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

View 35 Riveredge Drive 35 Winchester, CT MLS# 24147679
$159,500
2

Beds

1.1

Baths

992

Sq.Ft.

35 Riveredge Drive 35

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
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 720 Main Street Winchester, CT MLS# 24138050
$395,000
3

Beds

1.1

Baths

1,909

Sq.Ft.

720 Main Street

Winchester, CT

View 720 Main Street Winchester, CT MLS# 24138743
$395,000
1.1

Baths

1,909

Sq.Ft.

720 Main 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 436 Main Street Winchester, CT MLS# 24135027
$750,000
5,389

Sq.Ft.

436 Main Street

Winchester, CT

View 436 Main Street Winchester, CT MLS# 24135030
$750,000
4

Beds

2.2

Baths

5,389

Sq.Ft.

436 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

View 57 Main Street Winchester, CT MLS# 24112807
$375,000
3

Beds

0.0

Baths

3,660

Sq.Ft.

57 Main Street

Winchester, CT

View 57 Main Street Winchester, CT MLS# 24112471
$375,000
1.0

Baths

3,660

Sq.Ft.

57 Main Street

Winchester, CT

View 1 Lake Street Winchester, CT MLS# 24104685
$280,000
4,852

Sq.Ft.

1 Lake Street

Winchester, CT

View 115 Old Robertsville Road Winchester, CT MLS# 24104099
$649,900
Studio

Beds

0.0

Baths

115 Old Robertsville Road

Winchester, CT

View 00 Chapel Road Winchester, CT MLS# 24097613
$300,000
Studio

Beds

0.0

Baths

00 Chapel Road

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

50

Estimated median home price

$375,000
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 - 200K3
$200K - 300K9
$300K - 400K12
$400K - 500K5
$500K - 600K2
$600K - 700K2
$700K - 800K5
$800K - 900K3
$900K - 1M0
$1M - Max3

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family19
Townhouse0
Condo2
Commercial10
Rental20
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 4/16/2026)

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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