154 total properties
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View 12743 Garrett Highway Oakland, MD MLS# MDGA2008424
    Save 12743 Garrett Highway Oakland, MD MLS# MDGA2008424
    1 of 62
    $1,999,900
    32,544

    Sq.Ft.

    12743 Garrett Highway

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
      Save 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
      1 of 31
      $1,800,000
      4

      Beds

      4.2

      Baths

      5,117

      Sq.Ft.

      3898 3898 Underwood Rd

      Oakland, MD

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      Courtesy of CUSTER REALTY & AUCTION
      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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        Courtesy of RAILEY REALTY, INC.
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 272 Mccomas Beach Terrace Oakland, MD MLS# MDGA2010302
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        Save 272 Mccomas Beach Terrace Oakland, MD MLS# MDGA2010302
        1 of 71
        $1,589,000
        5

        Beds

        3.1

        Baths

        2,448

        Sq.Ft.

        272 Mccomas Beach Terrace

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 336 Paradise Heights Oakland, MD MLS# MDGA2010378
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        Save 336 Paradise Heights Oakland, MD MLS# MDGA2010378
        1 of 94
        $1,499,000
        5

        Beds

        3.0

        Baths

        2,826

        Sq.Ft.

        336 Paradise Heights

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        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 19956 Garrett Highway # 6 Oakland, MD MLS# MDGA2009898
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        Save 19956 Garrett Highway # 6 Oakland, MD MLS# MDGA2009898
        1 of 81
        $1,289,000
        4

        Beds

        4.0

        Baths

        3,000

        Sq.Ft.

        19956 Garrett Highway # 6

        Oakland, MD

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        View 444 Woodlands Hill Lane Oakland, MD MLS# MDGA2010802
          Save 444 Woodlands Hill Lane Oakland, MD MLS# MDGA2010802
          1 of 68
          $1,199,990
          4

          Beds

          4.2

          Baths

          4,744

          Sq.Ft.

          444 Woodlands Hill Lane

          Oakland, MD

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          View 127 Paradise Heights Oakland, MD MLS# MDGA2009010
            Save 127 Paradise Heights Oakland, MD MLS# MDGA2009010
            1 of 58
            $1,100,000
            3

            Beds

            2.1

            Baths

            2,240

            Sq.Ft.

            127 Paradise Heights

            Oakland, MD

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            Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
            View 1720 Pysell Crosscut Road Oakland, MD MLS# MDGA2010210
              Save 1720 Pysell Crosscut Road Oakland, MD MLS# MDGA2010210
              1 of 114
              $999,999
              5

              Beds

              5.1

              Baths

              8,000

              Sq.Ft.

              1720 Pysell Crosscut Road

              Oakland, MD

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              View 340 Grandview Drive Oakland, MD MLS# MDGA2010536
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              Save 340 Grandview Drive Oakland, MD MLS# MDGA2010536
              1 of 87
              $949,900
              6

              Beds

              4.0

              Baths

              2,536

              Sq.Ft.

              340 Grandview Drive

              Oakland, MD

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              View 39 Leo Friend Road Oakland, MD MLS# MDGA2010444
                Save 39 Leo Friend Road Oakland, MD MLS# MDGA2010444
                1 of 33
                $919,000
                3

                Beds

                3.1

                Baths

                3,897

                Sq.Ft.

                39 Leo Friend Road

                Oakland, MD

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                Courtesy of THE KW COLLECTIVE
                View 139 Overlook Ridge Drive Oakland, MD MLS# MDGA2009000
                  Save 139 Overlook Ridge Drive Oakland, MD MLS# MDGA2009000
                  1 of 73
                  $875,000
                  5

                  Beds

                  4.1

                  Baths

                  2,846

                  Sq.Ft.

                  139 Overlook Ridge 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
                    $865,000
                    4

                    Beds

                    4.1

                    Baths

                    2,970

                    Sq.Ft.

                    1909 Pysell Crosscut Road

                    Oakland, MD

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                    View 1001 Sutter Lane Oakland, MD MLS# MDGA2010778
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                    Save 1001 Sutter Lane Oakland, MD MLS# MDGA2010778
                    1 of 94
                    $829,000
                    5

                    Beds

                    4.2

                    Baths

                    6,550

                    Sq.Ft.

                    1001 Sutter Lane

                    Oakland, MD

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                    View George Washington Highway Oakland, MD MLS# MDGA2010274
                      Save George Washington Highway Oakland, MD MLS# MDGA2010274
                      1 of 16
                      $825,000
                      Studio

                      Beds

                      0.0

                      Baths

                      George Washington Highway

                      Oakland, MD

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                      Courtesy of THE KW COLLECTIVE
                      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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                        View 1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078
                          Save 1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078
                          1 of 67
                          $799,000
                          5

                          Beds

                          5.0

                          Baths

                          3,664

                          Sq.Ft.

                          1875 Pysell Crosscut Road

                          Oakland, MD

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                          View 222 Skippers Point Road Oakland, MD MLS# MDGA2010764
                            Save 222 Skippers Point Road Oakland, MD MLS# MDGA2010764
                            1 of 59
                            $779,000
                            5

                            Beds

                            1.1

                            Baths

                            1,278

                            Sq.Ft.

                            222 Skippers Point Road

                            Oakland, MD

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                            View 198 Grandview Drive Oakland, MD MLS# MDGA2010020
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                            Save 198 Grandview Drive Oakland, MD MLS# MDGA2010020
                            1 of 45
                            $775,000
                            3

                            Beds

                            3.0

                            Baths

                            2,744

                            Sq.Ft.

                            198 Grandview Drive

                            Oakland, MD

                            Bright
                            Courtesy of RE/MAX ONE

                            About Oakland

                            Listings in Oakland, MD

                            164

                            Estimated median home price

                            $297,000
                            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 - 100K37
                            $100K - 200K24
                            $200K - 300K24
                            $300K - 400K13
                            $400K - 500K10
                            $500K - 600K12
                            $600K - 700K8
                            $700K - 800K11
                            $800K - 900K4
                            $900K - 1M3
                            $1M - Max18

                            Homes for Sale by Type in Oakland, MD

                            Property TypeCount
                            Single Family68
                            Townhouse0
                            Condo22
                            Commercial10
                            Rental1
                            Lots and Land64
                            Condo/Town/CoOp0
                            CoOp0
                            Multi Family0
                            Mobile Home0
                            Farms0

                            (Data as of 12/16/2025)

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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.

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