View 436 Main Street Winchester, CT MLS# 24135027
$750,000
5,389

Sq.Ft.

436 Main Street

Winchester, CT

View 436 Main Street Winchester, CT MLS# 24135030
$750,000
4

Beds

2.2

Baths

5,389

Sq.Ft.

436 Main Street

Winchester, CT

View 151 Losaw Road Winchester, CT MLS# 24121140
$749,999
5

Beds

2.1

Baths

2,950

Sq.Ft.

151 Losaw Road

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
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 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 45 Elm Street Winchester, CT MLS# 24131609
$540,000
7.1

Baths

7,405

Sq.Ft.

45 Elm Street

Winchester, CT

View 440 Platt Hill Road Winchester, CT MLS# 24132598
$500,000
4

Beds

2.1

Baths

3,416

Sq.Ft.

440 Platt Hill Road

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

View 55 Walnut Street Winchester, CT MLS# 24071862
$499,999
5,016

Sq.Ft.

55 Walnut Street

Winchester, CT

View 197 Spencer Hill Road Winchester, CT MLS# 24134519
$499,000
3

Beds

2.0

Baths

2,167

Sq.Ft.

197 Spencer Hill 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 187 Torringford Street Winchester, CT MLS# 24138466
$419,000
4

Beds

1.1

Baths

2,365

Sq.Ft.

187 Torringford Street

Winchester, CT

View 208 Spencer Hill Road Winchester, CT MLS# 24142296
$399,000
3

Beds

1.1

Baths

1,969

Sq.Ft.

208 Spencer Hill Road

Winchester, CT

View 720 Main Street Winchester, CT MLS# 24138050
$395,000
3

Beds

1.1

Baths

1,909

Sq.Ft.

720 Main Street

Winchester, CT

View 720 Main Street Winchester, CT MLS# 24138743
$395,000
1.1

Baths

1,909

Sq.Ft.

720 Main Street

Winchester, CT

View 7 Stadler Heights Winchester, CT MLS# 24122124
$389,000
Studio

Beds

0.0

Baths

7 Stadler Heights

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

Beds

0.0

Baths

3,660

Sq.Ft.

57 Main 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

64

Estimated median home price

$319,900
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 - 100K10
$100K - 200K8
$200K - 300K13
$300K - 400K12
$400K - 500K6
$500K - 600K1
$600K - 700K2
$700K - 800K5
$800K - 900K4
$900K - 1M1
$1M - Max2

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family24
Townhouse0
Condo3
Commercial11
Rental16
Lots and Land16
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms0

(Data as of 12/11/2025)

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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