$389,016Average Value$248Average 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.
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
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Interested in learning more about homes in this area?
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On average, homes in Winchester, CT sell after 50 days on the market compared to the national average of 56 days. The median sale price for homes in Winchester, CT over the last 12 months is $345,000, down 10% from the median home sale price over the previous 12 months.
Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100' x 14' Brazilian hardwood deck, a 35' x 6' stationary Trex and steel dock, and a private cabana-perfect for relaxing, boating, swimming, and entertaining. Soak in panoramic water views from multiple vantage points, including
Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary bedroom, and a full bath w/laundry, providing the convenience of
Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family
Rare opportunity to build in a convenient in-town location! This level 0.41-acre lot is ideally situated close to downtown amenities while offering easy access to Highland Lake's public beach and boat launch. Formerly improved with a three-story Colonial home, the property presents a unique opportunity to redevelop an established homesite. Public water, public sewer, and natural gas are available
Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, pocket doors, built-ins, decorative moldings, and stunning stained-glass accents that capture the craftsmanship of a
Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with
Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch,
321 Colebrook Road is a rare opportunity to own beautiful land with natural features and self-sustaining potential. A natural spring gently rolls through the property, surrounded by mature oak, ash, birch, black walnut, pine, and abundant sugar maple trees - perfect for producing your own maple syrup. The land is rich with native granite and sparkling quartz throughout, adding character and
Welcome to 237 Wallens Hill Road, where comfort, quality, and exceptional entertaining spaces come together in a beautiful rural setting. This 9-room Colonial with a farmhouse front porch is set on .80 acres and offers 4 bedrooms and 2.5 baths. The main level features a formal dining room, large family room, mudroom, and an impressive eat-in kitchen with quartz countertops, stainless steel
Discover the perfect setting for your dream home on this private 2.0-acre parcel in the scenic hills of Colebrook. Featuring 236 feet of road frontage on quiet Pine Road, this property offers a beautiful building site situated on a gently elevated plateau with desirable southern and western exposures, providing excellent sunlight and the potential for stunning sunset views. Surrounded by nature
Wooded interior lot located at the end of a dead-end street, offering a private setting. The parcel is slightly sloped and accessed from the end of the road. Clients, do your homework , including but not limited to surveys, zoning, and building approvals. Convenient location with approximately a 15-minute walk to Resha Beach on Highland Lake for recreational enjoyment. Lake rights are granted to
Look no further for A Very Private location to build your Dream Home. A Wooded Hill top building site overlooking beautiful Winchester Center which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester. Convenient access agreement to the Rear lot is though 151 Chapel Rd. property.
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
Three bedroom apartment on the first floor. Large kitchen, light filled living room and a recently remodeled bath. Washer/dryer can be added for an additional $75 per month. Pets considered. Off-street parking. First month and two months security, if applicable. Credit and background check required.
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
Two bedroom, 1st flr apartment close to town. Private front porch. A washer-dryer can be provided for an extra $75 per month. Pets considered, and a background and credit check are required. Minimum credit score required. Showings only in the evening or on Sundays.
Welcome to your new home in Winsted, Winchester, CT! This charming property offers an inviting atmosphere perfect for comfortable living. Its convenient location places you near several great restaurants, making dining out a breeze. Plus, the Community Health & Wellness Center is just a short 14-minute drive away, ensuring easy access to health services.This property features essential
Large four bedroom apartment with one full bath and one half bath. Large kitchen, light filled living room. Washer/dryer can be added for an additional $75 per month. Pets considered. Off-street parking. First month and two months security, if applicable. Credit and background check required.
Charming 2-bedroom, 1-bath unit located in a quiet Winsted neighborhood on a spacious corner lot. This home features a well-appointed kitchen with ample cabinet space, a cozy island, and appliances. The unit includes beautiful hardwood floors throughout the living spaces and large windows that fill the rooms with natural light. Outside, enjoy a private entrance and a shared green space.
Private 1 bedroom apartment with its own porch and yard, off street parking. Washer/dryer can be added for an additional $75 per month. Pets considered. Conveniently located near the center of town and Highland Lake. First month's rent plus two months' security deposit required. Credit and background check performed by the listing office. Minimum credit score required.
-Modern 1-bedroom apartment -Kitchen with lots of cabinet space. -Spacious bathroom. -Tile floors-Plenty of closet space. -Freshly painted. -NO PETS!!!-Credit check required. -Reach out to Matthew at contacts listed (Email/Text message preferred)-Cozy, modern 1-bedroom/1-bathroom apartment-Unique & ergonomic floor-plan that maximizes usable space &
Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance to the property is being worked on now with 3 new homes to be put in front. The property will look much nicer when completed. This is the final phase. Beautiful free standing ranch style homes, 2 bedroom, 2 baths with attached closed porch available. There are 2 houses available
Nestled in the Hills of Litchfield County, our Large Town Homes Offer:• Updated eat in kitchen with dishwasher and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Bathroom.• Private Entrances with Slider to backyard • Over 1000 square feet of living space with heat and hot water included.Please come see why at Litchfield
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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