Outside the city center, quiet roads lead past country retreats on wooded lots with up to several acres of land. Prices for single-family homes generally range from $140,000 for fixer-uppers to $680,000 for larger homes in the countryside. Lakefront properties can be more expensive, selling for $500,000 to $1.2 million. Condos in Winsted fetch between $110,000 and $200,000. Winchester’s CAP Index Crime Score is 3 out of 10, below the national average of 4.
Winchester’s housing market includes fixer-uppers and luxury builds.
Winchester Center showcases historic New England-style homes.
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Winsted has shops, eateries and creative spaces in a walkable downtown
Main Street anchors downtown Winsted as a walkable corridor for shopping, dining and entertainment. Businesses include antique shops, salons and local favorites like The Curious Cat Bookshop. The dining scene offers casual spots and sit-down eateries, with slices from Kent Pizza and Italian dishes from Mario’s Tuscany Grill and Bar. Gilson Cafe & Cinema pairs dinner with a show, while Whiting Mills showcases the town’s creative community in a former industrial building that is now home to artists, photographers and artisans selling their crafts. Winsted’s American Mural Project stands out as the world’s largest indoor collaborative artwork, a tribute to American workers standing five stories high. Winsted is also home to the American Museum of Tort Law and hosts community events throughout the year, including the annual Fall Foliage Festival & Car Show. Essentials are available near downtown at CVS, Stop & Shop and Dollar General.
Downtown Winsted features antique shops and local boutiques.
Northwest Soup & Sandwich Co. is a highlight local dining option.
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Students go from the Winchester School District to The Gilbert School
The Winchester School District earns a B from Niche. Students in prekindergarten through second grade can attend Mary P. Hinsdale School, which reopened in 2022 after a $17.4 million renovation and does not yet have a Niche rating. The B-rated Pearson School covers third through sixth grades. The Gilbert School is a private secondary school that functions as the public middle and high school for Winchester residents, who attend tuition-free. It earns a B-plus and offers various sports programs, with its girls basketball team winning its first outright Berkshire League regular season title in 2025. Higher education can continue at CT State Northwestern, part of the Connecticut State Colleges and Universities system.
Pearson School provides education for grades three through six.
Mary P. Hinsdale School serves early learners in Winchester.
The Gilbert School receives an A- rating from Niche.
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Highways connect Winchester to Torrington, Hartford and beyond
This is a car-dependent area with few sidewalks and limited public transportation. The Northwestern CT Transit District runs weekday bus service between Winsted and Torrington, with its only stop outside Town Hall. U.S. Route 44 and state Route 8 are Winchester’s main roads. US 44 leads 30 miles southeast to Hartford, while Route 8 leads 8 miles south to Torrington and Charlotte Hungerford Hospital. Bradley International Airport is about 29 miles away. The Winsted Industrial Park features warehouses and manufacturing companies, while the Hartford HealthCare HealthCenter has a 24/7 emergency room.
Written By
Sian Syring
Photography Contributed By
Daniel Quattro
Video By
Daniel Willingham
Interested in learning more about homes in this area?
Reach out to
Lori Meyerson,
an experienced agent in this area.
GreatSchools:
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On average, homes in Winchester, CT sell after 48 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, CT over the last 12 months is $385,000, up 5% from the median home sale price over the previous 12 months.
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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
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