View 212 Spencer Hill Road Winchester, CT MLS# 24180470
  • Recently Listed
1 of 39
$369,000
2

Beds

1.1

Baths

1,440

Sq.Ft.

212 Spencer Hill Road

Winchester, CT

View 107 Roberts Avenue Winchester, CT MLS# 24177410
  • Recently Listed
1 of 19
$349,000
3

Beds

1.1

Baths

1,888

Sq.Ft.

107 Roberts Avenue

Winchester, CT

View 188 Glendale Avenue Winchester, CT MLS# 24179585
  • Recently Listed
1 of 29
$325,000
3

Beds

1.1

Baths

1,118

Sq.Ft.

188 Glendale Avenue

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 68 Wetmore Avenue Winchester, CT MLS# 24177338
  • Recently Listed
1 of 28
$349,999
6

Beds

2.1

Baths

2,555

Sq.Ft.

68 Wetmore Avenue

Winchester, CT

View 147 E. Wakefield Boulevard Winchester, CT MLS# 24175908
$299,900
2

Beds

1.0

Baths

702

Sq.Ft.

147 E. Wakefield Boulevard

Winchester, CT

View 63 Meadow Street Winchester, CT MLS# 24175107
$345,000
5

Beds

3.0

Baths

2,602

Sq.Ft.

63 Meadow Street

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 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 1 Hamill Drive Winchester, CT MLS# 24164318
    $349,900
    3

    Beds

    1.1

    Baths

    1,600

    Sq.Ft.

    1 Hamill Drive

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

    Beds

    0.0

    Baths

    32 Norfolk Road

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

    Beds

    2.0

    Baths

    2,699

    Sq.Ft.

    77 Hubbard Street

    Winchester, CT

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

    Beds

    0.0

    Baths

    393 Winchester 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

    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 6/2/2026)

    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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