88 total properties
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View 1021 E High Street Oakland, MD MLS# MDGA2010932
    Save 1021 E High Street Oakland, MD MLS# MDGA2010932
    1 of 58
    $234,000
    3

    Beds

    2.0

    Baths

    1,520

    Sq.Ft.

    1021 E High Street

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 62 Wild Turkey Court Oakland, MD MLS# MDGA2010810
    • New Construction
    Save 62 Wild Turkey Court Oakland, MD MLS# MDGA2010810
    1 of 30
    $249,000
    4

    Beds

    3.0

    Baths

    2,390

    Sq.Ft.

    62 Wild Turkey Court

    Oakland, MD

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    Courtesy of 1 REAL ESTATE SOURCE LLC
    View 565 Glendale Road # B206 Oakland, MD MLS# MDGA2010830
      Save 565 Glendale Road # B206 Oakland, MD MLS# MDGA2010830
      1 of 32
      $319,000
      2

      Beds

      1.0

      Baths

      780

      Sq.Ft.

      565 Glendale Road # B206

      Oakland, MD

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      Courtesy of JASON MITCHELL GROUP
      The time to sell is now! THE TIME TO SELL IS NOW!
      View LOT 2 Beaver Run Road Oakland, MD MLS# MDGA2010794
        Save LOT 2 Beaver Run Road Oakland, MD MLS# MDGA2010794
        1 of 9
        $3,500
        Studio

        Beds

        0.0

        Baths

        LOT 2 Beaver Run Road

        Oakland, MD

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        Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
        View Garrett Trail Oakland, MD MLS# MDGA2010758
          Save Garrett Trail Oakland, MD MLS# MDGA2010758
          1 of 4
          $29,900
          Studio

          Beds

          0.0

          Baths

          Garrett Trail

          Oakland, MD

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          Courtesy of 1 REAL ESTATE SOURCE LLC
          View 3257 George Washington Highway Oakland, MD MLS# MDGA2010760
            Save 3257 George Washington Highway Oakland, MD MLS# MDGA2010760
            1 of 8
            $280,000
            Studio

            Beds

            0.0

            Baths

            3257 George Washington Highway

            Oakland, MD

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            Courtesy of RAILEY REALTY, INC.
            View Rhododendron Drive Oakland, MD MLS# MDGA2010748
              Save Rhododendron Drive Oakland, MD MLS# MDGA2010748
              $4,000
              Studio

              Beds

              0.0

              Baths

              Rhododendron Drive

              Oakland, MD

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              Courtesy of RAILEY REALTY, INC.
              View 3.35 acres </> 4Th Street Oakland, MD MLS# MDGA2010746
                Save 3.35 acres </> 4Th Street Oakland, MD MLS# MDGA2010746
                1 of 3
                $150,000
                Studio

                Beds

                0.0

                Baths

                3.35 acres </> 4Th Street

                Oakland, MD

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                Courtesy of THE KW COLLECTIVE
                View 565 Glendale Road # 204 Oakland, MD MLS# MDGA2010718
                  Save 565 Glendale Road # 204 Oakland, MD MLS# MDGA2010718
                  1 of 51
                  $195,000
                  1

                  Beds

                  1.0

                  Baths

                  460

                  Sq.Ft.

                  565 Glendale Road # 204

                  Oakland, MD

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                  Courtesy of RAILEY REALTY, INC.
                  View 565 Glendale Road # 103B Oakland, MD MLS# MDGA2010720
                    Save 565 Glendale Road # 103B Oakland, MD MLS# MDGA2010720
                    1 of 54
                    $260,000
                    1

                    Beds

                    1.0

                    Baths

                    565 Glendale Road # 103B

                    Oakland, MD

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                    Courtesy of RAILEY REALTY, INC.
                    View 170 San Francisco Street Oakland, MD MLS# MDGA2010726
                      Save 170 San Francisco Street Oakland, MD MLS# MDGA2010726
                      1 of 12
                      $129,900
                      Studio

                      Beds

                      0.0

                      Baths

                      170 San Francisco Street

                      Oakland, MD

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                      Courtesy of COLDWELL BANKER REALTY
                      View Fox Tail Road Oakland, MD MLS# MDGA2010714
                        Save Fox Tail Road Oakland, MD MLS# MDGA2010714
                        1 of 4
                        $39,500
                        Studio

                        Beds

                        0.0

                        Baths

                        Fox Tail Road

                        Oakland, MD

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                        Courtesy of RAILEY REALTY, INC.
                        View Lot 40 Big Piney Drive Oakland, MD MLS# MDGA2010712
                          Save Lot 40 Big Piney Drive Oakland, MD MLS# MDGA2010712
                          1 of 8
                          $17,000
                          Studio

                          Beds

                          0.0

                          Baths

                          Lot 40 Big Piney Drive

                          Oakland, MD

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                          Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                          View 181 Jeffrey Lane # 23A Oakland, MD MLS# MDGA2010704
                            Save 181 Jeffrey Lane # 23A Oakland, MD MLS# MDGA2010704
                            1 of 25
                            $269,900
                            2

                            Beds

                            1.0

                            Baths

                            670

                            Sq.Ft.

                            181 Jeffrey Lane # 23A

                            Oakland, MD

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                            Courtesy of RAILEY REALTY, INC.
                            View Lot 13 Dogwood Drive Oakland, MD MLS# MDGA2010664
                              Save Lot 13 Dogwood Drive Oakland, MD MLS# MDGA2010664
                              1 of 26
                              $22,500
                              Studio

                              Beds

                              0.0

                              Baths

                              Lot 13 Dogwood Drive

                              Oakland, MD

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                              Courtesy of RAILEY REALTY, INC.
                              View 60 Gorman Street Oakland, MD MLS# MDGA2010692
                                Save 60 Gorman Street Oakland, MD MLS# MDGA2010692
                                1 of 15
                                $75,000
                                3

                                Beds

                                1.0

                                Baths

                                1,488

                                Sq.Ft.

                                60 Gorman Street

                                Oakland, MD

                                Bright
                                Courtesy of CHARIS REALTY GROUP
                                View Lot 18 Laurel Court Oakland, MD MLS# MDGA2010662
                                  Save Lot 18 Laurel Court Oakland, MD MLS# MDGA2010662
                                  1 of 35
                                  $95,000
                                  Studio

                                  Beds

                                  0.0

                                  Baths

                                  Lot 18 Laurel Court

                                  Oakland, MD

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                                  Courtesy of RAILEY REALTY, INC.
                                  View 63 Wallman Road Oakland, MD MLS# MDGA2010592
                                    Save 63 Wallman Road Oakland, MD MLS# MDGA2010592
                                    1 of 60
                                    $179,900
                                    3

                                    Beds

                                    1.0

                                    Baths

                                    816

                                    Sq.Ft.

                                    63 Wallman Road

                                    Oakland, MD

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                                    Courtesy of RAILEY REALTY, INC.
                                    View 102 Roanoke Avenue Oakland, MD MLS# MDGA2010452
                                      Save 102 Roanoke Avenue Oakland, MD MLS# MDGA2010452
                                      1 of 20
                                      $125,000
                                      4

                                      Beds

                                      1.1

                                      Baths

                                      1,932

                                      Sq.Ft.

                                      102 Roanoke Avenue

                                      Oakland, MD

                                      Bright
                                      Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                                      View 9 Timber Falls Road Oakland, MD MLS# MDGA2010352
                                        Save 9 Timber Falls Road Oakland, MD MLS# MDGA2010352
                                        1 of 25
                                        $34,000
                                        Studio

                                        Beds

                                        0.0

                                        Baths

                                        9 Timber Falls Road

                                        Oakland, MD

                                        Bright
                                        Courtesy of RAILEY REALTY, INC.

                                        About Oakland

                                        Listings in Oakland, MD

                                        153

                                        Estimated median home price

                                        $280,000
                                        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 - 100K35
                                        $100K - 200K22
                                        $200K - 300K26
                                        $300K - 400K13
                                        $400K - 500K8
                                        $500K - 600K10
                                        $600K - 700K8
                                        $700K - 800K6
                                        $800K - 900K5
                                        $900K - 1M3
                                        $1M - Max17

                                        Homes for Sale by Type in Oakland, MD

                                        Property TypeCount
                                        Single Family63
                                        Townhouse2
                                        Condo19
                                        Commercial11
                                        Rental4
                                        Lots and Land58
                                        Condo/Town/CoOp0
                                        CoOp0
                                        Multi Family0
                                        Mobile Home0
                                        Farms0

                                        (Data as of 2/6/2026)

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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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                                        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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