View 431 West Wakefield Boulevard Winchester, CT MLS# 24042374
$2,199,000
9

Beds

5.1

Baths

7,000

Sq.Ft.

431 West Wakefield Boulevard

Winchester, CT

View 722 Lake Drive Winchester, CT MLS# 24105754
  • Virtual Tour
1 of 49
$1,270,000
3

Beds

3.0

Baths

2,420

Sq.Ft.

722 Lake Drive

Winchester, CT

View 469 Platt Hill Road Winchester, CT MLS# 24089885
$920,000
4

Beds

2.0

Baths

3,088

Sq.Ft.

469 Platt Hill Road

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 354 Main Street Winchester, CT MLS# 24137086
$899,000
3.0

Baths

11,972

Sq.Ft.

354 Main Street

Winchester, CT

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

Beds

0.0

Baths

000000 Norfolk Road

Winchester, CT

View 119 West Wakefield Boulevard Winchester, CT MLS# 24058804
$849,900
4

Beds

2.0

Baths

1,781

Sq.Ft.

119 West Wakefield Boulevard

Winchester, CT

View 119 West Wakefield Boulevard Winchester, CT MLS# 24075940
$849,900
4

Beds

2.0

Baths

1,781

Sq.Ft.

119 West Wakefield Boulevard

Winchester, CT

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

Sq.Ft.

436 Main Street

Winchester, CT

View 436 Main Street Winchester, CT MLS# 24135030
$750,000
4

Beds

2.2

Baths

5,389

Sq.Ft.

436 Main Street

Winchester, CT

View 151 Losaw Road Winchester, CT MLS# 24121140
$749,999
5

Beds

2.1

Baths

2,950

Sq.Ft.

151 Losaw Road

Winchester, CT

View 39 South Main Street Winchester, CT MLS# 24083565
$749,900
7

Beds

3.0

Baths

3,486

Sq.Ft.

39 South Main Street

Winchester, CT

View Old Robertsville Road # Winchester, CT MLS# 24080217
$739,900
Studio

Beds

0.0

Baths

Old Robertsville Road #

Winchester, CT

View 115 Old Robertsville Road Winchester, CT MLS# 24104078
$649,900
5

Beds

1.1

Baths

2,304

Sq.Ft.

115 Old Robertsville Road

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

Baths

7,405

Sq.Ft.

45 Elm Street

Winchester, CT

View 440 Platt Hill Road Winchester, CT MLS# 24132598
$500,000
4

Beds

2.1

Baths

3,416

Sq.Ft.

440 Platt Hill Road

Winchester, CT

View 55 Walnut Street Winchester, CT MLS# 24071827
$499,999
5

Beds

1.3

Baths

5,016

Sq.Ft.

55 Walnut Street

Winchester, CT

View 55 Walnut Street Winchester, CT MLS# 24071862
$499,999
5,016

Sq.Ft.

55 Walnut Street

Winchester, CT

View 197 Spencer Hill Road Winchester, CT MLS# 24134519
$499,000
3

Beds

2.0

Baths

2,167

Sq.Ft.

197 Spencer Hill Road

Winchester, CT

View 117 South Road Winchester, CT MLS# 24096267
$419,000
3

Beds

3.0

Baths

2,747

Sq.Ft.

117 South 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

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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