View Address not provided Winchester, CT MLS# 24169258
$239,000
7

Beds

3.0

Baths

2,400

Sq.Ft.

Address not provided

Winchester, CT

View 350 Walnut Street Winchester, CT MLS# 24170101
$285,000
2

Beds

1.0

Baths

720

Sq.Ft.

350 Walnut Street

Winchester, CT

View 150 Oak Street Winchester, CT MLS# 24166332
$579,000
11

Beds

5.1

Baths

5,233

Sq.Ft.

150 Oak Street

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 51 Hinsdale Avenue Winchester, CT MLS# 24168665
$475,000
7

Beds

5.0

Baths

3,538

Sq.Ft.

51 Hinsdale Avenue

Winchester, CT

View 45 Willow Street Winchester, CT MLS# 24165997
$595,000
9,438

Sq.Ft.

45 Willow Street

Winchester, CT

View 121 West Wakefield Boulevard Winchester, CT MLS# 24159801
$749,000
4

Beds

3.1

Baths

2,265

Sq.Ft.

121 West Wakefield Boulevard

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 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 257-259 Torringford Street Winchester, CT MLS# 24157681
$799,000
Studio

Beds

0.0

Baths

257-259 Torringford Street

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 140 Willow Street STE 6 Winchester, CT MLS# 24143845
$89,000
1,165

Sq.Ft.

140 Willow Street STE 6

Winchester, CT

View 118 Meadow Street Winchester, CT MLS# 24140514
$269,999
3

Beds

2.0

Baths

1,652

Sq.Ft.

118 Meadow Street

Winchester, CT

View 605 East Wakefield Boulevard Winchester, CT MLS# 24139172
$12,500
Studio

Beds

0.0

Baths

605 East Wakefield Boulevard

Winchester, CT

View 354 Main Street Winchester, CT MLS# 24137086
$899,000
3.0

Baths

11,972

Sq.Ft.

354 Main Street

Winchester, CT

View 45 Elm Street Winchester, CT MLS# 24131609
$540,000
7.1

Baths

7,405

Sq.Ft.

45 Elm Street

Winchester, CT

View 32 Norfolk Road Winchester, CT MLS# 24130958
$299,900
Studio

Beds

0.0

Baths

32 Norfolk Road

Winchester, CT

View 000000 Norfolk Road Winchester, CT MLS# 24131284
$879,990
Studio

Beds

0.0

Baths

000000 Norfolk Road

Winchester, CT

View 7 Stadler Heights Winchester, CT MLS# 24122124
$389,000
Studio

Beds

0.0

Baths

7 Stadler Heights

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

71

Estimated median home price

$349,999
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 - 200K5
$200K - 300K14
$300K - 400K13
$400K - 500K8
$500K - 600K5
$600K - 700K1
$700K - 800K5
$800K - 900K3
$900K - 1M2
$1M - Max4

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family30
Townhouse0
Condo1
Commercial8
Rental16
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms0

(Data as of 6/17/2026)

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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