View 880 West Wakefield Boulevard Winchester, CT MLS# 24136631
$5,000
3

Beds

2.0

Baths

1,356

Sq.Ft.

880 West Wakefield Boulevard

Winchester, CT

View 91 Williams Avenue Winchester, CT MLS# 24160451
$2,450
3

Beds

2.0

Baths

1,600

Sq.Ft.

91 Williams Avenue

Winchester, CT

View 34 Rock Street Winchester, CT MLS# 24166316
$2,150
3

Beds

1.0

Baths

1,042

Sq.Ft.

34 Rock 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 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
$1,500
2,050

Sq.Ft.

277 North Main Street

Winchester, CT

View 936 Main Street 14 Winchester, CT MLS# 24176854
  • Recently Listed
1 of 9
$1,500
2

Beds

2.0

Baths

1,000

Sq.Ft.

936 Main Street 14

Winchester, CT

View 88 Spencer Street 2 Winchester, CT MLS# 24181102
$1,495
2

Beds

1.0

Baths

800

Sq.Ft.

88 Spencer Street 2

Winchester, CT

View 20-22 Allen Street 2nd flr rs Winchester, CT MLS# 24167330
$1,365
1

Beds

1.0

Baths

800

Sq.Ft.

20-22 Allen Street 2nd flr rs

Winchester, CT

View 267 Rockwell Street 1st fl Winchester, CT MLS# 24167283
$1,300
1

Beds

1.0

Baths

600

Sq.Ft.

267 Rockwell Street 1st fl

Winchester, CT

View 440 Main Street B Winchester, CT MLS# 24166050
$1,000
2

Beds

1.0

Baths

4,668

Sq.Ft.

440 Main Street B

Winchester, CT

View 277 N. Main Street #3 Winchester, CT MLS# 24167896
$900
1

Beds

1.0

Baths

650

Sq.Ft.

277 N. Main Street #3

Winchester, CT

View 40A High Street Winchester, CT MLS# 24160366
$850
1

Beds

1.0

Baths

450

Sq.Ft.

40A High Street

Winchester, CT

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

Sq.Ft.

452 Main Street

Winchester, CT

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

Sq.Ft.

Main Street #

Winchester, CT

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

Sq.Ft.

32 Lake 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

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
Rental17
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms0

(Data as of 6/7/2026)

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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