View 307 Gibson Hill Road Chester, NY MLS# 968972
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$350,000
2

Beds

1.0

Baths

1,272

Sq.Ft.

307 Gibson Hill Road

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 2203 Whispering Hills Chester, NY MLS# 954443
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1 of 14
$370,000
3

Beds

2.1

Baths

1,331

Sq.Ft.

2203 Whispering Hills

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 31 Hudson Street Chester, NY MLS# 963657
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$449,900
2

Beds

2.0

Baths

1,998

Sq.Ft.

31 Hudson Street

Chester, NY

Courtesy of BHG REAL ESTATE GREEN TEAM
The time to sell is now! THE TIME TO SELL IS NOW!
View 552 Pine Hill Road Chester, NY MLS# 958740
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$350,000
Studio

Beds

0.0

Baths

248,292

Sq.Ft.

552 Pine Hill Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC
View 1005 Whispering Hills Chester, NY MLS# 964957
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$249,900
2

Beds

1.1

Baths

1,053

Sq.Ft.

1005 Whispering Hills

Chester, NY

Courtesy of ARC REALTY 1 IN SALES
View 7 Hambletonian Avenue Chester, NY MLS# 964090
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1 of 23
$425,000
2

Beds

1.0

Baths

1,026

Sq.Ft.

7 Hambletonian Avenue

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES
View 2 Imperial Park Chester, NY MLS# 964115
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$149,900
Studio

Beds

0.0

Baths

8,875

Sq.Ft.

2 Imperial Park

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES
View 34 Booth Road Chester, NY MLS# 961100
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$699,000
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 487 Black Meadow Road Chester, NY MLS# 960665
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      1 of 35
      OPEN HOUSE: Saturday 3/14 12:00 PM - 3:00 PM
      $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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        1 of 26
        OPEN HOUSE: Sunday 3/15 1:00 PM - 3:00 PM
        $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 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
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            1 of 38
            $635,000
            3

            Beds

            2.1

            Baths

            1,954

            Sq.Ft.

            25 Sugarloaf Mountain Road

            Chester, NY

            Courtesy of CRONIN & COMPANY REAL ESTATE
            View 50 Elkay Drive Chester, NY MLS# 954329
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              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 4508 Whispering Hills Chester, NY MLS# 951306
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                  1 of 20
                  $299,999
                  2

                  Beds

                  1.1

                  Baths

                  1,072

                  Sq.Ft.

                  4508 Whispering Hills

                  Chester, NY

                  Courtesy of EXP REALTY
                  View 2113 Whispering Hills Chester, NY MLS# 950534
                    Save 2113 Whispering Hills Chester, NY MLS# 950534
                    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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                    $444,000
                    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
                      Save 3308 Whispering Hills Drive Chester, NY MLS# 924165
                      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

                        About Chester

                        Listings in Chester, NY

                        58

                        Estimated median home price

                        $505,000
                        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 - 200K3
                        $200K - 300K9
                        $300K - 400K10
                        $400K - 500K7
                        $500K - 600K1
                        $600K - 700K5
                        $700K - 800K6
                        $800K - 900K6
                        $900K - 1M4
                        $1M - Max7

                        Homes for Sale by Type in Chester, NY

                        Property TypeCount
                        Single Family30
                        Townhouse0
                        Condo11
                        Commercial5
                        Rental26
                        Lots and Land12
                        Condo/Town/CoOp0
                        CoOp0
                        Multi Family0
                        Mobile Home0
                        Farms0

                        (Data as of 3/14/2026)

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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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