$381,819Average Value$309Average Price per Sq Ft0Homes 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.
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.
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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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.
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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Explore Winchester's sister city, Winsted.
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.
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.
Colbrook Consolidated School focuses on providing a comprehensive educational experience.
Batcheller Elementary School serves area Winchester residents.
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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
Brandon Schulman
Video By
Daniel Willingham
Interested in learning more about homes in this area?
Reach out to
Joe Waters,
an experienced agent in this area.
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 $352,500, down 3% from the median home sale price over the previous 12 months.
TO SETTLE ESTATE: Available for Immediate Occupancy is this Immaculate 3 to 4 Bedroom Colonial tucked away on a quiet street. Features Hardwood Floors throughout the house, 24' x 14' Family Room with Propane Gas Stove, Country Kitchen. Primary Bedroom with it's own office area. Oversized Full Bath. 3-Season 21' x 8' Enclosed Porch. 26' x 10' Concrete Patio. Detached One Car Garage. Attractive
This stunning Renovated home is perfectly situated in the beautiful town of Winsted could be yours! Just a leisurely walk from the beautiful Highland Lake. Offering more than 2,200 square feet of thoughtfully designed living space, this home blends timeless charm with modern updates. The bright and spacious kitchen opens effortlessly into a welcoming dining area and a cozy yet expansive living
Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also
Victorian Charm Meets Modern Potential - 6-Bedroom Home Across from Pearson School Step into timeless elegance with this spacious 6-bedroom, 2.1-bath Victorian-style home located directly across from Pearson School in Winsted. Featuring hardwood floors throughout and a beautifully updated kitchen, this property blends classic character with modern convenience. From its distinctive architectural
Don't miss this unique opportunity to own a multi family residential property and an office space! (Owner currently has permission from the town to create a 2nd residential unit on the first floor) - will have 2.5 baths when completed. Great central location close to all amenities that Winsted has to offer including restaurants, parks, college, public transportation and shopping. First floor
TO SETTLE ESTATE: Available for Immediate Occupancy is this Immaculate 3 to 4 Bedroom Colonial tucked away on a quiet street. Features Hardwood Floors throughout the house, 24' x 14' Family Room with Propane Gas Stove, Country Kitchen. Primary Bedroom with it's own office area. Oversized Full Bath. 3-Season 21' x 8' Enclosed Porch. 26' x 10' Concrete Patio. Detached One Car Garage. Attractive
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
Discover lakeside living in this cozy 364 sq ft cottage available for lease on Shore Drive. This charming space includes a living room, kitchen, bedroom, and full bath-perfect for simple, comfortable living. Tenants will enjoy access to a limited portion of the waterfront, offering the chance to relax by the lake and take in the beautiful surroundings. An affordable opportunity to experience life
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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