View 107 Pine Hill Road Chester, NY MLS# 1003546
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    1 of 33
    OPEN HOUSE: Sunday 5/31 1:00 PM - 3:00 PM
    $549,000
    3

    Beds

    2.1

    Baths

    1,730

    Sq.Ft.

    107 Pine Hill Road

    Chester, NY

    Courtesy of HUDSON VALLEY GRIFFITH
    View 270 Bull Mill Road Chester, NY MLS# 1000373
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    1 of 25
    $779,000
    4

    Beds

    3.1

    Baths

    2,948

    Sq.Ft.

    270 Bull Mill Road

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 86 Long Vista Lane Chester, NY MLS# 1003760
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    1 of 47
    $985,000
    5

    Beds

    3.1

    Baths

    3,764

    Sq.Ft.

    86 Long Vista Lane

    Chester, NY

    Courtesy of RE/MAX TOWN & COUNTRY
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 102 Beverly Road Chester, NY MLS# 1005710
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    $1,090,000
    4

    Beds

    3.1

    Baths

    3,854

    Sq.Ft.

    102 Beverly Road

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 94 Booth Road Chester, NY MLS# 898870
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    OPEN HOUSE: Saturday 5/30 2:30 PM - 4:30 PM
    $590,000
    3

    Beds

    2.1

    Baths

    2,083

    Sq.Ft.

    94 Booth Road

    Chester, NY

    Courtesy of COMPASS GREATER NY, LLC
    View 45 Whitetail Run Chester, NY MLS# 999741
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    Save 45 Whitetail Run Chester, NY MLS# 999741
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    OPEN HOUSE: Sunday 5/31 11:00 AM - 1:00 PM
    $825,000
    4

    Beds

    2.1

    Baths

    2,732

    Sq.Ft.

    45 Whitetail Run

    Chester, NY

    Courtesy of HUDSON VALLEY HOME CONNECTION
    View 1 N Hudson Street Chester, NY MLS# 1001003
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    1 of 38
    $499,900
    3

    Beds

    2.0

    Baths

    1,778

    Sq.Ft.

    1 N Hudson Street

    Chester, NY

    Courtesy of KELLER WILLIAMS HUDSON VALLEY
    View 11 Oxford Depot Chester, NY MLS# 1002651
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    1 of 26
    $425,000
    3

    Beds

    2.0

    Baths

    1,748

    Sq.Ft.

    11 Oxford Depot

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 492 Black Meadow Road Chester, NY MLS# 1002697
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    1 of 17
    $399,000
    Studio

    Beds

    0.0

    Baths

    2,003,760

    Sq.Ft.

    492 Black Meadow Road

    Chester, NY

    Courtesy of EXP REALTY
    View 60 Whitetail Run Chester, NY MLS# 1002536
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    1 of 7
    $900,000
    4

    Beds

    2.1

    Baths

    2,588

    Sq.Ft.

    60 Whitetail Run

    Chester, NY

    Courtesy of REALTY BLUE CORP
    View 2722 Whispering Hills Chester, NY MLS# 994269
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    1 of 37
    $424,999
    3

    Beds

    2.1

    Baths

    1,331

    Sq.Ft.

    2722 Whispering Hills

    Chester, NY

    Courtesy of ARTISAN REALTY
    View 220 Oxford Road Chester, NY MLS# 000137
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    1 of 3
    $999,000
    3

    Beds

    3.1

    Baths

    3,535

    Sq.Ft.

    220 Oxford Road

    Chester, NY

    Courtesy of BLOOMING REALTY
    View 3815 Whispering Hills Drive Chester, NY MLS# 1000359
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    1 of 50
    $370,000
    3

    Beds

    2.1

    Baths

    1,331

    Sq.Ft.

    3815 Whispering Hills Drive

    Chester, NY

    Courtesy of MK REALTY INC
    View 4 Debbie Court Chester, NY MLS# 995223
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    1 of 49
    $799,000
    5

    Beds

    5.1

    Baths

    5,403

    Sq.Ft.

    4 Debbie Court

    Chester, NY

    Courtesy of FLAG REALTY GROUP
    View 2 Garnett Hill Road Chester, NY MLS# 999261
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    1 of 35
    $999,999
    5

    Beds

    2.1

    Baths

    4,772

    Sq.Ft.

    2 Garnett Hill Road

    Chester, NY

    Courtesy of PLATINUM REALTY ASSOCIATES
    View 63 Hubshop Road Chester, NY MLS# 997559
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    1 of 45
    $529,000
    4

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    2.1

    Baths

    2,060

    Sq.Ft.

    63 Hubshop Road

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 58 Nancy Lane Chester, NY MLS# 995624
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      1 of 46
      OPEN HOUSE: Sunday 5/31 12:00 PM - 2:00 PM
      $799,999
      3

      Beds

      2.1

      Baths

      2,718

      Sq.Ft.

      58 Nancy Lane

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View 208 Glenmere Road Chester, NY MLS# 996648
        Save 208 Glenmere Road Chester, NY MLS# 996648
        1 of 30
        $550,000
        5

        Beds

        2.1

        Baths

        1,815

        Sq.Ft.

        208 Glenmere Road

        Chester, NY

        Courtesy of MK REALTY INC
        View 151 Laroe Road Chester, NY MLS# 995916
          Save 151 Laroe Road Chester, NY MLS# 995916
          1 of 43
          $450,000
          3

          Beds

          1.1

          Baths

          1,177

          Sq.Ft.

          151 Laroe Road

          Chester, NY

          Courtesy of KELLER WILLIAMS REALTY
          View 19 High Street Chester, NY MLS# 995148
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          1 of 50
          $1,195,000
          9

          Beds

          6.1

          Baths

          4,965

          Sq.Ft.

          19 High Street

          Chester, NY

          Courtesy of KELLER WILLIAMS REALTY

          About Chester

          Listings in Chester, NY

          88

          Estimated median home price

          $637,500
          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 - 300K5
          $300K - 400K17
          $400K - 500K11
          $500K - 600K6
          $600K - 700K7
          $700K - 800K11
          $800K - 900K10
          $900K - 1M6
          $1M - Max12

          Homes for Sale by Type in Chester, NY

          Property TypeCount
          Single Family58
          Townhouse0
          Condo13
          Commercial5
          Rental23
          Lots and Land12
          Condo/Town/CoOp0
          CoOp0
          Multi Family0
          Mobile Home0
          Farms0

          (Data as of 5/29/2026)

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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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