View 144 Rowley Street Winchester, CT MLS# 24154804
$1,900,000
1.1

Baths

12,000

Sq.Ft.

144 Rowley Street

Winchester, CT

View 431 West Wakefield Boulevard Winchester, CT MLS# 24159989
$1,850,000
9

Beds

5.1

Baths

7,000

Sq.Ft.

431 West Wakefield Boulevard

Winchester, CT

View 424 East Wakefield Boulevard Winchester, CT MLS# 24171266
$1,595,000
5

Beds

2.0

Baths

3,693

Sq.Ft.

424 East Wakefield Boulevard

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 129 East Lake Street Winchester, CT MLS# 24166368
$1,495,000
3

Beds

3.1

Baths

2,699

Sq.Ft.

129 East Lake Street

Winchester, CT

View 748 Lake Drive Winchester, CT MLS# 24171778
$1,249,900
5

Beds

4.0

Baths

3,584

Sq.Ft.

748 Lake Drive

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 674 East Wakefield Boulevard Winchester, CT MLS# 24170488
$990,000
3

Beds

3.0

Baths

2,097

Sq.Ft.

674 East Wakefield Boulevard

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 469 Platt Hill Road Winchester, CT MLS# 24172121
$895,000
4

Beds

2.0

Baths

3,088

Sq.Ft.

469 Platt Hill Road

Winchester, CT

View 000000 Norfolk Road Winchester, CT MLS# 24131284
$879,990
Studio

Beds

0.0

Baths

000000 Norfolk Road

Winchester, CT

View 257-259 Torringford Street Winchester, CT MLS# 24157681
$799,000
Studio

Beds

0.0

Baths

257-259 Torringford Street

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 184 Smith Hill Road Winchester, CT MLS# 24173895
$765,000
3

Beds

2.1

Baths

4,387

Sq.Ft.

184 Smith Hill Road

Winchester, CT

View 660 East Wakefield Boulevard Winchester, CT MLS# 24174215
$749,999
2

Beds

2.0

Baths

1,320

Sq.Ft.

660 East Wakefield Boulevard

Winchester, CT

View 121 West Wakefield Boulevard Winchester, CT MLS# 24159801
$749,000
4

Beds

3.1

Baths

2,265

Sq.Ft.

121 West Wakefield Boulevard

Winchester, CT

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

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

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 - 200K7
$200K - 300K13
$300K - 400K13
$400K - 500K8
$500K - 600K5
$600K - 700K2
$700K - 800K5
$800K - 900K3
$900K - 1M2
$1M - Max5

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family34
Townhouse0
Condo3
Commercial8
Rental16
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms0

(Data as of 6/8/2026)

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.