View 27 South Pond Circle Cheshire, CT MLS# 24171642
$675,000
4

Beds

2.1

Baths

2,880

Sq.Ft.

27 South Pond 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 699 Andrea Court Cheshire, CT MLS# 24173103
$949,900
4

Beds

2.2

Baths

4,154

Sq.Ft.

699 Andrea Court

Cheshire, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 1274 Cheshire Street Cheshire, CT MLS# 24172072
$699,900
4

Beds

2.1

Baths

3,068

Sq.Ft.

1274 Cheshire Street

Cheshire, CT

View 15 Melrose Drive Cheshire, CT MLS# 24171652
$1,300,000
4

Beds

3.2

Baths

4,379

Sq.Ft.

15 Melrose Drive

Cheshire, CT

View 30 Soderman Way 30 Cheshire, CT MLS# 24171703
  • New Construction with Virtual Tour
1 of 37
$694,070
3

Beds

2.1

Baths

2,450

Sq.Ft.

30 Soderman Way 30

Cheshire, CT

View 5 Pondside Place Cheshire, CT MLS# 24171304
$699,900
5

Beds

2.1

Baths

2,310

Sq.Ft.

5 Pondside Place

Cheshire, CT

View 10 Colonial Court Cheshire, CT MLS# 24170129
$599,000
3

Beds

2.1

Baths

2,270

Sq.Ft.

10 Colonial Court

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 456 Castle Glenn Cheshire, CT MLS# 24167592
$769,900
3

Beds

2.1

Baths

3,740

Sq.Ft.

456 Castle Glenn

Cheshire, CT

View 456 Castle Glenn Cheshire, CT MLS# 24168866
$769,900
3

Beds

2.1

Baths

3,740

Sq.Ft.

456 Castle Glenn

Cheshire, CT

View 735 Cook Hill Road Cheshire, CT MLS# 24169111
$699,000
4

Beds

2.1

Baths

2,748

Sq.Ft.

735 Cook Hill Road

Cheshire, CT

View 140 Willow Street Cheshire, CT MLS# 24167158
$469,900
3

Beds

2.0

Baths

1,426

Sq.Ft.

140 Willow Street

Cheshire, CT

View 1830 Blackberry Place Cheshire, CT MLS# 24167067
$1,182,050
3

Beds

2.1

Baths

2,531

Sq.Ft.

1830 Blackberry Place

Cheshire, CT

View 303 Beacon Hill Drive Cheshire, CT MLS# 24165516
$744,900
4

Beds

3.1

Baths

2,884

Sq.Ft.

303 Beacon Hill Drive

Cheshire, CT

View 443 East Mitchell Avenue 443 Cheshire, CT MLS# 24166376
$134,900
1

Beds

1.0

Baths

853

Sq.Ft.

443 East Mitchell Avenue 443

Cheshire, CT

View 1 Mountaincrest Drive Cheshire, CT MLS# 24166356
$1,175,000
4

Beds

4.1

Baths

3,718

Sq.Ft.

1 Mountaincrest Drive

Cheshire, CT

View 773 Devonwood Drive Cheshire, CT MLS# 24166011
$799,900
4

Beds

3.1

Baths

3,984

Sq.Ft.

773 Devonwood Drive

Cheshire, CT

View 15 Shire Court Cheshire, CT MLS# 24157096
$1,085,000
4

Beds

2.1

Baths

4,437

Sq.Ft.

15 Shire Court

Cheshire, CT

View 10 Whispering Hollow Court Cheshire, CT MLS# 24165619
$1,080,888
4

Beds

4.1

Baths

4,163

Sq.Ft.

10 Whispering Hollow Court

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

113

Estimated median home price

$674,900
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 - 200K2
$200K - 300K5
$300K - 400K13
$400K - 500K15
$500K - 600K17
$600K - 700K13
$700K - 800K11
$800K - 900K12
$900K - 1M8
$1M - Max16

Homes for Sale by Type in Cheshire, CT

Property TypeCount
Single Family85
Townhouse0
Condo19
Commercial2
Rental23
Lots and Land6
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 6/20/2026)

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.