View 107 Pine Hill Road Chester, NY MLS# 1003546
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    1 of 33
    $549,000
    3

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    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 94 Booth Road Chester, NY MLS# 898870
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      OPEN HOUSE: Saturday 5/30 1:00 PM - 2:00 PM
      $590,000
      3

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      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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      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

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      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

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      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

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      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
      $425,000
      3

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      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

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      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

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      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

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      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

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      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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      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
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      1 of 30
      $550,000
      5

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      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
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      1 of 43
      $450,000
      3

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      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
      View 4 Greycourt Road Chester, NY MLS# 992700
        Save 4 Greycourt Road Chester, NY MLS# 992700
        1 of 12
        $640,000
        3

        Beds

        1.1

        Baths

        2,136

        Sq.Ft.

        4 Greycourt Road

        Chester, NY

        Courtesy of MK REALTY INC

        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 - 400K18
        $400K - 500K11
        $500K - 600K5
        $600K - 700K7
        $700K - 800K12
        $800K - 900K10
        $900K - 1M6
        $1M - Max11

        Homes for Sale by Type in Chester, NY

        Property TypeCount
        Single Family57
        Townhouse0
        Condo13
        Commercial5
        Rental24
        Lots and Land13
        Condo/Town/CoOp0
        CoOp0
        Multi Family0
        Mobile Home0
        Farms0

        (Data as of 5/27/2026)

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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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