$377,298Average 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
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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On average, homes in Winchester, CT sell after 50 days on the market compared to the national average of 55 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.
Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less
Spacious and full of potential, this 10-room home offers 4 bedrooms and 2.5 baths with plenty of room for everyone. Priced below current market value, this property presents a fantastic opportunity for buyers willing to make some cosmetic updates and build instant equity. Set in a quiet country location within a private development known for its large lots and peaceful surroundings, the home
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
Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of
Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less
FULLY RENOVATED! In addition this home is fully insulated, energy-efficient, and enhanced with solar panels for low utility costs. The open floor plan and cozy fireplace create the perfect space for gatherings, while multiple decks, an above-ground pool, and serene natural surroundings provide a tranquil retreat-ideal for year-round living or a weekend getaway. Located perfectly on a beautiful
Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows
Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor
Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your
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
Charming Riverview Townhouse with Patio Enjoy easy living in this well-located two-bedroom townhouse set on a slab and overlooking the river. The main level features a living room, dining room, and functional kitchen, perfect for everyday comfort and entertaining. Sliding glass doors lead to a private patio where you can relax and enjoy the peaceful water views. Upstairs offers two comfortable
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.
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
3 bedroom apartment close to down town. This unit has the living space on the first floor and the bedrooms and full bath on the second floor. There are hardwood floors through most of the unit. A walk-up attic and basement can be used for storage.
Bright and sunny, first floor, 2 bedroom apartment. Washer/dryer in the unit. Large, private porch. Pets considered. Off street parking. Minimum credit score required. Credit and background check done by listing office. required. Two months security, if applicable.
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
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
5 room, 1st floor apartment in well established neighborhood. Ranch style. Large eat-in kitchen, 2 bedrooms, den/office. 1 full bath. Ample closets, additional light storage is available in basement. Appliances include, gas range, refrigerator, washer & dryer (in basement). off street parking. Private rear yard.
FULLY RENOVATED! Be the first to move into this GEM in Colebrook. And guess what? Utilities included! Water, sewer, energy. The open floor plan and cozy fireplace create the perfect space for gatherings, while multiple decks, an above-ground pool, and serene natural surroundings provide a tranquil retreat-ideal for year-round living or a weekend getaway. Located perfectly on a
Welcome to this beautifully remodeled and spacious 3-bedroom, 2 full bathroom home in the heart of Winchester. Featuring hardwood floors throughout both the first and second levels, this home offers a warm and inviting layout with an eat-in kitchen that has a center island perfect for everyday living. Enjoy the convenience of a separate laundry room-washer and dryer included, high-efficiency gas
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