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

Beds

2.0

Baths

1,898

Sq.Ft.

102 Wallens Street

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

Beds

1.1

Baths

1,600

Sq.Ft.

1 Hamill Drive

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

View 94 Holabird Avenue Winchester, CT MLS# 24158795
$249,900
3

Beds

1.0

Baths

1,422

Sq.Ft.

94 Holabird Avenue

Winchester, CT

View 107 Birdsall Street Winchester, CT MLS# 24150688
$240,000
4

Beds

2.0

Baths

1,874

Sq.Ft.

107 Birdsall Street

Winchester, CT

View 230 East Wakefield Boulevard Winchester, CT MLS# 24150574
$314,000
3

Beds

2.0

Baths

1,536

Sq.Ft.

230 East Wakefield Boulevard

Winchester, CT

View 35 Riveredge Drive 35 Winchester, CT MLS# 24147679
$159,500
2

Beds

1.1

Baths

992

Sq.Ft.

35 Riveredge Drive 35

Winchester, CT

View 140 Willow Street STE 6 Winchester, CT MLS# 24143845
$89,000
1,165

Sq.Ft.

140 Willow Street STE 6

Winchester, CT

View 118 Meadow Street Winchester, CT MLS# 24140514
$269,999
3

Beds

2.0

Baths

1,652

Sq.Ft.

118 Meadow 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

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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