194 total properties
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View 62 Middleton Road Oakland, MD MLS# MDGA2011994
    Save 62 Middleton Road Oakland, MD MLS# MDGA2011994
    1 of 38
    $799,900
    3

    Beds

    2.1

    Baths

    1,929

    Sq.Ft.

    62 Middleton Road

    Oakland, MD

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    View 14 Commerce Drive Oakland, MD MLS# MDGA2010002
      Save 14 Commerce Drive Oakland, MD MLS# MDGA2010002
      1 of 99
      $800,000
      10,000

      Sq.Ft.

      14 Commerce Drive

      Oakland, MD

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      View 39 Leo Friend Road Oakland, MD MLS# MDGA2011668
        Save 39 Leo Friend Road Oakland, MD MLS# MDGA2011668
        1 of 59
        $875,000
        3

        Beds

        3.1

        Baths

        3,897

        Sq.Ft.

        39 Leo Friend Road

        Oakland, MD

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        The time to sell is now! THE TIME TO SELL IS NOW!
        View 62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182
          Save 62 Whispering Pines Lane Oakland, MD MLS# MDGA2011182
          1 of 77
          $899,000
          4

          Beds

          3.1

          Baths

          2,464

          Sq.Ft.

          62 Whispering Pines Lane

          Oakland, MD

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          View 113 Jubb Meadows Lane Oakland, MD MLS# MDGA2011494
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          Save 113 Jubb Meadows Lane Oakland, MD MLS# MDGA2011494
          1 of 69
          $899,900
          4

          Beds

          3.1

          Baths

          3,185

          Sq.Ft.

          113 Jubb Meadows Lane

          Oakland, MD

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          View 8 Hidden Cove Court Oakland, MD MLS# MDGA2011746
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          Save 8 Hidden Cove Court Oakland, MD MLS# MDGA2011746
          1 of 65
          $949,000
          4

          Beds

          3.0

          Baths

          2,856

          Sq.Ft.

          8 Hidden Cove Court

          Oakland, MD

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          View 164 Grandview Drive Oakland, MD MLS# MDGA2011052
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          Save 164 Grandview Drive Oakland, MD MLS# MDGA2011052
          1 of 54
          $950,000
          3

          Beds

          2.1

          Baths

          2,368

          Sq.Ft.

          164 Grandview Drive

          Oakland, MD

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          View 208 Cliff Drive Oakland, MD MLS# MDGA2011858
            Save 208 Cliff Drive Oakland, MD MLS# MDGA2011858
            1 of 80
            $950,000
            4

            Beds

            3.0

            Baths

            2,219

            Sq.Ft.

            208 Cliff Drive

            Oakland, MD

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            View 251 Robinwood Drive Oakland, MD MLS# MDGA2011890
              Save 251 Robinwood Drive Oakland, MD MLS# MDGA2011890
              1 of 61
              OPEN HOUSE: Friday 7/3 11:00 AM - 1:00 PM
              $969,000
              5

              Beds

              4.1

              Baths

              4,284

              Sq.Ft.

              251 Robinwood Drive

              Oakland, MD

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              View Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
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              Save Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
              1 of 21
              $975,000
              Studio

              Beds

              0.0

              Baths

              Glendale Rd Lot 12 Alpine Village Subdivision

              Oakland, MD

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              View 1250 Pergin Farm Road Oakland, MD MLS# MDGA2012178
                Save 1250 Pergin Farm Road Oakland, MD MLS# MDGA2012178
                1 of 110
                $975,000
                3

                Beds

                2.1

                Baths

                2,520

                Sq.Ft.

                1250 Pergin Farm Road

                Oakland, MD

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                View 137 Paradise Gardens Road Oakland, MD MLS# MDGA2011454
                  Save 137 Paradise Gardens Road Oakland, MD MLS# MDGA2011454
                  1 of 71
                  $999,000
                  4

                  Beds

                  2.0

                  Baths

                  2,730

                  Sq.Ft.

                  137 Paradise Gardens Road

                  Oakland, MD

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                  View 127 Paradise Heights Oakland, MD MLS# MDGA2011804
                    Save 127 Paradise Heights Oakland, MD MLS# MDGA2011804
                    1 of 24
                    $1,025,000
                    3

                    Beds

                    2.1

                    Baths

                    2,240

                    Sq.Ft.

                    127 Paradise Heights

                    Oakland, MD

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                    View 52 Dam View Drive Oakland, MD MLS# MDGA2011104
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                    Save 52 Dam View Drive Oakland, MD MLS# MDGA2011104
                    1 of 97
                    $1,074,900
                    4

                    Beds

                    4.2

                    Baths

                    3,032

                    Sq.Ft.

                    52 Dam View Drive

                    Oakland, MD

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                    View 660 Glendale Road Oakland, MD MLS# MDGA2011188
                      Save 660 Glendale Road Oakland, MD MLS# MDGA2011188
                      1 of 62
                      $1,100,000
                      5

                      Beds

                      3.0

                      Baths

                      2,592

                      Sq.Ft.

                      660 Glendale Road

                      Oakland, MD

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                      View 248 Tarn Drive Oakland, MD MLS# MDGA2011874
                      • New Construction
                      Save 248 Tarn Drive Oakland, MD MLS# MDGA2011874
                      1 of 70
                      $1,189,000
                      6

                      Beds

                      5.1

                      Baths

                      3,482

                      Sq.Ft.

                      248 Tarn Drive

                      Oakland, MD

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                      View 122 Woodlands Hill Lane Oakland, MD MLS# MDGA2011982
                        Save 122 Woodlands Hill Lane Oakland, MD MLS# MDGA2011982
                        1 of 56
                        $1,200,000
                        4

                        Beds

                        4.1

                        Baths

                        2,656

                        Sq.Ft.

                        122 Woodlands Hill Lane

                        Oakland, MD

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                        View 826 G Swauger Road Oakland, MD MLS# MDGA2012212
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                        Save 826 G Swauger Road Oakland, MD MLS# MDGA2012212
                        1 of 33
                        $1,200,000
                        2

                        Beds

                        2.1

                        Baths

                        2,914

                        Sq.Ft.

                        826 G Swauger Road

                        Oakland, MD

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                        View 439 Paradise Heights Oakland, MD MLS# MDGA2008472
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                        Save 439 Paradise Heights Oakland, MD MLS# MDGA2008472
                        1 of 45
                        $1,329,000
                        6

                        Beds

                        4.1

                        Baths

                        4,113

                        Sq.Ft.

                        439 Paradise Heights

                        Oakland, MD

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                        View 211 High Point Ridge Road Oakland, MD MLS# MDGA2011990
                          Save 211 High Point Ridge Road Oakland, MD MLS# MDGA2011990
                          1 of 99
                          $1,350,000
                          4

                          Beds

                          3.1

                          Baths

                          3,472

                          Sq.Ft.

                          211 High Point Ridge Road

                          Oakland, MD

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                          About Oakland

                          Listings in Oakland, MD

                          194

                          Estimated median home price

                          $295,000
                          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 - 100K45
                          $100K - 200K23
                          $200K - 300K32
                          $300K - 400K26
                          $400K - 500K7
                          $500K - 600K8
                          $600K - 700K8
                          $700K - 800K13
                          $800K - 900K3
                          $900K - 1M7
                          $1M - Max22

                          Homes for Sale by Type in Oakland, MD

                          Property TypeCount
                          Single Family86
                          Townhouse2
                          Condo24
                          Commercial14
                          Rental6
                          Lots and Land68
                          Condo/Town/CoOp0
                          CoOp0
                          Multi Family0
                          Mobile Home0
                          Farms0

                          (Data as of 7/2/2026)

                          Find Properties in Oakland, MD

                          Oakland, MD Information

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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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