21550 Homes for Sale

158 total properties
View 611 E Oak Street Oakland, MD MLS# MDGA2009308
    Save 611 E Oak Street Oakland, MD MLS# MDGA2009308
    1 of 14
    $295,000
    5

    Beds

    3.0

    Baths

    1,800

    Sq.Ft.

    611 E Oak Street

    Oakland, MD

    Bright
    Courtesy of RAILEY REALTY, INC.
    View Edgewater Drive # 4 Oakland, MD MLS# MDGA2009106
      Save Edgewater Drive # 4 Oakland, MD MLS# MDGA2009106
      1 of 16
      $299,000
      Studio

      Beds

      0.0

      Baths

      Edgewater Drive # 4

      Oakland, MD

      Bright
      Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
      View 1737 King Wildesen Road Oakland, MD MLS# MDGA2009574
        Save 1737 King Wildesen Road Oakland, MD MLS# MDGA2009574
        1 of 46
        $299,900
        3

        Beds

        2.0

        Baths

        1,736

        Sq.Ft.

        1737 King Wildesen Road

        Oakland, MD

        Bright
        Courtesy of RAILEY REALTY, INC.
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 143 Manor Drive Oakland, MD MLS# MDGA2010990
          Save 143 Manor Drive Oakland, MD MLS# MDGA2010990
          1 of 48
          $299,900
          3

          Beds

          1.1

          Baths

          1,786

          Sq.Ft.

          143 Manor Drive

          Oakland, MD

          Bright
          Courtesy of RAILEY REALTY, INC.
          View 163 Crestview Drive Oakland, MD MLS# MDGA2009776
            Save 163 Crestview Drive Oakland, MD MLS# MDGA2009776
            1 of 50
            $315,000
            3

            Beds

            2.1

            Baths

            1,416

            Sq.Ft.

            163 Crestview Drive

            Oakland, MD

            Bright
            Courtesy of RAILEY REALTY, INC.
            View 127 S Oakhall Drive Oakland, MD MLS# MDGA2010554
              Save 127 S Oakhall Drive Oakland, MD MLS# MDGA2010554
              1 of 29
              $315,000
              4

              Beds

              2.0

              Baths

              2,183

              Sq.Ft.

              127 S Oakhall Drive

              Oakland, MD

              Bright
              Courtesy of THE KW COLLECTIVE
              View Upperman Road Oakland, MD MLS# MDGA2010944
                Save Upperman Road Oakland, MD MLS# MDGA2010944
                1 of 4
                $325,000
                Studio

                Beds

                0.0

                Baths

                Upperman Road

                Oakland, MD

                Bright
                Courtesy of RAILEY REALTY, INC.
                View 565 Glendale Road # B206 Oakland, MD MLS# MDGA2010830
                  Save 565 Glendale Road # B206 Oakland, MD MLS# MDGA2010830
                  1 of 32
                  $329,000
                  2

                  Beds

                  1.0

                  Baths

                  780

                  Sq.Ft.

                  565 Glendale Road # B206

                  Oakland, MD

                  Bright
                  Courtesy of JASON MITCHELL GROUP
                  View 697 Monte Vista Road Oakland, MD MLS# MDGA2010454
                  • Virtual Tour
                  Save 697 Monte Vista Road Oakland, MD MLS# MDGA2010454
                  1 of 56
                  $339,000
                  5

                  Beds

                  3.1

                  Baths

                  3,682

                  Sq.Ft.

                  697 Monte Vista Road

                  Oakland, MD

                  Bright
                  Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                  View 931 Black Oak Drive Oakland, MD MLS# MDGA2010958
                  • Recently Listed
                  Save 931 Black Oak Drive Oakland, MD MLS# MDGA2010958
                  1 of 53
                  $359,000
                  3

                  Beds

                  1.0

                  Baths

                  990

                  Sq.Ft.

                  931 Black Oak Drive

                  Oakland, MD

                  Bright
                  Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                  View 531 Glendale Road # B302 Oakland, MD MLS# MDGA2009640
                    Save 531 Glendale Road # B302 Oakland, MD MLS# MDGA2009640
                    1 of 29
                    $369,000
                    2

                    Beds

                    1.0

                    Baths

                    887

                    Sq.Ft.

                    531 Glendale Road # B302

                    Oakland, MD

                    Bright
                    Courtesy of RAILEY REALTY, INC.
                    View 8946 Oakland Sang Run Road Oakland, MD MLS# MDGA2010780
                      Save 8946 Oakland Sang Run Road Oakland, MD MLS# MDGA2010780
                      $369,000
                      Studio

                      Beds

                      0.0

                      Baths

                      8946 Oakland Sang Run Road

                      Oakland, MD

                      Bright
                      Courtesy of EAGLE COMMERCIAL REALTY
                      View 961 Cedar Lane Oakland, MD MLS# MDGA2010426
                        Save 961 Cedar Lane Oakland, MD MLS# MDGA2010426
                        1 of 50
                        $379,000
                        4

                        Beds

                        2.1

                        Baths

                        1,920

                        Sq.Ft.

                        961 Cedar Lane

                        Oakland, MD

                        Bright
                        Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                        View 723 Kings Oakland, MD MLS# MDGA2009442
                          Save 723 Kings Oakland, MD MLS# MDGA2009442
                          1 of 67
                          $380,000
                          4

                          Beds

                          2.1

                          Baths

                          1,824

                          Sq.Ft.

                          723 Kings

                          Oakland, MD

                          Bright
                          Courtesy of LONG & FOSTER REAL ESTATE, INC.
                          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

                            Bright
                            Courtesy of RAILEY REALTY, INC.
                            View 216 E Alder Street Oakland, MD MLS# MDGA2010666
                              Save 216 E Alder Street Oakland, MD MLS# MDGA2010666
                              $399,000
                              4,791

                              Sq.Ft.

                              216 E Alder Street

                              Oakland, MD

                              Bright
                              Courtesy of EAGLE COMMERCIAL REALTY
                              View 16 Lemley Oakland, MD MLS# MDGA2010814
                              • Virtual Tour
                              Save 16 Lemley Oakland, MD MLS# MDGA2010814
                              1 of 65
                              $399,000
                              4

                              Beds

                              2.1

                              Baths

                              1,104

                              Sq.Ft.

                              16 Lemley

                              Oakland, MD

                              Bright
                              Courtesy of RAILEY REALTY, INC.
                              View 15 Village Drive # 1 Oakland, MD MLS# MDGA2008612
                              • Virtual Tour
                              Save 15 Village Drive # 1 Oakland, MD MLS# MDGA2008612
                              1 of 37
                              $425,000
                              2

                              Beds

                              1.0

                              Baths

                              15 Village Drive # 1

                              Oakland, MD

                              Bright
                              Courtesy of RAILEY REALTY, INC.
                              View 180 Paradise Ridge Road Oakland, MD MLS# MDGA2008834
                              • Virtual Tour
                              Save 180 Paradise Ridge Road Oakland, MD MLS# MDGA2008834
                              1 of 98
                              $425,000
                              3

                              Beds

                              2.0

                              Baths

                              1,152

                              Sq.Ft.

                              180 Paradise Ridge Road

                              Oakland, MD

                              Bright
                              Courtesy of RAILEY REALTY, INC.
                              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

                                Bright
                                Courtesy of 1 REAL ESTATE SOURCE LLC

                                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.