167 total properties
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View 565 Glendale Road # B206 Oakland, MD MLS# MDGA2010830
    Save 565 Glendale Road # B206 Oakland, MD MLS# MDGA2010830
    1 of 25
    $329,000
    Studio

    Beds

    0.0

    Baths

    780

    Sq.Ft.

    565 Glendale Road # B206

    Oakland, MD

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    Courtesy of JASON MITCHELL GROUP
    View 125 N 2Nd Oakland, MD MLS# MDGA2010832
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    1 of 4
    $115,000
    Studio

    Beds

    0.0

    Baths

    125 N 2Nd

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 16 Lemley Oakland, MD MLS# MDGA2010814
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    Save 16 Lemley Oakland, MD MLS# MDGA2010814
    1 of 65
    $399,000
    4

    Beds

    2.1

    Baths

    1,104

    Sq.Ft.

    16 Lemley

    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 2 Beaver Run Road Oakland, MD MLS# MDGA2010794
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    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 444 Woodlands Hill Lane Oakland, MD MLS# MDGA2010802
      Save 444 Woodlands Hill Lane Oakland, MD MLS# MDGA2010802
      1 of 68
      $1,199,990
      4

      Beds

      4.2

      Baths

      4,744

      Sq.Ft.

      444 Woodlands Hill Lane

      Oakland, MD

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      Courtesy of COMPASS
      View Penn Point Road Oakland, MD MLS# MDGA2010762
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      Save Penn Point Road Oakland, MD MLS# MDGA2010762
      1 of 13
      $199,900
      Studio

      Beds

      0.0

      Baths

      Penn Point Road

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      View 519 Paradise Heights Oakland, MD MLS# MDGA2010792
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      Save 519 Paradise Heights Oakland, MD MLS# MDGA2010792
      1 of 17
      $765,000
      4

      Beds

      3.0

      Baths

      2,112

      Sq.Ft.

      519 Paradise Heights

      Oakland, MD

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      Courtesy of APPALACHIAN REALTY
      View 222 Skippers Point Road Oakland, MD MLS# MDGA2010764
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      Save 222 Skippers Point Road Oakland, MD MLS# MDGA2010764
      1 of 59
      $779,000
      5

      Beds

      1.1

      Baths

      1,278

      Sq.Ft.

      222 Skippers Point Road

      Oakland, MD

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      Courtesy of THE KW COLLECTIVE
      View 1001 Sutter Lane Oakland, MD MLS# MDGA2010778
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      Save 1001 Sutter Lane Oakland, MD MLS# MDGA2010778
      1 of 94
      $829,000
      5

      Beds

      4.2

      Baths

      6,550

      Sq.Ft.

      1001 Sutter Lane

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      View 8946 Oakland Sang Run Road Oakland, MD MLS# MDGA2010780
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      Save 8946 Oakland Sang Run Road Oakland, MD MLS# MDGA2010780
      $369,000
      Studio

      Beds

      0.0

      Baths

      8946 Oakland Sang Run Road

      Oakland, MD

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      Courtesy of EAGLE COMMERCIAL REALTY
      View Garrett Trail Oakland, MD MLS# MDGA2010758
      • Recently Listed
      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
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      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 220 Woodlands Hill Lane Oakland, MD MLS# MDGA2010752
      • Recently Listed with Virtual Tour
      Save 220 Woodlands Hill Lane Oakland, MD MLS# MDGA2010752
      1 of 85
      $775,000
      5

      Beds

      3.0

      Baths

      2,660

      Sq.Ft.

      220 Woodlands Hill Lane

      Oakland, MD

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      Courtesy of RE/MAX REALTY GROUP
      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 141 Truesdale Road Oakland, MD MLS# MDGA2010742
            Save 141 Truesdale Road Oakland, MD MLS# MDGA2010742
            1 of 29
            $185,000
            3

            Beds

            2.1

            Baths

            1,834

            Sq.Ft.

            141 Truesdale Road

            Oakland, MD

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            Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
            View 34 Laurel Brook Drive # 34 Oakland, MD MLS# MDGA2010732
              Save 34 Laurel Brook Drive # 34 Oakland, MD MLS# MDGA2010732
              1 of 34
              $299,500
              3

              Beds

              3.0

              Baths

              34 Laurel Brook Drive # 34

              Oakland, MD

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              Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
              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 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

                    Bright
                    Courtesy of 1 REAL ESTATE SOURCE LLC

                    About Oakland

                    Listings in Oakland, MD

                    186

                    Estimated median home price

                    $320,000
                    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 - 100K37
                    $100K - 200K23
                    $200K - 300K29
                    $300K - 400K13
                    $400K - 500K13
                    $500K - 600K14
                    $600K - 700K9
                    $700K - 800K8
                    $800K - 900K5
                    $900K - 1M5
                    $1M - Max30

                    Homes for Sale by Type in Oakland, MD

                    Property TypeCount
                    Single Family88
                    Townhouse0
                    Condo28
                    Commercial10
                    Rental1
                    Lots and Land60
                    Condo/Town/CoOp0
                    CoOp0
                    Multi Family0
                    Mobile Home0
                    Farms0

                    (Data as of 11/11/2025)

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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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