View 35 Glendale Avenue Winchester, CT MLS# 24157783
$399,000
3

Beds

2.0

Baths

2,196

Sq.Ft.

35 Glendale Avenue

Winchester, CT

View 94 Holabird Avenue Winchester, CT MLS# 24158795
    1 of 1
    OPEN HOUSE: Saturday 3/21 11:00 AM - 1:00 PM
    $249,900
    3

    Beds

    1.0

    Baths

    1,422

    Sq.Ft.

    94 Holabird Avenue

    Winchester, CT

    View 257 Torringford Street Winchester, CT MLS# 24157681
    $859,000
    Studio

    Beds

    0.0

    Baths

    257 Torringford Street

    Winchester, CT

    The time to sell is now! THE TIME TO SELL IS NOW!
    View 9 John Street Winchester, CT MLS# 24154885
    $230,000
    2

    Beds

    1.1

    Baths

    1,172

    Sq.Ft.

    9 John Street

    Winchester, CT

    View 44 Lewis Street Winchester, CT MLS# 24155057
    $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

    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 9 Central Avenue Winchester, CT MLS# 24153231
    $274,900
    3

    Beds

    1.1

    Baths

    1,267

    Sq.Ft.

    9 Central Avenue

    Winchester, CT

    View 171 Wallens Street Winchester, CT MLS# 24152814
    $359,900
    2

    Beds

    2.0

    Baths

    1,274

    Sq.Ft.

    171 Wallens Street

    Winchester, CT

    View 107 Birdsall Street Winchester, CT MLS# 24150688
    $240,000
    4

    Beds

    2.0

    Baths

    1,874

    Sq.Ft.

    107 Birdsall Street

    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 230 East Wakefield Boulevard Winchester, CT MLS# 24150574
    $314,000
    3

    Beds

    2.0

    Baths

    1,536

    Sq.Ft.

    230 East Wakefield Boulevard

    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 140 Willow Street STE 6 Winchester, CT MLS# 24143845
    $89,000
    1,165

    Sq.Ft.

    140 Willow Street STE 6

    Winchester, CT

    View 118 Meadow Street Winchester, CT MLS# 24140514
    $269,999
    3

    Beds

    2.0

    Baths

    1,652

    Sq.Ft.

    118 Meadow Street

    Winchester, CT

    View 106 Rockwell Street Winchester, CT MLS# 24139930
    $299,900
    6

    Beds

    3.0

    Baths

    1,874

    Sq.Ft.

    106 Rockwell Street

    Winchester, CT

    View 720 Main Street Winchester, CT MLS# 24138050
    $395,000
    3

    Beds

    1.1

    Baths

    1,909

    Sq.Ft.

    720 Main Street

    Winchester, CT

    View 720 Main Street Winchester, CT MLS# 24138743
    $395,000
    1.1

    Baths

    1,909

    Sq.Ft.

    720 Main 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 354 Main Street Winchester, CT MLS# 24137086
    $899,000
    3.0

    Baths

    11,972

    Sq.Ft.

    354 Main 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

    47

    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 - 100K8
    $100K - 200K2
    $200K - 300K14
    $300K - 400K11
    $400K - 500K2
    $500K - 600K1
    $600K - 700K1
    $700K - 800K4
    $800K - 900K3
    $900K - 1M1
    $1M - Max0

    Homes for Sale by Type in Winchester, CT

    Property TypeCount
    Single Family13
    Townhouse0
    Condo2
    Commercial9
    Rental17
    Lots and Land16
    Condo/Town/CoOp0
    CoOp0
    Multi Family7
    Mobile Home0
    Farms0

    (Data as of 3/15/2026)

    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.