30

Winsted, CT Homes for Sale

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  • /31

    $339,000

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

    157 Elm St, Winsted, CT 06098

    Bring your vision to this spacious 6-bedroom, 2.5-bath home full of character and potential. Featuring a newer roof and boiler, this property offers peace of mind while leaving room for your personal touch. Enjoy the classic Victorian details and generous layout, perfect for creating your dream home. Situated on a sidewalk-lined street just steps from downtown eateries, a local brewery, and

    Agent Photo

    Doreen Gagnon

    Coldwell Banker Realty

    (860) 590-8606

    157 Elm 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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 453-5624

    48 Bridge St, Winsted, CT 06098
  • /22

    $179,900

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

    111 Riverton Rd Unit 90, Winsted, CT 06098

    Discover the ease of condo living with the charm of a riverside retreat at Riverwalk Condos. This beautifully cared-for 2-bedroom, 1.5-bath home offers an inviting layout designed for comfort and relaxation. The spacious living room with its warm fireplace opens to a private deck overlooking the Still River-an ideal spot to unwind at the end of the day or entertain with a view. The kitchen also

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 615-2545

    111 Riverton Rd Unit 90, 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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 891-6121

    124 Rockwell St, Winsted, CT 06098
  • /2

    $29,000

    • Land
    • 1.88 Acres
    • $15,426 per Acre

    52 White St, Winsted, CT 06098

    Discover the possibilities with this 1.8-acre parcel located on a peaceful in-town street. The property offers a convenient location close to town amenities while maintaining a quiet, private setting. Public water and sewer are available in the street, though not currently connected to the property. While the land is developable, the seller will retain easements for drainage and access to

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 856-5386

    52 White St, Winsted, CT 06098
  • /36

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,167 Sq Ft

    197 Spencer Hill Rd, Winsted, CT 06098

    Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a desirable rural neighborhood. Offering over 3,000 square feet of living space, this well-maintained home provides a flexible layout ideal for today's lifestyle. The main level features a formal living room, dining room, updated kitchen, den, sunroom with fireplace and hot tub, full bath, and convenient

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 419-0914

    197 Spencer Hill Rd, Winsted, CT 06098
  • /22

    $245,000

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    174 Wallens St Unit B6, Winsted, CT 06098

    Discover effortless, low-maintenance living in this inviting home located in the highly sought-after Clockmaker's Hill 55+ community. The thoughtfully designed open floor plan features 2 bedrooms and 2 full bathrooms, offering seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining area, ideal for hosting friends and family. The sun-filled kitchen

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 507-3542

    174 Wallens St Unit B6, Winsted, CT 06098
  • /30

    $329,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    107 Peck Rd, Winsted, CT 06098

    Turnkey 3 Bedroom, 1 bathroom home on almost an acre in Winchester. The home is sited up a long driveway in a quiet, wooded setting across from state land. Completely renovated by current owner, top to bottom. Updated kitchen & bath, new roof, new hot water heater, new Trex deck, new pellet stove, new ductless mini splits in living area and primary bedroom and much more! Attached one car garage

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (860) 855-0150

    107 Peck Rd, 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,

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 946-4468

    99 Hubbard St, Winsted, CT 06098
  • /37

    $499,999

    • 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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 390-5071

    55 Walnut St, Winsted, CT 06098
  • /38

    $1,270,000

    • 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
  • /40

    $419,000

    • 4 Beds
    • 1.5 Baths
    • 2,365 Sq Ft

    187 Torringford St, Winsted, CT 06098

    Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm,

    Jessica Washington William Raveis Real Estate

    187 Torringford St, 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
  • /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
  • /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
  • /40

    $2,199,000

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

    431 W Wakefield Blvd, Winsted, CT 06098

    LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. 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

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098
  • /38

    $395,000

    • 3 Beds
    • 1.5 Baths
    • 1,909 Sq Ft

    720 Main St, Winsted, CT 06098

    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,

    Ryan Marconi The Washington Agency

    720 Main St, 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
  • /23

    $230,000

    • 2 Beds
    • 1.5 Baths
    • 1,172 Sq Ft

    9 John St, Winsted, CT 06098

    Beautifully renovated 1870 Colonial offering 1,172 sq. ft. of updated and functional living space. The home features hardwood floors in the living room and both bedrooms, adding warmth and durability throughout. A convenient first-floor bedroom provides flexibility, while the spacious primary bedroom is located on the second level. The kitchen has been completely refreshed with new flooring,

    Michael Grady William Raveis Real Estate

    9 John St, Winsted, CT 06098
  • /13

    $649,900

    • Land
    • 41.23 Acres
    • $15,763 per Acre

    115 Old Robertsville Rd, Winsted, CT 06098

    Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The home

    Jared Tedesco Litchfield County Real Estate

    115 Old Robertsville Rd, Winsted, CT 06098
  • /24

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 2,356 Sq Ft

    95 Nalette Dr, Winsted, CT 06098

    Stunning Contemporary Home on a Quiet Corner Lot. This unique home offers a beautifully updated open floor plan that seamlessly blends the kitchen, dining, and living areas-perfect for modern living and entertaining. The kitchen features granite countertops, ample cabinetry, stainless steel appliances, and great flow into the main living space. The first floor includes a refinished half bathroom

    Jennifer Mitchell Northwest CT Realty

    95 Nalette Dr, Winsted, CT 06098
  • /11

    $179,900

    • 2 Beds
    • 1.5 Baths
    • 832 Sq Ft

    8 Oak St, Winsted, CT 06098

    Discover a low maintenance and hassle-free alternative to condo living with this easy-to-maintain, single-family home , perfect for investors, first-time buyers, or anyone seeking simplified living without the burden of HOA fees. Step inside to an efficient layout featuring brand-new WREN kitchen cabinets, granite countertops, a new gas stove, and a new refrigerator, offering a fresh and modern

    Austin Brochu Sullivan Real Estate Inc

    8 Oak St, 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
  • /39

    $920,000

    • 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
  • /12

    $750,000

    • 4 Beds
    • 2 Baths
    • 5,389 Sq Ft

    436 Main St, Winsted, CT 06098

    One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year

    Tony Goia The Washington Agency

    436 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
  • /17

    $269,000

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

    38 Upland Rd, Winsted, CT 06098

    TO SETTLE ESTATE: Available for Immediate Occupancy is this Immaculate 3 to 4 Bedroom Colonial tucked away on a quiet street. Features Hardwood Floors throughout the house, 24' x 14' Family Room with Propane Gas Stove, Country Kitchen. Primary Bedroom with it's own office area. Oversized Full Bath. 3-Season 21' x 8' Enclosed Porch. 26' x 10' Concrete Patio. Detached One Car Garage. Attractive

    Marshall Cohen Cohen Agency

    38 Upland Rd, 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
  • /16

    $290,000

    • 3 Beds
    • 2 Baths
    • 1,652 Sq Ft

    118 Meadow St, Winsted, CT 06098

    This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting. The home sits

    Ashley Henry The Washington Agency

    118 Meadow St, Winsted, CT 06098
  • /37

    $500,000

    • 4 Beds
    • 2.5 Baths
    • 3,416 Sq Ft

    440 Platt Hill Rd, Winsted, CT 06098

    Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque country acres, this unique property offers two homes and endless potential. The stone and stucco main residence features eight spacious rooms, including four bedrooms and four fireplaces, blending classic character with old-world charm. Rolling open land and mature trees surround the home, providing an ideal

    David D'Amore Northwest CT Realty

    440 Platt Hill 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. Winsted features a revitalized downtown with a 2-mile commercial corridor offering diverse shops, eateries and entertainment venues in historic buildings. Residents enjoy activities like antique shopping, duckpin 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 has services and activities for those aged 55 and over.

The city hosts the American Mural Project, a large collaborative indoor work of art, 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. The Winchester Public Schools system has a reputation for well-run science and engineering programs.

Commuting is common, with residents traveling to nearby towns like Hartford and Waterbury for work. Although flooding is possible due to the community's 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 $396,369.
How many homes have sold over the last 12 months in Winsted, CT?
115 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 $289,950. If you put a 20% down payment of $58,000 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $1,420 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $61K a year to afford the median home price in Winsted. Learn how much home you can afford with our Home Affordability Calculator.
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
$282,000
Median Single Family Sale Price
$319,900
Median Townhouse Sale Price
$157,500
Median 2 Bedroom Sale Price
$198,000
Median 1 Bedroom Sale Price
$127,500
Average Price Per Sq Ft
$238
Number of Homes for Sale
17
Last 12 months Home Sales
115
Months of Supply
1.80
Median List Price
$289,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-2%
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