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Winsted, CT Homes for Sale

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  • 548 E Wakefield Blvd, Winsted, CT 06098
    548 E Wakefield Blvd, Winsted, CT 06098
    548 E Wakefield Blvd, Winsted, CT 06098
    /30

    $394,900

    • 2 Beds
    • 1 Bath
    • 512 Sq Ft

    548 E Wakefield Blvd, Winsted, CT 06098

    Start your lakeside legacy at this rare waterfront cottage on Highland Lake. With stunning westerly views and a private dock, this is the perfect New England retreat for daily sunsets over the water. This intimate 512-square-foot home offers two bedrooms, a sunroom, Modern Eat-in Kitchen and a versatile loft space. with a newer roof, plumbing, electrical, and blown-in insulation, providing a

    Agent Photo

    Amy Rio

    Executive Real Estate Inc.

    (860) 777-1120

    548 E Wakefield Blvd, Winsted, CT 06098
  • 722 Lake Dr, Winsted, CT 06098
    722 Lake Dr, Winsted, CT 06098
    722 Lake Dr, Winsted, CT 06098
    /38

    $1,295,000

    • 3 Beds
    • 3 Baths
    • 2,420 Sq Ft

    722 Lake Dr, Winsted, CT 06098

    Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy

    Joanne Donne The Washington Agency

    722 Lake Dr, Winsted, CT 06098
  • 441 Platt Hill Rd, Winsted, CT 06098
    441 Platt Hill Rd, Winsted, CT 06098
    441 Platt Hill Rd, Winsted, CT 06098
    /34

    $625,000

    • 5 Beds
    • 3 Baths
    • 3,404 Sq Ft

    441 Platt Hill Rd, Winsted, CT 06098

    Welcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to make memories. This inviting residence features an open and airy layout filled with natural light thanks to large windows and multiple skylights. Solid hardwood floors and tile run throughout the main level, creating a timeless foundation for your personal touch. The spacious eat-in kitchen, while vintage in

    David Sartirana Northwest CT Realty

    441 Platt Hill Rd, Winsted, CT 06098
  • 51 Pratt St, Winsted, CT 06098
    51 Pratt St, Winsted, CT 06098
    51 Pratt St, Winsted, CT 06098
    /27

    $449,900

    • 4 Beds
    • 1.5 Baths
    • 2,239 Sq Ft

    51 Pratt St, Winsted, CT 06098

    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

    Arlene Gonzalez The Gonzalez Property Group

    51 Pratt St, Winsted, CT 06098
  • 111 South Rd, Winsted, CT 06098
    111 South Rd, Winsted, CT 06098
    111 South Rd, Winsted, CT 06098
    /39

    $779,900

    • 3 Beds
    • 3.5 Baths
    • 4,953 Sq Ft

    111 South Rd, Winsted, CT 06098

    Perched up higher than the rest with sweeping views up a private driveway in beautiful Winchester Center you'll find this custom built 4,953 sq ft Colonial nestled in on 3.97 serene & bucolic acres. For the car enthusiasts, you'll see a 3 bay garage that can fit up to at least 7 cars if lifts are installed including a bonus 2 car tandem garage within the 3 bays. Plenty of room for oversized

    Dawn Rousseau Showcase Realty, Inc.

    111 South Rd, Winsted, CT 06098
  • 117 South Rd, Winsted, CT 06098
    117 South Rd, Winsted, CT 06098
    117 South Rd, Winsted, CT 06098
    /35

    $475,000

    • 3 Beds
    • 3 Baths
    • 2,747 Sq Ft

    117 South Rd, Winsted, CT 06098

    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

    Christina Niziolek William Raveis Real Estate

    117 South Rd, Winsted, CT 06098
  • 55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    /37

    $515,000

    • 5 Beds
    • 4 Baths
    • 5,016 Sq Ft

    55 Walnut St, Winsted, CT 06098

    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

    David Sartirana Northwest CT Realty

    55 Walnut St, Winsted, CT 06098
  • 212 Spencer Hill Rd, Winsted, CT 06098
    212 Spencer Hill Rd, Winsted, CT 06098
    212 Spencer Hill Rd, Winsted, CT 06098
    /27

    $399,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    212 Spencer Hill Rd, Winsted, CT 06098

    Welcome to your peaceful retreat in the heart of Winchester - a quiet, scenic town surrounded by natural beauty. Tucked away on a private lot, this thoughtfully maintained home offers a perfect blend of rustic charm and modern comfort, with every detail designed to enhance your connection to the outdoors. Step inside to discover gleaming original hardwood floors that stretch across the sun-filled

    Tammy Powling Coldwell Banker Realty

    212 Spencer Hill Rd, Winsted, CT 06098
  • 62 Fruit St Unit 64, Winsted, CT 06098
    62 Fruit St Unit 64, Winsted, CT 06098
    62 Fruit St Unit 64, Winsted, CT 06098
    /14

    $325,000

    • 6 Beds
    • 2 Baths
    • 3,078 Sq Ft

    62 Fruit St Unit 64, Winsted, CT 06098

    62-64 Fruit Street in Winchester offers a rare opportunity to acquire a turnkey property located in one of the town's most desirable neighborhoods. This expansive residence is characterized by its classic New England architecture, making it a perfect fit for those seeking both charm and functionality. Both units offer spacious layouts and maintained interiors, ideal for entertaining and living

    Antonio De La Cruz Eagle Eye Realty PLLC

    62 Fruit St Unit 64, Winsted, CT 06098
  • 36 Whiting St, Winsted, CT 06098
    36 Whiting St, Winsted, CT 06098
    36 Whiting St, Winsted, CT 06098
    /39

    $299,999

    • 3 Beds
    • 2.5 Baths
    • 1,608 Sq Ft

    36 Whiting St, Winsted, CT 06098

    Newly updated 3 bedroom 2.5 bath colonial with large front porch overlooking the Mad River. Close to downtown and town center green. This home has an updated kitchen with new quartz counters, new furnace and hot water heater along with beautifully refinished hard wood floors through out the first floor. New carpet on second floor bedrooms and the primary bedroom has its own full bathroom. The

    Brandon Riley eXp Realty

    36 Whiting St, Winsted, CT 06098
  • 128 Danbury Quarter Rd, Winsted, CT 06098
    128 Danbury Quarter Rd, Winsted, CT 06098
    128 Danbury Quarter Rd, Winsted, CT 06098
    /40

    $295,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    128 Danbury Quarter Rd, Winsted, CT 06098

    First-time homebuyers and downsizers take notice!. Some improvements have been done in this cozy Ranch boasting a metal roof and well-maintained mechanics. What an incredible opportunity to pick your colors and let the cosmetic upgrades take shape. A 1-car detached garage and space for a garden or outbuilding are possible on this 2.5-acre country parcel. An As-Is sale is preferred.

    Kim Trumbull William Raveis Real Estate

    128 Danbury Quarter Rd, Winsted, CT 06098
  • 151 Losaw Rd, Winsted, CT 06098
    151 Losaw Rd, Winsted, CT 06098
    151 Losaw Rd, Winsted, CT 06098
    /40

    $799,000

    • 5 Beds
    • 2.5 Baths
    • 2,950 Sq Ft

    151 Losaw Rd, Winsted, CT 06098

    Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. This property is your personal sanctuary, complete with private trails for hiking your own land. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with

    Breanna Goebel Compass Connecticut, LLC

    151 Losaw Rd, Winsted, CT 06098
  • 14 Curtice St, Winsted, CT 06098
    14 Curtice St, Winsted, CT 06098
    14 Curtice St, Winsted, CT 06098
    /13

    $199,900

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    14 Curtice St, Winsted, CT 06098

    Attention investors and buyers looking to build equity! Welcome to 14 Curtice Street, a home has incredible value and potential in the heart of Winsted. This 3-bedroom, 1-bath home features approximately 1,248 square feet of living space and is ideal for sweat-equity seekers or rehab-minded buyers. Exterior updates have already been completed, including a newer roof, siding, and windows, giving

    Michael Johnson Lock and Key Realty, Inc

    14 Curtice St, Winsted, CT 06098
  • 166 Torringford St, Winsted, CT 06098
    166 Torringford St, Winsted, CT 06098
    166 Torringford St, Winsted, CT 06098
    /33

    $380,000

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft

    166 Torringford St, Winsted, CT 06098

    Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area

    Lana Van Valkenburgh Vision Real Estate

    166 Torringford St, Winsted, CT 06098
  • 14 Pratt St, Winsted, CT 06098
    14 Pratt St, Winsted, CT 06098
    14 Pratt St, Winsted, CT 06098
    /13

    $199,900

    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    14 Pratt St, Winsted, CT 06098

    Don't let the outside fool you! Perfect alternative to condominium living! No HOA and plenty of off street parking at this in-town location. Nice size living room; large kitchen/dining combination with access to the deck and the 1/2 bath laundry room make up the first floor of this cute home. Upstairs you will find 2 modest size bedrooms along with the large primary and the full bath which has a

    Amy Sartirana Northwest CT Realty

    14 Pratt St, Winsted, CT 06098
  • 674 E Wakefield Blvd, Winsted, CT 06098
    674 E Wakefield Blvd, Winsted, CT 06098
    674 E Wakefield Blvd, Winsted, CT 06098
    /40

    $1,149,000

    • 3 Beds
    • 3 Baths
    • 2,097 Sq Ft

    674 E Wakefield Blvd, Winsted, CT 06098

    Experience premier waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home offering stunning panoramic lake views and direct water access. Situated in the desirable 3rd Bay, this property boasts a private dock-perfect for boating, swimming, and enjoying all the lake lifestyle has to offer. Inside, you'll find an open and inviting layout with a spacious living

    Patrick Smith Smith & DeGroat Real Estate

    674 E Wakefield Blvd, Winsted, CT 06098
  • 174 Wallens St Unit H1, Winsted, CT 06098
    174 Wallens St Unit H1, Winsted, CT 06098
    174 Wallens St Unit H1, Winsted, CT 06098
    /27

    $235,000

    • 1 Bed
    • 2 Baths
    • 1,334 Sq Ft

    174 Wallens St Unit H1, Winsted, CT 06098

    Discover effortless living in this inviting home at the sought-after Clockmaker's Hill community. The thoughtfully designed open floor plan creates seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining room, perfect for hosting friends and family. The sun-drenched kitchen features a convenient breakfast bar for casual dining and morning coffee. The

    Kim D'Andrea William Pitt Sotheby's Int'l

    174 Wallens St Unit H1, Winsted, CT 06098
  • 57 Main St, Winsted, CT 06098
    57 Main St, Winsted, CT 06098
    57 Main St, Winsted, CT 06098
    /27

    $375,000

    • 3 Beds
    • 3,660 Sq Ft

    57 Main St, Winsted, CT 06098

    Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

    Stacy LaQuerre Regall Realty, LLC

    57 Main St, Winsted, CT 06098
  • 22 Curtice St, Winsted, CT 06098
    22 Curtice St, Winsted, CT 06098
    22 Curtice St, Winsted, CT 06098
    /20

    $255,000 Open Wed 4PM - 5PM

    • 3 Beds
    • 1 Bath
    • 1,334 Sq Ft

    22 Curtice St, Winsted, CT 06098

    Step into timeless elegance with this beautifully updated colonial-style home, where classic charm meets modern convenience. Gleaming hardwood floors flow seamlessly throughout the main living areas, creating a warm and inviting atmosphere. The fully renovated kitchen is a chef's dream, featuring premium finishes, sleek countertops, and top-of-the-line appliances. Upstairs, you'll find spacious

    Terence Dominick Complete Real Estate

    22 Curtice St, Winsted, CT 06098
  • 130 Stanton Ave, Winsted, CT 06098
    130 Stanton Ave, Winsted, CT 06098
    130 Stanton Ave, Winsted, CT 06098
    /10

    $225,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    130 Stanton Ave, Winsted, CT 06098

    Step right into effortless living with this charming 2bedroom ranch-style home, nestled right in town and wrapped in durable, lowmaintenance vinyl siding. As you approach, you'll appreciate the tidy curb appeal and generous driveway-perfect for guests or extra vehicles. Inside, an open concept living and dining area welcomes you with abundant natural light and easy flow, ideal for both everyday

    David D'Amore Northwest CT Realty

    130 Stanton Ave, Winsted, CT 06098
  • 99 Norfolk Rd, Winsted, CT 06098
    99 Norfolk Rd, Winsted, CT 06098
    99 Norfolk Rd, Winsted, CT 06098
    /14

    $214,900

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft

    99 Norfolk Rd, Winsted, CT 06098

    99 Norfolk Rd, Winsted CT - Opportunity Knocks! This cute 3-bedroom Cape sits proudly on 1.3 acres and is ready for its next chapter! With vinyl siding, replacement windows, and a lovely setting perched high up from the road, the bones are here-now it just needs your vision. For those seeking an investment opportunity or ready to roll up their sleeves and bring this gem back to life, this could

    Lisa McCarthy Coldwell Banker Realty

    99 Norfolk Rd, Winsted, CT 06098
  • 181 Torringford St, Winsted, CT 06098
    181 Torringford St, Winsted, CT 06098
    181 Torringford St, Winsted, CT 06098
    /27

    $355,000

    • 3 Beds
    • 1.5 Baths
    • 2,160 Sq Ft

    181 Torringford St, Winsted, CT 06098

    Motivated seller! Charming Colonial on Nearly an Acre! Discover the perfect blend of comfort and space in this 3-bedroom, 1.5-bathroom Colonial home. Situated on almost an acre of flat, usable land, the property features a brand new grand circular driveway and a detached two-car garage. The inviting exterior, with its covered front porch, welcomes you into a home ready for its next chapter.

    Michelle Grant Coldwell Banker Premier Real Estate

    181 Torringford St, Winsted, CT 06098
  • 38 Upland Rd, Winsted, CT 06098
    38 Upland Rd, Winsted, CT 06098
    38 Upland Rd, Winsted, CT 06098
    /36

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 1,736 Sq Ft

    38 Upland Rd, Winsted, CT 06098

    Estate Owned 3 to 4 Bedroom Colonial in Immaculate Move In Condition! Tucked away on a quiet street but within walking distance of Schools, Medical Facilities and Shopping. Special features include a huge cedar closet, Hardwood floors throughout the entire house, bay windows, 24' x 14' Family Room with Propane Gas Stove and an Oversized Full Bath The Master Bedroom features its own office.

    Holly Blinkoff Cohen Agency

    38 Upland Rd, Winsted, CT 06098
  • 130 Alpha Ave, Winsted, CT 06098
    130 Alpha Ave, Winsted, CT 06098
    130 Alpha Ave, Winsted, CT 06098
    /4

    $39,000

    • Land
    • 0.41 Acre
    • $95,122 per Acre

    130 Alpha Ave, Winsted, CT 06098

    Discover the Perfect Canvas for Your Dream Home in Winchester, Connecticut! This exceptional .41-acre parcel (owner reports closer to .5 ac) combines eight contiguous lots to create a prime opportunity for building your ideal residence. Nestled in the serene surroundings of the Highland Lake neighborhood, the property is lightly wooded with mature, straight-standing hardwoods and features a

    Suzie Larson Turning Point Realty, LLC

    130 Alpha Ave, Winsted, CT 06098
  • 469 Platt Hill Rd, Winsted, CT 06098
    469 Platt Hill Rd, Winsted, CT 06098
    469 Platt Hill Rd, Winsted, CT 06098
    /39

    $995,000

    • 4 Beds
    • 2 Baths
    • 3,088 Sq Ft

    469 Platt Hill Rd, Winsted, CT 06098

    HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

    Marshall Cohen Cohen Agency

    469 Platt Hill Rd, Winsted, CT 06098
  • 39 S Main St, Winsted, CT 06098
    39 S Main St, Winsted, CT 06098
    39 S Main St, Winsted, CT 06098
    /34

    $749,900

    • 7 Beds
    • 3 Baths
    • 3,486 Sq Ft

    39 S Main St, Winsted, CT 06098

    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

    RYAN HORVAY Smith & DeGroat Real Estate

    39 S Main St, Winsted, CT 06098
  • 129 Shore Dr, Winsted, CT 06098
    129 Shore Dr, Winsted, CT 06098
    129 Shore Dr, Winsted, CT 06098
    /3

    $225,000

    • Land
    • 0.23 Acre
    • $978,261 per Acre

    129 Shore Dr, Winsted, CT 06098

    A RARE OPPORTUNITY on HIGHLAND LAKE! This approved buildable lot is ready and waiting for you to build your dream! Lake life is a great life, make it yours!

    Annie Simard LPT Realty

    129 Shore Dr, Winsted, CT 06098
  • 119 W Wakefield Blvd, Winsted, CT 06098
    119 W Wakefield Blvd, Winsted, CT 06098
    119 W Wakefield Blvd, Winsted, CT 06098
    /35

    $849,900

    • 4 Beds
    • 2 Baths
    • 1,781 Sq Ft

    119 W Wakefield Blvd, Winsted, CT 06098

    Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

    Mela Veltri Case KW Legacy Partners

    119 W Wakefield Blvd, Winsted, CT 06098
  • 119 W Wakefield Blvd, Winsted, CT 06098
    119 W Wakefield Blvd, Winsted, CT 06098
    119 W Wakefield Blvd, Winsted, CT 06098
    /36

    $849,900

    • 4 Beds
    • 2 Baths
    • 1,781 Sq Ft

    119 W Wakefield Blvd, Winsted, CT 06098

    Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

    Mela Veltri Case KW Legacy Partners

    119 W Wakefield Blvd, Winsted, CT 06098
  • 99 Hubbard St, Winsted, CT 06098
    99 Hubbard St, Winsted, CT 06098
    /2

    $49,000

    • Land
    • 0.37 Acre
    • $132,432 per Acre

    99 Hubbard St, Winsted, CT 06098

    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,

    David Sartirana Northwest CT Realty

    99 Hubbard St, Winsted, CT 06098
  • 124 Rockwell St, Winsted, CT 06098
    124 Rockwell St, Winsted, CT 06098
    /2

    $29,000

    • Land
    • 0.44 Acre
    • $65,909 per Acre

    124 Rockwell St, Winsted, CT 06098

    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

    David Sartirana Northwest CT Realty

    124 Rockwell St, Winsted, CT 06098
  • 431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    /40

    $2,199,000

    • 9 Beds
    • 5.5 Baths
    • 7,000 Sq Ft

    431 W Wakefield Blvd, Winsted, CT 06098

    This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098
  • 393 Winchester Rd, Winsted, CT 06098
    393 Winchester Rd, Winsted, CT 06098
    393 Winchester Rd, Winsted, CT 06098
    /5

    $295,000

    • Land
    • 51 Acres
    • $5,784 per Acre

    393 Winchester Rd, Winsted, CT 06098

    WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

    Tom McGowan Elyse Harney Real Estate

    393 Winchester Rd, Winsted, CT 06098
  • 503 N Main St, Winsted, CT 06098
    503 N Main St, Winsted, CT 06098
    /2

    $69,000

    • Land
    • 2.00 Acres
    • $34,500 per Acre

    503 N Main St, Winsted, CT 06098

    Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

    Charles Albertario William Raveis Real Estate

    503 N Main St, Winsted, CT 06098
  • 48 Bridge St, Winsted, CT 06098
    48 Bridge St, Winsted, CT 06098
    /2

    $23,900

    • Land
    • 0.15 Acre
    • $159,333 per Acre

    48 Bridge St, Winsted, CT 06098

    Nestled just steps from downtown, this .15-acre lot offers a fantastic opportunity in a highly convenient location. The property is fairly level and provides easy access to shopping, restaurants, The Gilson Theater, and Little Red Barn Brewery. With city water and sewer available, this lot is ready for your vision. Whether you're looking to build or invest, this prime spot puts you right in the

    David Sartirana Northwest CT Realty

    48 Bridge St, Winsted, CT 06098
  • 19 Hill St, Winsted, CT 06098
    19 Hill St, Winsted, CT 06098
    /2

    $23,900

    • Land
    • 0.22 Acre
    • $108,636 per Acre

    19 Hill St, Winsted, CT 06098

    Located on a lightly traveled side street, this .22-acre lot offers a peaceful getaway with easy access to downtown. The property features a flat area at the street before gently sloping upward, creating a unique setting for potential future use. City water and sewer are available in the street, but buyers should conduct their own due diligence regarding buildability. Whether you're looking for a

    David Sartirana Northwest CT Realty

    19 Hill St, Winsted, CT 06098
  • 126 Forest Ave, Winsted, CT 06098
    126 Forest Ave, Winsted, CT 06098
    126 Forest Ave, Winsted, CT 06098
    /5

    $355,750 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,833 Sq Ft

    126 Forest Ave, Winsted, CT 06098

    Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath Cape Cod home offering over 1,800 sq. ft. of living space on nearly one acre of land. Owned by the original family. This property has been lovingly maintained and thoughtfully update. Step inside to find a fully appliance kitchen, fresh carpeting, and updated windows and gutters. The flexible seven- room

    Joanne Donne The Washington Agency

    126 Forest Ave, Winsted, CT 06098
  • 27 Thibault Ave, Winsted, CT 06098
    27 Thibault Ave, Winsted, CT 06098
    27 Thibault Ave, Winsted, CT 06098
    /18

    $399,900 Coming Soon

    • 8 Beds
    • 5 Baths
    • 7,372 Sq Ft

    27 Thibault Ave, Winsted, CT 06098

    Here is your perfect chance to build your investment portfolio! 2 houses and a vacant lot create the perfect investment opportunity! Comprised of a 4 unit apartment building and a single unit house with a 4 car garage under and an adjacent vacant lot. The vacant lot is perfect for additional parking and or play area! All tenants have been there long term and pay regularly.

    Cathy Macias Northwest CT Realty

    27 Thibault Ave, Winsted, CT 06098
  • 111 Riverton Rd Unit 37, Winsted, CT 06098
    111 Riverton Rd Unit 37, Winsted, CT 06098
    111 Riverton Rd Unit 37, Winsted, CT 06098
    /23

    $197,500 Coming Soon

    • 2 Beds
    • 1.5 Baths
    • 1,204 Sq Ft

    111 Riverton Rd Unit 37, Winsted, CT 06098

    Picture yourselves in this bright, roomy end unit condominium with room to spare! Totally renovated bathtub and fixtures in the full bath. Lovely, updated kitchen that not only has a pantry but sliding glass doors that lead out to the brand-new deck. 3-year-old pellet stove that will keep your entire unit toasty all winter long. The living room features beautiful sliding glass doors that also

    Sandra Marchetti The Washington Agency

    111 Riverton Rd Unit 37, Winsted, CT 06098
  • 157 Elm St, Winsted, CT 06098
    157 Elm St, Winsted, CT 06098
    /2

    $350,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 2,376 Sq Ft

    157 Elm St, Winsted, CT 06098

    Victorian Charm Meets Modern Potential - 5-Bedroom Home Across from Pearson School Step into timeless elegance with this spacious 5-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

    Doreen Gagnon Coldwell Banker Realty

    157 Elm St, Winsted, CT 06098

Showing Results 1 - 40, Page 1 of 2

Connecticut Litchfield County Winsted

Real Estate & Homes for Sale in Winsted, CT

Why Live in Winsted

Winsted, Connecticut, situated at the edge of the Berkshire Mountains, is part of the town of Winchester and home to about 7,200 residents. Known for its affordability, Winsted features a revitalized downtown with a two-mile commercial corridor offering diverse shops, eateries, and entertainment venues in historic buildings. Residents enjoy activities like antique shopping, duck pin bowling, and Go-Kart racing. Highland Lake, one of Connecticut’s largest waterways, is popular for fishing, swimming, and boating, while East End Park provides a walking path, memorials, and a bandstand. The Winsted Senior Center offers services and activities for those aged 55 and over.

The city hosts the American Mural Project, a large collaborative indoor artwork, and the Soldier’s Monument and Memorial Park, a Civil War memorial. The Winchester Historical Society, in an 1813 Colonial Revival mansion, showcases Civil War memorabilia and Victorian artifacts. Housing options include detached single-family homes, apartments, and townhouses, with many properties predating 1970. Northwestern Regional School District No. 7 is highly rated, offering programs in agricultural education.

Commuting is common, with residents traveling to nearby towns like Hartford and Waterbury for work. Winsted’s crime rate is 13% below the national average, indicating a safer environment compared to many areas. Although prone to flooding due to its proximity to lakes and rivers, the town has implemented measures like retaining walls and dams to mitigate risks.

Learn more about living in Winsted

Frequently Asked Questions

What is the average home price in Winsted, CT?
Homes for sale in Winsted, CT have an average home price of $378,469.
How many homes have sold over the last 12 months in Winsted, CT?
114 homes have sold in Winsted, CT over the last 12 months.
What are the most popular zip codes in Winsted, CT?
The most popular zip codes in Winsted, CT include 06098, 06063, 06021, 06057 and 06790.
How much do you need to make to afford a house in Winsted?
The median home price in Winsted is $299,999. If you put a 20% down payment of $60,000 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $1,530 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $66K a year to afford the median home price in Winsted.
How are the schools in Winsted, CT?
Winsted, CT has highly rated public and private schools. Some of the best schools in Winsted based on Niche Grades are Northwestern Regional Middle School, Northwestern Regional High School and Barkhamsted Elementary School. Browse all the schools in Winsted, CT to learn more.

Home Trends in Winsted, CT

On average, homes in Winsted, CT sell after 56 days on the market compared to the national average of 52 days. The median sale price for homes in Winsted, CT over the last 12 months is $290,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$290,000
Median Single Family Sale Price
$321,000
Median Townhouse Sale Price
$157,500
Median 2 Bedroom Sale Price
$197,500
Median 1 Bedroom Sale Price
$127,500
Average Price Per Sq Ft
$234
Number of Homes for Sale
26
Last 12 months Home Sales
114
Months of Supply
2.70
Median List Price
$299,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
How to Buy a Home How to Finance a Home How to Sell a Home

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