Winchester Connecticut Homes for Rent

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View 23 Allen Street Winchester, CT MLS# 24218562
  • Recently Listed
1 of 19
$1,350
2

Beds

1.0

Baths

1,100

Sq.Ft.

23 Allen Street

Winchester, CT

View 20 Center Street 2 Winchester, CT MLS# 24217473
  • Recently Listed
1 of 16
$1,450
3

Beds

1.0

Baths

1,223

Sq.Ft.

20 Center Street 2

Winchester, CT

View 50 High Street Winchester, CT MLS# 24214145
  • Recently Listed
1 of 11
$1,800
3

Beds

1.0

Baths

1,424

Sq.Ft.

50 High Street

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 14-A Gay Street Winchester, CT MLS# 24216160
  • Recently Listed
1 of 9
$875
1

Beds

1.0

Baths

625

Sq.Ft.

14-A Gay Street

Winchester, CT

View 5 Chestnut Street Winchester, CT MLS# 24216215
  • Recently Listed
1 of 15
$1,700
3

Beds

1.0

Baths

2,300

Sq.Ft.

5 Chestnut Street

Winchester, CT

View 71 Wheeler Street 2nd Floor Winchester, CT MLS# 24215564
$1,400
2

Beds

1.0

Baths

920

Sq.Ft.

71 Wheeler Street 2nd Floor

Winchester, CT

View 130 Shore Drive Winchester, CT MLS# 24213925
$2,750
2

Beds

1.0

Baths

624

Sq.Ft.

130 Shore Drive

Winchester, CT

View 98 Spencer Street 3N Winchester, CT MLS# 24211813
$1,495
2

Beds

1.0

Baths

800

Sq.Ft.

98 Spencer Street 3N

Winchester, CT

View 425 Winchester Road 2 Winchester, CT MLS# 24211423
$1,350
2

Beds

1.0

Baths

721

Sq.Ft.

425 Winchester Road 2

Winchester, CT

View 840 Main Street 2 Winchester, CT MLS# 24209997
$1,500
3

Beds

1.0

Baths

922

Sq.Ft.

840 Main Street 2

Winchester, CT

View 220 Walnut Street Winchester, CT MLS# 24210041
$2,250
3

Beds

1.1

Baths

1,654

Sq.Ft.

220 Walnut Street

Winchester, CT

View 68 Wetmore Avenue 1 Winchester, CT MLS# 24206556
$2,000
3

Beds

1.1

Baths

1,258

Sq.Ft.

68 Wetmore Avenue 1

Winchester, CT

View 18 Pratt Street 2 Winchester, CT MLS# 24204173
$1,475
2

Beds

1.0

Baths

900

Sq.Ft.

18 Pratt Street 2

Winchester, CT

View 188 East Lake Street Winchester, CT MLS# 24202936
$2,500
2

Beds

1.0

Baths

1,040

Sq.Ft.

188 East Lake Street

Winchester, CT

View 59 Cook Street 7 Winchester, CT MLS# 24197809
$1,900
2

Beds

2.0

Baths

1,289

Sq.Ft.

59 Cook Street 7

Winchester, CT

View 57 Main Street Winchester, CT MLS# 24196835
$2,000

57 Main Street

Winchester, CT

View 936 Main Street LOT 12 Winchester, CT MLS# 24195927
$1,500
2

Beds

1.1

Baths

950

Sq.Ft.

936 Main Street LOT 12

Winchester, CT

View 936 Main Street LOT 14 Winchester, CT MLS# 24195926
$1,500
2

Beds

2.0

Baths

950

Sq.Ft.

936 Main Street LOT 14

Winchester, CT

View 144 Rowley Street Winchester, CT MLS# 24169925
$1,700
12,000

Sq.Ft.

144 Rowley Street

Winchester, CT

View 277 North Main Street Winchester, CT MLS# 24155599
$1,375
2,050

Sq.Ft.

277 North 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

66

Estimated median home price

$350,000
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 - 100K6
$100K - 200K4
$200K - 300K14
$300K - 400K16
$400K - 500K7
$500K - 600K5
$600K - 700K2
$700K - 800K2
$800K - 900K4
$900K - 1M3
$1M - Max3

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family34
Townhouse0
Condo3
Commercial7
Rental21
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms0

(Data as of 11/3/2026)

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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