182 total properties
Did you mean the neighborhood Oakland?
View 586 Bray School Road Oakland, MD MLS# MDGA2012712
    Save 586 Bray School Road Oakland, MD MLS# MDGA2012712
    1 of 32
    $289,000
    4

    Beds

    2.0

    Baths

    2,240

    Sq.Ft.

    586 Bray School Road

    Oakland, MD

    Bright
    Courtesy of THE KW COLLECTIVE
    View 20160 Garett Highway # 105A Oakland, MD MLS# MDGA2012720
      Save 20160 Garett Highway # 105A Oakland, MD MLS# MDGA2012720
      1 of 25
      $296,500
      1

      Beds

      1.0

      Baths

      600

      Sq.Ft.

      20160 Garett Highway # 105A

      Oakland, MD

      Bright
      Courtesy of RAILEY REALTY, INC.
      View 2849 Shingle Camp Road Oakland, MD MLS# MDGA2012730
        Save 2849 Shingle Camp Road Oakland, MD MLS# MDGA2012730
        1 of 74
        $1,100,000
        3

        Beds

        2.0

        Baths

        2,034

        Sq.Ft.

        2849 Shingle Camp Road

        Oakland, MD

        Bright
        Courtesy of RAILEY REALTY, INC.
        The time to sell is now! THE TIME TO SELL IS NOW!
        View Wild Turkey Lane # LOT 28 Oakland, MD MLS# MDGA2012728
          Save Wild Turkey Lane # LOT 28 Oakland, MD MLS# MDGA2012728
          1 of 26
          $37,500
          0.0

          Baths

          Wild Turkey Lane # LOT 28

          Oakland, MD

          Bright
          Courtesy of RAILEY REALTY, INC.
          View Cedar Lane # LOT 66 Oakland, MD MLS# MDGA2012732
            Save Cedar Lane # LOT 66 Oakland, MD MLS# MDGA2012732
            1 of 12
            $6,500
            0.0

            Baths

            Cedar Lane # LOT 66

            Oakland, MD

            Bright
            Courtesy of TAYLOR-MADE DEEP CREEK SALES
            View 1158 Kings Run Road Oakland, MD MLS# MDGA2012684
              Save 1158 Kings Run Road Oakland, MD MLS# MDGA2012684
              1 of 54
              $290,000
              2

              Beds

              1.0

              Baths

              912

              Sq.Ft.

              1158 Kings Run Road

              Oakland, MD

              Bright
              Courtesy of RAILEY REALTY, INC.
              View 102 Roanoke Avenue Oakland, MD MLS# MDGA2012700
                Save 102 Roanoke Avenue Oakland, MD MLS# MDGA2012700
                1 of 38
                $69,990
                3

                Beds

                1.0

                Baths

                1,932

                Sq.Ft.

                102 Roanoke Avenue

                Oakland, MD

                Bright
                Courtesy of SAMSON PROPERTIES
                View Yough View Drive Oakland, MD MLS# MDGA2012690
                  Save Yough View Drive Oakland, MD MLS# MDGA2012690
                  1 of 27
                  $40,000
                  0.0

                  Baths

                  Yough View Drive

                  Oakland, MD

                  Bright
                  Courtesy of RAILEY REALTY, INC.
                  View 482 Pergin Farm Road Oakland, MD MLS# MDGA2012680
                    Save 482 Pergin Farm Road Oakland, MD MLS# MDGA2012680
                    1 of 55
                    $449,000
                    3

                    Beds

                    1.1

                    Baths

                    2,160

                    Sq.Ft.

                    482 Pergin Farm Road

                    Oakland, MD

                    Bright
                    Courtesy of TAYLOR-MADE DEEP CREEK SALES
                    View Lot 4 Hunters Ridge Drive Oakland, MD MLS# MDGA2012688
                      Save Lot 4 Hunters Ridge Drive Oakland, MD MLS# MDGA2012688
                      1 of 7
                      $65,000
                      0.0

                      Baths

                      Lot 4 Hunters Ridge Drive

                      Oakland, MD

                      Bright
                      Courtesy of TAYLOR-MADE DEEP CREEK SALES
                      View 184 Upper Penn Point Drive Oakland, MD MLS# MDGA2012648
                        Save 184 Upper Penn Point Drive Oakland, MD MLS# MDGA2012648
                        1 of 53
                        $895,000
                        3

                        Beds

                        2.0

                        Baths

                        1,152

                        Sq.Ft.

                        184 Upper Penn Point Drive

                        Oakland, MD

                        Bright
                        Courtesy of RAILEY REALTY, INC.
                        View 1407 Broadford Road Oakland, MD MLS# MDGA2012662
                        • New Construction
                        Save 1407 Broadford Road Oakland, MD MLS# MDGA2012662
                        1 of 52
                        $399,900
                        3

                        Beds

                        2.0

                        Baths

                        1,464

                        Sq.Ft.

                        1407 Broadford Road

                        Oakland, MD

                        Bright
                        Courtesy of TAYLOR-MADE DEEP CREEK SALES
                        View 395 Woodlands Hill Lane Oakland, MD MLS# MDGA2012628
                          Save 395 Woodlands Hill Lane Oakland, MD MLS# MDGA2012628
                          1 of 68
                          $899,900
                          5

                          Beds

                          6.0

                          Baths

                          3,160

                          Sq.Ft.

                          395 Woodlands Hill Lane

                          Oakland, MD

                          Bright
                          Courtesy of RAILEY REALTY, INC.
                          View 1001 Penn Point Road Oakland, MD MLS# MDGA2012654
                            Save 1001 Penn Point Road Oakland, MD MLS# MDGA2012654
                            1 of 61
                            $1,449,900
                            4

                            Beds

                            3.0

                            Baths

                            1,592

                            Sq.Ft.

                            1001 Penn Point Road

                            Oakland, MD

                            Bright
                            Courtesy of TAYLOR-MADE DEEP CREEK SALES
                            View Lot 8 Stool Rock Road Oakland, MD MLS# MDGA2012542
                              Save Lot 8 Stool Rock Road Oakland, MD MLS# MDGA2012542
                              1 of 16
                              $10,000
                              0.0

                              Baths

                              Lot 8 Stool Rock Road

                              Oakland, MD

                              Bright
                              Courtesy of RAILEY REALTY, INC.
                              View 333 Sloan Tract Road Oakland, MD MLS# MDGA2012576
                              • 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

                              Bright
                              Courtesy of LONG & FOSTER REAL ESTATE, INC.
                              View Boyd Paugh Lane Oakland, MD MLS# MDGA2012630
                                Save Boyd Paugh Lane Oakland, MD MLS# MDGA2012630
                                1 of 11
                                $989,000
                                0.0

                                Baths

                                Boyd Paugh Lane

                                Oakland, MD

                                Bright
                                Courtesy of TAYLOR-MADE DEEP CREEK SALES
                                View 20698 Garrett Highway Oakland, MD MLS# MDGA2012616
                                • Virtual Tour
                                Save 20698 Garrett Highway Oakland, MD MLS# MDGA2012616
                                1 of 53
                                $1,199,000
                                4

                                Beds

                                3.0

                                Baths

                                1,844

                                Sq.Ft.

                                20698 Garrett Highway

                                Oakland, MD

                                Bright
                                Courtesy of TAYLOR-MADE DEEP CREEK SALES
                                View Lot 7 Heron Cove Oakland, MD MLS# MDGA2012608
                                  Save Lot 7 Heron Cove Oakland, MD MLS# MDGA2012608
                                  1 of 46
                                  $489,900
                                  0.0

                                  Baths

                                  Lot 7 Heron Cove

                                  Oakland, MD

                                  Bright
                                  Courtesy of TAYLOR-MADE DEEP CREEK SALES
                                  View 704 Old Crellin Road Oakland, MD MLS# MDGA2012604
                                    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

                                    Bright
                                    Courtesy of THE KW COLLECTIVE

                                    About Oakland

                                    Listings in Oakland, MD

                                    189

                                    Estimated median home price

                                    $289,000
                                    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 - 100K43
                                    $100K - 200K23
                                    $200K - 300K33
                                    $300K - 400K18
                                    $400K - 500K14
                                    $500K - 600K5
                                    $600K - 700K14
                                    $700K - 800K10
                                    $800K - 900K6
                                    $900K - 1M4
                                    $1M - Max19

                                    Homes for Sale by Type in Oakland, MD

                                    Property TypeCount
                                    Single Family86
                                    Townhouse1
                                    Condo17
                                    Commercial11
                                    Rental7
                                    Lots and Land73
                                    Condo/Town/CoOp0
                                    CoOp0
                                    Multi Family1
                                    Mobile Home0
                                    Farms0

                                    (Data as of 10/2/2026)

                                    Find Properties in Oakland, MD

                                    Oakland, MD Information

                                    Find Properties by Zip

                                    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.