138 total properties
Did you mean the neighborhood Oakland?
View 126 Leo Friend Road Oakland, MD MLS# MDGA2009940
    Save 126 Leo Friend Road Oakland, MD MLS# MDGA2009940
    1 of 50
    $499,900
    4

    Beds

    3.0

    Baths

    2,235

    Sq.Ft.

    126 Leo Friend Road

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 101 Sobriety Way Oakland, MD MLS# MDGA2012278
    • Virtual Tour
    Save 101 Sobriety Way Oakland, MD MLS# MDGA2012278
    1 of 72
    $499,900
    3

    Beds

    2.0

    Baths

    1,920

    Sq.Ft.

    101 Sobriety Way

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 0 George Washington Highway Oakland, MD MLS# MDGA2006062
      Save 0 George Washington Highway Oakland, MD MLS# MDGA2006062
      1 of 77
      $490,000
      Studio

      Beds

      0.0

      Baths

      0 George Washington Highway

      Oakland, MD

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      Courtesy of WHITETAIL PROPERTIES REAL ESTATE, LLC
      The time to sell is now! THE TIME TO SELL IS NOW!
      View Lot 7 Heron Cove Oakland, MD MLS# MDGA2012608
      • Recently Listed
      Save Lot 7 Heron Cove Oakland, MD MLS# MDGA2012608
      1 of 46
      $489,900
      Studio

      Beds

      0.0

      Baths

      Lot 7 Heron Cove

      Oakland, MD

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      Courtesy of TAYLOR-MADE DEEP CREEK SALES
      View 256 Jeffrey Lane # 28 Oakland, MD MLS# MDGA2012248
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      Save 256 Jeffrey Lane # 28 Oakland, MD MLS# MDGA2012248
      1 of 65
      $464,900
      3

      Beds

      3.1

      Baths

      1,838

      Sq.Ft.

      256 Jeffrey Lane # 28

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      View 5154 Maryland Highway Oakland, MD MLS# MDGA2012262
        Save 5154 Maryland Highway Oakland, MD MLS# MDGA2012262
        1 of 70
        $460,000
        5

        Beds

        2.0

        Baths

        2,860

        Sq.Ft.

        5154 Maryland Highway

        Oakland, MD

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        Courtesy of COLDWELL BANKER HOME TOWN REALTY
        View 718 Boy Scout Crosscut Road Oakland, MD MLS# MDGA2012430
          Save 718 Boy Scout Crosscut Road Oakland, MD MLS# MDGA2012430
          1 of 58
          $459,900
          3

          Beds

          2.0

          Baths

          1,458

          Sq.Ft.

          718 Boy Scout Crosscut Road

          Oakland, MD

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          Courtesy of RAILEY REALTY, INC.
          View 333 Sloan Tract Road Oakland, MD MLS# MDGA2012576
          • Recently Listed with Virtual Tour
          Save 333 Sloan Tract Road Oakland, MD MLS# MDGA2012576
          1 of 61
          $444,700
          4

          Beds

          3.1

          Baths

          1,585

          Sq.Ft.

          333 Sloan Tract Road

          Oakland, MD

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          Courtesy of LONG & FOSTER REAL ESTATE, INC.
          View 401 Dave Turney Street Oakland, MD MLS# MDGA2011080
            Save 401 Dave Turney Street Oakland, MD MLS# MDGA2011080
            1 of 61
            $439,000
            5,328

            Sq.Ft.

            401 Dave Turney Street

            Oakland, MD

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            Courtesy of JASON MITCHELL GROUP
            View 704 Old Crellin Road Oakland, MD MLS# MDGA2012604
            • Recently Listed
            Save 704 Old Crellin Road Oakland, MD MLS# MDGA2012604
            1 of 31
            $430,000
            5

            Beds

            2.1

            Baths

            2,507

            Sq.Ft.

            704 Old Crellin Road

            Oakland, MD

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            Courtesy of THE KW COLLECTIVE
            View 3257 George Washington Highway Oakland, MD MLS# MDGA2010760
              Save 3257 George Washington Highway Oakland, MD MLS# MDGA2010760
              1 of 55
              $400,000
              Studio

              Beds

              0.0

              Baths

              3257 George Washington Highway

              Oakland, MD

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              Courtesy of RAILEY REALTY, INC.
              View 2967 Pysell Crosscut Road Oakland, MD MLS# MDGA2012022
                Save 2967 Pysell Crosscut Road Oakland, MD MLS# MDGA2012022
                1 of 64
                $400,000
                2

                Beds

                1.0

                Baths

                1,800

                Sq.Ft.

                2967 Pysell Crosscut Road

                Oakland, MD

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                View 565 Glendale Road # 303B Oakland, MD MLS# MDGA2011808
                  Save 565 Glendale Road # 303B Oakland, MD MLS# MDGA2011808
                  1 of 34
                  $399,900
                  2

                  Beds

                  1.0

                  Baths

                  887

                  Sq.Ft.

                  565 Glendale Road # 303B

                  Oakland, MD

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                  Courtesy of TAYLOR-MADE DEEP CREEK SALES
                  View 511 Hilltop Road Oakland, MD MLS# MDGA2012082
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                  Save 511 Hilltop Road Oakland, MD MLS# MDGA2012082
                  1 of 51
                  $399,900
                  4

                  Beds

                  3.0

                  Baths

                  2,406

                  Sq.Ft.

                  511 Hilltop Road

                  Oakland, MD

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                  Courtesy of TAYLOR-MADE DEEP CREEK SALES
                  View 181 Glotfelty Drive Oakland, MD MLS# MDGA2012496
                    Save 181 Glotfelty Drive Oakland, MD MLS# MDGA2012496
                    1 of 51
                    $399,000
                    3

                    Beds

                    2.0

                    Baths

                    1,456

                    Sq.Ft.

                    181 Glotfelty Drive

                    Oakland, MD

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                    Courtesy of RAILEY REALTY, INC.
                    View 560 Glendale Road Oakland, MD MLS# MDGA2011856
                      Save 560 Glendale Road Oakland, MD MLS# MDGA2011856
                      1 of 24
                      $398,000
                      2

                      Beds

                      1.0

                      Baths

                      700

                      Sq.Ft.

                      560 Glendale Road

                      Oakland, MD

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                      Courtesy of RAILEY REALTY, INC.
                      View 5024 Cranesville Road Oakland, MD MLS# MDGA2010510
                      • Virtual Tour
                      Save 5024 Cranesville Road Oakland, MD MLS# MDGA2010510
                      1 of 67
                      $385,000
                      3

                      Beds

                      2.1

                      Baths

                      2,128

                      Sq.Ft.

                      5024 Cranesville Road

                      Oakland, MD

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                      Courtesy of RAILEY REALTY, INC.
                      View 321 Deer Park Hotel Road Oakland, MD MLS# MDGA2012166
                        Save 321 Deer Park Hotel Road Oakland, MD MLS# MDGA2012166
                        1 of 47
                        $384,500
                        3

                        Beds

                        2.0

                        Baths

                        2,476

                        Sq.Ft.

                        321 Deer Park Hotel Road

                        Oakland, MD

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                        Courtesy of HOUWZER, LLC
                        View 654 N Bradley Lane Oakland, MD MLS# MDGA2011266
                        • New Construction
                        Save 654 N Bradley Lane Oakland, MD MLS# MDGA2011266
                        1 of 41
                        $379,999
                        3

                        Beds

                        2.0

                        Baths

                        1,464

                        Sq.Ft.

                        654 N Bradley Lane

                        Oakland, MD

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                        Courtesy of TAYLOR-MADE DEEP CREEK SALES
                        View 20160 Garrett Highway # C307 Oakland, MD MLS# MDGA2012092
                          Save 20160 Garrett Highway # C307 Oakland, MD MLS# MDGA2012092
                          1 of 49
                          $379,500
                          1

                          Beds

                          1.0

                          Baths

                          636

                          Sq.Ft.

                          20160 Garrett Highway # C307

                          Oakland, MD

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                          Courtesy of RAILEY REALTY, INC.

                          About Oakland

                          Listings in Oakland, MD

                          208

                          Estimated median home price

                          $309,000
                          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 - 100K44
                          $100K - 200K28
                          $200K - 300K31
                          $300K - 400K25
                          $400K - 500K10
                          $500K - 600K12
                          $600K - 700K10
                          $700K - 800K15
                          $800K - 900K5
                          $900K - 1M4
                          $1M - Max24

                          Homes for Sale by Type in Oakland, MD

                          Property TypeCount
                          Single Family92
                          Townhouse1
                          Condo25
                          Commercial11
                          Rental6
                          Lots and Land79
                          Condo/Town/CoOp0
                          CoOp0
                          Multi Family0
                          Mobile Home0
                          Farms0

                          (Data as of 8/25/2026)

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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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