View 34 Booth Road Chester, NY MLS# 961100
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1 of 42
$720,000
4

Beds

2.1

Baths

2,506

Sq.Ft.

34 Booth Road

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
View 2913 Whispering Hills Chester, NY MLS# 962709
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1 of 29
$279,900
2

Beds

1.0

Baths

1,084

Sq.Ft.

2913 Whispering Hills

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES
View 4 Debbie Court Chester, NY MLS# 962813
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$849,999
5

Beds

5.1

Baths

5,403

Sq.Ft.

4 Debbie Court

Chester, NY

Courtesy of FLAG REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 487 Black Meadow Road Chester, NY MLS# 960665
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1 of 30
$725,000
6

Beds

3.1

Baths

4,204

Sq.Ft.

487 Black Meadow Road

Chester, NY

Courtesy of JOSEPH BARATTA COMPANY REALTY
View 5 Bens Way Chester, NY MLS# 959390
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$744,999
4

Beds

2.1

Baths

2,544

Sq.Ft.

5 Bens Way

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 34 Mountainside Drive Chester, NY MLS# 956879
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    1 of 8
    $699,990
    4

    Beds

    3.0

    Baths

    1,867

    Sq.Ft.

    34 Mountainside Drive

    Chester, NY

    Courtesy of OUR HOUSE REAL ESTATE GROUP
    View 50 Elkay Drive Chester, NY MLS# 954329
      Save 50 Elkay Drive Chester, NY MLS# 954329
      1 of 3
      $675,000
      Studio

      Beds

      0.0

      Baths

      87,120

      Sq.Ft.

      50 Elkay Drive

      Chester, NY

      Courtesy of POINT REALTY USA
      View 1367 Kings Highway Chester, NY MLS# 951876
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        1 of 13
        $460,000
        3

        Beds

        1.1

        Baths

        1,728

        Sq.Ft.

        1367 Kings Highway

        Chester, NY

        Courtesy of KARTEN REAL ESTATE SVCS LLC
        View 5 Gabriels Drive Chester, NY MLS# 952148
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        1 of 49
        $899,000
        4

        Beds

        2.1

        Baths

        2,722

        Sq.Ft.

        5 Gabriels Drive

        Chester, NY

        Courtesy of KELLER WILLIAMS REALTY
        View 2113 Whispering Hills Chester, NY MLS# 950534
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          1 of 24
          $295,000
          2

          Beds

          1.0

          Baths

          1,084

          Sq.Ft.

          2113 Whispering Hills

          Chester, NY

          Courtesy of KELLER WILLIAMS REALTY
          View 108 Pine Hill Road Chester, NY MLS# 944582
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          1 of 37
          $449,000
          4

          Beds

          1.1

          Baths

          1,780

          Sq.Ft.

          108 Pine Hill Road

          Chester, NY

          Courtesy of AVION
          View 3308 Whispering Hills Drive Chester, NY MLS# 924165
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            1 of 30
            $289,000
            2

            Beds

            1.1

            Baths

            1,072

            Sq.Ft.

            3308 Whispering Hills Drive

            Chester, NY

            Courtesy of HOWARD HANNA RAND REALTY
            View Oxford Road Chester, NY MLS# 946546
              Save Oxford Road Chester, NY MLS# 946546
              1 of 2
              $199,000
              Studio

              Beds

              0.0

              Baths

              313,632

              Sq.Ft.

              Oxford Road

              Chester, NY

              Courtesy of BLOOMING REALTY
              View Oxford Road Chester, NY MLS# 945194
                Save Oxford Road Chester, NY MLS# 945194
                1 of 1
                $199,000
                Studio

                Beds

                0.0

                Baths

                113,256

                Sq.Ft.

                Oxford Road

                Chester, NY

                Courtesy of BLOOMING REALTY
                View 360 Prospect Road Chester, NY MLS# 944607
                  Save 360 Prospect Road Chester, NY MLS# 944607
                  1 of 50
                  $699,000
                  3

                  Beds

                  3.0

                  Baths

                  3,000

                  Sq.Ft.

                  360 Prospect Road

                  Chester, NY

                  Courtesy of EREALTY ADVISORS, INC
                  View 6 Vista Drive Chester, NY MLS# 944968
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                  1 of 45
                  $499,900
                  3

                  Beds

                  2.1

                  Baths

                  1,934

                  Sq.Ft.

                  6 Vista Drive

                  Chester, NY

                  Courtesy of KELLER WILLIAMS REALTY
                  View 3120 Whispering Hills Chester, NY MLS# 941582
                    Save 3120 Whispering Hills Chester, NY MLS# 941582
                    1 of 18
                    $299,000
                    2

                    Beds

                    1.1

                    Baths

                    1,072

                    Sq.Ft.

                    3120 Whispering Hills

                    Chester, NY

                    Courtesy of JOHN J LEASE REALTORS INC
                    View 44 Cedar Pond Lane Chester, NY MLS# 942578
                      Save 44 Cedar Pond Lane Chester, NY MLS# 942578
                      1 of 42
                      $600,000
                      3

                      Beds

                      2.0

                      Baths

                      1,876

                      Sq.Ft.

                      44 Cedar Pond Lane

                      Chester, NY

                      Courtesy of EXP REALTY
                      View 101 Oxford Road Chester, NY MLS# 943068
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                      Save 101 Oxford Road Chester, NY MLS# 943068
                      1 of 1
                      $669,000
                      3

                      Beds

                      1.1

                      Baths

                      1,816

                      Sq.Ft.

                      101 Oxford Road

                      Chester, NY

                      Courtesy of LOOP REALTY INC
                      View 3917 Whispering Hills Chester, NY MLS# 942965
                        Save 3917 Whispering Hills Chester, NY MLS# 942965
                        1 of 28
                        $314,000
                        2

                        Beds

                        1.1

                        Baths

                        1,072

                        Sq.Ft.

                        3917 Whispering Hills

                        Chester, NY

                        Courtesy of KELLER WILLIAMS HUDSON VALLEY

                        About Chester

                        Listings in Chester, NY

                        57

                        Estimated median home price

                        $600,000
                        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 - 100K0
                        $100K - 200K2
                        $200K - 300K8
                        $300K - 400K8
                        $400K - 500K8
                        $500K - 600K3
                        $600K - 700K4
                        $700K - 800K8
                        $800K - 900K3
                        $900K - 1M3
                        $1M - Max10

                        Homes for Sale by Type in Chester, NY

                        Property TypeCount
                        Single Family32
                        Townhouse0
                        Condo9
                        Commercial5
                        Rental25
                        Lots and Land10
                        Condo/Town/CoOp0
                        CoOp0
                        Multi Family1
                        Mobile Home0
                        Farms0

                        (Data as of 2/22/2026)

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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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