21550 Homes for Sale

210 total properties
View 2 Overlook Ridge Drive Oakland, MD MLS# MDGA2007374
    Save 2 Overlook Ridge Drive Oakland, MD MLS# MDGA2007374
    1 of 11
    $199,900
    Studio

    Beds

    0.0

    Baths

    2 Overlook Ridge Drive

    Oakland, MD

    Bright
    Courtesy of RAILEY REALTY, INC.
    View 0 Lake Shore Drive Oakland, MD MLS# MDGA2010464
      Save 0 Lake Shore Drive Oakland, MD MLS# MDGA2010464
      1 of 28
      $199,900
      Studio

      Beds

      0.0

      Baths

      0 Lake Shore Drive

      Oakland, MD

      Bright
      Courtesy of THE MIKE HAYWOOD GROUP
      View 8956 Oakland Sang Run Road Oakland, MD MLS# MDGA2011566
        Save 8956 Oakland Sang Run Road Oakland, MD MLS# MDGA2011566
        1 of 69
        $191,409
        3

        Beds

        2.0

        Baths

        1,064

        Sq.Ft.

        8956 Oakland Sang Run Road

        Oakland, MD

        Bright
        Courtesy of TAYLOR PROPERTIES
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 729 E Oak Street Oakland, MD MLS# MDGA2011048
          Save 729 E Oak Street Oakland, MD MLS# MDGA2011048
          1 of 62
          $185,000
          3

          Beds

          1.1

          Baths

          1,170

          Sq.Ft.

          729 E Oak Street

          Oakland, MD

          Bright
          Courtesy of RAILEY REALTY, INC.
          View 2918 Oakland Sang Run Road Oakland, MD MLS# MDGA2012034
            Save 2918 Oakland Sang Run Road Oakland, MD MLS# MDGA2012034
            1 of 29
            $185,000
            3

            Beds

            1.0

            Baths

            1,382

            Sq.Ft.

            2918 Oakland Sang Run Road

            Oakland, MD

            Bright
            Courtesy of RAILEY REALTY, INC.
            View Pysell Crosscut Road Oakland, MD MLS# MDGA2012040
              Save Pysell Crosscut Road Oakland, MD MLS# MDGA2012040
              1 of 19
              $185,000
              Studio

              Beds

              0.0

              Baths

              Pysell Crosscut Road

              Oakland, MD

              Bright
              Courtesy of RAILEY REALTY, INC.
              View 565 Glendale Road # 212A Oakland, MD MLS# MDGA2008680
                Save 565 Glendale Road # 212A Oakland, MD MLS# MDGA2008680
                1 of 20
                $175,000
                1

                Beds

                1.0

                Baths

                527

                Sq.Ft.

                565 Glendale Road # 212A

                Oakland, MD

                Bright
                Courtesy of RAILEY REALTY, INC.
                View Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
                • Recently Listed
                Save Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
                1 of 3
                $175,000
                Studio

                Beds

                0.0

                Baths

                Robinwood Drive # 9

                Oakland, MD

                Bright
                Courtesy of TAYLOR-MADE DEEP CREEK SALES
                View 9.75 AC. Dennett Road Oakland, MD MLS# MDGA2011844
                  Save 9.75 AC. Dennett Road Oakland, MD MLS# MDGA2011844
                  1 of 30
                  $169,000
                  Studio

                  Beds

                  0.0

                  Baths

                  9.75 AC. Dennett Road

                  Oakland, MD

                  Bright
                  Courtesy of RAILEY REALTY, INC.
                  View 63 Wallman Road Oakland, MD MLS# MDGA2010592
                    Save 63 Wallman Road Oakland, MD MLS# MDGA2010592
                    1 of 60
                    $164,000
                    3

                    Beds

                    1.0

                    Baths

                    816

                    Sq.Ft.

                    63 Wallman Road

                    Oakland, MD

                    Bright
                    Courtesy of RAILEY REALTY, INC.
                    View Dennett Rd, 10.10 Acres To Oakland Dr Oakland, MD MLS# MDGA2011252
                      Save Dennett Rd, 10.10 Acres To Oakland Dr Oakland, MD MLS# MDGA2011252
                      1 of 21
                      $160,000
                      Studio

                      Beds

                      0.0

                      Baths

                      Dennett Rd, 10.10 Acres To Oakland Dr

                      Oakland, MD

                      Bright
                      Courtesy of THE KW COLLECTIVE
                      View 132 &132A Tarn Drive Oakland, MD MLS# MDGA2011528
                        Save 132 &132A Tarn Drive Oakland, MD MLS# MDGA2011528
                        1 of 28
                        $160,000
                        Studio

                        Beds

                        0.0

                        Baths

                        132 &132A Tarn Drive

                        Oakland, MD

                        Bright
                        Courtesy of RAILEY REALTY, INC.
                        View 22 Woodlands Hill Lane Oakland, MD MLS# MDGA2012334
                        • Recently Listed
                        Save 22 Woodlands Hill Lane Oakland, MD MLS# MDGA2012334
                        1 of 22
                        $159,000
                        Studio

                        Beds

                        0.0

                        Baths

                        22 Woodlands Hill Lane

                        Oakland, MD

                        Bright
                        Courtesy of RAILEY REALTY, INC.
                        View Sanders Lane Oakland, MD MLS# MDGA2011678
                          Save Sanders Lane Oakland, MD MLS# MDGA2011678
                          1 of 46
                          $150,000
                          Studio

                          Beds

                          0.0

                          Baths

                          Sanders Lane

                          Oakland, MD

                          Bright
                          Courtesy of RAILEY REALTY, INC.
                          View 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
                          • Recently Listed
                          Save 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
                          1 of 15
                          $149,000
                          Studio

                          Beds

                          0.0

                          Baths

                          16 Woodlands Hill Court

                          Oakland, MD

                          Bright
                          Courtesy of RAILEY REALTY, INC.
                          View 1099 Table Rock Road Oakland, MD MLS# MDGA2011978
                            Save 1099 Table Rock Road Oakland, MD MLS# MDGA2011978
                            1 of 44
                            $145,000
                            1

                            Beds

                            1.0

                            Baths

                            1,728

                            Sq.Ft.

                            1099 Table Rock Road

                            Oakland, MD

                            Bright
                            Courtesy of RAILEY REALTY, INC.
                            View Paradise Point Road Oakland, MD MLS# MDGA2003916
                              Save Paradise Point Road Oakland, MD MLS# MDGA2003916
                              $134,000
                              Studio

                              Beds

                              0.0

                              Baths

                              Paradise Point Road

                              Oakland, MD

                              Bright
                              Courtesy of EAGLE COMMERCIAL REALTY
                              View 170 San Francisco Street Oakland, MD MLS# MDGA2010726
                                Save 170 San Francisco Street Oakland, MD MLS# MDGA2010726
                                1 of 12
                                $125,000
                                Studio

                                Beds

                                0.0

                                Baths

                                170 San Francisco Street

                                Oakland, MD

                                Bright
                                Courtesy of COLDWELL BANKER REALTY
                                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 Lot 20 Paradise Ridge Road Oakland, MD MLS# MDGA2010926
                                    Save Lot 20 Paradise Ridge Road Oakland, MD MLS# MDGA2010926
                                    1 of 31
                                    $124,000
                                    Studio

                                    Beds

                                    0.0

                                    Baths

                                    Lot 20 Paradise Ridge Road

                                    Oakland, MD

                                    Bright
                                    Courtesy of RAILEY REALTY, INC.

                                    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.

                                    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

                                    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.

                                    © 2026 BrightMLS. All Rights Reserved.