View 25 Center Street Winchester, CT MLS# 24131211
$319,900
2.1

Baths

2,754

Sq.Ft.

25 Center Street

Winchester, CT

View 25 Center Street Winchester, CT MLS# 24131214
$319,900
3

Beds

2.1

Baths

2,754

Sq.Ft.

25 Center 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

The time to sell is now! THE TIME TO SELL IS NOW!
View 00 Chapel Road Winchester, CT MLS# 24097613
$300,000
Studio

Beds

0.0

Baths

00 Chapel Road

Winchester, CT

View 77 Hubbard Street Winchester, CT MLS# 24059312
$299,900
6

Beds

2.0

Baths

2,699

Sq.Ft.

77 Hubbard Street

Winchester, CT

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

Beds

0.0

Baths

32 Norfolk Road

Winchester, CT

View 106 Rockwell Street Winchester, CT MLS# 24139930
$299,900
6

Beds

3.0

Baths

1,874

Sq.Ft.

106 Rockwell Street

Winchester, CT

View 393 Winchester Road Winchester, CT MLS# 170078080
$295,000
Studio

Beds

0.0

Baths

393 Winchester 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 95 Colony Drive Winchester, CT MLS# 24150993
$285,000
3

Beds

1.1

Baths

1,008

Sq.Ft.

95 Colony Drive

Winchester, CT

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

Sq.Ft.

1 Lake Street

Winchester, CT

View 44 Lewis Street Winchester, CT MLS# 24155057
$279,900
3

Beds

2.0

Baths

1,604

Sq.Ft.

44 Lewis Street

Winchester, CT

View 9 Central Avenue Winchester, CT MLS# 24153231
$274,900
3

Beds

1.1

Baths

1,267

Sq.Ft.

9 Central Avenue

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 94 Holabird Avenue Winchester, CT MLS# 24158795
$249,900
3

Beds

1.0

Baths

1,422

Sq.Ft.

94 Holabird Avenue

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 9 John Street Winchester, CT MLS# 24154885
$230,000
2

Beds

1.1

Baths

1,172

Sq.Ft.

9 John Street

Winchester, CT

View 35 Riveredge Drive 35 Winchester, CT MLS# 24147679
$164,000
2

Beds

1.1

Baths

992

Sq.Ft.

35 Riveredge Drive 35

Winchester, CT

View 843-845 (lots - 10A,10 &1 East wakefield Boulevard Winchester, CT MLS# 24003236
$158,000
Studio

Beds

0.0

Baths

843-845 (lots - 10A,10 &1 East wakefield Boulevard

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

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

47

Estimated median home price

$300,000
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 - 100K8
$100K - 200K2
$200K - 300K14
$300K - 400K11
$400K - 500K2
$500K - 600K1
$600K - 700K1
$700K - 800K4
$800K - 900K3
$900K - 1M1
$1M - Max0

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family13
Townhouse0
Condo2
Commercial9
Rental17
Lots and Land16
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 3/15/2026)

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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