160 total properties
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View George Washington Highway Oakland, MD MLS# MDGA2010274
    Save George Washington Highway Oakland, MD MLS# MDGA2010274
    1 of 16
    $675,000
    Studio

    Beds

    0.0

    Baths

    George Washington Highway

    Oakland, MD

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    Courtesy of THE KW COLLECTIVE
    View 104 Pine Top Trail Oakland, MD MLS# MDGA2010178
      Save 104 Pine Top Trail Oakland, MD MLS# MDGA2010178
      1 of 13
      $425,000
      3

      Beds

      3.1

      Baths

      1,596

      Sq.Ft.

      104 Pine Top Trail

      Oakland, MD

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      Courtesy of 1 REAL ESTATE SOURCE LLC
      View LOT 25 Holy Cross Drive Oakland, MD MLS# MDGA2010144
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      Save LOT 25 Holy Cross Drive Oakland, MD MLS# MDGA2010144
      1 of 26
      $475,000
      Studio

      Beds

      0.0

      Baths

      LOT 25 Holy Cross Drive

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      The time to sell is now! THE TIME TO SELL IS NOW!
      View Lot 13 Bray Run Road Oakland, MD MLS# MDGA2010142
        Save Lot 13 Bray Run Road Oakland, MD MLS# MDGA2010142
        1 of 23
        $44,900
        Studio

        Beds

        0.0

        Baths

        Lot 13 Bray Run Road

        Oakland, MD

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        View 565 Glendale Road # 116 Oakland, MD MLS# MDGA2010152
          Save 565 Glendale Road # 116 Oakland, MD MLS# MDGA2010152
          1 of 29
          $169,000
          1

          Beds

          1.0

          Baths

          484

          Sq.Ft.

          565 Glendale Road # 116

          Oakland, MD

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          View 65 Enterprise Drive Oakland, MD MLS# MDGA2010098
            Save 65 Enterprise Drive Oakland, MD MLS# MDGA2010098
            1 of 67
            $2,799,900
            30,000

            Sq.Ft.

            65 Enterprise Drive

            Oakland, MD

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            View Lot 53 Mountainview Drive Oakland, MD MLS# MDGA2010146
              Save Lot 53 Mountainview Drive Oakland, MD MLS# MDGA2010146
              1 of 5
              $124,900
              Studio

              Beds

              0.0

              Baths

              Lot 53 Mountainview Drive

              Oakland, MD

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              Courtesy of SAMSON PROPERTIES
              View Lot 7 Backbone Ridge Road Oakland, MD MLS# MDGA2010076
                Save Lot 7 Backbone Ridge Road Oakland, MD MLS# MDGA2010076
                1 of 7
                $29,950
                Studio

                Beds

                0.0

                Baths

                Lot 7 Backbone Ridge Road

                Oakland, MD

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                View 1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078
                  Save 1875 Pysell Crosscut Road Oakland, MD MLS# MDGA2010078
                  1 of 67
                  $769,000
                  5

                  Beds

                  5.0

                  Baths

                  3,664

                  Sq.Ft.

                  1875 Pysell Crosscut Road

                  Oakland, MD

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                  Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
                  View 14 Commerce Drive Oakland, MD MLS# MDGA2010002
                    Save 14 Commerce Drive Oakland, MD MLS# MDGA2010002
                    1 of 99
                    $800,000
                    10,000

                    Sq.Ft.

                    14 Commerce Drive

                    Oakland, MD

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                    View 1019 Lake Shore Drive Oakland, MD MLS# MDGA2010014
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                    Save 1019 Lake Shore Drive Oakland, MD MLS# MDGA2010014
                    1 of 75
                    $1,749,000
                    4

                    Beds

                    4.1

                    Baths

                    2,605

                    Sq.Ft.

                    1019 Lake Shore Drive

                    Oakland, MD

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                    View 565 Glendale Road # 106 B Oakland, MD MLS# MDGA2010012
                      Save 565 Glendale Road # 106 B Oakland, MD MLS# MDGA2010012
                      1 of 27
                      $229,900
                      1

                      Beds

                      1.0

                      Baths

                      565 Glendale Road # 106 B

                      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
                        $529,900
                        4

                        Beds

                        3.0

                        Baths

                        2,235

                        Sq.Ft.

                        126 Leo Friend Road

                        Oakland, MD

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                        View 163 Crestview Drive Oakland, MD MLS# MDGA2009776
                          Save 163 Crestview Drive Oakland, MD MLS# MDGA2009776
                          1 of 50
                          $315,000
                          3

                          Beds

                          2.1

                          Baths

                          1,416

                          Sq.Ft.

                          163 Crestview Drive

                          Oakland, MD

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                          View 8Th & Dennett Road Street Oakland, MD MLS# MDGA2009886
                            Save 8Th & Dennett Road Street Oakland, MD MLS# MDGA2009886
                            1 of 15
                            $199,900
                            Studio

                            Beds

                            0.0

                            Baths

                            8Th & Dennett Road Street

                            Oakland, MD

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                            Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
                            View Yough View Drive # 12 Oakland, MD MLS# MDGA2009840
                              Save Yough View Drive # 12 Oakland, MD MLS# MDGA2009840
                              1 of 5
                              $34,000
                              Studio

                              Beds

                              0.0

                              Baths

                              Yough View Drive # 12

                              Oakland, MD

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                              Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
                              View ±9 ACRES Cranesville Road Oakland, MD MLS# MDGA2009854
                                Save ±9 ACRES Cranesville Road Oakland, MD MLS# MDGA2009854
                                1 of 10
                                $99,000
                                Studio

                                Beds

                                0.0

                                Baths

                                ±9 ACRES Cranesville Road

                                Oakland, MD

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                                View ±18 ACRES Cranesville Road Oakland, MD MLS# MDGA2009858
                                  Save ±18 ACRES Cranesville Road Oakland, MD MLS# MDGA2009858
                                  1 of 13
                                  $249,000
                                  Studio

                                  Beds

                                  0.0

                                  Baths

                                  ±18 ACRES Cranesville Road

                                  Oakland, MD

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                                  View 333 Sloan Tract Road Oakland, MD MLS# MDGA2009836
                                  • Virtual Tour
                                  Save 333 Sloan Tract Road Oakland, MD MLS# MDGA2009836
                                  1 of 43
                                  $475,000
                                  4

                                  Beds

                                  3.1

                                  Baths

                                  1,492

                                  Sq.Ft.

                                  333 Sloan Tract Road

                                  Oakland, MD

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                                  Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
                                  View 609 Southern Pines Drive Oakland, MD MLS# MDGA2009816
                                    Save 609 Southern Pines Drive Oakland, MD MLS# MDGA2009816
                                    1 of 59
                                    $425,000
                                    4

                                    Beds

                                    2.1

                                    Baths

                                    2,030

                                    Sq.Ft.

                                    609 Southern Pines Drive

                                    Oakland, MD

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                                    Courtesy of BHHS TOUCHDOWN HOME PROS REALTY

                                    About Oakland

                                    Listings in Oakland, MD

                                    162

                                    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 - 100K36
                                    $100K - 200K20
                                    $200K - 300K31
                                    $300K - 400K14
                                    $400K - 500K7
                                    $500K - 600K10
                                    $600K - 700K10
                                    $700K - 800K7
                                    $800K - 900K4
                                    $900K - 1M3
                                    $1M - Max20

                                    Homes for Sale by Type in Oakland, MD

                                    Property TypeCount
                                    Single Family69
                                    Townhouse2
                                    Condo22
                                    Commercial14
                                    Rental6
                                    Lots and Land55
                                    Condo/Town/CoOp0
                                    CoOp0
                                    Multi Family0
                                    Mobile Home0
                                    Farms0

                                    (Data as of 3/12/2026)

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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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