Winchester Connecticut Homes for Rent

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View 131 Willow Street Winchester, CT MLS# 24151297
  • Recently Listed
1 of 4
$1,695
3

Beds

1.0

Baths

1,080

Sq.Ft.

131 Willow Street

Winchester, CT

View 55 Wetmore Avenue Winchester, CT MLS# 24149606
  • Recently Listed
1 of 12
$825
1

Beds

1.0

Baths

650

Sq.Ft.

55 Wetmore Avenue

Winchester, CT

View 139 North Main Street Winchester, CT MLS# 24148694
$1,695
3

Beds

1.0

Baths

1,059

Sq.Ft.

139 North Main Street

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 180 Holabird Avenue Winchester, CT MLS# 24148456
$1,700
2,200

Sq.Ft.

180 Holabird Avenue

Winchester, CT

View 115 Main Street Winchester, CT MLS# 24144617
$4,000
2,400

Sq.Ft.

115 Main Street

Winchester, CT

View 135 Elm Street 1 Winchester, CT MLS# 24142806
$1,700
2

Beds

1.0

Baths

3,303

Sq.Ft.

135 Elm Street 1

Winchester, CT

View 31 Benton Street Winchester, CT MLS# 24141638
$1,600
2

Beds

2.0

Baths

1,890

Sq.Ft.

31 Benton Street

Winchester, CT

View 22 Upson Avenue Winchester, CT MLS# 24139617
$1,500
2

Beds

1.0

Baths

1,199

Sq.Ft.

22 Upson Avenue

Winchester, CT

View 880 West Wakefield Boulevard Winchester, CT MLS# 24136631
$4,000
3

Beds

2.0

Baths

1,356

Sq.Ft.

880 West Wakefield Boulevard

Winchester, CT

View 452 Main Street Winchester, CT MLS# 24108119
$750
1,300

Sq.Ft.

452 Main Street

Winchester, CT

View 32 Lake Street Winchester, CT MLS# 24106629
$14
4,800

Sq.Ft.

32 Lake Street

Winchester, CT

View 19 Rowley Street Winchester, CT MLS# 24106674
$10
2,400

Sq.Ft.

19 Rowley Street

Winchester, CT

View Main Street # Winchester, CT MLS# 24111564
$750
317

Sq.Ft.

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

59

Estimated median home price

$315,000
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 - 200K5
$200K - 300K14
$300K - 400K13
$400K - 500K5
$500K - 600K1
$600K - 700K2
$700K - 800K5
$800K - 900K2
$900K - 1M1
$1M - Max1

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family23
Townhouse0
Condo2
Commercial10
Rental13
Lots and Land16
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms0

(Data as of 1/30/2026)

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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