View 3409 Whispering Hills Chester, NY MLS# 1032618
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    1 of 24
    $360,000
    3

    Beds

    2.1

    Baths

    1,331

    Sq.Ft.

    3409 Whispering Hills

    Chester, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 2124 Whispering Hills Chester, NY MLS# 1042658
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    1 of 18
    $299,000
    2

    Beds

    1.0

    Baths

    1,084

    Sq.Ft.

    2124 Whispering Hills

    Chester, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 260 Gibson Hill Road Chester, NY MLS# 1044316
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    1 of 22
    $374,900
    3

    Beds

    1.1

    Baths

    1,644

    Sq.Ft.

    260 Gibson Hill Road

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 2921 Whispering Hills Chester, NY MLS# 1043986
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    1 of 42
    $374,900
    3

    Beds

    2.1

    Baths

    1,331

    Sq.Ft.

    2921 Whispering Hills

    Chester, NY

    Courtesy of ARC REALTY 1 IN SALES
    View 50 Hambletonian Avenue Chester, NY MLS# 1042882
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    Save 50 Hambletonian Avenue Chester, NY MLS# 1042882
    1 of 45
    $550,000
    3

    Beds

    2.0

    Baths

    1,583

    Sq.Ft.

    50 Hambletonian Avenue

    Chester, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 1005 Whispering Hills Chester, NY MLS# 1043197
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    1 of 28
    $290,000
    2

    Beds

    1.1

    Baths

    1,053

    Sq.Ft.

    1005 Whispering Hills

    Chester, NY

    Courtesy of CENTURY 21 FULL SERVICE REALTY
    View 6 Main Street Chester, NY MLS# 1043650
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    1 of 5
    $25,000
    700

    Sq.Ft.

    6 Main Street

    Chester, NY

    Courtesy of HOMESMART HOMES & ESTATES
    View 63 Hubshop Road Chester, NY MLS# 1039933
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    Save 63 Hubshop Road Chester, NY MLS# 1039933
    1 of 19
    $459,000
    4

    Beds

    2.1

    Baths

    2,060

    Sq.Ft.

    63 Hubshop Road

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 32 Surrey Road Chester, NY MLS# 1040785
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    1 of 39
    $489,000
    4

    Beds

    1.1

    Baths

    1,820

    Sq.Ft.

    32 Surrey Road

    Chester, NY

    Courtesy of EXP REALTY
    View 1367 Kings Highway Chester, NY MLS# 1036770
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    1 of 16
    $440,000
    3

    Beds

    1.1

    Baths

    1,728

    Sq.Ft.

    1367 Kings Highway

    Chester, NY

    Courtesy of GREENE REALTY GROUP
    View 166 Bull Mill Road Chester, NY MLS# 1030923
      Save 166 Bull Mill Road Chester, NY MLS# 1030923
      1 of 37
      $340,000
      2

      Beds

      1.0

      Baths

      1,004

      Sq.Ft.

      166 Bull Mill Road

      Chester, NY

      Courtesy of KELLER WILLIAMS VALLEY REALTY
      View 21 Trotting Drive Chester, NY MLS# 1030740
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      1 of 50
      $475,000
      3

      Beds

      2.0

      Baths

      1,624

      Sq.Ft.

      21 Trotting Drive

      Chester, NY

      Courtesy of KELLER WILLIAMS REALTY
      View 70 Main Street Chester, NY MLS# 1034449
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        1 of 27
        $469,000
        3

        Beds

        1.2

        Baths

        1,357

        Sq.Ft.

        70 Main Street

        Chester, NY

        Courtesy of CURASI REALTY, INC.
        View 66 Whitetail Run Chester, NY MLS# 1033721
          Save 66 Whitetail Run Chester, NY MLS# 1033721
          1 of 50
          $449,000
          3

          Beds

          1.1

          Baths

          1,500

          Sq.Ft.

          66 Whitetail Run

          Chester, NY

          Courtesy of HOWARD HANNA RAND REALTY
          View 2522 Whispering Hills Chester, NY MLS# 1027103
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            1 of 35
            $369,000
            3

            Beds

            2.1

            Baths

            1,331

            Sq.Ft.

            2522 Whispering Hills

            Chester, NY

            Courtesy of HOWARD HANNA RAND REALTY
            View 151 Main Street Chester, NY MLS# 1031155
              Save 151 Main Street Chester, NY MLS# 1031155
              1 of 16
              $299,000
              4

              Beds

              1.0

              Baths

              1,504

              Sq.Ft.

              151 Main Street

              Chester, NY

              Courtesy of HUDSON VALLEY GRIFFITH
              View 4008 Whispering Hills Drive Chester, NY MLS# 1027838
                Save 4008 Whispering Hills Drive Chester, NY MLS# 1027838
                1 of 33
                $290,000
                2

                Beds

                1.1

                Baths

                1,072

                Sq.Ft.

                4008 Whispering Hills Drive

                Chester, NY

                Courtesy of HOWARD HANNA RAND REALTY
                View 185 Oxford Road Chester, NY MLS# 1019170
                  Save 185 Oxford Road Chester, NY MLS# 1019170
                  1 of 49
                  $389,000
                  3

                  Beds

                  1.0

                  Baths

                  1,062

                  Sq.Ft.

                  185 Oxford Road

                  Chester, NY

                  Courtesy of KELLER WILLIAMS HUDSON VALLEY
                  View 7 Lakeview Drive Chester, NY MLS# 1028872
                    Save 7 Lakeview Drive Chester, NY MLS# 1028872
                    1 of 29
                    $549,999
                    4

                    Beds

                    2.1

                    Baths

                    2,098

                    Sq.Ft.

                    7 Lakeview Drive

                    Chester, NY

                    Courtesy of HOWARD HANNA RAND REALTY
                    View 4114 Whispering Hills Chester, NY MLS# 1027245
                      Save 4114 Whispering Hills Chester, NY MLS# 1027245
                      1 of 29
                      $389,900
                      3

                      Beds

                      2.0

                      Baths

                      1,393

                      Sq.Ft.

                      4114 Whispering Hills

                      Chester, NY

                      Courtesy of COLDWELL BANKER REALTY

                      About Chester

                      Listings in Chester, NY

                      109

                      Estimated median home price

                      $699,000
                      Chester NY Homes for Sale & Properties

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

                      Homes for Sale by Price in Chester, NY

                      PriceCount
                      $0 - 100K1
                      $100K - 200K0
                      $200K - 300K8
                      $300K - 400K18
                      $400K - 500K12
                      $500K - 600K9
                      $600K - 700K12
                      $700K - 800K20
                      $800K - 900K10
                      $900K - 1M6
                      $1M - Max13

                      Homes for Sale by Type in Chester, NY

                      Property TypeCount
                      Single Family79
                      Townhouse0
                      Condo17
                      Commercial6
                      Rental23
                      Lots and Land5
                      Condo/Town/CoOp0
                      CoOp0
                      Multi Family2
                      Mobile Home0
                      Farms0

                      (Data as of 8/30/2026)

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                      Information deemed reliable but not guaranteed.

                      The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

                      The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

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