169 total properties
Did you mean the neighborhood Oakland?
View 815 Chadderton School Road Oakland, MD MLS# MDGA2011092
    Save 815 Chadderton School Road Oakland, MD MLS# MDGA2011092
    1 of 110
    $1,900,000
    5

    Beds

    3.1

    Baths

    4,619

    Sq.Ft.

    815 Chadderton School Road

    Oakland, MD

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    View 62 Duck Cove Road Oakland, MD MLS# MDGA2011402
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    Save 62 Duck Cove Road Oakland, MD MLS# MDGA2011402
    1 of 74
    $1,899,000
    4

    Beds

    4.0

    Baths

    4,150

    Sq.Ft.

    62 Duck Cove Road

    Oakland, MD

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    View 499 Oakland Drive Oakland, MD MLS# MDGA2003394
      Save 499 Oakland Drive Oakland, MD MLS# MDGA2003394
      1 of 103
      $1,750,000
      15,000

      Sq.Ft.

      499 Oakland Drive

      Oakland, MD

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      The time to sell is now! THE TIME TO SELL IS NOW!
      View 1544 Stockslager Road Oakland, MD MLS# MDGA2011420
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      Save 1544 Stockslager Road Oakland, MD MLS# MDGA2011420
      1 of 64
      $1,750,000
      5

      Beds

      4.0

      Baths

      3,456

      Sq.Ft.

      1544 Stockslager Road

      Oakland, MD

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      Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
      View 17848 Garrett Highway Oakland, MD MLS# MDGA2011286
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      Save 17848 Garrett Highway Oakland, MD MLS# MDGA2011286
      1 of 122
      $1,700,000
      6,477

      Sq.Ft.

      17848 Garrett Highway

      Oakland, MD

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      View 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
        Save 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
        1 of 31
        $1,650,000
        4

        Beds

        4.2

        Baths

        5,117

        Sq.Ft.

        3898 3898 Underwood Rd

        Oakland, MD

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        View 2332 Paradise Point Road Oakland, MD MLS# MDGA2011510
          Save 2332 Paradise Point Road Oakland, MD MLS# MDGA2011510
          1 of 74
          $1,399,000
          3

          Beds

          2.0

          Baths

          2,064

          Sq.Ft.

          2332 Paradise Point Road

          Oakland, MD

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          View 439 Paradise Heights Oakland, MD MLS# MDGA2008472
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          Save 439 Paradise Heights Oakland, MD MLS# MDGA2008472
          1 of 45
          $1,329,000
          6

          Beds

          4.1

          Baths

          4,113

          Sq.Ft.

          439 Paradise Heights

          Oakland, MD

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          View 660 Glendale Road Oakland, MD MLS# MDGA2011188
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          1 of 62
          $1,300,000
          5

          Beds

          3.0

          Baths

          2,592

          Sq.Ft.

          660 Glendale Road

          Oakland, MD

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          View 285 Lake Shore Drive Oakland, MD MLS# MDGA2010466
            Save 285 Lake Shore Drive Oakland, MD MLS# MDGA2010466
            1 of 47
            $1,149,800
            5

            Beds

            4.1

            Baths

            2,593

            Sq.Ft.

            285 Lake Shore Drive

            Oakland, MD

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            Courtesy of KELLER WILLIAMS CAPITAL PROPERTIES
            View 52 Dam View Drive Oakland, MD MLS# MDGA2011104
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            Save 52 Dam View Drive Oakland, MD MLS# MDGA2011104
            1 of 75
            $1,087,900
            4

            Beds

            4.2

            Baths

            3,032

            Sq.Ft.

            52 Dam View Drive

            Oakland, MD

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            View 137 Paradise Gardens Road Oakland, MD MLS# MDGA2011454
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            Save 137 Paradise Gardens Road Oakland, MD MLS# MDGA2011454
            1 of 71
            $1,049,000
            4

            Beds

            2.0

            Baths

            2,730

            Sq.Ft.

            137 Paradise Gardens Road

            Oakland, MD

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            Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
            View Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
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            Save Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
            1 of 10
            $995,000
            Studio

            Beds

            0.0

            Baths

            Glendale Rd Lot 12 Alpine Village Subdivision

            Oakland, MD

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            View 164 Grandview Drive Oakland, MD MLS# MDGA2011052
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            Save 164 Grandview Drive Oakland, MD MLS# MDGA2011052
            1 of 54
            $950,000
            3

            Beds

            2.1

            Baths

            2,368

            Sq.Ft.

            164 Grandview Drive

            Oakland, MD

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            View 62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182
              Save 62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182
              1 of 77
              $930,000
              4

              Beds

              3.1

              Baths

              2,464

              Sq.Ft.

              62 Whispering Pines Lane

              Oakland, MD

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              View 267 San Francisco Street Oakland, MD MLS# MDGA2011040
                Save 267 San Francisco Street Oakland, MD MLS# MDGA2011040
                1 of 30
                $899,900
                4

                Beds

                2.1

                Baths

                3,278

                Sq.Ft.

                267 San Francisco Street

                Oakland, MD

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                View 113 Jubb Meadows Lane Oakland, MD MLS# MDGA2011494
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                Save 113 Jubb Meadows Lane Oakland, MD MLS# MDGA2011494
                1 of 69
                $899,900
                4

                Beds

                3.1

                Baths

                3,185

                Sq.Ft.

                113 Jubb Meadows Lane

                Oakland, MD

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                View 891 Mountainview Drive Oakland, MD MLS# MDGA2011344
                  Save 891 Mountainview Drive Oakland, MD MLS# MDGA2011344
                  1 of 82
                  $875,000
                  3

                  Beds

                  4.0

                  Baths

                  3,990

                  Sq.Ft.

                  891 Mountainview Drive

                  Oakland, MD

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                  View 1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462
                    Save 1909 Pysell Crosscut Road Oakland, MD MLS# MDGA2010462
                    1 of 85
                    $825,000
                    4

                    Beds

                    4.1

                    Baths

                    2,970

                    Sq.Ft.

                    1909 Pysell Crosscut Road

                    Oakland, MD

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                    View 14 Commerce Drive Oakland, MD MLS# MDGA2010002
                      Save 14 Commerce Drive Oakland, MD MLS# MDGA2010002
                      1 of 99
                      $800,000
                      10,000

                      Sq.Ft.

                      14 Commerce Drive

                      Oakland, MD

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                      About Oakland

                      Listings in Oakland, MD

                      177

                      Estimated median home price

                      $295,000
                      Oakland MD Homes for Sale & Properties

                      Weichert Realtors is one of the nation's leading providers of Oakland, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Oakland, MD.

                      Homes for Sale by Price in Oakland, MD

                      PriceCount
                      $0 - 100K43
                      $100K - 200K20
                      $200K - 300K32
                      $300K - 400K19
                      $400K - 500K8
                      $500K - 600K9
                      $600K - 700K8
                      $700K - 800K9
                      $800K - 900K4
                      $900K - 1M3
                      $1M - Max22

                      Homes for Sale by Type in Oakland, MD

                      Property TypeCount
                      Single Family78
                      Townhouse2
                      Condo23
                      Commercial14
                      Rental6
                      Lots and Land60
                      Condo/Town/CoOp0
                      CoOp0
                      Multi Family0
                      Mobile Home0
                      Farms0

                      (Data as of 4/18/2026)

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                      Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

                      Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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                      Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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