View 105 Deepwood Drive Cheshire, CT MLS# 24220055
    1 of 40
    OPEN HOUSE: Saturday 11/14 12:00 PM - 2:00 PM
    $429,900
    2

    Beds

    2.0

    Baths

    1,104

    Sq.Ft.

    105 Deepwood Drive

    Cheshire, CT

    View 1430 South Main Street Cheshire, CT MLS# 24216659
    • Recently Listed
    1 of 40
    $524,900
    3

    Beds

    2.1

    Baths

    1,932

    Sq.Ft.

    1430 South Main Street

    Cheshire, CT

    View 7 Edith Place Cheshire, CT MLS# 24216201
    $479,900
    4

    Beds

    4.1

    Baths

    3,839

    Sq.Ft.

    7 Edith Place

    Cheshire, CT

    The time to sell is now! THE TIME TO SELL IS NOW!
    View 4 Cherrywood Circle Cheshire, CT MLS# 24216017
      1 of 1
      OPEN HOUSE: Saturday 11/14 11:00 AM - 1:00 PM
      $525,000
      3

      Beds

      2.0

      Baths

      2,043

      Sq.Ft.

      4 Cherrywood Circle

      Cheshire, CT

      View 120 Hilltop Road Cheshire, CT MLS# 24215666
      $519,900
      3

      Beds

      2.0

      Baths

      1,564

      Sq.Ft.

      120 Hilltop Road

      Cheshire, CT

      View 3 Racebrook Court Cheshire, CT MLS# 24214282
      $538,000
      2

      Beds

      2.0

      Baths

      1,960

      Sq.Ft.

      3 Racebrook Court

      Cheshire, CT

      View 72 Quarry Village Road 72 Cheshire, CT MLS# 24214748
      $425,000
      2

      Beds

      2.1

      Baths

      1,700

      Sq.Ft.

      72 Quarry Village Road 72

      Cheshire, CT

      View 50 Foxwood Court Cheshire, CT MLS# 24210432
      $465,000
      3

      Beds

      1.1

      Baths

      2,120

      Sq.Ft.

      50 Foxwood Court

      Cheshire, CT

      View 68 Pleasant Drive Cheshire, CT MLS# 24214579
      $469,000
      4

      Beds

      3.0

      Baths

      1,478

      Sq.Ft.

      68 Pleasant Drive

      Cheshire, CT

      View 268 Eastgate Drive Cheshire, CT MLS# 24213257
      $499,999
      3

      Beds

      2.1

      Baths

      1,642

      Sq.Ft.

      268 Eastgate Drive

      Cheshire, CT

      View 1016 Sperry Road Cheshire, CT MLS# 24212500
      $399,000
      2

      Beds

      1.0

      Baths

      974

      Sq.Ft.

      1016 Sperry Road

      Cheshire, CT

      View 388 Sharon Drive Cheshire, CT MLS# 24210609
      $409,900
      3

      Beds

      2.0

      Baths

      1,512

      Sq.Ft.

      388 Sharon Drive

      Cheshire, CT

      View 72 Willow Street Cheshire, CT MLS# 24203699
      $484,900
      4

      Beds

      2.0

      Baths

      1,824

      Sq.Ft.

      72 Willow Street

      Cheshire, CT

      View 190 Remus Road Cheshire, CT MLS# 24207733
      $469,900
      4

      Beds

      2.0

      Baths

      2,033

      Sq.Ft.

      190 Remus Road

      Cheshire, CT

      View 122 Green Hill Lane Cheshire, CT MLS# 24208667
      $439,900
      3

      Beds

      1.1

      Baths

      1,572

      Sq.Ft.

      122 Green Hill Lane

      Cheshire, CT

      View 2 Saxon Woods Court Cheshire, CT MLS# 24207223
      $497,700
      3

      Beds

      2.0

      Baths

      2,459

      Sq.Ft.

      2 Saxon Woods Court

      Cheshire, CT

      View 110 Green Hill Lane Cheshire, CT MLS# 24206251
      $399,900
      5

      Beds

      2.0

      Baths

      1,584

      Sq.Ft.

      110 Green Hill Lane

      Cheshire, CT

      View 1338 Avon Boulevard Cheshire, CT MLS# 24199826
      • Virtual Tour
      1 of 40
      $439,900
      3

      Beds

      2.0

      Baths

      1,619

      Sq.Ft.

      1338 Avon Boulevard

      Cheshire, CT

      View 445 Lincoln Drive Cheshire, CT MLS# 24203408
      • Virtual Tour
      1 of 29
      $455,000
      3

      Beds

      1.0

      Baths

      1,764

      Sq.Ft.

      445 Lincoln Drive

      Cheshire, CT

      View 16 Deepwood Drive Cheshire, CT MLS# 24182948
      • Virtual Tour
      1 of 40
      $465,000
      3

      Beds

      2.0

      Baths

      1,566

      Sq.Ft.

      16 Deepwood Drive

      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

      95

      Estimated median home price

      $550,000
      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 - 200K7
      $200K - 300K5
      $300K - 400K15
      $400K - 500K14
      $500K - 600K15
      $600K - 700K7
      $700K - 800K8
      $800K - 900K6
      $900K - 1M2
      $1M - Max15

      Homes for Sale by Type in Cheshire, CT

      Property TypeCount
      Single Family60
      Townhouse0
      Condo23
      Commercial6
      Rental19
      Lots and Land5
      Condo/Town/CoOp0
      CoOp0
      Multi Family1
      Mobile Home0
      Farms0

      (Data as of 11/11/2026)

      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.

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