View 4508 Whispering Hills Chester, NY MLS# 951306
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OPEN HOUSE: Sunday 1/18 12:00 PM - 2:00 PM
$325,000
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
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$295,000
2

Beds

1.0

Baths

1,084

Sq.Ft.

2113 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 3910 Whispering Hills Chester, NY MLS# 946789
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OPEN HOUSE: Saturday 1/17 11:30 AM - 2:00 PM
$369,900
3

Beds

2.1

Baths

1,331

Sq.Ft.

3910 Whispering Hills

Chester, NY

Courtesy of EXP REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 108 Pine Hill Road Chester, NY MLS# 944582
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$449,000
4

Beds

1.1

Baths

1,780

Sq.Ft.

108 Pine Hill Road

Chester, NY

Courtesy of AVION
View 3308 Whispering Hills Drive Chester, NY MLS# 924165
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OPEN HOUSE: Saturday 1/17 12:00 PM - 2:00 PM
$299,000
2

Beds

1.1

Baths

1,072

Sq.Ft.

3308 Whispering Hills Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 25 Oakland Avenue Chester, NY MLS# 949886
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$28,000,000
270,000

Sq.Ft.

25 Oakland Avenue

Chester, NY

Courtesy of EREALTY ADVISORS, INC
View 2 Garnett Hill Road Chester, NY MLS# 931380
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$999,999
5

Beds

3.1

Baths

4,772

Sq.Ft.

2 Garnett Hill Road

Chester, NY

Courtesy of PLATINUM REALTY ASSOCIATES
View Oxford Road Chester, NY MLS# 946546
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$199,000
Studio

Beds

0.0

Baths

313,632

Sq.Ft.

Oxford Road

Chester, NY

Courtesy of BLOOMING REALTY
View Oxford Road Chester, NY MLS# 945194
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$199,000
Studio

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0.0

Baths

113,256

Sq.Ft.

Oxford Road

Chester, NY

Courtesy of BLOOMING REALTY
View 360 Prospect Road Chester, NY MLS# 944607
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    $699,000
    3

    Beds

    3.0

    Baths

    3,000

    Sq.Ft.

    360 Prospect Road

    Chester, NY

    Courtesy of EREALTY ADVISORS, INC
    View 6 Vista Drive Chester, NY MLS# 944968
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    $499,900
    3

    Beds

    2.1

    Baths

    1,934

    Sq.Ft.

    6 Vista Drive

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 4 Debbie Court Chester, NY MLS# 942910
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      1 of 41
      $849,000
      5

      Beds

      5.1

      Baths

      5,403

      Sq.Ft.

      4 Debbie Court

      Chester, NY

      Courtesy of FLAG REALTY GROUP
      View 23 White Oak Drive Chester, NY MLS# 943245
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        $3,000
        1,150

        Sq.Ft.

        23 White Oak Drive

        Chester, NY

        Courtesy of KELLER WILLIAMS REALTY
        View 3120 Whispering Hills Chester, NY MLS# 941582
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          1 of 18
          $310,000
          2

          Beds

          1.1

          Baths

          1,072

          Sq.Ft.

          3120 Whispering Hills

          Chester, NY

          Courtesy of JOHN J LEASE REALTORS INC
          View 101 Oxford Road Chester, NY MLS# 943068
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          $669,000
          3

          Beds

          1.1

          Baths

          1,816

          Sq.Ft.

          101 Oxford Road

          Chester, NY

          Courtesy of LOOP REALTY INC
          View 3917 Whispering Hills Chester, NY MLS# 942965
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            1 of 28
            $319,000
            2

            Beds

            1.1

            Baths

            1,072

            Sq.Ft.

            3917 Whispering Hills

            Chester, NY

            Courtesy of KELLER WILLIAMS HUDSON VALLEY
            View 2948 State Route 94 Chester, NY MLS# 940751
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              OPEN HOUSE: Saturday 1/17 1:00 PM - 3:00 PM
              $1,395,000
              4

              Beds

              2.1

              Baths

              3,866

              Sq.Ft.

              2948 State Route 94

              Chester, NY

              Courtesy of TUXEDO HUDSON REALTY CORP
              View 23 Pewter Circle Chester, NY MLS# 939836
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              $650,000
              4

              Beds

              2.1

              Baths

              2,318

              Sq.Ft.

              23 Pewter Circle

              Chester, NY

              Courtesy of EXP REALTY
              View 16 Oakland Avenue Chester, NY MLS# 939522
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                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 65 Oxford Springs Road Chester, NY MLS# 938744
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                  1 of 50
                  $650,000
                  5

                  Beds

                  3.1

                  Baths

                  3,617

                  Sq.Ft.

                  65 Oxford Springs Road

                  Chester, NY

                  Courtesy of EXP REALTY

                  About Chester

                  Listings in Chester, NY

                  63

                  Estimated median home price

                  $515,000
                  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 - 200K2
                  $200K - 300K7
                  $300K - 400K12
                  $400K - 500K8
                  $500K - 600K4
                  $600K - 700K8
                  $700K - 800K4
                  $800K - 900K3
                  $900K - 1M1
                  $1M - Max13

                  Homes for Sale by Type in Chester, NY

                  Property TypeCount
                  Single Family34
                  Townhouse0
                  Condo11
                  Commercial7
                  Rental26
                  Lots and Land9
                  Condo/Town/CoOp0
                  CoOp0
                  Multi Family2
                  Mobile Home0
                  Farms0

                  (Data as of 1/15/2026)

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                  Information deemed reliable but not guaranteed.

                  All information provided is deemed reliable but is not guaranteed and should be independently verified.

                  Copyright 2026 by the Multiple Listing service of Ulster County, Inc. All Rights Reserved.

                  The data relating to real estate on this web site comes in part from the IDX of the Multiple Listing service of Ulster County, Inc. Real estate listings held by brokerage firms other that Weichert Realtors are marked with IDX logo and the detailed information about them includes the name of the listing broker.

                  The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

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