169 total properties
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View 615 E Oak Street Oakland, MD MLS# MDGA2012446
    Save 615 E Oak Street Oakland, MD MLS# MDGA2012446
    1 of 9
    $365,000
    5

    Beds

    3.0

    Baths

    2,652

    Sq.Ft.

    615 E Oak Street

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View Bear Drive E Oakland, MD MLS# MDGA2012426
    • Recently Listed
    Save Bear Drive E Oakland, MD MLS# MDGA2012426
    1 of 5
    $19,900
    Studio

    Beds

    0.0

    Baths

    Bear Drive E

    Oakland, MD

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    Courtesy of LONG & FOSTER REAL ESTATE, INC.
    View 22 Shady Hill Drive Oakland, MD MLS# MDGA2012314
    • Recently Listed
    Save 22 Shady Hill Drive Oakland, MD MLS# MDGA2012314
    1 of 55
    $210,000
    2

    Beds

    1.0

    Baths

    1,056

    Sq.Ft.

    22 Shady Hill 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 718 Boy Scout Crosscut Road Oakland, MD MLS# MDGA2012430
    • Recently Listed
    Save 718 Boy Scout Crosscut Road Oakland, MD MLS# MDGA2012430
    1 of 58
    $459,900
    3

    Beds

    2.0

    Baths

    1,458

    Sq.Ft.

    718 Boy Scout Crosscut Road

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 995 Betts Lane Oakland, MD MLS# MDGA2012114
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    Save 995 Betts Lane Oakland, MD MLS# MDGA2012114
    1 of 45
    $549,900
    4

    Beds

    2.1

    Baths

    2,548

    Sq.Ft.

    995 Betts Lane

    Oakland, MD

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    Courtesy of TAYLOR-MADE DEEP CREEK SALES
    View 5 Laurel Brook Drive # 5 Oakland, MD MLS# MDGA2012388
    • Recently Listed
    Save 5 Laurel Brook Drive # 5 Oakland, MD MLS# MDGA2012388
    1 of 29
    $269,900
    2

    Beds

    2.0

    Baths

    1,400

    Sq.Ft.

    5 Laurel Brook Drive # 5

    Oakland, MD

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    Courtesy of TAYLOR-MADE DEEP CREEK SALES
    View 520 Palmer Lane Oakland, MD MLS# MDGA2012340
      Save 520 Palmer Lane Oakland, MD MLS# MDGA2012340
      1 of 72
      $325,000
      3

      Beds

      2.0

      Baths

      1,978

      Sq.Ft.

      520 Palmer Lane

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      View 635 Dennett Road Oakland, MD MLS# MDGA2012374
        Save 635 Dennett Road Oakland, MD MLS# MDGA2012374
        1 of 50
        $290,000
        3

        Beds

        2.0

        Baths

        1,512

        Sq.Ft.

        635 Dennett Road

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
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        Save Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
        1 of 6
        $175,000
        Studio

        Beds

        0.0

        Baths

        Robinwood Drive # 9

        Oakland, MD

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        Courtesy of TAYLOR-MADE DEEP CREEK SALES
        View 610 Harvey Winters Drive Oakland, MD MLS# MDGA2012326
        • Recently Listed
        Save 610 Harvey Winters Drive Oakland, MD MLS# MDGA2012326
        1 of 38
        $325,000
        3

        Beds

        2.0

        Baths

        1,539

        Sq.Ft.

        610 Harvey Winters Drive

        Oakland, MD

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        Courtesy of TAYLOR-MADE DEEP CREEK SALES
        View 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
        • Recently Listed
        Save 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
        1 of 15
        $149,000
        Studio

        Beds

        0.0

        Baths

        16 Woodlands Hill Court

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 22 Woodlands Hill Lane Oakland, MD MLS# MDGA2012334
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        Save 22 Woodlands Hill Lane Oakland, MD MLS# MDGA2012334
        1 of 22
        $159,000
        Studio

        Beds

        0.0

        Baths

        22 Woodlands Hill Lane

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View Robinwood Drive # 13 Oakland, MD MLS# MDGA2012320
        • Recently Listed
        Save Robinwood Drive # 13 Oakland, MD MLS# MDGA2012320
        1 of 21
        $99,000
        Studio

        Beds

        0.0

        Baths

        Robinwood Drive # 13

        Oakland, MD

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        Courtesy of TAYLOR-MADE DEEP CREEK SALES
        View Bethlehem Rd Oakland, MD MLS# MDGA2012316
          Save Bethlehem Rd Oakland, MD MLS# MDGA2012316
          1 of 7
          $119,000
          Studio

          Beds

          0.0

          Baths

          Bethlehem Rd

          Oakland, MD

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          Courtesy of CUSTER REALTY & AUCTION
          View 135 Rock Ridge Lane # 13 Oakland, MD MLS# MDGA2012086
            Save 135 Rock Ridge Lane # 13 Oakland, MD MLS# MDGA2012086
            1 of 49
            $575,000
            4

            Beds

            3.0

            Baths

            2,383

            Sq.Ft.

            135 Rock Ridge Lane # 13

            Oakland, MD

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            Courtesy of RAILEY REALTY, INC.
            View 112 E Pennington Street Oakland, MD MLS# MDGA2012308
            • Recently Listed
            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
            • Virtual Tour
            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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            Courtesy of RAILEY REALTY, INC.
            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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              Courtesy of RAILEY REALTY, INC.
              View 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
              • Recently Listed
              Save 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
              1 of 21
              $599,000
              Studio

              Beds

              0.0

              Baths

              97 acres Lot C Garrett Road

              Oakland, MD

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              Courtesy of RAILEY REALTY, INC.
              View 104 Roman Ridge Road # 21 Oakland, MD MLS# MDGA2012268
              • Recently Listed
              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

              Bright
              Courtesy of RAILEY REALTY, INC.

              About Oakland

              Listings in Oakland, MD

              206

              Estimated median home price

              $301,950
              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 - 200K23
              $200K - 300K35
              $300K - 400K27
              $400K - 500K9
              $500K - 600K10
              $600K - 700K9
              $700K - 800K16
              $800K - 900K4
              $900K - 1M5
              $1M - Max23

              Homes for Sale by Type in Oakland, MD

              Property TypeCount
              Single Family93
              Townhouse1
              Condo26
              Commercial12
              Rental6
              Lots and Land74
              Condo/Town/CoOp0
              CoOp0
              Multi Family0
              Mobile Home0
              Farms0

              (Data as of 7/23/2026)

              Find Properties in Oakland, MD

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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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