7

Winsted, CT Houses for Sale

Section Image Section Image
  • 55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    /37

    $469,000

    • 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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 390-5071

    55 Walnut St, Winsted, CT 06098
  • 123 Old North Rd, Winsted, CT 06098
    123 Old North Rd, Winsted, CT 06098
    123 Old North Rd, Winsted, CT 06098
    /28

    $425,000

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

    123 Old North Rd, Winsted, CT 06098

    This one-of-a-kind custom Ranch is tucked well back from the road for exceptional privacy and was thoughtfully designed for its present owner. The stunning kitchen is truly the heart of the home, featuring a dramatic floor-to-ceiling stone fireplace, an expansive island with breakfast bar, an endless array of cabinets, and a built-in range with gas cooktop. The dining area flows seamlessly from

    Rick Berkenstock Century 21 AllPoints Realty

    123 Old North Rd, Winsted, CT 06098
  • 1 Hamill Dr, Winsted, CT 06098
    1 Hamill Dr, Winsted, CT 06098
    1 Hamill Dr, Winsted, CT 06098
    /29

    $359,900

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft

    1 Hamill Dr, Winsted, CT 06098

    Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less

    Paul Duh Realty ONE Group Connect

    1 Hamill Dr, Winsted, CT 06098
  • 90 Colony Dr, Winsted, CT 06098
    90 Colony Dr, Winsted, CT 06098
    90 Colony Dr, Winsted, CT 06098
    /22

    $349,900

    • 3 Beds
    • 1 Bath
    • 1,282 Sq Ft

    90 Colony Dr, Winsted, CT 06098

    Turnkey Winsted gem completely renovated inside & out! Get ready to just move and and not worry. Here is a beautifully reimagined 3-bedroom, 1-bathroom property in Winsted, offering the perfect blend of modern luxury and ultimate peace of mind. Every detail has been thoughtfully updated to create a true turnkey experience. Step inside to a bright, inviting space where the wall between the

    Michelle Grant Coldwell Banker Premier Real Estate

    90 Colony Dr, Winsted, CT 06098
  • 121 W Wakefield Blvd, Winsted, CT 06098
    121 W Wakefield Blvd, Winsted, CT 06098
    121 W Wakefield Blvd, Winsted, CT 06098
    /38

    $769,000

    • 4 Beds
    • 3.5 Baths
    • 2,265 Sq Ft

    121 W Wakefield Blvd, Winsted, CT 06098

    Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or

    Elizabeth Stockwell Coldwell Banker Realty

    121 W Wakefield Blvd, Winsted, CT 06098
  • 156 Shore Dr, Winsted, CT 06098
    156 Shore Dr, Winsted, CT 06098
    156 Shore Dr, Winsted, CT 06098
    /37

    $779,900

    • 5 Beds
    • 1.5 Baths
    • 1,258 Sq Ft

    156 Shore Dr, Winsted, CT 06098

    Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor

    Bryan Palladino Showcase Realty, Inc.

    156 Shore Dr, Winsted, CT 06098
  • 431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    431 W Wakefield Blvd, Winsted, CT 06098
    /36

    $1,850,000

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

    431 W Wakefield Blvd, Winsted, CT 06098

    Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

    Lisa Ogren Berkshire Hathaway NE Prop.

    431 W Wakefield Blvd, Winsted, CT 06098
Connecticut Litchfield County Winsted

Houses 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. 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.

Learn more about living in Winsted

Home Trends in Winsted, CT

On average, homes in Winsted, CT sell after 58 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 $287,278, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$287,278
Median Single Family Sale Price
$315,500
Median Townhouse Sale Price
$160,000
Median 2 Bedroom Sale Price
$224,000
Median 1 Bedroom Sale Price
$127,900
Average Price Per Sq Ft
$243
Number of Homes for Sale
10
Last 12 months Home Sales
112
Months of Supply
1.10
Median List Price
$289,450
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
0%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winsted, there are currently 7 houses for sale, offering an array of options for potential buyers. With houses priced between $349,900 to $1,850,000, there's a range to accomodate every budget. As of April, 2026 the median home price in Winsted is $289,450, while the average sale price is $352,086, offering insights into the local housing market. On average, houses spend 58 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Winsted, CT and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group