6

Winsted, CT Homes for Sale under $400,000

Section Image Section Image
  • 621 Wynne Rd, Winsted, CT 06098
    621 Wynne Rd, Winsted, CT 06098
    621 Wynne Rd, Winsted, CT 06098
    /35

    $339,900

    • 2 Beds
    • 1 Bath
    • 975 Sq Ft

    621 Wynne Rd, Winsted, CT 06098

    Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 385-6622

    621 Wynne 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
  • 262 Holabird Ave, Winsted, CT 06098
    262 Holabird Ave, Winsted, CT 06098
    262 Holabird Ave, Winsted, CT 06098
    /21

    $360,000

    • 3 Beds
    • 1.5 Baths
    • 1,312 Sq Ft

    262 Holabird Ave, Winsted, CT 06098

    Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows

    Mary Anne Casey D. Beckley Realty

    262 Holabird Ave, Winsted, CT 06098
  • 720 Main St, Winsted, CT 06098
    720 Main St, Winsted, CT 06098
    720 Main St, 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
  • 7 Stadler Heights, Winsted, CT 06098
    7 Stadler Heights, Winsted, CT 06098
    7 Stadler Heights, 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 minutes

    Hector Ortiz KW Legacy Partners

    7 Stadler Heights, Winsted, CT 06098
  • 90 Colony Dr, Winsted, CT 06098
    90 Colony Dr, Winsted, CT 06098
    90 Colony Dr, Winsted, CT 06098
    /6

    $349,900 Coming Soon

    • 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
Connecticut Litchfield County Winsted

Real Estate & Homes in Winsted, CT under $400,000

Home Trends in Winsted, CT

On average, homes in Winsted, CT sell after 59 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
$319,950
Median Townhouse Sale Price
$161,250
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
11
Last 12 months Home Sales
110
Months of Supply
1.20
Median List Price
$298,000
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

Explore the array of homes and houses for sale under $400,000 in Winsted, where you'll find 6 options tailored for those seeking affordable real estate opportunities. Whether you're interested in spacious family homes, modern townhouses, or cozy bungalows, Winsted offers a diverse range of choices to match your needs and financial considerations. Take advantage of these affordably-priced properties to make your move into the real estate market in Winsted, CT.

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