162 total properties
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View 112 E Pennington Street Oakland, MD MLS# MDGA2012308
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Save 112 E Pennington Street Oakland, MD MLS# MDGA2012308
1 of 63
$350,000
5

Beds

3.0

Baths

2,165

Sq.Ft.

112 E Pennington Street

Oakland, MD

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Courtesy of LAKE HOMES REALTY, LLC
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 Cranesville Road Oakland, MD MLS# MDGA2012284
    Save Cranesville Road Oakland, MD MLS# MDGA2012284
    1 of 17
    $115,000
    Studio

    Beds

    0.0

    Baths

    Cranesville Road

    Oakland, MD

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    The time to sell is now! THE TIME TO SELL IS NOW!
    View 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
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    Save 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
    1 of 21
    $599,000
    Studio

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    0.0

    Baths

    97 acres Lot C Garrett Road

    Oakland, MD

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    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 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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      View 102 N 3Rd Street Oakland, MD MLS# MDGA2012246
        Save 102 N 3Rd Street Oakland, MD MLS# MDGA2012246
        1 of 43
        $259,900
        3

        Beds

        2.0

        Baths

        1,998

        Sq.Ft.

        102 N 3Rd Street

        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 953 Bray School Road Oakland, MD MLS# MDGA2012238
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          Save 953 Bray School Road Oakland, MD MLS# MDGA2012238
          1 of 63
          $299,900
          3

          Beds

          1.0

          Baths

          1,008

          Sq.Ft.

          953 Bray School Road

          Oakland, MD

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          View 2189 Table Rock Road Oakland, MD MLS# MDGA2012226
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          Save 2189 Table Rock Road Oakland, MD MLS# MDGA2012226
          1 of 65
          $299,000
          4

          Beds

          2.0

          Baths

          1,736

          Sq.Ft.

          2189 Table Rock Road

          Oakland, MD

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          View Lot B Loch Deer Road Oakland, MD MLS# MDGA2012224
            Save Lot B Loch Deer Road Oakland, MD MLS# MDGA2012224
            1 of 27
            $259,000
            Studio

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            0.0

            Baths

            Lot B Loch Deer Road

            Oakland, MD

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            View Quentin Lane Oakland, MD MLS# MDGA2012218
              Save Quentin Lane Oakland, MD MLS# MDGA2012218
              1 of 7
              $84,369
              Studio

              Beds

              0.0

              Baths

              Quentin Lane

              Oakland, MD

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              View 321 Deer Park Hotel Road Oakland, MD MLS# MDGA2012166
                Save 321 Deer Park Hotel Road Oakland, MD MLS# MDGA2012166
                1 of 47
                $399,900
                3

                Beds

                2.0

                Baths

                2,476

                Sq.Ft.

                321 Deer Park Hotel Road

                Oakland, MD

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                View 509 Southern Pines Drive Oakland, MD MLS# MDGA2012208
                  Save 509 Southern Pines Drive Oakland, MD MLS# MDGA2012208
                  $399,000
                  4

                  Beds

                  3.0

                  Baths

                  2,681

                  Sq.Ft.

                  509 Southern Pines Drive

                  Oakland, MD

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                  View 308 Winding Trail Lane # 11B Oakland, MD MLS# MDGA2012146
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                  Save 308 Winding Trail Lane # 11B Oakland, MD MLS# MDGA2012146
                  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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                  View 254 Little Mountain Road Oakland, MD MLS# MDGA2012150
                    Save 254 Little Mountain Road Oakland, MD MLS# MDGA2012150
                    1 of 54
                    $340,000
                    4

                    Beds

                    2.0

                    Baths

                    1,792

                    Sq.Ft.

                    254 Little Mountain Road

                    Oakland, MD

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                    View Lot 18 Buck Drive Oakland, MD MLS# MDGA2011342
                      Save Lot 18 Buck Drive Oakland, MD MLS# MDGA2011342
                      1 of 6
                      $19,900
                      Studio

                      Beds

                      0.0

                      Baths

                      Lot 18 Buck Drive

                      Oakland, MD

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                      View Maple Del Lane Oakland, MD MLS# MDGA2012116
                        Save Maple Del Lane Oakland, MD MLS# MDGA2012116
                        1 of 7
                        $42,000
                        Studio

                        Beds

                        0.0

                        Baths

                        Maple Del Lane

                        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 1499 Foster Road Oakland, MD MLS# MDGA2012068
                          Save 1499 Foster Road Oakland, MD MLS# MDGA2012068
                          1 of 64
                          $375,000
                          4

                          Beds

                          2.0

                          Baths

                          2,234

                          Sq.Ft.

                          1499 Foster Road

                          Oakland, MD

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                          About Oakland

                          Listings in Oakland, MD

                          210

                          Estimated median home price

                          $306,500
                          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 - 200K26
                          $200K - 300K35
                          $300K - 400K28
                          $400K - 500K9
                          $500K - 600K11
                          $600K - 700K9
                          $700K - 800K17
                          $800K - 900K4
                          $900K - 1M5
                          $1M - Max23

                          Homes for Sale by Type in Oakland, MD

                          Property TypeCount
                          Single Family98
                          Townhouse1
                          Condo26
                          Commercial12
                          Rental6
                          Lots and Land73
                          Condo/Town/CoOp0
                          CoOp0
                          Multi Family0
                          Mobile Home0
                          Farms0

                          (Data as of 7/26/2026)

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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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                          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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