Located at the edge of the Berkshire Mountains, Winsted was founded at the junction of the Mad and Still Rivers, and its moniker combines the names of the neighboring towns of Winchester and Barkhamsted. In fact, it’s part of the town of Winchester, and the two share a town meeting form of government. “Winchester is a big town with a small city as the downtown. That’s Winsted. It’s got a community college, and students commute from around the area up and down Route 8. There’s also Highland Lake. It has small beaches you can access and a marina where you can launch a boat,” says David Sartirana, a real estate broker with over 20 years of experience and the owner of Northwest CT Realty. Situated 24 miles from Hartford and 97 from New York City, Winsted was one of Connecticut’s earliest industrial centers, with numerous mills and factories. Today, it’s home to 7,200 residents, according to the 2020 Census.
Businesses operate in historic buildings in Winsted.
Downtown Winsted corridors support community living near local homes.
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Shopping and dining in town or nearby cities
Downtown began a revitalization through an enhancement plan in the early 2000s, and the plan has worked to bring in new businesses. In 2023, the Friends of Main Street organization began hanging flower baskets from lampposts to beautify the area. The two-mile commercial corridor is home to diverse shops, eateries and entertainment venues housed in turn-of-the-century buildings. Locals can shop for antiques, go duck pin bowling or take a spin on the Go-Kart course. For groceries, the Shops at Ledgebrook contains the Stop & Shop grocery store. The one-stop-shop sells produce, pantry items, pet supplies and alcohol. Winsted eateries offer everything from boba teas to Vietnamese fare to Italian ristorantes. The majority of them are clustered along U.S. Route 44. For even more shopping and dining options, residents travel ten miles to nearby Torrington Commons Shopping Center or Torrington Plaza.
Norbrook Farm Brewery serves customers near Winsted.
Northwest Soup and Sandwich Co. is located in Winsted.
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Local lakes, summer camps and a bandstand
At 444 acres, Highland Lake is one of Connecticut’s largest waterways and is a popular spot for fishing, swimming and boating. Filled with maple and oak trees, East End Park can be found in Winsted’s historic downtown. The park’s walking path takes guests past several soldier’s memorials, an 1800s fountain and a bandstand. The parks department also oversees recreational programs like children’s basketball camps, adult tennis lessons and summer camps. The Winsted Senior Center caters to the needs of those aged 55 and over. It operates a daily lunch program, a paratransit service for local medical trips and free exercise classes. Seniors can also play Bingo and card games on certain days of the week.
Highland Lake offers boating access near Winsted.
Highland Lake’s boat launch expands recreation options for Winsted residents.
Lakeside homes on Highland Lake enhance Winsted’s waterfront real estate.
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Memorials, murals and memorabilia
Winsted is home to the American Mural Project. This 120-foot-long artwork is one of the largest collaborative indoor pieces in the world. It’s next to Whiting Mills, a collection of art galleries and retail spaces. The Soldier’s Monument and Memorial Park is one of the city’s most notable features. The castle-like tower is a striking memorial to the more than 300 local soldiers who served in the Civil War. Closed for much of the year, it opens for tours on national holidays like the Fourth of July, Memorial Day and Veterans Day. The Winchester Historical Society occupies an 1813 Colonial Revival mansion and doubles as a museum. It has an impressive collection of Civil War memorabilia and military items, a historic dollhouse and other Victorian artifacts.
Winsted functions as the downtown district for Winchester.
Downtown Winsted features antique shops and local boutiques.
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Turn-of-the-century housing in Litchfield County
Winsted has more than 3,650 places to live, including detached single-family dwellings, apartments and townhouses. Being close to several colleges means Winsted has a fair number of renters. In fact, 37% of people rent here, while 63% own their homes. Most were built before 1970, with a substantial number being older than the 1940s. From March 2023 to March 2024, 54 homes were sold in Winsted after 49 days on the market. The town has less than one month of available housing supply, selling for an average price of $327,000. “Single-family houses across Connecticut are in short supply, and Winsted inventory is wicked low, making it competitive for buyers. A lot of houses go for more than asking after multiple bids,” says Mr. Sartirana.
Turn‑of‑the‑century homes reinforce Winsted’s historic residential character.
Historic multifamily homes in Winsted add variety to local real estate.
Apartment buildings in Winsted expand housing options for local residents.
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Commuting to Connecticut’s capital city
Many workers in Winsted commute to the surrounding towns of Hartford, Springfield and Waterbury for healthcare, manufacturing and retail jobs. Typically, it’s a 28-minute one-way commute, with most workers driving alone over U.S. Route 44 and Connecticut Routes 8, 183 and 263. This is a car-dependent area, although the Northwestern Connecticut Transit District provides a fixed-route bus service and a demand-response service for residents aged 60 and older. Also, park-and-ride lots are located throughout town to help locals reach destinations like Charlotte Hungerford Hospital, 8 miles away or Bradley International Airport, 25 miles away.
Science and engineering programs in highly ranked schools
Winchester Public Schools holds a B from Niche, enrolls over 550 students and is known for its innovative science and engineering programs. It operates two schools for students from prekindergarten through sixth grade. Mary P. Hinsdale School serves prekindergarten through third grade and is unrated by Niche, while the B-rated Pearson School teaches third grade through sixth grade. The A-minus-rated Gilbert School is a private school that serves as the system's public-school option for grades 7 through 12. For higher-education options, Westfield State College, the University of Hartford and Naugatuck Valley Community College have campuses nearby and offer two- or four-year degrees and professional certificates.
Hinsdale Elementary School is in the heart of downtown Winsted.
Pearson Middle School serves grades 3 through 6 near Winsted.
The Gilbert School is a private high school in Winsted, CT.
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Environmental factors
Its location near lakes and two rivers significantly increases the town’s chances of flooding. Historically, the worst flooding happened in the 1950s and destroyed much of Winsted. Since then, the town has built back stronger, partly thanks to the Winsted Local Protection Project. Spearheaded by the Army Corps of Engineers, the project built retaining walls along the riverbanks and widened Main Street. The Corps maintains two dams along the rivers to help control water levels during extreme weather events. The state of Connecticut also oversees the CT Alert program, which will email, text or call registered citizens with updates for a variety of emergencies.
Anglers fish in the waterways surrounding Winsted.
Highland Lake views highlight Winsted living near one of its key outdoor amenities.
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Photography Contributed By
Francisco de la Vera
Video By
Francisco de la Vera
Interested in learning more about homes in this area?
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On average, homes in Winsted, CT sell after 57 days on the market compared to the national average of 55 days. The median sale price for homes in Winsted, CT over the last 12 months is $320,000, up 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 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated eat-in kitchen with updated cabinetry, countertops, and finishes, perfect for everyday living and gathering. The comfortable layout includes a spacious living room and dining area, while four bedrooms offer flexibility for family, guests, or a home office. Enjoy the large yard,
Enjoy the best of Highland Lake living with this unique property offering a spacious home directly across the street from the lake along with your own separate waterfront parcel! The main house features 7 rooms, 3-4 bedrooms and 2 full baths, providing plenty of space for year-round living or a relaxing lake retreat. A deck overlooking the waterfront offers the perfect spot to enjoy the lake
Welcome to 180 Shore Dr - your own beautifully renovated waterfront retreat on highly desirable Lake! This exceptional year-round home offers the perfect combination of modern comfort, stunning water views, and the lake lifestyle you've been dreaming about. Featuring 3 bedrooms and 2 full bathrooms, the home has been extensively remodeled with quality finishes and thoughtful attention to detail
Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors
Well-maintained two-family home offering excellent owner-occupant or investment potential. First-floor unit features 3 bedrooms, kitchen, and living room and is currently rented. Second-floor unit is vacant and offers 2 bedrooms, living room, and kitchen. Separate utilities and laundry for each unit. Full basement provides additional storage. Entire home has undergone lead remediation. Great
Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. Both units have been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the bedrooms.
Amy Rio
Better Homes and Gardens Real Estate Executive Real Estate
Welcome to 136 Losaw Rd! Built in 1984, this nicely maintained and updated home offers 1,977 sq. ft. of living space with 4 bedrooms, 2 full baths, and a comfortable open floor plan, all set on 1.76 acres. The main living level features an open dining area and kitchen with breakfast bar overlooking the sunken living room, highlighted by a beautiful arched fieldstone fireplace with propane log
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
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
Two bedroom, second floor apartment with laundry hook-up in the unit. Washer/dryer can be added for an additional $100 per month. Close to downtown. Off street parking, pets considered. Electric heat. First month, two months security required. Background and credit check done by listing office.
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
Cozy one-bedroom apartment with a practical layout. Features a living room, kitchen, bedroom, and in-unit washer and dryer. Pets considered. First month and 2 months security, if applicable. Credit and background check through Rentspree.
Litchfield Heights Apartments is nestled quietly in the greenery of the Berkshires. We are situated close to the border of Massachusetts with easy access from Routes 8 & 44. We offer generously sized 1 bedroom flats, and 2 or 3 bedroom Townhouse. Enjoy the ease of maintenance free living when you make Litchfield Heights Apartments your home. Call Litchfield Heights Apartments today for further
Two bedroom, first floor apartment with laundry hook-up in the unit. Washer/dryer can be added for an additional $100 per month. Close to downtown. Off street parking, pets considered. Gas and electric heat. First month, two months security required. Background and credit check done by listing office.
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
Spacious two-bedroom, 1.5-bath apartment conveniently located close to downtown. The kitchen features a convenient pantry for additional storage and offers direct access to a covered rear porch-perfect for enjoying your morning coffee or relaxing outdoors. The apartment also offers plenty of storage, including dedicated basement storage space and a walk-up attic with additional room for your
4-bedroom house with rooms available for rent. Each room is $950 per month. Spacious shared living areas and a full kitchen. A comfortable and peaceful place to call home.
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. Beautiful free standing ranch style homes, 2 bedroom, 2 baths with attached closed porch available. There are 2 houses available at this time for the same price. The other is larger with 2 bedrooms and
2 bedroom apartment located on first floor with yard, pets considered at owners discretion(one time non refundable pet fee is applicable) -off street parking -washer dryer hookups in unit. Gas Heat and Gas Stove (tenant pays all utilities) No Smoking Walking distance to downtown Winsted restaurants and stores-One Year lease required-must fill out no fee application prior to viewing Please
Fully Furnished Top-Floor Retreat with Beautiful Lake Views Enjoy beautiful lake views and easy, turnkey living from the top floor of 188 E Lake Street in Winsted. This fully furnished 2-bedroom, 1-bath rental offers a comfortable, private place to call home with everything you need already in place. The bright and inviting living space takes advantage of the elevated setting and wonderful views
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 walk out basements and washer/dryer hookups.• Over 1000 square feet of living space with heat and hot water included.Please come see
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