157 total properties
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View 13209 Garrett Highway Oakland, MD MLS# MDGA2006142
    Save 13209 Garrett Highway Oakland, MD MLS# MDGA2006142
    1 of 10
    $649,000

    13209 Garrett Highway

    Oakland, MD

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    View 231 Santa Fe Trail Oakland, MD MLS# MDGA2011082
      Save 231 Santa Fe Trail Oakland, MD MLS# MDGA2011082
      1 of 38
      $629,000
      4

      Beds

      3.0

      Baths

      2,280

      Sq.Ft.

      231 Santa Fe Trail

      Oakland, MD

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      View 308 Winding Trail Lane # 11B Oakland, MD MLS# MDGA2012146
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      1 of 61
      $615,000
      5

      Beds

      4.1

      Baths

      3,300

      Sq.Ft.

      308 Winding Trail Lane # 11B

      Oakland, MD

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      The time to sell is now! THE TIME TO SELL IS NOW!
      View 104 Roman Ridge Road # 21 Oakland, MD MLS# MDGA2012268
        Save 104 Roman Ridge Road # 21 Oakland, MD MLS# MDGA2012268
        1 of 61
        $605,000
        5

        Beds

        4.1

        Baths

        2,582

        Sq.Ft.

        104 Roman Ridge Road # 21

        Oakland, MD

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        View Boy Scout Road Oakland, MD MLS# MDGA2012474
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        1 of 21
        $599,900
        Studio

        Beds

        0.0

        Baths

        Boy Scout Road

        Oakland, MD

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        View 428 Sam Snead Circle Oakland, MD MLS# MDGA2012104
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        Save 428 Sam Snead Circle Oakland, MD MLS# MDGA2012104
        1 of 86
        $599,000
        5

        Beds

        3.1

        Baths

        3,542

        Sq.Ft.

        428 Sam Snead Circle

        Oakland, MD

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        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
          $599,000
          Studio

          Beds

          0.0

          Baths

          97 acres Lot C Garrett Road

          Oakland, MD

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          View 193 Red Run Road # 1-B-3 Oakland, MD MLS# MDGA2012232
            Save 193 Red Run Road # 1-B-3 Oakland, MD MLS# MDGA2012232
            1 of 57
            $595,000
            2

            Beds

            2.0

            Baths

            1,340

            Sq.Ft.

            193 Red Run Road # 1-B-3

            Oakland, MD

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            View 55 Village Drive # 5 Oakland, MD MLS# MDGA2011682
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            Save 55 Village Drive # 5 Oakland, MD MLS# MDGA2011682
            1 of 45
            $585,000
            3

            Beds

            3.0

            Baths

            2,280

            Sq.Ft.

            55 Village Drive # 5

            Oakland, MD

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            View 20160 Garrett Highway # F501-701 Oakland, MD MLS# MDGA2010702
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            1 of 68
            $575,000
            3

            Beds

            2.0

            Baths

            1,700

            Sq.Ft.

            20160 Garrett Highway # F501-701

            Oakland, MD

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            View 135 Rock Ridge Lane # 13 Oakland, MD MLS# MDGA2012086
              Save 135 Rock Ridge Lane # 13 Oakland, MD MLS# MDGA2012086
              1 of 49
              $575,000
              4

              Beds

              3.0

              Baths

              2,383

              Sq.Ft.

              135 Rock Ridge Lane # 13

              Oakland, MD

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              View 355 Markwood Drive Oakland, MD MLS# MDGA2012466
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              Save 355 Markwood Drive Oakland, MD MLS# MDGA2012466
              1 of 72
              $569,000
              3

              Beds

              2.1

              Baths

              1,654

              Sq.Ft.

              355 Markwood Drive

              Oakland, MD

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              View 178 Winding Trail Lane # 5B Oakland, MD MLS# MDGA2010960
                Save 178 Winding Trail Lane # 5B Oakland, MD MLS# MDGA2010960
                1 of 47
                $559,000
                5

                Beds

                4.1

                Baths

                3,300

                Sq.Ft.

                178 Winding Trail Lane # 5B

                Oakland, MD

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                View 98 Bear Run Road Oakland, MD MLS# MDGA2010728
                  Save 98 Bear Run Road Oakland, MD MLS# MDGA2010728
                  1 of 30
                  $550,000
                  3

                  Beds

                  2.0

                  Baths

                  1,080

                  Sq.Ft.

                  98 Bear Run Road

                  Oakland, MD

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                  View 995 Betts Lane Oakland, MD MLS# MDGA2012114
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                  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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                  View 328 Stool Rock Road Oakland, MD MLS# MDGA2009150
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                  1 of 137
                  $545,000
                  4

                  Beds

                  2.1

                  Baths

                  1,860

                  Sq.Ft.

                  328 Stool Rock Road

                  Oakland, MD

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                  View 126 Leo Friend Road Oakland, MD MLS# MDGA2009940
                    Save 126 Leo Friend Road Oakland, MD MLS# MDGA2009940
                    1 of 50
                    $499,900
                    4

                    Beds

                    3.0

                    Baths

                    2,235

                    Sq.Ft.

                    126 Leo Friend Road

                    Oakland, MD

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                    View 101 Sobriety Way Oakland, MD MLS# MDGA2012278
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                    Save 101 Sobriety Way Oakland, MD MLS# MDGA2012278
                    1 of 72
                    $499,900
                    3

                    Beds

                    2.0

                    Baths

                    1,920

                    Sq.Ft.

                    101 Sobriety Way

                    Oakland, MD

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                    View 0 George Washington Highway Oakland, MD MLS# MDGA2006062
                      Save 0 George Washington Highway Oakland, MD MLS# MDGA2006062
                      1 of 77
                      $490,000
                      Studio

                      Beds

                      0.0

                      Baths

                      0 George Washington Highway

                      Oakland, MD

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                      View 256 Jeffrey Lane # 28 Oakland, MD MLS# MDGA2012248
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                      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

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                      About Oakland

                      Listings in Oakland, MD

                      208

                      Estimated median home price

                      $301,950
                      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 - 100K44
                      $100K - 200K26
                      $200K - 300K34
                      $300K - 400K27
                      $400K - 500K10
                      $500K - 600K12
                      $600K - 700K9
                      $700K - 800K16
                      $800K - 900K4
                      $900K - 1M4
                      $1M - Max22

                      Homes for Sale by Type in Oakland, MD

                      Property TypeCount
                      Single Family95
                      Townhouse1
                      Condo26
                      Commercial11
                      Rental6
                      Lots and Land75
                      Condo/Town/CoOp0
                      CoOp0
                      Multi Family0
                      Mobile Home0
                      Farms0

                      (Data as of 7/31/2026)

                      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.

                      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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                      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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