View 188 Glendale Avenue Winchester, CT MLS# 24179585
$325,000
3

Beds

1.1

Baths

1,118

Sq.Ft.

188 Glendale Avenue

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

The time to sell is now! THE TIME TO SELL IS NOW!
View 393 Winchester Road Winchester, CT MLS# 170078080
$295,000
Studio

Beds

0.0

Baths

393 Winchester Road

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 147 E. Wakefield Boulevard Winchester, CT MLS# 24175908
$279,900
2

Beds

1.0

Baths

702

Sq.Ft.

147 E. Wakefield Boulevard

Winchester, CT

View 104 Maloney Court Winchester, CT MLS# 24172219
    1 of 30
    OPEN HOUSE: Sunday 6/14 1:00 PM - 3:00 PM
    $279,000
    3

    Beds

    1.0

    Baths

    1,008

    Sq.Ft.

    104 Maloney Court

    Winchester, CT

    View 149 East Mountain Avenue Winchester, CT MLS# 24170791
    $274,900
    2

    Beds

    1.0

    Baths

    993

    Sq.Ft.

    149 East Mountain Avenue

    Winchester, CT

    View 69 Prospect Street Winchester, CT MLS# 24173658
    $274,900
    7

    Beds

    3.0

    Baths

    2,204

    Sq.Ft.

    69 Prospect Street

    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 436 Main Street Winchester, CT MLS# 24170540
    $250,000
    2,177

    Sq.Ft.

    436 Main Street

    Winchester, CT

    View 321 Colebrook Road Winchester, CT MLS# 24178092
    • Recently Listed
    1 of 39
    $250,000
    Studio

    Beds

    0.0

    Baths

    321 Colebrook Road

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

    Beds

    3.0

    Baths

    2,400

    Sq.Ft.

    Address not provided

    Winchester, CT

    View 30 Upland Road Winchester, CT MLS# 24176921
    $220,000
    4

    Beds

    2.0

    Baths

    1,844

    Sq.Ft.

    30 Upland Road

    Winchester, CT

    View 00 Chapel Road Winchester, CT MLS# 24171867
    $200,000
    Studio

    Beds

    0.0

    Baths

    00 Chapel Road

    Winchester, CT

    View 111 Torringford Street 33 Winchester, CT MLS# 24174220
    $189,900
    2

    Beds

    2.0

    Baths

    1,102

    Sq.Ft.

    111 Torringford Street 33

    Winchester, CT

    View 111 Torringford Street 7 Winchester, CT MLS# 24173166
    $179,900
    2

    Beds

    2.0

    Baths

    1,156

    Sq.Ft.

    111 Torringford Street 7

    Winchester, CT

    View 624 Wynne Road Winchester, CT MLS# 24174996
    $174,900
    2

    Beds

    1.0

    Baths

    672

    Sq.Ft.

    624 Wynne Road

    Winchester, CT

    View 624 Wynne Road Winchester, CT MLS# 24175027
    $174,900
    Studio

    Beds

    0.0

    Baths

    624 Wynne 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

    75

    Estimated median home price

    $349,900
    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 - 200K6
    $200K - 300K14
    $300K - 400K15
    $400K - 500K8
    $500K - 600K5
    $600K - 700K2
    $700K - 800K5
    $800K - 900K3
    $900K - 1M2
    $1M - Max4

    Homes for Sale by Type in Winchester, CT

    Property TypeCount
    Single Family33
    Townhouse0
    Condo2
    Commercial8
    Rental16
    Lots and Land21
    Condo/Town/CoOp0
    CoOp0
    Multi Family11
    Mobile Home0
    Farms0

    (Data as of 6/12/2026)

    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.

    Information on this this page is provided by the Smart Multiple Listing Service, Inc. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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