5

Winsted, CT Homes for Sale with Acreage

Section Image
  • 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

    Hector Ortiz KW Legacy Partners

    7 Stadler Heights, 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
  • 503 N Main St, Winsted, CT 06098
    503 N 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
  • 469 Platt Hill Rd, Winsted, CT 06098
    469 Platt Hill Rd, Winsted, CT 06098
    469 Platt Hill 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
  • 10 Meeting House Rd, Winsted, CT 06063
    10 Meeting House Rd, Winsted, CT 06063
    10 Meeting House Rd, Winsted, CT 06063
    /36

    $469,000

    • 3 Beds
    • 2 Baths
    • 1,556 Sq Ft

    10 Meeting House Rd, Winsted, CT 06063

    Enjoy the quiet setting and backyard privacy of this totally renovated three bedroom, two bath home. Everything is new, including every electric receptacle and switch. New kitchen with quartz countertops and stainless appliances, complete bathrooms and fixtures, flooring, furnace and AC, septic system, windows, composite decks, 200 amp service, well tank, water heater, plumbing, footing drains,

    Keith Meyer Northwest CT Realty

    10 Meeting House Rd, Winsted, CT 06063
Connecticut Litchfield County Winsted

Homes for Sale with Acreage in Winsted, CT

Home Trends in Winsted, CT

On average, homes in Winsted, CT sell after 55 days on the market compared to the national average of 53 days. The median sale price for homes in Winsted, CT over the last 12 months is $279,950, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$279,950
Median Single Family Sale Price
$305,000
Median Townhouse Sale Price
$162,000
Median 2 Bedroom Sale Price
$224,000
Median 1 Bedroom Sale Price
$135,000
Average Price Per Sq Ft
$239
Number of Homes for Sale
9
Last 12 months Home Sales
110
Months of Supply
1.00
Median List Price
$287,700
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winsted, there are currently 5 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Winsted, CT offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Winsted and discover the potential and freedom that comes with owning your own piece of property.

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