View 217 Walnut Street Winchester, CT MLS# 24168016
  • Recently Listed
1 of 34
$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
  • Recently Listed
1 of 9
$250,000
2,177

Sq.Ft.

436 Main Street

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View Address not provided Winchester, CT MLS# 24169258
  • Recently Listed
1 of 26
$239,000
7

Beds

3.0

Baths

2,400

Sq.Ft.

Address not provided

Winchester, CT

View 350 Walnut Street Winchester, CT MLS# 24170101
  • Recently Listed
1 of 34
$279,999
2

Beds

1.0

Baths

720

Sq.Ft.

350 Walnut Street

Winchester, CT

View 9 Colony Drive Winchester, CT MLS# 24168127
$329,900
3

Beds

2.0

Baths

1,582

Sq.Ft.

9 Colony Drive

Winchester, CT

View 150 Oak Street Winchester, CT MLS# 24166332
  • Recently Listed
1 of 8
$579,000
11

Beds

5.1

Baths

5,233

Sq.Ft.

150 Oak Street

Winchester, CT

View 51 Hinsdale Avenue Winchester, CT MLS# 24168665
  • Recently Listed
1 of 40
OPEN HOUSE: Sunday 5/3 11:00 AM - 3:00 PM
$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 57 Bridge Street Winchester, CT MLS# 24167580
$275,000
4

Beds

1.1

Baths

1,416

Sq.Ft.

57 Bridge Street

Winchester, CT

View 26 Elm Street Winchester, CT MLS# 24164370
$398,000
5

Beds

3.0

Baths

2,496

Sq.Ft.

26 Elm Street

Winchester, CT

View 45 Willow Street Winchester, CT MLS# 24165997
  • Recently Listed
1 of 3
$595,000
9,438

Sq.Ft.

45 Willow Street

Winchester, CT

View 111 Riverton Road 28 Winchester, CT MLS# 24165512
$184,900
2

Beds

1.1

Baths

1,204

Sq.Ft.

111 Riverton Road 28

Winchester, CT

View 123 Old North Road Winchester, CT MLS# 24164624
$425,000
3

Beds

2.0

Baths

1,781

Sq.Ft.

123 Old North Road

Winchester, CT

View 1 Hamill Drive Winchester, CT MLS# 24164318
$349,900
3

Beds

1.1

Baths

1,600

Sq.Ft.

1 Hamill Drive

Winchester, CT

View 121 West Wakefield Boulevard Winchester, CT MLS# 24159801
$749,000
4

Beds

3.1

Baths

2,265

Sq.Ft.

121 West Wakefield Boulevard

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 262 Holabird Avenue Winchester, CT MLS# 24162992
$360,000
3

Beds

1.1

Baths

1,312

Sq.Ft.

262 Holabird Avenue

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

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

54

Estimated median home price

$354,950
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 - 100K5
$100K - 200K3
$200K - 300K13
$300K - 400K14
$400K - 500K5
$500K - 600K3
$600K - 700K2
$700K - 800K3
$800K - 900K3
$900K - 1M0
$1M - Max3

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family22
Townhouse0
Condo2
Commercial10
Rental22
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 4/30/2026)

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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