View 107 Roberts Avenue Winchester, CT MLS# 24177410
  • Recently Listed
1 of 19
$349,000
3

Beds

1.1

Baths

1,888

Sq.Ft.

107 Roberts Avenue

Winchester, CT

View 257 Wallens Hill Road Winchester, CT MLS# 24179574
  • Recently Listed
1 of 38
$539,900
3

Beds

2.1

Baths

2,011

Sq.Ft.

257 Wallens Hill Road

Winchester, CT

View 32 Hubbard Street Winchester, CT MLS# 24179637
$45,000
Studio

Beds

0.0

Baths

32 Hubbard Street

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 132 Florence Street Winchester, CT MLS# 24179755
$45,000
Studio

Beds

0.0

Baths

132 Florence Street

Winchester, CT

View 17 Birdsall Street Winchester, CT MLS# 24179758
  • Recently Listed
1 of 2
$29,900
Studio

Beds

0.0

Baths

17 Birdsall Street

Winchester, CT

View 82-84 Rockwell Street Winchester, CT MLS# 24179760
$29,000
Studio

Beds

0.0

Baths

82-84 Rockwell Street

Winchester, CT

View 188 Glendale Avenue Winchester, CT MLS# 24179585
  • Recently Listed
1 of 29
$325,000
3

Beds

1.1

Baths

1,118

Sq.Ft.

188 Glendale Avenue

Winchester, CT

View 878 West Wakefield Boulevard Winchester, CT MLS# 24176238
$998,000
4

Beds

3.0

Baths

3,330

Sq.Ft.

878 West Wakefield Boulevard

Winchester, CT

View 71-73 Wheeler Street Winchester, CT MLS# 24178174
  • Recently Listed
1 of 17
$450,000
8

Beds

4.0

Baths

2,000

Sq.Ft.

71-73 Wheeler Street

Winchester, CT

View 441 Platt Hill Road Winchester, CT MLS# 24178677
  • Recently Listed
1 of 25
$499,900
5

Beds

3.0

Baths

3,404

Sq.Ft.

441 Platt Hill Road

Winchester, CT

View 319 White Oak Trail Winchester, CT MLS# 24177619
  • Recently Listed
1 of 5
$70,000
Studio

Beds

0.0

Baths

319 White Oak Trail

Winchester, CT

View 205 Old New Hartford Road Winchester, CT MLS# 24178149
$499,900
6

Beds

5.0

Baths

2,864

Sq.Ft.

205 Old New Hartford Road

Winchester, CT

View 68 Wetmore Avenue Winchester, CT MLS# 24177338
  • Recently Listed
1 of 28
$349,999
6

Beds

2.1

Baths

2,555

Sq.Ft.

68 Wetmore Avenue

Winchester, CT

View 535,538 West Wakefield Boulevard Winchester, CT MLS# 24037015
$795,000
Studio

Beds

0.0

Baths

535,538 West Wakefield Boulevard

Winchester, CT

View 30 Upland Road Winchester, CT MLS# 24176921
$220,000
4

Beds

2.0

Baths

1,844

Sq.Ft.

30 Upland Road

Winchester, CT

View 736 West Wakefield Boulevard Winchester, CT MLS# 24098872
$544,000
1

Beds

1.1

Baths

1,308

Sq.Ft.

736 West Wakefield Boulevard

Winchester, CT

View 147 E. Wakefield Boulevard Winchester, CT MLS# 24175908
$299,900
2

Beds

1.0

Baths

702

Sq.Ft.

147 E. Wakefield Boulevard

Winchester, CT

View 9 Loomis Street Winchester, CT MLS# 24175936
  • Recently Listed
1 of 20
$469,900
3

Beds

2.0

Baths

1,768

Sq.Ft.

9 Loomis Street

Winchester, CT

View 63 Meadow Street Winchester, CT MLS# 24175107
$345,000
5

Beds

3.0

Baths

2,602

Sq.Ft.

63 Meadow Street

Winchester, CT

View 624 Wynne Road Winchester, CT MLS# 24174996
  • Recently Listed
1 of 23
$199,900
2

Beds

1.0

Baths

672

Sq.Ft.

624 Wynne 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

76

Estimated median home price

$349,900
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 - 200K8
$200K - 300K14
$300K - 400K11
$400K - 500K9
$500K - 600K5
$600K - 700K2
$700K - 800K6
$800K - 900K3
$900K - 1M2
$1M - Max5

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family34
Townhouse0
Condo4
Commercial9
Rental17
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms0

(Data as of 5/31/2026)

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.

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