View 111 Ayr Road Chester, NY MLS# 1049653
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$599,000
4

Beds

4.1

Baths

3,326

Sq.Ft.

111 Ayr Road

Chester, NY

Courtesy of CURASI REALTY, INC.
View 985 Craigville Road Chester, NY MLS# 1057348
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1 of 36
$750,000
4

Beds

3.1

Baths

3,100

Sq.Ft.

985 Craigville Road

Chester, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 3706 Whispering Hills Chester, NY MLS# 1039289
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$339,900
2

Beds

1.1

Baths

1,086

Sq.Ft.

3706 Whispering Hills

Chester, NY

Courtesy of EXP REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2107 Whispering Hills Chester, NY MLS# 1050213
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1 of 34
$309,000
2

Beds

1.1

Baths

1,086

Sq.Ft.

2107 Whispering Hills

Chester, NY

Courtesy of WANSOR REALTY
View 94 Booth Road Chester, NY MLS# 1050173
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$525,000
3

Beds

2.1

Baths

2,441

Sq.Ft.

94 Booth Road

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 147 Main Street Chester, NY MLS# 1052484
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$549,000
4

Beds

2.0

Baths

2,824

Sq.Ft.

147 Main Street

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 19 Meadow Avenue Chester, NY MLS# 1050131
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$525,000
2

Beds

2.0

Baths

1,910

Sq.Ft.

19 Meadow Avenue

Chester, NY

Courtesy of RE/MAX TOWN & COUNTRY
View 1212 Whispering Hills Chester, NY MLS# 1048656
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1 of 48
$269,000
2

Beds

1.0

Baths

1,084

Sq.Ft.

1212 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 18 Schueler Road Chester, NY MLS# 1046033
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1 of 43
$339,900
2

Beds

1.0

Baths

960

Sq.Ft.

18 Schueler Road

Chester, NY

Courtesy of Weichert Realtors - Monroe
View 1168 Craigville Road Chester, NY MLS# 1050193
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$779,900
4

Beds

2.1

Baths

2,616

Sq.Ft.

1168 Craigville Road

Chester, NY

Courtesy of ARC REALTY 1 IN SALES
View 3211 Whispering Hills Chester, NY MLS# 1046996
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$370,000
3

Beds

2.0

Baths

1,316

Sq.Ft.

3211 Whispering Hills

Chester, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 5 Red Fox Run Chester, NY MLS# 1046418
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    1 of 47
    $679,000
    4

    Beds

    3.1

    Baths

    2,960

    Sq.Ft.

    5 Red Fox Run

    Chester, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 3409 Whispering Hills Chester, NY MLS# 1032618
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      1 of 24
      $360,000
      3

      Beds

      2.1

      Baths

      1,331

      Sq.Ft.

      3409 Whispering Hills

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View 4704 Whispering Hills Chester, NY MLS# 1038636
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        1 of 19
        $370,000
        3

        Beds

        2.1

        Baths

        1,331

        Sq.Ft.

        4704 Whispering Hills

        Chester, NY

        Courtesy of SAHAGIAN REALTY LLC
        View 188 Creamery Pond Road Chester, NY MLS# 1038759
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        1 of 45
        $675,000
        3

        Beds

        2.1

        Baths

        3,202

        Sq.Ft.

        188 Creamery Pond Road

        Chester, NY

        Courtesy of KELLER WILLIAMS REALTY
        View 3561 Rte 94 Chester, NY MLS# 1041906
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        OPEN HOUSE: Saturday 10/3 11:00 AM - 1:00 PM
        $619,999
        3

        Beds

        3.0

        Baths

        2,902

        Sq.Ft.

        3561 Rte 94

        Chester, NY

        Courtesy of HOWARD HANNA RAND REALTY
        View 2124 Whispering Hills Chester, NY MLS# 1042658
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        1 of 18
        $289,000
        2

        Beds

        1.0

        Baths

        1,084

        Sq.Ft.

        2124 Whispering Hills

        Chester, NY

        Courtesy of HOWARD HANNA RAND REALTY
        View 260 Gibson Hill Road Chester, NY MLS# 1044316
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          1 of 22
          $374,900
          3

          Beds

          1.1

          Baths

          1,644

          Sq.Ft.

          260 Gibson Hill Road

          Chester, NY

          Courtesy of KELLER WILLIAMS REALTY
          View 2921 Whispering Hills Chester, NY MLS# 1043986
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            1 of 42
            $364,900
            3

            Beds

            2.1

            Baths

            1,331

            Sq.Ft.

            2921 Whispering Hills

            Chester, NY

            Courtesy of ARC REALTY 1 IN SALES
            View 50 Hambletonian Avenue Chester, NY MLS# 1042882
              Save 50 Hambletonian Avenue Chester, NY MLS# 1042882
              1 of 1
              $550,000
              3

              Beds

              2.0

              Baths

              1,583

              Sq.Ft.

              50 Hambletonian Avenue

              Chester, NY

              Courtesy of HOWARD HANNA RAND REALTY

              About Chester

              Listings in Chester, NY

              101

              Estimated median home price

              $675,000
              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 - 100K1
              $100K - 200K0
              $200K - 300K10
              $300K - 400K18
              $400K - 500K8
              $500K - 600K9
              $600K - 700K11
              $700K - 800K17
              $800K - 900K10
              $900K - 1M6
              $1M - Max11

              Homes for Sale by Type in Chester, NY

              Property TypeCount
              Single Family67
              Townhouse0
              Condo21
              Commercial6
              Rental22
              Lots and Land4
              Condo/Town/CoOp0
              CoOp0
              Multi Family3
              Mobile Home0
              Farms0

              (Data as of 10/2/2026)

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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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