207 total properties
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View 47 Holy Cross Oakland, MD MLS# MDGA2010560
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$6,499,900
8

Beds

8.1

Baths

11,417

Sq.Ft.

47 Holy Cross

Oakland, MD

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View 4009 Mayhew Inn Oakland, MD MLS# MDGA2007236
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$6,000,000

4009 Mayhew Inn

Oakland, MD

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Courtesy of JASON MITCHELL GROUP
View 1010 Holy Cross Drive Oakland, MD MLS# MDGA2011388
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1 of 147
$5,150,000
8

Beds

8.1

Baths

10,300

Sq.Ft.

1010 Holy Cross Drive

Oakland, MD

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The time to sell is now! THE TIME TO SELL IS NOW!
View 65 Enterprise Drive Oakland, MD MLS# MDGA2010098
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    1 of 67
    $2,799,900
    30,000

    Sq.Ft.

    65 Enterprise Drive

    Oakland, MD

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    View 19530 Garrett Highway Oakland, MD MLS# MDGA2010798
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      1 of 43
      $2,500,000
      7,200

      Sq.Ft.

      19530 Garrett Highway

      Oakland, MD

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      View 83 Bethlehem Road Oakland, MD MLS# MDGA2011892
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      1 of 44
      $2,499,900
      4

      Beds

      1.1

      Baths

      2,190

      Sq.Ft.

      83 Bethlehem Road

      Oakland, MD

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      View 2725 Stockslager Road Oakland, MD MLS# MDGA2008312
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      1 of 115
      $2,350,000
      5

      Beds

      6.1

      Baths

      5,376

      Sq.Ft.

      2725 Stockslager Road

      Oakland, MD

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      View 209 Glendale Road Oakland, MD MLS# MDGA2010922
        Save 209 Glendale Road Oakland, MD MLS# MDGA2010922
        1 of 89
        $2,100,000
        6

        Beds

        4.1

        Baths

        3,882

        Sq.Ft.

        209 Glendale Road

        Oakland, MD

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        View 1038 S Blakeslee Road Oakland, MD MLS# MDGA2011370
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          1 of 69
          $2,100,000
          5

          Beds

          5.0

          Baths

          4,074

          Sq.Ft.

          1038 S Blakeslee Road

          Oakland, MD

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          View 12743 Garrett Highway Oakland, MD MLS# MDGA2008424
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            $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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            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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              $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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              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
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                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
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                  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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                  About Oakland

                  Listings in Oakland, MD

                  207

                  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 - 500K13
                  $500K - 600K7
                  $600K - 700K8
                  $700K - 800K11
                  $800K - 900K6
                  $900K - 1M7
                  $1M - Max27

                  Homes for Sale by Type in Oakland, MD

                  Property TypeCount
                  Single Family94
                  Townhouse2
                  Condo23
                  Commercial16
                  Rental6
                  Lots and Land72
                  Condo/Town/CoOp0
                  CoOp0
                  Multi Family0
                  Mobile Home0
                  Farms0

                  (Data as of 6/9/2026)

                  Find Properties in Oakland, MD

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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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                  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.

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