View 9 John Street Winchester, CT MLS# 24154885
  • Recently Listed
1 of 26
$230,000
2

Beds

1.1

Baths

1,172

Sq.Ft.

9 John Street

Winchester, CT

View 44 Lewis Street Winchester, CT MLS# 24155057
  • Recently Listed
1 of 25
$279,900
3

Beds

2.0

Baths

1,604

Sq.Ft.

44 Lewis Street

Winchester, CT

View 351 Platt Hill Road Winchester, CT MLS# 24154916
$370,000
3

Beds

2.0

Baths

1,715

Sq.Ft.

351 Platt Hill Road

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 174 Wallens Street APT A5 Winchester, CT MLS# 24153820
$289,000
2

Beds

2.1

Baths

1,946

Sq.Ft.

174 Wallens Street APT A5

Winchester, CT

View 160 Williams Avenue Winchester, CT MLS# 24150736
  • Recently Listed with Virtual Tour
1 of 40
$385,000
6

Beds

3.1

Baths

3,302

Sq.Ft.

160 Williams Avenue

Winchester, CT

View 9 Central Avenue Winchester, CT MLS# 24153231
    1 of 23
    OPEN HOUSE: Sunday 2/22 1:00 PM - 3:00 PM
    $274,900
    3

    Beds

    1.1

    Baths

    1,267

    Sq.Ft.

    9 Central Avenue

    Winchester, CT

    View 171 Wallens Street Winchester, CT MLS# 24152814
    • Recently Listed
    1 of 24
    $359,900
    2

    Beds

    2.0

    Baths

    1,274

    Sq.Ft.

    171 Wallens Street

    Winchester, CT

    View 107 Birdsall Street Winchester, CT MLS# 24150688
    $250,000
    4

    Beds

    2.0

    Baths

    1,874

    Sq.Ft.

    107 Birdsall Street

    Winchester, CT

    View 343 East Wakefield Boulevard Winchester, CT MLS# 24151049
    $270,000
    2

    Beds

    1.0

    Baths

    1,218

    Sq.Ft.

    343 East Wakefield Boulevard

    Winchester, CT

    View 95 Colony Drive Winchester, CT MLS# 24150993
    $285,000
    3

    Beds

    1.1

    Baths

    1,008

    Sq.Ft.

    95 Colony Drive

    Winchester, CT

    View 155 Rockwell Street Winchester, CT MLS# 24150627
    $159,000
    3

    Beds

    1.0

    Baths

    1,317

    Sq.Ft.

    155 Rockwell Street

    Winchester, CT

    View 230 East Wakefield Boulevard Winchester, CT MLS# 24150574
    $319,000
    3

    Beds

    2.0

    Baths

    1,536

    Sq.Ft.

    230 East Wakefield Boulevard

    Winchester, CT

    View 123 Wetmore Avenue Winchester, CT MLS# 24150199
    $339,900
    4

    Beds

    2.0

    Baths

    2,345

    Sq.Ft.

    123 Wetmore Avenue

    Winchester, CT

    View 21 Riveredge Drive 21 Winchester, CT MLS# 24149186
    $170,000
    2

    Beds

    1.1

    Baths

    992

    Sq.Ft.

    21 Riveredge Drive 21

    Winchester, CT

    View 35 Riveredge Drive 35 Winchester, CT MLS# 24147679
    $164,000
    2

    Beds

    1.1

    Baths

    992

    Sq.Ft.

    35 Riveredge Drive 35

    Winchester, CT

    View 43 Wallens Street Winchester, CT MLS# 24146596
    $275,000
    4

    Beds

    2.0

    Baths

    1,971

    Sq.Ft.

    43 Wallens 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 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 157 Elm Street Winchester, CT MLS# 24142357
    $339,000
    6

    Beds

    2.1

    Baths

    2,376

    Sq.Ft.

    157 Elm Street

    Winchester, CT

    View 8 Oak Street Winchester, CT MLS# 24140653
    $159,000
    2

    Beds

    1.1

    Baths

    832

    Sq.Ft.

    8 Oak 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

    59

    Estimated median home price

    $299,900
    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 - 200K5
    $200K - 300K17
    $300K - 400K14
    $400K - 500K3
    $500K - 600K1
    $600K - 700K2
    $700K - 800K4
    $800K - 900K2
    $900K - 1M1
    $1M - Max0

    Homes for Sale by Type in Winchester, CT

    Property TypeCount
    Single Family21
    Townhouse0
    Condo3
    Commercial10
    Rental13
    Lots and Land16
    Condo/Town/CoOp0
    CoOp0
    Multi Family9
    Mobile Home0
    Farms0

    (Data as of 2/19/2026)

    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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