View 25 Oakland Avenue Chester, NY MLS# 949886
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1 of 17
$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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1 of 35
$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
The time to sell is now! THE TIME TO SELL IS NOW!
View Oxford Road Chester, NY MLS# 945194
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$199,000
Studio

Beds

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
    Save 4 Debbie Court Chester, NY MLS# 942910
    1 of 41
    OPEN HOUSE: Sunday 1/11 2:00 PM - 4:00 PM
    $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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      1 of 23
      $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
        Save 3120 Whispering Hills Chester, NY MLS# 941582
        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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        1 of 1
        $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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            1 of 45
            OPEN HOUSE: Saturday 1/10 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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            1 of 37
            $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
              Save 16 Oakland Avenue Chester, NY MLS# 939522
              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
                Save 65 Oxford Springs Road Chester, NY MLS# 938744
                1 of 50
                $650,000
                5

                Beds

                3.1

                Baths

                3,617

                Sq.Ft.

                65 Oxford Springs Road

                Chester, NY

                Courtesy of EXP REALTY
                View 2812 Whispering Hills Chester, NY MLS# 936470
                  Save 2812 Whispering Hills Chester, NY MLS# 936470
                  1 of 30
                  $290,000
                  2

                  Beds

                  1.0

                  Baths

                  1,084

                  Sq.Ft.

                  2812 Whispering Hills

                  Chester, NY

                  Courtesy of EXIT REALTY CONNECTIONS
                  View 16 Oxford Springs Road Chester, NY MLS# 935115
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                  1 of 48
                  OPEN HOUSE: Sunday 1/11 12:00 PM - 2:00 PM
                  $750,000
                  3

                  Beds

                  3.0

                  Baths

                  2,870

                  Sq.Ft.

                  16 Oxford Springs Road

                  Chester, NY

                  Courtesy of RE/MAX BENCHMARK REALTY GROUP
                  View 80 Pewter Circle Chester, NY MLS# 913254
                    Save 80 Pewter Circle Chester, NY MLS# 913254
                    1 of 49
                    $534,900
                    3

                    Beds

                    2.1

                    Baths

                    1,946

                    Sq.Ft.

                    80 Pewter Circle

                    Chester, NY

                    Courtesy of BHG REAL ESTATE GREEN TEAM
                    View 1503 Whispering Hills Chester, NY MLS# 937839
                      Save 1503 Whispering Hills Chester, NY MLS# 937839
                      1 of 17
                      $309,900
                      3

                      Beds

                      2.1

                      Baths

                      1,331

                      Sq.Ft.

                      1503 Whispering Hills

                      Chester, NY

                      Courtesy of CENTURY 21 E & M WILLIAMS RLTY
                      View 2912 Whispering Hills Chester, NY MLS# 937375
                        Save 2912 Whispering Hills Chester, NY MLS# 937375
                        1 of 1
                        $304,900
                        2

                        Beds

                        1.0

                        Baths

                        1,084

                        Sq.Ft.

                        2912 Whispering Hills

                        Chester, NY

                        Courtesy of KELLER WILLIAMS REALTY

                        About Chester

                        Listings in Chester, NY

                        60

                        Estimated median home price

                        $592,450
                        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 - 300K5
                        $300K - 400K12
                        $400K - 500K7
                        $500K - 600K3
                        $600K - 700K9
                        $700K - 800K4
                        $800K - 900K3
                        $900K - 1M1
                        $1M - Max13

                        Homes for Sale by Type in Chester, NY

                        Property TypeCount
                        Single Family33
                        Townhouse0
                        Condo9
                        Commercial7
                        Rental27
                        Lots and Land9
                        Condo/Town/CoOp0
                        CoOp0
                        Multi Family2
                        Mobile Home0
                        Farms0

                        (Data as of 1/9/2026)

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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.

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                        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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