139 total properties
Did you mean the neighborhood Oakland?
View 504 San Francisco Street Oakland, MD MLS# MDGA2012432
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$39,900
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504 San Francisco Street

Oakland, MD

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Courtesy of RAILEY REALTY, INC.
View 5154 Maryland Highway Oakland, MD MLS# MDGA2012262
    Save 5154 Maryland Highway Oakland, MD MLS# MDGA2012262
    1 of 26
    $460,000
    5

    Beds

    2.0

    Baths

    2,860

    Sq.Ft.

    5154 Maryland Highway

    Oakland, MD

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    Courtesy of COLDWELL BANKER HOME TOWN REALTY
    View 14 Yough View Drive Oakland, MD MLS# MDGA2012410
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    Save 14 Yough View Drive Oakland, MD MLS# MDGA2012410
    1 of 25
    $45,000
    Studio

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    0.0

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    14 Yough View 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 926 Hutton Road Oakland, MD MLS# MDGA2012442
      Save 926 Hutton Road Oakland, MD MLS# MDGA2012442
      1 of 10
      $115,000
      Studio

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      0.0

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      926 Hutton Road

      Oakland, MD

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      Courtesy of TAYLOR-MADE DEEP CREEK SALES
      View 40 Sunshine Oakland, MD MLS# MDGA2012436
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      Save 40 Sunshine Oakland, MD MLS# MDGA2012436
      1 of 43
      $179,000
      3

      Beds

      1.0

      Baths

      1,516

      Sq.Ft.

      40 Sunshine

      Oakland, MD

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      View 206 W Liberty Street Oakland, MD MLS# MDGA2012412
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      Save 206 W Liberty Street Oakland, MD MLS# MDGA2012412
      1 of 35
      $199,000
      2

      Beds

      1.0

      Baths

      2,008

      Sq.Ft.

      206 W Liberty Street

      Oakland, MD

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      View 615 E Oak Street Oakland, MD MLS# MDGA2012446
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      Save 615 E Oak Street Oakland, MD MLS# MDGA2012446
      1 of 60
      $365,000
      5

      Beds

      3.0

      Baths

      2,652

      Sq.Ft.

      615 E Oak Street

      Oakland, MD

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      View Bear Drive E Oakland, MD MLS# MDGA2012426
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      Save Bear Drive E Oakland, MD MLS# MDGA2012426
      1 of 5
      $19,900
      Studio

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      0.0

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      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
        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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        View 718 Boy Scout Crosscut Road Oakland, MD MLS# MDGA2012430
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        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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        View 5 Laurel Brook Drive # 5 Oakland, MD MLS# MDGA2012388
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        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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        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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          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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            View 610 Harvey Winters Drive Oakland, MD MLS# MDGA2012326
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            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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            View 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
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            Save 16 Woodlands Hill Court Oakland, MD MLS# MDGA2012332
            1 of 15
            $149,000
            Studio

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            0.0

            Baths

            16 Woodlands Hill Court

            Oakland, MD

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            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

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            0.0

            Baths

            22 Woodlands Hill Lane

            Oakland, MD

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            View Robinwood Drive # 13 Oakland, MD MLS# MDGA2012320
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            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 112 E Pennington Street Oakland, MD MLS# MDGA2012308
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              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

              About Oakland

              Listings in Oakland, MD

              204

              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 - 100K44
              $100K - 200K26
              $200K - 300K32
              $300K - 400K27
              $400K - 500K10
              $500K - 600K12
              $600K - 700K9
              $700K - 800K16
              $800K - 900K4
              $900K - 1M4
              $1M - Max20

              Homes for Sale by Type in Oakland, MD

              Property TypeCount
              Single Family94
              Townhouse1
              Condo26
              Commercial9
              Rental6
              Lots and Land74
              Condo/Town/CoOp0
              CoOp0
              Multi Family0
              Mobile Home0
              Farms0

              (Data as of 8/1/2026)

              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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