141 total properties
Did you mean the neighborhood Oakland?
View 18948 Garrett Highway Oakland, MD MLS# MDGA2012540
    Save 18948 Garrett Highway Oakland, MD MLS# MDGA2012540
    1 of 41
    $375,000
    2

    Beds

    2.0

    Baths

    1,404

    Sq.Ft.

    18948 Garrett Highway

    Oakland, MD

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    Courtesy of 1 REAL ESTATE SOURCE LLC
    View 2560 Bray School Road Oakland, MD MLS# MDGA2012546
      Save 2560 Bray School Road Oakland, MD MLS# MDGA2012546
      1 of 1
      $230,000
      0.0

      Baths

      2560 Bray School Road

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      View Mayhew Inn Road Oakland, MD MLS# MDGA2012550
        Save Mayhew Inn Road Oakland, MD MLS# MDGA2012550
        1 of 7
        $169,900
        0.0

        Baths

        Mayhew Inn Road

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 181 Glotfelty Drive Oakland, MD MLS# MDGA2012496
          Save 181 Glotfelty Drive Oakland, MD MLS# MDGA2012496
          1 of 51
          $374,900
          3

          Beds

          2.0

          Baths

          1,456

          Sq.Ft.

          181 Glotfelty Drive

          Oakland, MD

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          Courtesy of RAILEY REALTY, INC.
          View 565 Glendale Road # 213 Oakland, MD MLS# MDGA2012506
            Save 565 Glendale Road # 213 Oakland, MD MLS# MDGA2012506
            1 of 24
            $215,000
            1

            Beds

            1.0

            Baths

            565 Glendale Road # 213

            Oakland, MD

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            Courtesy of THE KW COLLECTIVE
            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 40 Sunshine Oakland, MD MLS# MDGA2012436
                Save 40 Sunshine Oakland, MD MLS# MDGA2012436
                1 of 43
                $159,000
                3

                Beds

                1.0

                Baths

                1,516

                Sq.Ft.

                40 Sunshine

                Oakland, MD

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                Courtesy of TAYLOR-MADE DEEP CREEK SALES
                View 206 W Liberty Street Oakland, MD MLS# MDGA2012412
                  Save 206 W Liberty Street Oakland, MD MLS# MDGA2012412
                  1 of 35
                  $149,000
                  2

                  Beds

                  1.0

                  Baths

                  2,008

                  Sq.Ft.

                  206 W Liberty Street

                  Oakland, MD

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                  Courtesy of RAILEY REALTY, INC.
                  View 615 E Oak Street Oakland, MD MLS# MDGA2012446
                    Save 615 E Oak Street Oakland, MD MLS# MDGA2012446
                    1 of 60
                    $365,000
                    5

                    Beds

                    3.0

                    Baths

                    2,652

                    Sq.Ft.

                    615 E Oak Street

                    Oakland, MD

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                    Courtesy of RAILEY REALTY, INC.
                    View Bear Drive E Oakland, MD MLS# MDGA2012426
                      Save Bear Drive E Oakland, MD MLS# MDGA2012426
                      1 of 5
                      $19,900
                      0.0

                      Baths

                      Bear Drive E

                      Oakland, MD

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                      Courtesy of LONG & FOSTER REAL ESTATE, INC.
                      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 995 Betts Lane Oakland, MD MLS# MDGA2012114
                          Save 995 Betts Lane Oakland, MD MLS# MDGA2012114
                          1 of 45
                          $549,900
                          4

                          Beds

                          2.1

                          Baths

                          2,548

                          Sq.Ft.

                          995 Betts Lane

                          Oakland, MD

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                          Courtesy of TAYLOR-MADE DEEP CREEK SALES
                          View 5 Laurel Brook Drive # 5 Oakland, MD MLS# MDGA2012388
                            Save 5 Laurel Brook Drive # 5 Oakland, MD MLS# MDGA2012388
                            1 of 29
                            $259,900
                            2

                            Beds

                            2.0

                            Baths

                            1,400

                            Sq.Ft.

                            5 Laurel Brook Drive # 5

                            Oakland, MD

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                            Courtesy of TAYLOR-MADE DEEP CREEK SALES
                            View Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
                              Save Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
                              1 of 6
                              $175,000
                              0.0

                              Baths

                              Robinwood Drive # 9

                              Oakland, MD

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                              Courtesy of TAYLOR-MADE DEEP CREEK SALES
                              View 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
                                Save 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
                                1 of 15
                                $149,000
                                0.0

                                Baths

                                16 Woodlands Hill Court

                                Oakland, MD

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                                Courtesy of RAILEY REALTY, INC.
                                View 22 Woodlands Hill Lane Oakland, MD MLS# MDGA2012334
                                  Save 22 Woodlands Hill Lane Oakland, MD MLS# MDGA2012334
                                  1 of 22
                                  $159,000
                                  0.0

                                  Baths

                                  22 Woodlands Hill Lane

                                  Oakland, MD

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                                  View Robinwood Drive # 13 Oakland, MD MLS# MDGA2012320
                                    Save Robinwood Drive # 13 Oakland, MD MLS# MDGA2012320
                                    1 of 21
                                    $99,000
                                    0.0

                                    Baths

                                    Robinwood Drive # 13

                                    Oakland, MD

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                                    Courtesy of TAYLOR-MADE DEEP CREEK SALES
                                    View 112 E Pennington Street Oakland, MD MLS# MDGA2012308
                                      Save 112 E Pennington Street Oakland, MD MLS# MDGA2012308
                                      1 of 63
                                      $325,000
                                      5

                                      Beds

                                      3.0

                                      Baths

                                      2,165

                                      Sq.Ft.

                                      112 E Pennington Street

                                      Oakland, MD

                                      Bright
                                      Courtesy of LAKE HOMES REALTY, LLC
                                      View 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
                                        Save 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
                                        1 of 21
                                        $499,000
                                        0.0

                                        Baths

                                        97 acres Lot C Garrett Road

                                        Oakland, MD

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                                        Courtesy of RAILEY REALTY, INC.
                                        View 256 Jeffrey Lane # 28 Oakland, MD MLS# MDGA2012248
                                        • Virtual Tour
                                        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

                                        Bright
                                        Courtesy of RAILEY REALTY, INC.

                                        About Oakland

                                        Listings in Oakland, MD

                                        183

                                        Estimated median home price

                                        $285,000
                                        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 - 200K22
                                        $200K - 300K33
                                        $300K - 400K16
                                        $400K - 500K14
                                        $500K - 600K3
                                        $600K - 700K14
                                        $700K - 800K10
                                        $800K - 900K6
                                        $900K - 1M4
                                        $1M - Max18

                                        Homes for Sale by Type in Oakland, MD

                                        Property TypeCount
                                        Single Family82
                                        Townhouse1
                                        Condo16
                                        Commercial11
                                        Rental7
                                        Lots and Land72
                                        Condo/Town/CoOp0
                                        CoOp0
                                        Multi Family1
                                        Mobile Home0
                                        Farms0

                                        (Data as of 10/7/2026)

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                                        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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