178 total properties
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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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    Courtesy of RAILEY REALTY, INC.
    View 19530 Garrett Highway Oakland, MD MLS# MDGA2010798
      Save 19530 Garrett Highway Oakland, MD MLS# MDGA2010798
      1 of 43
      $2,500,000
      7,200

      Sq.Ft.

      19530 Garrett Highway

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      View 2411 Lake Shore Drive Oakland, MD MLS# MDGA2011610
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      Save 2411 Lake Shore Drive Oakland, MD MLS# MDGA2011610
      1 of 69
      $2,390,000
      5

      Beds

      4.0

      Baths

      3,463

      Sq.Ft.

      2411 Lake Shore Drive

      Oakland, MD

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      The time to sell is now! THE TIME TO SELL IS NOW!
      View 2725 Stockslager Road Oakland, MD MLS# MDGA2008312
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      Save 2725 Stockslager Road Oakland, MD MLS# MDGA2008312
      1 of 115
      $2,350,000
      5

      Beds

      6.1

      Baths

      5,376

      Sq.Ft.

      2725 Stockslager Road

      Oakland, MD

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      Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
      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
          Save 1038 S Blakeslee Road Oakland, MD MLS# MDGA2011370
          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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          Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
          View 815 Chadderton School Road Oakland, MD MLS# MDGA2011092
            Save 815 Chadderton School Road Oakland, MD MLS# MDGA2011092
            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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            Save 62 Duck Cove Road Oakland, MD MLS# MDGA2011402
            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 1544 Stockslager Road Oakland, MD MLS# MDGA2011420
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              Save 1544 Stockslager Road Oakland, MD MLS# MDGA2011420
              1 of 64
              $1,750,000
              5

              Beds

              4.0

              Baths

              3,456

              Sq.Ft.

              1544 Stockslager Road

              Oakland, MD

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              View 17848 Garrett Highway Oakland, MD MLS# MDGA2011286
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              Save 17848 Garrett Highway Oakland, MD MLS# MDGA2011286
              1 of 122
              $1,700,000
              6,477

              Sq.Ft.

              17848 Garrett Highway

              Oakland, MD

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              View 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
                Save 3898 3898 Underwood Rd Oakland, MD MLS# MDGA2010508
                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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                Courtesy of CUSTER REALTY & AUCTION
                View 2332 Paradise Point Road Oakland, MD MLS# MDGA2011510
                  Save 2332 Paradise Point Road Oakland, MD MLS# MDGA2011510
                  1 of 74
                  $1,399,000
                  3

                  Beds

                  2.0

                  Baths

                  2,064

                  Sq.Ft.

                  2332 Paradise 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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                  View 660 Glendale Road Oakland, MD MLS# MDGA2011188
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                  Save 660 Glendale Road Oakland, MD MLS# MDGA2011188
                  1 of 62
                  $1,300,000
                  5

                  Beds

                  3.0

                  Baths

                  2,592

                  Sq.Ft.

                  660 Glendale Road

                  Oakland, MD

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                  View 285 Lake Shore Drive Oakland, MD MLS# MDGA2010466
                    Save 285 Lake Shore Drive Oakland, MD MLS# MDGA2010466
                    1 of 47
                    $1,149,800
                    5

                    Beds

                    4.1

                    Baths

                    2,593

                    Sq.Ft.

                    285 Lake Shore Drive

                    Oakland, MD

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                    Courtesy of KELLER WILLIAMS CAPITAL PROPERTIES
                    View 52 Dam View Drive Oakland, MD MLS# MDGA2011104
                    • New Construction with Virtual Tour
                    Save 52 Dam View Drive Oakland, MD MLS# MDGA2011104
                    1 of 75
                    $1,087,900
                    4

                    Beds

                    4.2

                    Baths

                    3,032

                    Sq.Ft.

                    52 Dam View Drive

                    Oakland, MD

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                    View 137 Paradise Gardens Road Oakland, MD MLS# MDGA2011454
                    • Recently Listed
                    Save 137 Paradise Gardens Road Oakland, MD MLS# MDGA2011454
                    1 of 71
                    $1,049,000
                    4

                    Beds

                    2.0

                    Baths

                    2,730

                    Sq.Ft.

                    137 Paradise Gardens Road

                    Oakland, MD

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                    Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
                    View Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
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                    Save Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
                    1 of 10
                    $995,000
                    Studio

                    Beds

                    0.0

                    Baths

                    Glendale Rd Lot 12 Alpine Village Subdivision

                    Oakland, MD

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                    View 164 Grandview Drive Oakland, MD MLS# MDGA2011052
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                    Save 164 Grandview Drive Oakland, MD MLS# MDGA2011052
                    1 of 54
                    $950,000
                    3

                    Beds

                    2.1

                    Baths

                    2,368

                    Sq.Ft.

                    164 Grandview Drive

                    Oakland, MD

                    Bright
                    Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE

                    About Oakland

                    Listings in Oakland, MD

                    182

                    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 - 100K45
                    $100K - 200K20
                    $200K - 300K32
                    $300K - 400K20
                    $400K - 500K8
                    $500K - 600K9
                    $600K - 700K10
                    $700K - 800K8
                    $800K - 900K5
                    $900K - 1M3
                    $1M - Max22

                    Homes for Sale by Type in Oakland, MD

                    Property TypeCount
                    Single Family80
                    Townhouse2
                    Condo24
                    Commercial14
                    Rental6
                    Lots and Land62
                    Condo/Town/CoOp0
                    CoOp0
                    Multi Family0
                    Mobile Home0
                    Farms0

                    (Data as of 4/20/2026)

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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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