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Connecticut · Real Estate

Homes for Sale in
Winchester, CT

There are currently 17 homes for sale in Winchester, Connecticut with an average list price of $557,741.

Winchester is a Litchfield County town of about 10,700 centered on the village of Winsted, with Highland Lake as the town's natural centerpiece — a popular destination for boating, fishing, and swimming. Home prices are affordable for Litchfield County, and Route 44 provides easy access to Torrington and the broader northwest hills. A genuine small-town character with four-season recreational appeal.

For Sale

17

active listings

Avg. Sale Price

$334K

$8K–$1.6M

Avg. Size Sold

1,744 sf

last 12 mo

vs. Ask Price

-0.1%

avg. paid vs. ask

Stats based on 141 closings in the last 12 months

Showing 12 of 17 listings in Winchester

621 Wynne Road, Winchester, CT Coming Soon
$339,900
2 bd · 1.00 ba · 975 sqft
621 Wynne Road
Winchester, CT 06098
Northwest CT Realty SmartMLS
156 Shore Drive, Winchester, CT
$789,000
5 bd · 2.00 ba · 1,258 sqft
156 Shore Drive
Winchester, CT 06098
Showcase Realty, Inc. SmartMLS
431 West Wakefield Boulevard, Winchester, CT
$1,850,000
9 bd · 6.00 ba · 7,000 sqft
431 West Wakefield Boulevard
Winchester, CT 06098
Berkshire Hathaway NE Prop. SmartMLS
5 Stadler Heights, Winchester, CT
$499,000
4 bd · 3.00 ba · 3,556 sqft
5 Stadler Heights
Winchester, CT 06098
Northwest CT Realty SmartMLS
257-259 Torringford Street, Winchester, CT
$859,000
Residential Land
257-259 Torringford Street
Winchester, CT 06098
Home Valley Realty, LLC SmartMLS
Photos coming soon
$395,000
3 bd · 2.00 ba · 1,909 sqft  ·  2 Family
720 Main Street
Winchester, CT 06098
The Washington Agency SmartMLS
Photos coming soon
$750,000
4 bd · 2.00 ba · 5,389 sqft  ·  2 Family
436 Main Street
Winchester, CT 06098
The Washington Agency SmartMLS
Photos coming soon
$879,990
Residential Land
000000 Norfolk Road
Winchester, CT 06098
William Pitt Sotheby's Int'l SmartMLS
Photos coming soon
$389,000
Residential Land
7 Stadler Heights
Winchester, CT 06098
KW Legacy Partners SmartMLS
Photos coming soon
$300,000
Residential Land
00 Chapel Road
Winchester, CT 06098
Borla & Associates Real Estate SmartMLS
Photos coming soon
$920,000
4 bd · 2.00 ba · 3,088 sqft
469 Platt Hill Road
Winchester, CT 06098
Cohen Agency SmartMLS
Photos coming soon
$749,900
7 bd · 3.00 ba · 3,486 sqft  ·  Other
39 South Main Street
Winchester, CT 06098
Smith & DeGroat Real Estate SmartMLS
See All 17 Homes in Winchester

Buying a Home in Winchester, CT

Current Market Snapshot

Entry Price
$25K
lowest listed
Avg. Price
$558K
list price
Top of Market
$1.9M
highest listed
Listings by Bedroom Count
2 beds
1
3 beds
1
4 beds
3
5 beds
2
7 beds
1
9 beds
1
Property Types Available
Land · 8 Single Family · 6 Multi-Family For Sale · 3

The Winchester real estate market currently has 17 active listings with an average list price of $557,741 and a price range from $24,900 to $1,850,000. Land homes make up the largest share of available inventory. Most listings are 4-bedroom homes. The average home size is 1,863 sq ft. All listings are sourced directly from SmartMLS and updated every 15 minutes.

Frequently Asked Questions

How many homes are for sale in Winchester, CT right now?
As of March 2026, there are 17 active listings in Winchester, CT. All listings are updated every 15 minutes directly from SmartMLS.
What is the average home price in Winchester, CT?
The average list price in Winchester is $557,741. Homes currently range from $24,900 to $1,850,000.
What size homes are most common in Winchester, CT?
The most common listing in Winchester is a 4-bedroom home (3 listings). Other common sizes include 5-bedroom (2) and 2-bedroom (1). The average home size is 1,863 sq ft.
What types of homes are available in Winchester, CT?
Current listings in Winchester include: Land (8), Single Family (6), Multi-Family For Sale (3).
Is Winchester, CT a good place to buy a home?
Winchester is a Litchfield County town of about 10,700 centered on the village of Winsted, with Highland Lake as the town's natural centerpiece — a popular destination for boating, fishing, and swimming. Home prices are affordable for Litchfield County, and Route 44 provides easy access to Torrington and the broader northwest hills. A genuine small-town character with four-season recreational appeal.
Does RYZE Realty Group serve Winchester, CT?
Yes — RYZE Realty Group is a Connecticut real estate team serving buyers and sellers across Litchfield County and the greater Connecticut market, including Winchester. Contact us for a free consultation.

Nearby Towns

Torrington, CT 77 listings
Plymouth, CT 28 listings
Roxbury, CT 28 listings
Woodbury, CT 27 listings
Watertown, CT 26 listings
Salisbury, CT 22 listings

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