View 16 Oxford Springs Road Chester, NY MLS# 935115
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$750,000
3

Beds

3.0

Baths

2,870

Sq.Ft.

16 Oxford Springs Road

Chester, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 5 Bens Way Chester, NY MLS# 959390
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    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 7 Park Place Chester, NY MLS# 927218
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      1 of 48
      $730,000
      4

      Beds

      3.1

      Baths

      2,780

      Sq.Ft.

      7 Park Place

      Chester, NY

      Courtesy of CENTURY 21 FULL SERVICE REALTY
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 9 Country Woods Drive Chester, NY MLS# 925049
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      $725,000
      5

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      2.1

      Baths

      3,124

      Sq.Ft.

      9 Country Woods Drive

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View 487 Black Meadow Road Chester, NY MLS# 960665
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        $725,000
        6

        Beds

        3.1

        Baths

        4,204

        Sq.Ft.

        487 Black Meadow Road

        Chester, NY

        Courtesy of JOSEPH BARATTA COMPANY REALTY
        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 360 Prospect Road Chester, NY MLS# 944607
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            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 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 50 Elkay Drive Chester, NY MLS# 954329
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              $675,000
              Studio

              Beds

              0.0

              Baths

              87,120

              Sq.Ft.

              50 Elkay Drive

              Chester, NY

              Courtesy of POINT REALTY USA
              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 391 Bull Mill Road Chester, NY MLS# 880804
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                $509,999
                2

                Beds

                2.0

                Baths

                1,714

                Sq.Ft.

                391 Bull Mill Road

                Chester, NY

                Courtesy of CENTURY 21 REALTY CENTER
                View Main Street Chester, NY MLS# H6204360
                  Save Main Street Chester, NY MLS# H6204360
                  1 of 2
                  $500,000
                  Studio

                  Beds

                  0.0

                  Baths

                  36,098

                  Sq.Ft.

                  Main Street

                  Chester, NY

                  Courtesy of KELLER WILLIAMS REALTY
                  View 70 Main Street Chester, NY MLS# 914556
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                    1 of 23
                    $475,000
                    4

                    Beds

                    2.1

                    Baths

                    1,357

                    Sq.Ft.

                    70 Main Street

                    Chester, NY

                    Courtesy of KELLER WILLIAMS HUDSON VALLEY
                    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 31 Hudson Street Chester, NY MLS# 963657
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                      1 of 25
                      $449,900
                      2

                      Beds

                      2.0

                      Baths

                      1,998

                      Sq.Ft.

                      31 Hudson Street

                      Chester, NY

                      Courtesy of BHG REAL ESTATE GREEN TEAM
                      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 16 Oakland Avenue Chester, NY MLS# 939522
                        Save 16 Oakland Avenue Chester, NY MLS# 939522
                        1 of 49
                        $425,000
                        4

                        Beds

                        2.1

                        Baths

                        2,090

                        Sq.Ft.

                        16 Oakland Avenue

                        Chester, NY

                        Courtesy of BHG REAL ESTATE GREEN TEAM
                        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 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 2915 Whispering Hills Chester, NY MLS# 927990
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                        1 of 23
                        $369,000
                        3

                        Beds

                        2.1

                        Baths

                        1,331

                        Sq.Ft.

                        2915 Whispering Hills

                        Chester, NY

                        Courtesy of CENTURY 21 FULL SERVICE 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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