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
  • Recently Listed
1 of 40
OPEN HOUSE: Saturday 5/16 1:00 PM - 3:00 PM
$895,000
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 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
$859,000
Studio

Beds

0.0

Baths

257-259 Torringford Street

Winchester, CT

View 258 Perch Rock Trail Winchester, CT MLS# 24171657
$795,000
4

Beds

2.0

Baths

1,373

Sq.Ft.

258 Perch Rock Trail

Winchester, CT

View 156 Shore Drive Winchester, CT MLS# 24160676
$779,900
5

Beds

1.1

Baths

1,258

Sq.Ft.

156 Shore Drive

Winchester, CT

View 184 Smith Hill Road Winchester, CT MLS# 24173895
  • Recently Listed
1 of 37
$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 45 Elm Street Winchester, CT MLS# 24131609
$540,000
7.1

Baths

7,405

Sq.Ft.

45 Elm Street

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

Beds

2.0

Baths

1,768

Sq.Ft.

9 Loomis 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

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

67

Estimated median home price

$360,000
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 - 100K7
$100K - 200K8
$200K - 300K13
$300K - 400K12
$400K - 500K6
$500K - 600K3
$600K - 700K2
$700K - 800K5
$800K - 900K4
$900K - 1M1
$1M - Max6

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family32
Townhouse0
Condo4
Commercial10
Rental19
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 5/15/2026)

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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