View 247 North Main Street Winchester, CT MLS# 24013422
$525,000
7

Beds

5.1

Baths

5,093

Sq.Ft.

247 North Main Street

Winchester, CT

View 25 Hillside Avenue Winchester, CT MLS# 24012978
  • Recently Listed
1 of 39
$599,900
6

Beds

5.0

Baths

5,001

Sq.Ft.

25 Hillside Avenue

Winchester, CT

View 136 Glendale Avenue Winchester, CT MLS# 24012477
$279,925
4

Beds

1.0

Baths

1,114

Sq.Ft.

136 Glendale Avenue

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 213 Spencer Hill Road Winchester, CT MLS# 24008613
$399,900
3

Beds

2.0

Baths

1,836

Sq.Ft.

213 Spencer Hill Road

Winchester, CT

View 287 Colebrook Road Winchester, CT MLS# 24010400
  • Recently Listed
1 of 8
$54,500
Studio

Beds

0.0

Baths

287 Colebrook Road

Winchester, CT

View 246 Kingsbury Avenue Winchester, CT MLS# 24010266
$69,900
Studio

Beds

0.0

Baths

246 Kingsbury Avenue

Winchester, CT

View 28 Maloney Court Winchester, CT MLS# 24009516
  • Recently Listed
1 of 40
$259,900
3

Beds

2.0

Baths

1,485

Sq.Ft.

28 Maloney Court

Winchester, CT

View 88 Munro Place Winchester, CT MLS# 24008867
  • Recently Listed with Virtual Tour
1 of 30
OPEN HOUSE: Saturday 4/27 9:00 AM - 11:00 AM
$319,000
4

Beds

2.0

Baths

2,800

Sq.Ft.

88 Munro Place

Winchester, CT

View 27 Benton Street Winchester, CT MLS# 24009455
  • Recently Listed
1 of 16
$226,900
2

Beds

1.1

Baths

1,109

Sq.Ft.

27 Benton Street

Winchester, CT

View 107 Oakdale Avenue Winchester, CT MLS# 170625095
$368,000
3

Beds

2.1

Baths

2,521

Sq.Ft.

107 Oakdale Avenue

Winchester, CT

View 80 John Street Winchester, CT MLS# 24008788
  • Recently Listed
1 of 36
$349,999
2

Beds

2.0

Baths

1,514

Sq.Ft.

80 John Street

Winchester, CT

View 339 West Wakefield Boulevard Winchester, CT MLS# 24002936
$650,000
3

Beds

2.0

Baths

1,322

Sq.Ft.

339 West Wakefield Boulevard

Winchester, CT

View 638 & 640 Jewel Rd Winchester, CT MLS# 24006520
$15,000
Studio

Beds

0.0

Baths

638 & 640 Jewel Rd

Winchester, CT

View 817 E Wakefield Boulevard Winchester, CT MLS# 24006473
$399,900
2

Beds

1.1

Baths

1,051

Sq.Ft.

817 E Wakefield Boulevard

Winchester, CT

View 100 Colony Drive Winchester, CT MLS# 24005790
$259,000
3

Beds

2.0

Baths

1,092

Sq.Ft.

100 Colony Drive

Winchester, CT

View 2 Herman Road Winchester, CT MLS# 24004977
$234,900
3

Beds

2.0

Baths

1,872

Sq.Ft.

2 Herman Road

Winchester, CT

View 843-845 (lots - 10A,10 &1 East wakefield Winchester, CT MLS# 24003236
$169,000
Studio

Beds

0.0

Baths

843-845 (lots - 10A,10 &1 East wakefield

Winchester, CT

View 209 1/2 Rockwell Street Winchester, CT MLS# 24004037
$229,000
2

Beds

1.0

Baths

1,920

Sq.Ft.

209 1/2 Rockwell Street

Winchester, CT

View 114 Oak Street Winchester, CT MLS# 24004000
$275,000
3

Beds

1.1

Baths

2,192

Sq.Ft.

114 Oak Street

Winchester, CT

View 361 Winchester Road Winchester, CT MLS# 24002497
$329,900
3

Beds

1.0

Baths

1,786

Sq.Ft.

361 Winchester Road

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

56

Estimated median home price

$287,463
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 - 300K15
$300K - 400K15
$400K - 500K0
$500K - 600K1
$600K - 700K4
$700K - 800K2
$800K - 900K1
$900K - 1M0
$1M - Max3

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family27
Townhouse0
Condo1
Commercial8
Rental10
Lots and Land16
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 4/26/2024)

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.

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