197 total properties
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View 12743 Garrett Highway Oakland, MD MLS# MDGA2008424
    Save 12743 Garrett Highway Oakland, MD MLS# MDGA2008424
    1 of 62
    $1,999,900
    32,544

    Sq.Ft.

    12743 Garrett Highway

    Oakland, MD

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    View 815 Chadderton School Road Oakland, MD MLS# MDGA2011092
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    1 of 110
    $1,900,000
    5

    Beds

    3.1

    Baths

    4,619

    Sq.Ft.

    815 Chadderton School Road

    Oakland, MD

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    View 62 Duck Cove Road Oakland, MD MLS# MDGA2011402
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    1 of 74
    $1,899,000
    4

    Beds

    4.0

    Baths

    4,150

    Sq.Ft.

    62 Duck Cove Road

    Oakland, MD

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    The time to sell is now! THE TIME TO SELL IS NOW!
    View 499 Oakland Drive Oakland, MD MLS# MDGA2003394
      Save 499 Oakland Drive Oakland, MD MLS# MDGA2003394
      1 of 103
      $1,750,000
      15,000

      Sq.Ft.

      499 Oakland Drive

      Oakland, MD

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      View 17848 Garrett Highway Oakland, MD MLS# MDGA2011286
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      Save 17848 Garrett Highway Oakland, MD MLS# MDGA2011286
      1 of 122
      $1,700,000
      6,477

      Sq.Ft.

      17848 Garrett Highway

      Oakland, MD

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      View 670 Woodlands Hill Lane Oakland, MD MLS# MDGA2011904
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      Save 670 Woodlands Hill Lane Oakland, MD MLS# MDGA2011904
      1 of 72
      $1,689,000
      5

      Beds

      4.1

      Baths

      3,714

      Sq.Ft.

      670 Woodlands Hill Lane

      Oakland, MD

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      View 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
        Save 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
        1 of 31
        $1,650,000
        4

        Beds

        4.2

        Baths

        5,117

        Sq.Ft.

        3898 3898 Underwood Rd

        Oakland, MD

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        View 2311 Boy Scout Road Oakland, MD MLS# MDGA2012046
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        1 of 78
        $1,579,900
        4

        Beds

        3.0

        Baths

        3,278

        Sq.Ft.

        2311 Boy Scout Road

        Oakland, MD

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        View 211 High Point Ridge Road Oakland, MD MLS# MDGA2011990
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        1 of 99
        $1,495,000
        4

        Beds

        3.1

        Baths

        3,472

        Sq.Ft.

        211 High Point Ridge Road

        Oakland, MD

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        View 827 Penn Point Road Oakland, MD MLS# MDGA2011664
          Save 827 Penn Point Road Oakland, MD MLS# MDGA2011664
          1 of 64
          $1,400,000
          5

          Beds

          3.1

          Baths

          2,832

          Sq.Ft.

          827 Penn Point 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 122 Woodlands Hill Lane Oakland, MD MLS# MDGA2011982
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          1 of 54
          $1,200,000
          4

          Beds

          4.1

          Baths

          2,656

          Sq.Ft.

          122 Woodlands Hill Lane

          Oakland, MD

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          View 209 Black Angus Drive Oakland, MD MLS# MDGA2012018
            Save 209 Black Angus Drive Oakland, MD MLS# MDGA2012018
            1 of 50
            $1,200,000
            2

            Beds

            2.0

            Baths

            1,156

            Sq.Ft.

            209 Black Angus Drive

            Oakland, MD

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            View 248 Tarn Drive Oakland, MD MLS# MDGA2011874
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            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 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 588 Lake Forest Drive Oakland, MD MLS# MDGA2011898
                Save 588 Lake Forest Drive Oakland, MD MLS# MDGA2011898
                1 of 39
                $1,089,000
                3

                Beds

                2.0

                Baths

                1,411

                Sq.Ft.

                588 Lake Forest Drive

                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 91
                $1,074,900
                4

                Beds

                4.2

                Baths

                3,032

                Sq.Ft.

                52 Dam View Drive

                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 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 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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                    About Oakland

                    Listings in Oakland, MD

                    206

                    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 - 100K49
                    $100K - 200K27
                    $200K - 300K30
                    $300K - 400K22
                    $400K - 500K12
                    $500K - 600K7
                    $600K - 700K8
                    $700K - 800K11
                    $800K - 900K6
                    $900K - 1M7
                    $1M - Max27

                    Homes for Sale by Type in Oakland, MD

                    Property TypeCount
                    Single Family93
                    Townhouse2
                    Condo23
                    Commercial16
                    Rental6
                    Lots and Land72
                    Condo/Town/CoOp0
                    CoOp0
                    Multi Family0
                    Mobile Home0
                    Farms0

                    (Data as of 6/10/2026)

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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.

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