$378,327Average Value$233Average 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
Sian Syring
Photography Contributed By
Daniel Quattro
Video By
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Interested in learning more about homes in this area?
Reach out to
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an experienced agent in this area.
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On average, homes in Winchester, CT sell after 59 days on the market compared to the national average of 54 days. The median sale price for homes in Winchester, CT over the last 12 months is $320,000, down 17% from the median home sale price over the previous 12 months.
Welcome to this spacious and well-maintained 2,196 sq. ft. one-owner home offering comfortable living in a convenient in-town location. This 3-bedroom, 2-bath residence features an open floor plan on the main living level, highlighted by a large formal living room with fireplace, dining room, expansive family room, and an updated kitchen-perfect for both everyday living and entertaining.
Welcome to this charming New England Colonial that blends classic character with comfortable living. Step inside to an inviting, oversized living room featuring beautiful new vinyl flooring-perfect for relaxing, entertaining guests, or gathering with family. The main living level offers two convenient bedrooms and a laundry area, making everyday living easy and practical. Upstairs, you'll find
124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless
99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,
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
This Highland Lake house is in great condition, remodeled 4 years ago. Lower level has a separate entrance and was revamped with large living room and full bathroom. Walk to the Association beach in 5 mins.
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 minutes
THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas
Uncover this hidden gem - 65 pristine acres of raw land, with natural beauty and endless potential. This picturesque parcel features serene ponds and mature trees. Distant views can be enjoyed from the property. Much site work has been done to date. A driveway with a binder coarse is already in place offering easy access into and throughout the property. Many acres are cleared, stumps have been
1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL CONSIDER
Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe,
Spacious colonial with 4 bedrooms, 2 full baths, generous size living room, dining room, sitting room, sunroom. Looking for space, this home definitely has it. Harwood floors thorough, granite countertops, marble backsplash, Island in kitchen. Short walk to highland Lake With a little TLC this home will be a GEM! Home being sold AS-IS.
Private 1bedroom apartment with its own porch and yard, plus in-unit washer/dryer. 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.
Large 3 bedroom apartment with sun porch. Eat-in kitchen, dining room, living room and attic storage. Washer/dryer can be added for an additional $75 per month. No off street parking. Close to town, walk to NCCC. Pets considered. Credit and background check required.
Bright and sunny 3-bedroom duplex, ideally located close to town. This spacious home features a large eat-in kitchen, a separate dining room, and a cozy living room. Enjoy the convenience of gas heat, with washer/dryer hook-up available in the basement, or can be provided for an extra $75 per month. Minimum credit score of 700. Pets considered, and a background and credit check are required.
Raised Ranch rental close to town on 1.33 wooded acres. The lower level features two large rooms with new vinyl plank flooring, fresh paint, and a spacious storage/utility room with laundry. The main floor includes a living room and an updated kitchen with quartz countertops and stainless steel appliances. Sliders lead to a large deck overlooking the private wooded yard. There is a large primary
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
Beautiful First-Floor Apartment with Classic Charm and Modern Updates! This spacious first-floor apartment features gleaming hardwood floors, fresh paint, and an updated kitchen. Enjoy the high ceilings and beautiful woodwork that add character and warmth throughout. Conveniently located close to downtown, offering easy access to shopping, dining, and commuting routes.
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
Discover lakeside living at its finest with this fully renovated, fully furnished 3 bedroom, sleeps 10, 2 full-baths, family estate set on a half acre of professionally landscaped grounds overlooking picturesque Highland Lake. Located just 0.6 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of
Property Id: 1615805Total 8 - 1 BED ROOM UNITS in the building CLOSE to Route 8 & WINSTED Mainstreet, on-site parking, coin operated laundry, REAR BALCONY.
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