Homes for Sale in Winchester, CT | RYZE Realty Group
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Connecticut · Real Estate

Homes for Sale in
Winchester, CT

There are currently 41 homes for sale in Winchester, Connecticut with an average list price of $520,548.

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

41

active listings

Avg. Sale Price

$384K

$27K–$1.9M

Avg. Size Sold

1,691 sf

last 12 mo

vs. Ask Price

+0.9%

avg. paid vs. ask

Stats based on 141 closings in the last 12 months

Showing 12 of 41 listings in Winchester

95 Williams Avenue, Winchester, CT
Active
$374,900
6 bd · 3.00 ba · 2,887 sqft  ·  2 Family
95 Williams Avenue
Winchester, CT 06098
LPT Realty SmartMLS
359 Winchester Road, Winchester, CT
Active
$850,000
3 bd · 3.00 ba · 2,943 sqft
359 Winchester Road
Winchester, CT 06098
William Pitt Sotheby's Int'l SmartMLS
150 East Lake Street, Winchester, CT
Coming Soon OH 9/27 · 12pm–2pm
$449,000
3 bd · 3.00 ba · 1,659 sqft
150 East Lake Street
Winchester, CT 06098
Sullivan Real Estate Inc SmartMLS
50 Palmer Avenue, Winchester, CT
Active
$489,000
3 bd · 2.00 ba · 1,680 sqft
50 Palmer Avenue
Winchester, CT 06098
Berkshire Hathaway NE Prop. SmartMLS
120 Moore Avenue, Winchester, CT
Active
$425,000
3 bd · 2.00 ba · 1,952 sqft
120 Moore Avenue
Winchester, CT 06098
Elyse Harney Real Estate SmartMLS
100 Norfolk Road, Winchester, CT
Active
$350,000
4 bd · 2.00 ba · 2,914 sqft
100 Norfolk Road
Winchester, CT 06098
Northwest CT Realty SmartMLS
118 Meadow Street, Winchester, CT
Active
$260,000
3 bd · 2.00 ba · 1,652 sqft
118 Meadow Street
Winchester, CT 06098
The Washington Agency SmartMLS
180 Shore Drive, Winchester, CT
Active
$749,900
3 bd · 2.00 ba · 1,131 sqft
180 Shore Drive
Winchester, CT 06098
Berkshire Hathaway NE Prop. SmartMLS
77 Hubbard Street, Winchester, CT
Active
$359,900
4 bd · 2.00 ba · 2,699 sqft  ·  2 Family
77 Hubbard Street
Winchester, CT 06098
Better Homes and Gardens Real Estate Executive Real Estate SmartMLS
414 East Wakefield Boulevard, Winchester, CT
Active
$850,000
Residential Land
414 East Wakefield Boulevard
Winchester, CT 06098
LPT Realty SmartMLS
130 Riverton Road, Winchester, CT
Active OH 9/27 · 1pm–3pm
$450,000
3 bd · 2.00 ba · 1,430 sqft
130 Riverton Road
Winchester, CT 06098
William Raveis Real Estate SmartMLS
347 West Wakefield Boulevard, Winchester, CT
Active
$289,000
2 bd · 1.00 ba · 596 sqft
347 West Wakefield Boulevard
Winchester, CT 06098
Berkshire Hathaway NE Prop. SmartMLS
See All 41 Homes in Winchester

Buying a Home in Winchester, CT

Current Market Snapshot

Entry Price
$38K
lowest listed
Avg. Price
$521K
list price
Top of Market
$1.6M
highest listed
Listings by Bedroom Count
2 beds
5
3 beds
11
4 beds
10
5 beds
1
6 beds
2
8 beds
1
11 beds
1
Property Types Available
Single Family · 23 Land · 10 Multi-Family For Sale · 8

The Winchester real estate market currently has 41 active listings with an average list price of $520,548 and a price range from $37,900 to $1,550,000. Single Family homes make up the largest share of available inventory. Most listings are 3-bedroom homes. The average home size is 1,672 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 September 2026, there are 41 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 $520,548. Homes currently range from $37,900 to $1,550,000.
What size homes are most common in Winchester, CT?
The most common listing in Winchester is a 3-bedroom home (11 listings). Other common sizes include 4-bedroom (10) and 2-bedroom (5). The average home size is 1,672 sq ft.
What types of homes are available in Winchester, CT?
Current listings in Winchester include: Single Family (23), Land (10), Multi-Family For Sale (8).
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.