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

Beds

0.0

Baths

624 Wynne Road

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 34 Hannifin Road Winchester, CT MLS# 24171237
$85,000
3

Beds

1.0

Baths

1,435

Sq.Ft.

34 Hannifin Road

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
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 104 Maloney Court Winchester, CT MLS# 24172219
    1 of 30
    OPEN HOUSE: Sunday 6/7 1:00 PM - 3:00 PM
    $284,000
    3

    Beds

    1.0

    Baths

    1,008

    Sq.Ft.

    104 Maloney Court

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

    Beds

    0.0

    Baths

    00 Chapel Road

    Winchester, CT

    View 217 Walnut Street Winchester, CT MLS# 24168016
    $399,000
    5

    Beds

    2.2

    Baths

    2,779

    Sq.Ft.

    217 Walnut Street

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

    Sq.Ft.

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

    Beds

    1.0

    Baths

    720

    Sq.Ft.

    350 Walnut Street

    Winchester, CT

    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 102 Wallens Street Winchester, CT MLS# 24168531
    $349,900
    3

    Beds

    2.0

    Baths

    1,898

    Sq.Ft.

    102 Wallens Street

    Winchester, CT

    View 111 Riverton Road 28 Winchester, CT MLS# 24165512
    $184,900
    2

    Beds

    1.1

    Baths

    1,204

    Sq.Ft.

    111 Riverton Road 28

    Winchester, CT

    View 90 Colony Drive Winchester, CT MLS# 24164163
    $335,000
    3

    Beds

    1.0

    Baths

    1,282

    Sq.Ft.

    90 Colony Drive

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

    Beds

    2.1

    Baths

    3,556

    Sq.Ft.

    5 Stadler Heights

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

    Beds

    1.1

    Baths

    992

    Sq.Ft.

    35 Riveredge Drive 35

    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

    76

    Estimated median home price

    $349,450
    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 - 200K8
    $200K - 300K14
    $300K - 400K12
    $400K - 500K8
    $500K - 600K5
    $600K - 700K2
    $700K - 800K6
    $800K - 900K3
    $900K - 1M2
    $1M - Max5

    Homes for Sale by Type in Winchester, CT

    Property TypeCount
    Single Family34
    Townhouse0
    Condo4
    Commercial9
    Rental16
    Lots and Land19
    Condo/Town/CoOp0
    CoOp0
    Multi Family10
    Mobile Home0
    Farms0

    (Data as of 6/4/2026)

    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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