35

Winsted, CT Homes for Sale

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  • /31

    $350,000

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

    157 Elm St, Winsted, CT 06098

    Victorian Charm Meets Modern Potential - 6-Bedroom Home Across from Pearson School Step into timeless elegance with this spacious 6-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

    Agent Photo

    Doreen Gagnon

    Coldwell Banker Realty

    (860) 590-4676

    157 Elm St, 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
  • /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
  • /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
  • /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
  • /35

    $450,000

    • 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
  • /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
  • /36

    $499,000 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,892 Sq Ft

    819 E Wakefield Blvd, Winsted, CT 06098

    Perched directly across the street from Highland Lake's 3rd Bay, this charming 1,900 sq. ft. Cape offers sweeping lake views and the enjoyment of a permanent right-of-way to access the water. The home features 7 rooms, including 3 bedrooms and 1.5 baths, and has been thoughtfully maintained with important updates: new propane heating and hot water systems (2022), a new roof on both the house and

    David Sartirana Northwest CT Realty

    819 E Wakefield Blvd, Winsted, CT 06098
  • /10

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft

    15 John St, Winsted, CT 06098

    Feels Like New - Without the New Construction Price! Looking for a move-in ready home that won't break the bank? This freshly renovated 3-bedroom, 2-bath home has been updated from top to bottom - with a brand-new roof, siding, doors (inside and out), electrical, plumbing, carpet, kitchen, and two full bathrooms. Everything's done and ready for you to move in. It sits on a nice, level yard on a

    Amanda Balaski Northwest CT Realty

    15 John St, Winsted, CT 06098
  • /33

    $315,000

    • 2 Beds
    • 1 Bath
    • 1,880 Sq Ft

    101 Norfolk Rd, Winsted, CT 06098

    Beautifully updated Raised- Ranch retreat on 1.33 wooded acres! Nestled in a serene, natural setting yet conveniently close to local amenities. When you enter the home you will find two generous sized rooms with new vinyl plank flooring, fresh paint & a mini split as well as a spacious storage/utility room with laundry. The main floor includes the living room with a stone accent wall & great

    Jackie Desmarais Showcase Realty, Inc.

    101 Norfolk Rd, Winsted, CT 06098
  • /40

    $355,750

    • 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
  • /8

    $389,000

    • Land
    • 20.87 Acres
    • $18,639 per Acre

    7 Stadler Heights, Winsted, CT 06098

    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

    Hector Ortiz KW Legacy Partners

    7 Stadler Heights, Winsted, CT 06098
  • /27

    $399,900 Open Sat 11AM - 1PM

    • 2 Beds
    • 1.5 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /20

    $255,000

    • 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
  • /26

    $365,000

    • 4 Beds
    • 2 Baths
    • 1,910 Sq Ft

    147 Smith Hill Rd, Winsted, CT 06098

    Tucked away on a wooded lot, this meticulously maintained Cape features 4 spacious bedrooms and a full bathroom on each floor. Enjoy watching the birds & other wildlife on the huge rear deck or enjoy the peaceful setting on the enclosed porch. They don't make them like this anymore! The grounds have been lovingly maintained. You will want to move right in.

    SHARON GILSON Northwest CT Realty

    147 Smith Hill 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
  • /27

    $345,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /2

    $69,000

    • Land
    • 2 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
  • /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
  • /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
  • /2

    $280,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft

    331 Colebrook Rd, Winsted, CT 06098

    Nestled in the scenic Litchfield Hills, this charming 2-bedroom, 1.5-bath Cape has been lovingly restored over the past 11 years and thoughtfully updated with room to expand. Combining modern convenience with timeless character, recent improvements include refinished hardwood floors and fresh paint throughout, making it truly move-in ready. Cozy up by the wood-burning stove on crisp autumn

    Alison Malkin Essentia Realty

    331 Colebrook Rd, Winsted, CT 06098

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.

Frequently Asked Questions

What is the average home price in Winsted, CT?
Homes for sale in Winsted, CT have an average home price of $403,793.
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 $300,000. If you put a 20% down payment of $60,000 and had a 30-year fixed mortgage with an interest rate of 6.35%, your estimated principal and interest payment would be $1,490 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $64K 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 High School, Barkhamsted Elementary School and Northwestern Regional Middle School. Browse all the schools in Winsted, CT to learn more.

Home Trends in Winsted, CT

Housing Trends

Median Sale Price
$289,950
Median Single Family Sale Price
$321,000
Median Townhouse Sale Price
$157,500
Median 1 Bedroom Sale Price
$127,500
Average Price Per Sq Ft
$225
Number of Homes for Sale
25
Last 12 months Home Sales
114
Months of Supply
2.60
Median List Price
$300,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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