167 total properties
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View 20160 Garrett Highway # G507 Oakland, MD MLS# MDGA2010360
    Save 20160 Garrett Highway # G507 Oakland, MD MLS# MDGA2010360
    1 of 34
    $399,000
    2

    Beds

    1.0

    Baths

    912

    Sq.Ft.

    20160 Garrett Highway # G507

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View Longview Lane Oakland, MD MLS# MDGA2010356
      Save Longview Lane Oakland, MD MLS# MDGA2010356
      1 of 9
      $49,900
      Studio

      Beds

      0.0

      Baths

      Longview Lane

      Oakland, MD

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      Courtesy of APPALACHIAN REALTY
      View Sam Snead Circle # 1 Oakland, MD MLS# MDGA2010358
      • New Construction
      Save Sam Snead Circle # 1 Oakland, MD MLS# MDGA2010358
      1 of 3
      $425,000
      3

      Beds

      2.0

      Baths

      1,500

      Sq.Ft.

      Sam Snead Circle # 1

      Oakland, MD

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      Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
      The time to sell is now! THE TIME TO SELL IS NOW!
      View Santa Fe Trail Oakland, MD MLS# MDGA2010334
        Save Santa Fe Trail Oakland, MD MLS# MDGA2010334
        1 of 5
        $30,000
        Studio

        Beds

        0.0

        Baths

        Santa Fe Trail

        Oakland, MD

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        Courtesy of CUMMINGS & CO. REALTORS
        View 1010 Holy Cross Drive Oakland, MD MLS# MDGA2010180
        • Virtual Tour
        Save 1010 Holy Cross Drive Oakland, MD MLS# MDGA2010180
        1 of 147
        $5,150,000
        8

        Beds

        8.1

        Baths

        10,300

        Sq.Ft.

        1010 Holy Cross Drive

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 1 Lowes Drive Oakland, MD MLS# MDGA2010298
          Save 1 Lowes Drive Oakland, MD MLS# MDGA2010298
          1 of 15
          $175,000

          1 Lowes Drive

          Oakland, MD

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          Courtesy of RAILEY REALTY, INC.
          View 66 Paradise Ridge Road Oakland, MD MLS# MDGA2010278
            Save 66 Paradise Ridge Road Oakland, MD MLS# MDGA2010278
            1 of 24
            $650,000
            4

            Beds

            4.0

            Baths

            2,550

            Sq.Ft.

            66 Paradise Ridge Road

            Oakland, MD

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            Courtesy of HAWKINS REAL ESTATE COMPANY
            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 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

                Bright
                Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                View 104 Pine Top Trail Oakland, MD MLS# MDGA2010178
                  Save 104 Pine Top Trail Oakland, MD MLS# MDGA2010178
                  1 of 13
                  $425,000
                  3

                  Beds

                  3.1

                  Baths

                  1,596

                  Sq.Ft.

                  104 Pine Top Trail

                  Oakland, MD

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                  Courtesy of 1 REAL ESTATE SOURCE LLC
                  View 503 E Alder Street E Oakland, MD MLS# MDGA2010182
                    Save 503 E Alder Street E Oakland, MD MLS# MDGA2010182
                    1 of 8
                    $266,691
                    4

                    Beds

                    2.0

                    Baths

                    2,496

                    Sq.Ft.

                    503 E Alder Street E

                    Oakland, MD

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                    Courtesy of COLDWELL BANKER REALTY
                    View LOT 25 Holy Cross Drive Oakland, MD MLS# MDGA2010144
                    • Virtual Tour
                    Save LOT 25 Holy Cross Drive Oakland, MD MLS# MDGA2010144
                    1 of 25
                    $499,999
                    Studio

                    Beds

                    0.0

                    Baths

                    LOT 25 Holy Cross Drive

                    Oakland, MD

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                    Courtesy of RAILEY REALTY, INC.
                    View Lot 13 Bray Run Road Oakland, MD MLS# MDGA2010142
                      Save Lot 13 Bray Run Road Oakland, MD MLS# MDGA2010142
                      1 of 23
                      $44,900
                      Studio

                      Beds

                      0.0

                      Baths

                      Lot 13 Bray Run Road

                      Oakland, MD

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                      Courtesy of RAILEY REALTY, INC.
                      View 5202 Hutton Road Oakland, MD MLS# MDGA2010148
                        Save 5202 Hutton Road Oakland, MD MLS# MDGA2010148
                        1 of 50
                        $239,000
                        3

                        Beds

                        1.0

                        Baths

                        1,199

                        Sq.Ft.

                        5202 Hutton Road

                        Oakland, MD

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                        Courtesy of RAILEY REALTY, INC.
                        View 565 Glendale Road # 116 Oakland, MD MLS# MDGA2010152
                          Save 565 Glendale Road # 116 Oakland, MD MLS# MDGA2010152
                          1 of 29
                          $169,000
                          1

                          Beds

                          1.0

                          Baths

                          484

                          Sq.Ft.

                          565 Glendale Road # 116

                          Oakland, MD

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                          Courtesy of RAILEY REALTY, INC.
                          View 65 Enterprise Drive Oakland, MD MLS# MDGA2010098
                            Save 65 Enterprise Drive Oakland, MD MLS# MDGA2010098
                            1 of 67
                            $2,799,900
                            30,000

                            Sq.Ft.

                            65 Enterprise Drive

                            Oakland, MD

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                            Courtesy of RAILEY REALTY, INC.
                            View Lot 53 Mountainview Drive Oakland, MD MLS# MDGA2010146
                              Save Lot 53 Mountainview Drive Oakland, MD MLS# MDGA2010146
                              1 of 5
                              $124,900
                              Studio

                              Beds

                              0.0

                              Baths

                              Lot 53 Mountainview Drive

                              Oakland, MD

                              Bright
                              Courtesy of SAMSON PROPERTIES
                              View 939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096
                                Save 939 Glendale Road # 19 Oakland, MD MLS# MDGA2010096
                                1 of 30
                                $765,000
                                3

                                Beds

                                2.0

                                Baths

                                1,432

                                Sq.Ft.

                                939 Glendale Road # 19

                                Oakland, MD

                                Bright
                                Courtesy of RICHARD DAVIS & ASSOCIATES
                                View Lot 7 Backbone Ridge Road Oakland, MD MLS# MDGA2010076
                                  Save Lot 7 Backbone Ridge Road Oakland, MD MLS# MDGA2010076
                                  1 of 7
                                  $29,950
                                  Studio

                                  Beds

                                  0.0

                                  Baths

                                  Lot 7 Backbone Ridge Road

                                  Oakland, MD

                                  Bright
                                  Courtesy of RAILEY REALTY, INC.
                                  View 198 Grandview Drive Oakland, MD MLS# MDGA2010020
                                  • Virtual Tour
                                  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

                                  167

                                  Estimated median home price

                                  $299,500
                                  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 - 100K38
                                  $100K - 200K24
                                  $200K - 300K23
                                  $300K - 400K13
                                  $400K - 500K12
                                  $500K - 600K12
                                  $600K - 700K8
                                  $700K - 800K11
                                  $800K - 900K4
                                  $900K - 1M4
                                  $1M - Max18

                                  Homes for Sale by Type in Oakland, MD

                                  Property TypeCount
                                  Single Family68
                                  Townhouse0
                                  Condo24
                                  Commercial10
                                  Rental1
                                  Lots and Land65
                                  Condo/Town/CoOp0
                                  CoOp0
                                  Multi Family0
                                  Mobile Home0
                                  Farms0

                                  (Data as of 12/9/2025)

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                                  Information deemed reliable but not guaranteed.

                                  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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