View 624 Wynne Road Winchester, CT MLS# 24175027
$174,900
Studio

Beds

0.0

Baths

624 Wynne Road

Winchester, CT

View 69 Prospect Street Winchester, CT MLS# 24173658
$274,900
7

Beds

3.0

Baths

2,204

Sq.Ft.

69 Prospect Street

Winchester, CT

View 34 Hannifin Road Winchester, CT MLS# 24171237
$85,000
3

Beds

1.0

Baths

1,435

Sq.Ft.

34 Hannifin Road

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 111 Torringford Street 33 Winchester, CT MLS# 24174220
$189,900
2

Beds

2.0

Baths

1,102

Sq.Ft.

111 Torringford Street 33

Winchester, CT

View 104 Maloney Court Winchester, CT MLS# 24172219
$279,000
3

Beds

1.0

Baths

1,008

Sq.Ft.

104 Maloney Court

Winchester, CT

View 111 Torringford Street 7 Winchester, CT MLS# 24173166
$179,900
2

Beds

2.0

Baths

1,156

Sq.Ft.

111 Torringford Street 7

Winchester, CT

View 00 Chapel Road Winchester, CT MLS# 24171867
$200,000
Studio

Beds

0.0

Baths

00 Chapel Road

Winchester, CT

View 217 Walnut Street Winchester, CT MLS# 24168016
$399,000
5

Beds

2.2

Baths

2,779

Sq.Ft.

217 Walnut Street

Winchester, CT

View 149 East Mountain Avenue Winchester, CT MLS# 24170791
$274,900
2

Beds

1.0

Baths

993

Sq.Ft.

149 East Mountain Avenue

Winchester, CT

View 436 Main Street Winchester, CT MLS# 24170540
$250,000
2,177

Sq.Ft.

436 Main Street

Winchester, CT

View Address not provided Winchester, CT MLS# 24169258
$239,000
7

Beds

3.0

Baths

2,400

Sq.Ft.

Address not provided

Winchester, CT

View 350 Walnut Street Winchester, CT MLS# 24170101
$285,000
2

Beds

1.0

Baths

720

Sq.Ft.

350 Walnut Street

Winchester, CT

View 150 Oak Street Winchester, CT MLS# 24166332
$579,000
11

Beds

5.1

Baths

5,233

Sq.Ft.

150 Oak Street

Winchester, CT

View 51 Hinsdale Avenue Winchester, CT MLS# 24168665
$475,000
7

Beds

5.0

Baths

3,538

Sq.Ft.

51 Hinsdale Avenue

Winchester, CT

View 102 Wallens Street Winchester, CT MLS# 24168531
$349,900
3

Beds

2.0

Baths

1,898

Sq.Ft.

102 Wallens Street

Winchester, CT

View 162 Spencer Hill Road Winchester, CT MLS# 24167312
$625,000
3

Beds

2.1

Baths

2,144

Sq.Ft.

162 Spencer Hill Road

Winchester, CT

View 45 Willow Street Winchester, CT MLS# 24165997
$595,000
9,438

Sq.Ft.

45 Willow Street

Winchester, CT

View 90 Colony Drive Winchester, CT MLS# 24164163
$335,000
3

Beds

1.0

Baths

1,282

Sq.Ft.

90 Colony Drive

Winchester, CT

View 621 Wynne Road Winchester, CT MLS# 24161635
$339,900
2

Beds

1.0

Baths

975

Sq.Ft.

621 Wynne Road

Winchester, CT

View 5 Stadler Heights Winchester, CT MLS# 24159478
$499,000
4

Beds

2.1

Baths

3,556

Sq.Ft.

5 Stadler Heights

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

$349,900
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 - 200K7
$200K - 300K13
$300K - 400K13
$400K - 500K8
$500K - 600K5
$600K - 700K2
$700K - 800K5
$800K - 900K3
$900K - 1M2
$1M - Max5

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family34
Townhouse0
Condo3
Commercial8
Rental16
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms0

(Data as of 6/8/2026)

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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