View 140 Willow Street STE 6 Winchester, CT MLS# 24143845
$99,000
1,165

Sq.Ft.

140 Willow Street STE 6

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 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

The time to sell is now! THE TIME TO SELL IS NOW!
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 8 Oak Street Winchester, CT MLS# 24140653
  • Recently Listed
1 of 11
$179,900
2

Beds

1.1

Baths

832

Sq.Ft.

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

    Beds

    3.0

    Baths

    1,874

    Sq.Ft.

    106 Rockwell Street

    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 605 East Wakefield Boulevard Winchester, CT MLS# 24139172
    $12,500
    Studio

    Beds

    0.0

    Baths

    605 East Wakefield Boulevard

    Winchester, CT

    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 32 Charles Street Winchester, CT MLS# 24136816
    $229,900
    3

    Beds

    1.0

    Baths

    1,044

    Sq.Ft.

    32 Charles Street

    Winchester, CT

    View 156 Lincoln Avenue Winchester, CT MLS# 24135385
    $299,900
    2

    Beds

    1.0

    Baths

    702

    Sq.Ft.

    156 Lincoln Avenue

    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 52 White Street Winchester, CT MLS# 24132699
    $29,000
    Studio

    Beds

    0.0

    Baths

    52 White Street

    Winchester, CT

    View 25 Center Street Winchester, CT MLS# 24131211
    $319,900
    2.1

    Baths

    2,754

    Sq.Ft.

    25 Center Street

    Winchester, CT

    View 25 Center Street Winchester, CT MLS# 24131214
    $319,900
    3

    Beds

    2.1

    Baths

    2,754

    Sq.Ft.

    25 Center Street

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

      Beds

      0.0

      Baths

      32 Norfolk Road

      Winchester, CT

      View 111 Riverton Road Apt 61 Winchester, CT MLS# 24130574
      $194,900
      2

      Beds

      1.1

      Baths

      1,204

      Sq.Ft.

      111 Riverton Road Apt 61

      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

      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

      67

      Estimated median home price

      $300,000
      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 - 200K9
      $200K - 300K15
      $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 Family26
      Townhouse0
      Condo4
      Commercial11
      Rental16
      Lots and Land16
      Condo/Town/CoOp0
      CoOp0
      Multi Family10
      Mobile Home0
      Farms0

      (Data as of 12/9/2025)

      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.

      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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