View 139 Contour Drive Cheshire, CT MLS# 24175579
  • Virtual Tour
1 of 37
$489,900
3

Beds

2.1

Baths

1,808

Sq.Ft.

139 Contour Drive

Cheshire, CT

View 20 Watch Hill Road Cheshire, CT MLS# 24178385
  • Recently Listed
1 of 19
$459,900
4

Beds

2.1

Baths

2,086

Sq.Ft.

20 Watch Hill Road

Cheshire, CT

View 58 Old Towne Road 58 Cheshire, CT MLS# 24175597
  • Recently Listed
1 of 54
$549,000
3

Beds

2.1

Baths

2,160

Sq.Ft.

58 Old Towne Road 58

Cheshire, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 2175 Plank Road Cheshire, CT MLS# 24178038
  • Recently Listed
1 of 44
$519,900
4

Beds

2.1

Baths

2,496

Sq.Ft.

2175 Plank Road

Cheshire, CT

View 405 Sheridan Drive Cheshire, CT MLS# 24177386
$529,900
6

Beds

3.0

Baths

2,015

Sq.Ft.

405 Sheridan Drive

Cheshire, CT

View 43 Hawthorne Drive Cheshire, CT MLS# 24174204
$519,900
3

Beds

2.0

Baths

2,346

Sq.Ft.

43 Hawthorne Drive

Cheshire, CT

View 375 Sycamore Lane Cheshire, CT MLS# 24174238
$559,000
4

Beds

2.1

Baths

2,057

Sq.Ft.

375 Sycamore Lane

Cheshire, CT

View 230 Wallingford Road Cheshire, CT MLS# 24173978
$559,900
3

Beds

2.1

Baths

2,462

Sq.Ft.

230 Wallingford Road

Cheshire, CT

View 1006 King Road Cheshire, CT MLS# 24165798
$499,000
3

Beds

2.1

Baths

1,577

Sq.Ft.

1006 King Road

Cheshire, CT

View 1241 Rice Avenue Cheshire, CT MLS# 24174634
$499,900
3

Beds

2.0

Baths

2,146

Sq.Ft.

1241 Rice Avenue

Cheshire, CT

View 39 Fernwood Lane Cheshire, CT MLS# 24163245
$430,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

39 Fernwood Lane

Cheshire, CT

View 649 Maple Avenue Cheshire, CT MLS# 24174035
  • Virtual Tour
1 of 36
$524,900
4

Beds

2.0

Baths

1,719

Sq.Ft.

649 Maple Avenue

Cheshire, CT

View 181 Crescent Circle Cheshire, CT MLS# 24172505
  • Virtual Tour
1 of 37
$439,900
3

Beds

1.0

Baths

1,601

Sq.Ft.

181 Crescent Circle

Cheshire, CT

View 39 Winslow Road Cheshire, CT MLS# 24168914
$449,900
3

Beds

2.0

Baths

1,758

Sq.Ft.

39 Winslow Road

Cheshire, CT

View 568 Wiese Road Cheshire, CT MLS# 24172497
$540,000
4

Beds

2.0

Baths

1,633

Sq.Ft.

568 Wiese Road

Cheshire, CT

View 2192 Waterbury Road Cheshire, CT MLS# 24172189
$510,000
6

Beds

3.0

Baths

2,960

Sq.Ft.

2192 Waterbury Road

Cheshire, CT

View 960 Peck Lane Cheshire, CT MLS# 24167821
$439,900
3

Beds

1.1

Baths

1,450

Sq.Ft.

960 Peck Lane

Cheshire, CT

View 611 Ives Row Cheshire, CT MLS# 24168897
$435,000
3

Beds

2.0

Baths

1,788

Sq.Ft.

611 Ives Row

Cheshire, CT

View 200 Chipman Drive Cheshire, CT MLS# 24159847
  • Virtual Tour
1 of 44
$495,000
3

Beds

2.0

Baths

1,933

Sq.Ft.

200 Chipman Drive

Cheshire, CT

View 140 Willow Street Cheshire, CT MLS# 24167158
$499,900
3

Beds

2.0

Baths

1,810

Sq.Ft.

140 Willow Street

Cheshire, CT

About Cheshire

The residential suburban community of Cheshire enjoys a strong tax base supported by a significant industrial and commercial community.  Known as the “bedding plant capital of Connecticut,” the town has been able to retain much of its rural flavor by preserving thousands of acres of open space.  Just 14 miles north of New Haven and 25 miles southwest of Hartford, Cheshire enjoys access to Interstates 84, 91, and 691.

Listings in Cheshire, CT

117

Estimated median home price

$639,900
Cheshire CT Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Cheshire, Connecticut real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Cheshire, CT.

Homes for Sale by Price in Cheshire, CT

PriceCount
$0 - 100K1
$100K - 200K4
$200K - 300K6
$300K - 400K12
$400K - 500K15
$500K - 600K16
$600K - 700K18
$700K - 800K10
$800K - 900K11
$900K - 1M7
$1M - Max17

Homes for Sale by Type in Cheshire, CT

Property TypeCount
Single Family86
Townhouse0
Condo19
Commercial4
Rental23
Lots and Land6
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms0

(Data as of 5/26/2026)

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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