View 385 Sir Walter Drive Cheshire, CT MLS# 24211153
    1 of 40
    OPEN HOUSE: Sunday 10/11 1:00 PM - 3:00 PM
    $649,900
    3

    Beds

    2.1

    Baths

    2,214

    Sq.Ft.

    385 Sir Walter Drive

    Cheshire, CT

    View 1 Mountaincrest Drive Cheshire, CT MLS# 24206472
    • Recently Listed
    1 of 42
    $1,375,000
    4

    Beds

    4.1

    Baths

    3,718

    Sq.Ft.

    1 Mountaincrest Drive

    Cheshire, CT

    View 273 Winthrop Drive Cheshire, CT MLS# 24210901
    • Recently Listed
    1 of 35
    $454,900
    3

    Beds

    2.0

    Baths

    1,357

    Sq.Ft.

    273 Winthrop Drive

    Cheshire, CT

    The time to sell is now! THE TIME TO SELL IS NOW!
    View 388 Sharon Drive Cheshire, CT MLS# 24210609
    • Recently Listed
    1 of 39
    $419,900
    3

    Beds

    2.0

    Baths

    1,512

    Sq.Ft.

    388 Sharon Drive

    Cheshire, CT

    View 21 Berkshire Court Cheshire, CT MLS# 24210753
    $725,000
    4

    Beds

    2.1

    Baths

    2,873

    Sq.Ft.

    21 Berkshire Court

    Cheshire, CT

    View 662 Coleman Road Cheshire, CT MLS# 24211310
    • Recently Listed
    1 of 40
    $775,000
    4

    Beds

    2.1

    Baths

    3,143

    Sq.Ft.

    662 Coleman Road

    Cheshire, CT

    View 980 Notch Road Cheshire, CT MLS# 24210481
    • Recently Listed
    1 of 37
    $434,900
    3

    Beds

    2.0

    Baths

    1,729

    Sq.Ft.

    980 Notch Road

    Cheshire, CT

    View 190 Remus Road Cheshire, CT MLS# 24207733
    • Recently Listed
    1 of 35
    $525,000
    4

    Beds

    2.0

    Baths

    2,033

    Sq.Ft.

    190 Remus Road

    Cheshire, CT

    View 368 Charles Drive Cheshire, CT MLS# 24208525
    • Recently Listed with Virtual Tour
    1 of 46
    $769,000
    4

    Beds

    3.0

    Baths

    2,324

    Sq.Ft.

    368 Charles Drive

    Cheshire, CT

    View 531 Blacks Road Cheshire, CT MLS# 24209218
    • Recently Listed
    1 of 41
    $645,000
    3

    Beds

    2.2

    Baths

    2,308

    Sq.Ft.

    531 Blacks Road

    Cheshire, CT

    View 8 Applewood Drive Cheshire, CT MLS# 24209466
    $735,000
    4

    Beds

    2.1

    Baths

    2,900

    Sq.Ft.

    8 Applewood Drive

    Cheshire, CT

    View 488 Radmere Road A Cheshire, CT MLS# 24203083
    • Virtual Tour
    1 of 25
    $249,900
    2

    Beds

    1.1

    Baths

    1,514

    Sq.Ft.

    488 Radmere Road A

    Cheshire, CT

    View 1100 Coleman Road Cheshire, CT MLS# 24205288
    • Recently Listed
    1 of 38
    $695,000
    4

    Beds

    2.1

    Baths

    2,280

    Sq.Ft.

    1100 Coleman Road

    Cheshire, CT

    View 233 Forest Lane Cheshire, CT MLS# 24208227
    • Recently Listed
    1 of 27
    $319,900
    3

    Beds

    1.1

    Baths

    1,413

    Sq.Ft.

    233 Forest Lane

    Cheshire, CT

    View 70 Heritage Drive Cheshire, CT MLS# 24208189
    $649,900
    3

    Beds

    2.1

    Baths

    2,605

    Sq.Ft.

    70 Heritage Drive

    Cheshire, CT

    View 70 Southwick Court 311 Cheshire, CT MLS# 24206360
    • Adult Community
    1 of 15
    $305,000
    2

    Beds

    2.0

    Baths

    1,132

    Sq.Ft.

    70 Southwick Court 311

    Cheshire, CT

    View 122 Green Hill Lane Cheshire, CT MLS# 24208667
    • Recently Listed
    1 of 40
    $439,900
    3

    Beds

    1.1

    Baths

    1,572

    Sq.Ft.

    122 Green Hill Lane

    Cheshire, CT

    View 644 South Brooksvale Road Cheshire, CT MLS# 24207257
    $1,630,000
    5

    Beds

    4.1

    Baths

    6,361

    Sq.Ft.

    644 South Brooksvale Road

    Cheshire, CT

    View 114 Broadview Road Cheshire, CT MLS# 24207774
    $339,900
    2

    Beds

    1.0

    Baths

    816

    Sq.Ft.

    114 Broadview Road

    Cheshire, CT

    View 295 Towpath Lane Cheshire, CT MLS# 24208080
    $725,000
    4

    Beds

    2.1

    Baths

    2,256

    Sq.Ft.

    295 Towpath Lane

    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

    94

    Estimated median home price

    $562,500
    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 - 200K6
    $200K - 300K6
    $300K - 400K11
    $400K - 500K20
    $500K - 600K7
    $600K - 700K9
    $700K - 800K12
    $800K - 900K6
    $900K - 1M1
    $1M - Max15

    Homes for Sale by Type in Cheshire, CT

    Property TypeCount
    Single Family62
    Townhouse0
    Condo20
    Commercial6
    Rental17
    Lots and Land5
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms0

    (Data as of 10/5/2026)

    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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