View 162 Spencer Hill Road Winchester, CT MLS# 24167312
  • Recently Listed
1 of 35
OPEN HOUSE: Saturday 4/18 1:00 PM - 3:00 PM
$625,000
3

Beds

2.1

Baths

2,144

Sq.Ft.

162 Spencer Hill Road

Winchester, CT

View 57 Bridge Street Winchester, CT MLS# 24167580
  • Recently Listed
1 of 33
$275,000
4

Beds

1.1

Baths

1,416

Sq.Ft.

57 Bridge Street

Winchester, CT

View 118 South Road Winchester, CT MLS# 24167287
  • Recently Listed
1 of 36
OPEN HOUSE: Sunday 4/19 11:00 AM - 2:00 PM
$419,000
4

Beds

3.0

Baths

2,240

Sq.Ft.

118 South Road

Winchester, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 26 Elm Street Winchester, CT MLS# 24164370
  • Recently Listed
1 of 14
$398,000
5

Beds

3.0

Baths

2,496

Sq.Ft.

26 Elm Street

Winchester, CT

View 45 Willow Street Winchester, CT MLS# 24165997
  • Recently Listed
1 of 3
$595,000
9,438

Sq.Ft.

45 Willow Street

Winchester, CT

View 111 Riverton Road 28 Winchester, CT MLS# 24165512
$184,900
2

Beds

1.1

Baths

1,204

Sq.Ft.

111 Riverton Road 28

Winchester, CT

View 123 Old North Road Winchester, CT MLS# 24164624
$425,000
3

Beds

2.0

Baths

1,781

Sq.Ft.

123 Old North Road

Winchester, CT

View 1 Hamill Drive Winchester, CT MLS# 24164318
  • Recently Listed
1 of 29
$359,900
3

Beds

1.1

Baths

1,600

Sq.Ft.

1 Hamill Drive

Winchester, CT

View 90 Colony Drive Winchester, CT MLS# 24164163
  • Recently Listed
1 of 22
$335,000
3

Beds

1.0

Baths

1,282

Sq.Ft.

90 Colony Drive

Winchester, CT

View 262 Holabird Avenue Winchester, CT MLS# 24162992
$360,000
3

Beds

1.1

Baths

1,312

Sq.Ft.

262 Holabird Avenue

Winchester, CT

View 621 Wynne Road Winchester, CT MLS# 24161635
$339,900
2

Beds

1.0

Baths

975

Sq.Ft.

621 Wynne 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 94 Holabird Avenue Winchester, CT MLS# 24158795
$249,900
3

Beds

1.0

Baths

1,422

Sq.Ft.

94 Holabird Avenue

Winchester, CT

View 351 Platt Hill Road Winchester, CT MLS# 24154916
$370,000
3

Beds

2.0

Baths

1,715

Sq.Ft.

351 Platt Hill Road

Winchester, CT

View 107 Birdsall Street Winchester, CT MLS# 24150688
$240,000
4

Beds

2.0

Baths

1,874

Sq.Ft.

107 Birdsall Street

Winchester, CT

View 230 East Wakefield Boulevard Winchester, CT MLS# 24150574
$314,000
3

Beds

2.0

Baths

1,536

Sq.Ft.

230 East Wakefield Boulevard

Winchester, CT

View 35 Riveredge Drive 35 Winchester, CT MLS# 24147679
$159,500
2

Beds

1.1

Baths

992

Sq.Ft.

35 Riveredge Drive 35

Winchester, CT

View 140 Willow Street STE 6 Winchester, CT MLS# 24143845
$89,000
1,165

Sq.Ft.

140 Willow Street STE 6

Winchester, CT

View 118 Meadow Street Winchester, CT MLS# 24140514
$269,999
3

Beds

2.0

Baths

1,652

Sq.Ft.

118 Meadow Street

Winchester, CT

View 720 Main Street Winchester, CT MLS# 24138050
$395,000
3

Beds

1.1

Baths

1,909

Sq.Ft.

720 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

50

Estimated median home price

$375,000
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 - 100K6
$100K - 200K3
$200K - 300K9
$300K - 400K12
$400K - 500K5
$500K - 600K2
$600K - 700K2
$700K - 800K5
$800K - 900K3
$900K - 1M0
$1M - Max3

Homes for Sale by Type in Winchester, CT

Property TypeCount
Single Family19
Townhouse0
Condo2
Commercial10
Rental20
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 4/16/2026)

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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