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

The time to sell is now! THE TIME TO SELL IS NOW!
View 49 Walnut Street Winchester, CT MLS# 24137315
$299,900
5

Beds

2.0

Baths

2,344

Sq.Ft.

49 Walnut Street

Winchester, CT

View 106 Rockwell Street Winchester, CT MLS# 24139930
$299,900
4

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 1 Lake Street Winchester, CT MLS# 24104685
$290,000
4,852

Sq.Ft.

1 Lake Street

Winchester, CT

View 118 Meadow Street Winchester, CT MLS# 24140514
    1 of 16
    OPEN HOUSE: Saturday 12/13 12:00 PM - 2:00 PM
    $290,000
    3

    Beds

    2.0

    Baths

    1,652

    Sq.Ft.

    118 Meadow Street

    Winchester, CT

    View 73 Norfolk Road Winchester, CT MLS# 24133158
    $279,999
    3

    Beds

    2.1

    Baths

    1,542

    Sq.Ft.

    73 Norfolk Road

    Winchester, CT

    View 38 Upland Road Winchester, CT MLS# 24131432
      1 of 17
      OPEN HOUSE: Saturday 12/13 1:00 PM - 3:00 PM
      $269,000
      3

      Beds

      1.1

      Baths

      1,736

      Sq.Ft.

      38 Upland Road

      Winchester, CT

      View 10 Crescent Street Winchester, CT MLS# 24139201
      $259,000
      4

      Beds

      2.0

      Baths

      2,444

      Sq.Ft.

      10 Crescent Street

      Winchester, CT

      View 9 John Street Winchester, CT MLS# 24141326
      • Recently Listed
      1 of 23
      $230,000
      2

      Beds

      1.1

      Baths

      1,172

      Sq.Ft.

      9 John Street

      Winchester, CT

      View 817 East Wakefield Boulevard Winchester, CT MLS# 24143747
      $225,000
      2

      Beds

      1.0

      Baths

      1,051

      Sq.Ft.

      817 East Wakefield Boulevard

      Winchester, CT

      View 115 Willow Street Winchester, CT MLS# 24070789
      $200,000
      1.1

      Baths

      780

      Sq.Ft.

      115 Willow Street

      Winchester, CT

      View 14 Curtice Street Winchester, CT MLS# 24120651
      $189,900
      3

      Beds

      1.0

      Baths

      1,248

      Sq.Ft.

      14 Curtice Street

      Winchester, CT

      View 99 Norfolk Road Winchester, CT MLS# 24107073
      $184,900
      3

      Beds

      1.0

      Baths

      980

      Sq.Ft.

      99 Norfolk Road

      Winchester, CT

      View 111 Riverton Road APT 90 Winchester, CT MLS# 24129959
      $179,900
      2

      Beds

      1.1

      Baths

      1,204

      Sq.Ft.

      111 Riverton Road APT 90

      Winchester, CT

      View 8 Oak Street Winchester, CT MLS# 24140653
        1 of 11
        OPEN HOUSE: Sunday 12/14 12:00 PM - 2:00 PM
        $179,900
        2

        Beds

        1.1

        Baths

        832

        Sq.Ft.

        8 Oak Street

        Winchester, CT

        View 45 Riveredge Drive 45 Winchester, CT MLS# 24140645
        $175,000
        2

        Beds

        1.1

        Baths

        992

        Sq.Ft.

        45 Riveredge Drive 45

        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

        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

        64

        Estimated median home price

        $319,900
        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 - 100K10
        $100K - 200K8
        $200K - 300K13
        $300K - 400K12
        $400K - 500K6
        $500K - 600K1
        $600K - 700K2
        $700K - 800K5
        $800K - 900K4
        $900K - 1M1
        $1M - Max2

        Homes for Sale by Type in Winchester, CT

        Property TypeCount
        Single Family24
        Townhouse0
        Condo3
        Commercial11
        Rental16
        Lots and Land16
        Condo/Town/CoOp0
        CoOp0
        Multi Family10
        Mobile Home0
        Farms0

        (Data as of 12/11/2025)

        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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