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 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

    The time to sell is now! THE TIME TO SELL IS NOW!
    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 102 Wallens Street Winchester, CT MLS# 24168531
    $349,900
    3

    Beds

    2.0

    Baths

    1,898

    Sq.Ft.

    102 Wallens Street

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

    Beds

    0.0

    Baths

    32 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 124 Rockwell Street Winchester, CT MLS# 24073710
    $24,900
    Studio

    Beds

    0.0

    Baths

    124 Rockwell Street

    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

    74

    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 - 200K7
    $200K - 300K14
    $300K - 400K13
    $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
    Condo3
    Commercial8
    Rental16
    Lots and Land20
    Condo/Town/CoOp0
    CoOp0
    Multi Family10
    Mobile Home0
    Farms0

    (Data as of 6/10/2026)

    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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