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

The time to sell is now! THE TIME TO SELL IS NOW!
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 118 Meadow Street Winchester, CT MLS# 24140514
$269,999
3

Beds

2.0

Baths

1,652

Sq.Ft.

118 Meadow Street

Winchester, CT

View 38 Upland Road Winchester, CT MLS# 24131432
$269,000
3

Beds

1.1

Baths

1,736

Sq.Ft.

38 Upland Road

Winchester, CT

View 174 Wallens Street APT B6 Winchester, CT MLS# 24144757
$245,000
2

Beds

2.0

Baths

1,352

Sq.Ft.

174 Wallens Street APT B6

Winchester, CT

View 9 John Street Winchester, CT MLS# 24141326
$230,000
2

Beds

1.1

Baths

1,172

Sq.Ft.

9 John Street

Winchester, CT

View 18 Curtice Street Winchester, CT MLS# 24145729
$229,000
2

Beds

1.1

Baths

1,252

Sq.Ft.

18 Curtice 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 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 21 Riveredge Drive 21 Winchester, CT MLS# 24149186
  • Recently Listed
1 of 12
$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
    1 of 3
    OPEN HOUSE: Sunday 1/25 12:00 PM - 2:00 PM
    $164,000
    2

    Beds

    1.1

    Baths

    992

    Sq.Ft.

    35 Riveredge Drive 35

    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

    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

    View 508 Main Street Winchester, CT MLS# 24125194
    $99,000
    4,679

    Sq.Ft.

    508 Main Street

    Winchester, CT

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

    Sq.Ft.

    140 Willow Street STE 6

    Winchester, CT

    View 503 North Main Street Winchester, CT MLS# 24101761
    $69,000
    Studio

    Beds

    0.0

    Baths

    503 North Main Street

    Winchester, CT

    View 105,107 Mountain Road Winchester, CT MLS# 170616672
    $59,900
    Studio

    Beds

    0.0

    Baths

    105,107 Mountain Road

    Winchester, CT

    View 99 Hubbard Street Winchester, CT MLS# 24073744
    $49,000
    Studio

    Beds

    0.0

    Baths

    99 Hubbard 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

    $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 - 200K5
    $200K - 300K13
    $300K - 400K12
    $400K - 500K5
    $500K - 600K1
    $600K - 700K2
    $700K - 800K5
    $800K - 900K4
    $900K - 1M1
    $1M - Max1

    Homes for Sale by Type in Winchester, CT

    Property TypeCount
    Single Family20
    Townhouse0
    Condo4
    Commercial10
    Rental14
    Lots and Land16
    Condo/Town/CoOp0
    CoOp0
    Multi Family9
    Mobile Home0
    Farms0

    (Data as of 1/16/2026)

    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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