View 57 Main Street Winchester, CT MLS# 24112807
$375,000
3

Beds

0.0

Baths

3,660

Sq.Ft.

57 Main Street

Winchester, CT

View 57 Main Street Winchester, CT MLS# 24112471
$375,000
1.0

Baths

3,660

Sq.Ft.

57 Main Street

Winchester, CT

View 722 Lake Drive Winchester, CT MLS# 24105754
  • Virtual Tour
1 of 49
$1,270,000
3

Beds

3.0

Baths

2,420

Sq.Ft.

722 Lake Drive

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 99 Norfolk Road Winchester, CT MLS# 24107073
$184,900
3

Beds

1.0

Baths

980

Sq.Ft.

99 Norfolk Road

Winchester, CT

View 1 Lake Street Winchester, CT MLS# 24104685
$290,000
4,852

Sq.Ft.

1 Lake Street

Winchester, CT

View 115 Old Robertsville Road Winchester, CT MLS# 24104078
$649,900
5

Beds

1.1

Baths

2,304

Sq.Ft.

115 Old Robertsville Road

Winchester, CT

View 115 Old Robertsville Road Winchester, CT MLS# 24104099
$649,900
Studio

Beds

0.0

Baths

115 Old Robertsville Road

Winchester, CT

View 503 North Main Street Winchester, CT MLS# 24101761
$69,000
Studio

Beds

0.0

Baths

503 North Main Street

Winchester, CT

View 00 Chapel Road Winchester, CT MLS# 24097613
$300,000
Studio

Beds

0.0

Baths

00 Chapel Road

Winchester, CT

View 256 Colebrook Road Winchester, CT MLS# 24096527
$39,900
Studio

Beds

0.0

Baths

256 Colebrook Road

Winchester, CT

View 117 South Road Winchester, CT MLS# 24096267
$419,000
3

Beds

3.0

Baths

2,747

Sq.Ft.

117 South Road

Winchester, CT

View 469 Platt Hill Road Winchester, CT MLS# 24089885
$920,000
4

Beds

2.0

Baths

3,088

Sq.Ft.

469 Platt Hill Road

Winchester, CT

View 39 South Main Street Winchester, CT MLS# 24083565
$749,900
7

Beds

3.0

Baths

3,486

Sq.Ft.

39 South Main Street

Winchester, CT

View Old Robertsville Road # Winchester, CT MLS# 24080217
$739,900
Studio

Beds

0.0

Baths

Old Robertsville Road #

Winchester, CT

View 119 West Wakefield Boulevard Winchester, CT MLS# 24058804
$849,900
4

Beds

2.0

Baths

1,781

Sq.Ft.

119 West Wakefield Boulevard

Winchester, CT

View 119 West Wakefield Boulevard Winchester, CT MLS# 24075940
$849,900
4

Beds

2.0

Baths

1,781

Sq.Ft.

119 West Wakefield Boulevard

Winchester, CT

View 124 Rockwell Street Winchester, CT MLS# 24073710
$29,000
Studio

Beds

0.0

Baths

124 Rockwell Street

Winchester, CT

View 48 Bridge Street Winchester, CT MLS# 24073721
$23,900
Studio

Beds

0.0

Baths

48 Bridge Street

Winchester, CT

View 99 Hubbard Street Winchester, CT MLS# 24073744
$49,000
Studio

Beds

0.0

Baths

99 Hubbard Street

Winchester, CT

View 55 Walnut Street Winchester, CT MLS# 24071827
$499,999
5

Beds

1.3

Baths

5,016

Sq.Ft.

55 Walnut Street

Winchester, CT

About Winchester

Often called the “Gateway to the Berkshire Mountains,” Winchester blends the natural beauty of lakes and freshwater springs with more than 650 flourishing businesses.  The result is a strong local economy within a relaxed small-town lifestyle.  Winsted is the downtown district of Winchester, home to the campus for Northwestern Connecticut Community Technical College.  The town is noted for its magnificent ecclesiastical architecture and for one of the state’s largest lakes.

Listings in Winchester, CT

74

Estimated median home price

$314,900
Winchester CT Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Connecticut real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, CT.

Homes for Sale by Price in Winchester, CT

PriceCount
$0 - 100K11
$100K - 200K9
$200K - 300K16
$300K - 400K14
$400K - 500K6
$500K - 600K2
$600K - 700K1
$700K - 800K5
$800K - 900K4
$900K - 1M2
$1M - Max4

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family31
Townhouse0
Condo5
Commercial9
Rental15
Lots and Land18
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms0

(Data as of 11/11/2025)

Information deemed reliable but not guaranteed.

Listing information has been assembled from various sources of varying degrees of reliability. Any information critical to a buying decision should be independently verified.

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