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 9 John Street Winchester, CT MLS# 24141326
  • Recently Listed
1 of 23
$230,000
2

Beds

1.1

Baths

1,172

Sq.Ft.

9 John Street

Winchester, CT

View 208 Spencer Hill Road Winchester, CT MLS# 24142296
  • Recently Listed
1 of 40
$399,000
3

Beds

1.1

Baths

1,969

Sq.Ft.

208 Spencer Hill Road

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 157 Elm Street Winchester, CT MLS# 24142357
  • Recently Listed
1 of 31
$339,000
6

Beds

2.1

Baths

2,376

Sq.Ft.

157 Elm Street

Winchester, CT

View 107 Peck Road Winchester, CT MLS# 24142199
  • Recently Listed
1 of 39
OPEN HOUSE: Sunday 12/7 12:00 PM - 2:00 PM
$339,000
3

Beds

1.0

Baths

960

Sq.Ft.

107 Peck Road

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 8 Oak Street Winchester, CT MLS# 24140653
  • Recently Listed
1 of 11
$179,900
2

Beds

1.1

Baths

832

Sq.Ft.

8 Oak Street

Winchester, CT

View 95 Nalette Drive Winchester, CT MLS# 24140441
  • Recently Listed
1 of 24
$365,000
3

Beds

2.1

Baths

2,356

Sq.Ft.

95 Nalette Drive

Winchester, CT

View 118 Meadow Street Winchester, CT MLS# 24140514
  • Recently Listed
1 of 16
$290,000
3

Beds

2.0

Baths

1,652

Sq.Ft.

118 Meadow Street

Winchester, CT

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 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 10 Crescent Street Winchester, CT MLS# 24139201
$259,000
4

Beds

2.0

Baths

2,444

Sq.Ft.

10 Crescent 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 187 Torringford Street Winchester, CT MLS# 24138466
$419,000
4

Beds

1.1

Baths

2,365

Sq.Ft.

187 Torringford Street

Winchester, CT

View 148 Danbury Quarter Road Winchester, CT MLS# 24138604
$339,900
4

Beds

2.0

Baths

1,999

Sq.Ft.

148 Danbury Quarter Road

Winchester, CT

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

Baths

11,972

Sq.Ft.

354 Main Street

Winchester, CT

View 49 Walnut Street Winchester, CT MLS# 24137315
$299,900
5

Beds

2.0

Baths

2,344

Sq.Ft.

49 Walnut Street

Winchester, CT

View 32 Charles Street Winchester, CT MLS# 24136816
$229,900
3

Beds

1.0

Baths

1,044

Sq.Ft.

32 Charles Street

Winchester, CT

View 436 Main Street Winchester, CT MLS# 24135027
$750,000
5,389

Sq.Ft.

436 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

74

Estimated median home price

$314,900
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 - 200K9
$200K - 300K16
$300K - 400K14
$400K - 500K6
$500K - 600K2
$600K - 700K1
$700K - 800K5
$800K - 900K4
$900K - 1M2
$1M - Max4

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family31
Townhouse0
Condo5
Commercial9
Rental15
Lots and Land18
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms0

(Data as of 11/11/2025)

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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