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 32 Hubbard Street Winchester, CT MLS# 24179637
$45,000
Studio

Beds

0.0

Baths

32 Hubbard Street

Winchester, CT

View 132 Florence Street Winchester, CT MLS# 24179755
$45,000
Studio

Beds

0.0

Baths

132 Florence Street

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 17 Birdsall Street Winchester, CT MLS# 24179758
  • Recently Listed
1 of 2
$29,900
Studio

Beds

0.0

Baths

17 Birdsall Street

Winchester, CT

View 82-84 Rockwell Street Winchester, CT MLS# 24179760
$29,000
Studio

Beds

0.0

Baths

82-84 Rockwell Street

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

View 71-73 Wheeler Street Winchester, CT MLS# 24178174
  • Recently Listed
1 of 17
$450,000
8

Beds

4.0

Baths

2,000

Sq.Ft.

71-73 Wheeler Street

Winchester, CT

View 319 White Oak Trail Winchester, CT MLS# 24177619
  • Recently Listed
1 of 5
$70,000
Studio

Beds

0.0

Baths

319 White Oak Trail

Winchester, CT

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 30 Upland Road Winchester, CT MLS# 24176921
$220,000
4

Beds

2.0

Baths

1,844

Sq.Ft.

30 Upland Road

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 9 Loomis Street Winchester, CT MLS# 24175936
  • Recently Listed
1 of 20
$469,900
3

Beds

2.0

Baths

1,768

Sq.Ft.

9 Loomis Street

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 624 Wynne Road Winchester, CT MLS# 24174996
  • Recently Listed
1 of 23
$199,900
2

Beds

1.0

Baths

672

Sq.Ft.

624 Wynne Road

Winchester, CT

View 624 Wynne Road Winchester, CT MLS# 24175027
  • Recently Listed
1 of 24
$199,900
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

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

    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

    $349,900
    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 - 100K11
    $100K - 200K8
    $200K - 300K14
    $300K - 400K11
    $400K - 500K9
    $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
    Rental17
    Lots and Land19
    Condo/Town/CoOp0
    CoOp0
    Multi Family10
    Mobile Home0
    Farms0

    (Data as of 5/31/2026)

    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.

    © Copyright 2026 Smart Multiple Listing Service, Inc.