View 115 Old Robertsville Road Winchester, CT MLS# 24104099
$649,900
Studio

Beds

0.0

Baths

115 Old Robertsville Road

Winchester, CT

View 162 Spencer Hill Road Winchester, CT MLS# 24167312
$625,000
3

Beds

2.1

Baths

2,144

Sq.Ft.

162 Spencer Hill Road

Winchester, CT

View 45 Willow Street Winchester, CT MLS# 24165997
$595,000
9,438

Sq.Ft.

45 Willow Street

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 150 Oak Street Winchester, CT MLS# 24166332
$579,000
11

Beds

5.1

Baths

5,233

Sq.Ft.

150 Oak Street

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 45 Elm Street Winchester, CT MLS# 24131609
$540,000
7.1

Baths

7,405

Sq.Ft.

45 Elm Street

Winchester, CT

View 257 Wallens Hill Road Winchester, CT MLS# 24179574
$539,900
3

Beds

2.1

Baths

2,011

Sq.Ft.

257 Wallens Hill Road

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 5 Stadler Heights Winchester, CT MLS# 24159478
$499,000
4

Beds

2.1

Baths

3,556

Sq.Ft.

5 Stadler Heights

Winchester, CT

View 51 Hinsdale Avenue Winchester, CT MLS# 24168665
$475,000
7

Beds

5.0

Baths

3,538

Sq.Ft.

51 Hinsdale Avenue

Winchester, CT

View 441 Platt Hill Road Winchester, CT MLS# 24178677
$474,900
5

Beds

3.0

Baths

3,404

Sq.Ft.

441 Platt Hill Road

Winchester, CT

View 9 Loomis Street Winchester, CT MLS# 24175936
$469,900
3

Beds

2.0

Baths

1,768

Sq.Ft.

9 Loomis Street

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 55 Walnut Street Winchester, CT MLS# 24071827
$449,000
5

Beds

1.3

Baths

5,016

Sq.Ft.

55 Walnut Street

Winchester, CT

View 55 Walnut Street Winchester, CT MLS# 24071862
$449,000
5,016

Sq.Ft.

55 Walnut Street

Winchester, CT

View 217 Walnut Street Winchester, CT MLS# 24168016
$399,000
5

Beds

2.2

Baths

2,779

Sq.Ft.

217 Walnut Street

Winchester, CT

View 26 Elm Street Winchester, CT MLS# 24182777
  • Recently Listed
1 of 13
$398,000
5

Beds

3.0

Baths

2,496

Sq.Ft.

26 Elm Street

Winchester, CT

View 7 Stadler Heights Winchester, CT MLS# 24122124
$389,000
Studio

Beds

0.0

Baths

7 Stadler Heights

Winchester, CT

View 00 Main Street Winchester, CT MLS# 24182990
  • Recently Listed
1 of 7
$386,000
Studio

Beds

0.0

Baths

00 Main Street

Winchester, CT

View 57 Main Street Winchester, CT MLS# 24112471
$375,000
1.0

Baths

3,660

Sq.Ft.

57 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

$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 - 200K6
$200K - 300K14
$300K - 400K14
$400K - 500K8
$500K - 600K5
$600K - 700K2
$700K - 800K5
$800K - 900K3
$900K - 1M2
$1M - Max4

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family33
Townhouse0
Condo2
Commercial8
Rental16
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms0

(Data as of 6/11/2026)

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.