View 174 Main Street 1 Winchester, CT MLS# 24166022
$1,495
3

Beds

1.0

Baths

1,000

Sq.Ft.

174 Main Street 1

Winchester, CT

View 5 Brookside Avenue Winchester, CT MLS# 24163534
  • Recently Listed
1 of 7
$1,350
2

Beds

1.0

Baths

1,250

Sq.Ft.

5 Brookside Avenue

Winchester, CT

View 34 Rock Street Winchester, CT MLS# 24166316
  • Recently Listed
1 of 21
$2,200
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 440 Main Street B Winchester, CT MLS# 24166050
  • Recently Listed
1 of 5
$1,200
2

Beds

1.0

Baths

4,668

Sq.Ft.

440 Main Street B

Winchester, CT

View 43 Wallens Street 1 Winchester, CT MLS# 24165404
  • Recently Listed
1 of 13
$1,300
1

Beds

1.0

Baths

595

Sq.Ft.

43 Wallens Street 1

Winchester, CT

View 40A High Street Winchester, CT MLS# 24160366
  • Recently Listed
1 of 11
$850
1

Beds

1.0

Baths

450

Sq.Ft.

40A High Street

Winchester, CT

View 102 Elm Street Winchester, CT MLS# 24164141
  • Recently Listed
1 of 21
$1,550
3

Beds

1.1

Baths

1,178

Sq.Ft.

102 Elm Street

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 112 Rockwell Street 1 Winchester, CT MLS# 24159483
$1,395
2

Beds

1.0

Baths

704

Sq.Ft.

112 Rockwell Street 1

Winchester, CT

View 188 East Lake Street Winchester, CT MLS# 24159128
$2,500
2

Beds

1.0

Baths

1,100

Sq.Ft.

188 East Lake Street

Winchester, CT

View 112 Rockwell Street LL Winchester, CT MLS# 24158088
$1,150
1

Beds

1.0

Baths

1,400

Sq.Ft.

112 Rockwell Street LL

Winchester, CT

View 101 Norfolk Road Winchester, CT MLS# 24158090
$2,375
3

Beds

1.0

Baths

1,860

Sq.Ft.

101 Norfolk Road

Winchester, CT

View 277 North Main Street Winchester, CT MLS# 24155599
$1,500
2,050

Sq.Ft.

277 North Main Street

Winchester, CT

View 131-133 Willow Street Winchester, CT MLS# 24151297
$1,695
3

Beds

1.0

Baths

1,080

Sq.Ft.

131-133 Willow Street

Winchester, CT

View 180 Holabird Avenue Winchester, CT MLS# 24148456
$1,700
2,200

Sq.Ft.

180 Holabird Avenue

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 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

48

Estimated median home price

$372,500
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 - 200K3
$200K - 300K9
$300K - 400K13
$400K - 500K4
$500K - 600K2
$600K - 700K1
$700K - 800K5
$800K - 900K3
$900K - 1M0
$1M - Max2

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family16
Townhouse0
Condo3
Commercial10
Rental20
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 4/11/2026)

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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