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Connecticut · Real Estate

Homes for Sale in
Winchester, CT

As of November 10, 2026, per SmartMLS, there are 37 homes for sale in Winchester, Connecticut with an average list price of $460,951.

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

37

active listings

Median Sale Price

$330K

$27K–$1.9M

Avg. Size Sold

1,693 sf

last 12 mo

vs. Ask Price

-0.3%

avg. paid vs. ask

Stats based on 133 closings in the last 12 months · SmartMLS, as of Nov 10, 2026

Showing 12 of 37 listings in Winchester

18 Pratt Street, Winchester, CT
Active
$299,900
5 bd · 2 ba · 2,016 sqft  ·  2 Family
18 Pratt Street
Winchester, CT 06098
Northwest CT Realty SmartMLS
435 Platt Hill Road, Winchester, CT
Active
$110,000
Residential Land
435 Platt Hill Road
Winchester, CT 06098
Berkshire Hathaway NE Prop. SmartMLS
510 Reaching Hill Road, Winchester, CT
Active
$199,000
Residential Land
510 Reaching Hill Road
Winchester, CT 06098
Berkshire Hathaway NE Prop. SmartMLS
19 Hill Street, Winchester, CT
Active
$23,900
Residential Land
19 Hill Street
Winchester, CT 06098
Northwest CT Realty SmartMLS
Photos coming soon
Active
$35,000
Residential Land
16 Brook Street
Winchester, CT 06098
Northwest CT Realty SmartMLS
120 Hollow Hill Road, Winchester, CT
Active
$450,000
Residential Land
120 Hollow Hill Road
Winchester, CT 06098
William Raveis Real Estate SmartMLS
19 Walnut Street, Winchester, CT
Active OH 11/15 · 12pm–2pm
$285,000
4 bd · 3 ba · 2,868 sqft
19 Walnut Street
Winchester, CT 06098
Sullivan Real Estate Inc SmartMLS
264 Florence Street, Winchester, CT
Active
$265,000
3 bd · 2 ba · 1,417 sqft
264 Florence Street
Winchester, CT 06098
The Washington Agency SmartMLS
111 Riverton Road #22, Winchester, CT
Active
$185,000
2 bd · 2 ba · 1,204 sqft  ·  Condominium
111 Riverton Road #22
Winchester, CT 06098
KW Legacy Partners SmartMLS
139 Grantville Road, Winchester, CT
Active
$950,000
5 bd · 5 ba · 4,212 sqft
139 Grantville Road
Winchester, CT 06098
Country House Realty CT Inc. SmartMLS
218 Oak Street, Winchester, CT
Active
$225,000
3 bd · 1 ba · 1,155 sqft
218 Oak Street
Winchester, CT 06098
Northwest CT Realty SmartMLS
205 Perch Rock Trail, Winchester, CT
Active
$350,000
4 bd · 3 ba · 2,407 sqft
205 Perch Rock Trail
Winchester, CT 06098
Find Real Estate LLC SmartMLS
Read our Living in Winchester, CT guide
See All 37 Homes in Winchester

Buying a Home in Winchester, CT

Current Market Snapshot

Entry Price
$24K
lowest listed
Avg. Price
$461K
list price
Top of Market
$1.6M
highest listed
Listings by Bedroom Count
2 beds
1
3 beds
7
4 beds
9
5 beds
3
6 beds
2
8 beds
1
14 beds
1
Property Types Available
Single Family · 15 Land · 13 Multi-Family For Sale · 8 Condo / Co-Op · 1

As of November 10, 2026, the Winchester real estate market has 37 active listings with an average list price of $460,951 and a price range from $23,900 to $1,550,000. Single Family homes make up the largest share of available inventory. Most listings are 4-bedroom homes. The average home size is 1,560 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 November 10, 2026, per SmartMLS, there are 37 active listings in Winchester, CT. All listings are updated every 15 minutes directly from SmartMLS.
What is the average home price in Winchester, CT?
As of November 10, 2026, per SmartMLS, the average list price in Winchester is $460,951. Homes currently range from $23,900 to $1,550,000.
What size homes are most common in Winchester, CT?
The most common listing in Winchester is a 4-bedroom home (9 listings). Other common sizes include 3-bedroom (7) and 5-bedroom (3). The average home size is 1,560 sq ft.
What types of homes are available in Winchester, CT?
Current listings in Winchester include: Single Family (15), Land (13), Multi-Family For Sale (8), Condo / Co-Op (1).
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.