View 1414 Kings Highway Chester, NY MLS# 965992
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1 of 7
$879,900
4

Beds

2.1

Baths

3,200

Sq.Ft.

1414 Kings Highway

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View * Lot #4 Wells Sweep Lane Chester, NY MLS# 966048
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1 of 6
$869,900
4

Beds

2.1

Baths

3,000

Sq.Ft.

* Lot #4 Wells Sweep Lane

Chester, NY

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

Beds

1.1

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 558 Pine Hill Road Chester, NY MLS# 958731
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1 of 50
$850,000
4

Beds

2.1

Baths

3,120

Sq.Ft.

558 Pine Hill Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC
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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1 of 1
$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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Save 7 Hambletonian Avenue Chester, NY MLS# 964090
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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1 of 9
$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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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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1 of 46
$849,999
5

Beds

5.1

Baths

5,403

Sq.Ft.

4 Debbie Court

Chester, NY

Courtesy of FLAG REALTY GROUP
View 487 Black Meadow Road Chester, NY MLS# 960665
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1 of 35
$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 3/8 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
      Save 34 Mountainside Drive Chester, NY MLS# 956879
      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
        Save 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
        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
          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
            Save 1367 Kings Highway Chester, NY MLS# 951876
            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
            OPEN HOUSE: Sunday 3/8 1:00 PM - 3:00 PM
            $899,000
            4

            Beds

            2.1

            Baths

            2,722

            Sq.Ft.

            5 Gabriels Drive

            Chester, NY

            Courtesy of KELLER WILLIAMS REALTY
            View 4508 Whispering Hills Chester, NY MLS# 951306
              Save 4508 Whispering Hills Chester, NY MLS# 951306
              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

                About Chester

                Listings in Chester, NY

                59

                Estimated median home price

                $500,000
                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 - 300K10
                $300K - 400K8
                $400K - 500K9
                $500K - 600K2
                $600K - 700K5
                $700K - 800K7
                $800K - 900K5
                $900K - 1M3
                $1M - Max7

                Homes for Sale by Type in Chester, NY

                Property TypeCount
                Single Family33
                Townhouse0
                Condo10
                Commercial4
                Rental26
                Lots and Land12
                Condo/Town/CoOp0
                CoOp0
                Multi Family0
                Mobile Home0
                Farms0

                (Data as of 3/2/2026)

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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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