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 45 Willow Street Winchester, CT MLS# 24165997
  • Recently Listed
1 of 3
$595,000
9,438

Sq.Ft.

45 Willow Street

Winchester, CT

View 111 Riverton Road 28 Winchester, CT MLS# 24165512
  • Recently Listed
1 of 22
OPEN HOUSE: Sunday 4/12 12:00 PM - 2:00 PM
$184,900
2

Beds

1.1

Baths

1,204

Sq.Ft.

111 Riverton Road 28

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 123 Old North Road Winchester, CT MLS# 24164624
  • Recently Listed
1 of 28
$425,000
3

Beds

2.0

Baths

1,781

Sq.Ft.

123 Old North Road

Winchester, CT

View 1 Hamill Drive Winchester, CT MLS# 24164318
  • Recently Listed
1 of 29
$359,900
3

Beds

1.1

Baths

1,600

Sq.Ft.

1 Hamill Drive

Winchester, CT

View 121 West Wakefield Boulevard Winchester, CT MLS# 24159801
$769,000
4

Beds

3.1

Baths

2,265

Sq.Ft.

121 West Wakefield Boulevard

Winchester, CT

View 90 Colony Drive Winchester, CT MLS# 24164163
  • Recently Listed
1 of 22
$349,900
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 156 Shore Drive Winchester, CT MLS# 24160676
  • Recently Listed
1 of 37
$779,900
5

Beds

1.1

Baths

1,258

Sq.Ft.

156 Shore Drive

Winchester, CT

View 431 West Wakefield Boulevard Winchester, CT MLS# 24159989
$1,850,000
9

Beds

5.1

Baths

7,000

Sq.Ft.

431 West Wakefield Boulevard

Winchester, CT

View 144 Rowley Street Winchester, CT MLS# 24154804
$1,900,000
1.1

Baths

12,000

Sq.Ft.

144 Rowley Street

Winchester, CT

View 5 Stadler Heights Winchester, CT MLS# 24159478
$499,000
4

Beds

2.1

Baths

3,556

Sq.Ft.

5 Stadler Heights

Winchester, CT

View 35 Glendale Avenue Winchester, CT MLS# 24157783
$399,000
3

Beds

2.0

Baths

2,196

Sq.Ft.

35 Glendale Avenue

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 257-259 Torringford Street Winchester, CT MLS# 24157681
$859,000
Studio

Beds

0.0

Baths

257-259 Torringford Street

Winchester, CT

View 351 Platt Hill Road Winchester, CT MLS# 24154916
$370,000
3

Beds

2.0

Baths

1,715

Sq.Ft.

351 Platt Hill Road

Winchester, CT

View 174 Wallens Street APT A5 Winchester, CT MLS# 24153820
$289,000
2

Beds

2.1

Baths

1,946

Sq.Ft.

174 Wallens Street APT A5

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

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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