201 total properties
Did you mean the neighborhood Oakland?
View 181 Glotfelty Drive Oakland, MD MLS# MDGA2012496
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1 of 51
$399,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

181 Glotfelty Drive

Oakland, MD

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Courtesy of RAILEY REALTY, INC.
View 504 San Francisco Street Oakland, MD MLS# MDGA2012432
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1 of 17
$39,900
Studio

Beds

0.0

Baths

504 San Francisco Street

Oakland, MD

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Courtesy of RAILEY REALTY, INC.
View 565 Glendale Road # 213 Oakland, MD MLS# MDGA2012506
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1 of 24
$225,000
1

Beds

1.0

Baths

565 Glendale Road # 213

Oakland, MD

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Courtesy of THE KW COLLECTIVE
The time to sell is now! THE TIME TO SELL IS NOW!
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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    1 of 25
    $45,000
    Studio

    Beds

    0.0

    Baths

    14 Yough View Drive

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 355 Markwood Drive Oakland, MD MLS# MDGA2012466
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    Save 355 Markwood Drive Oakland, MD MLS# MDGA2012466
    1 of 72
    $569,000
    3

    Beds

    2.1

    Baths

    1,654

    Sq.Ft.

    355 Markwood Drive

    Oakland, MD

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    Courtesy of TAYLOR-MADE DEEP CREEK SALES
    View 15 Byran Dr Oakland, MD MLS# MDGA2012464
    • New Construction
    Save 15 Byran Dr Oakland, MD MLS# MDGA2012464
    1 of 1
    $799,900
    4

    Beds

    4.0

    Baths

    15 Byran Dr

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View Boy Scout Road Oakland, MD MLS# MDGA2012474
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    Save Boy Scout Road Oakland, MD MLS# MDGA2012474
    1 of 21
    $599,900
    Studio

    Beds

    0.0

    Baths

    Boy Scout Road

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 926 Hutton Road Oakland, MD MLS# MDGA2012442
      Save 926 Hutton Road Oakland, MD MLS# MDGA2012442
      1 of 10
      $115,000
      Studio

      Beds

      0.0

      Baths

      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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      1 of 43
      $179,000
      3

      Beds

      1.0

      Baths

      1,516

      Sq.Ft.

      40 Sunshine

      Oakland, MD

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      Courtesy of TAYLOR-MADE DEEP CREEK SALES
      View 206 W Liberty Street Oakland, MD MLS# MDGA2012412
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      1 of 35
      $199,000
      2

      Beds

      1.0

      Baths

      2,008

      Sq.Ft.

      206 W Liberty Street

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      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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      Courtesy of RAILEY REALTY, INC.
      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

      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
        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.
        View 718 Boy Scout Crosscut Road Oakland, MD MLS# MDGA2012430
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        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 325 Markwood Drive Oakland, MD MLS# MDGA2012328
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        1 of 65
        $799,000
        4

        Beds

        3.1

        Baths

        3,376

        Sq.Ft.

        325 Markwood Drive

        Oakland, MD

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        Courtesy of TAYLOR-MADE DEEP CREEK SALES
        View 187 Lower Penn Point Drive Oakland, MD MLS# MDGA2012396
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        Save 187 Lower Penn Point Drive Oakland, MD MLS# MDGA2012396
        1 of 44
        $1,450,000
        3

        Beds

        2.0

        Baths

        1,695

        Sq.Ft.

        187 Lower Penn Point Drive

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 995 Betts Lane Oakland, MD MLS# MDGA2012114
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        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
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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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        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.

          About Oakland

          Listings in Oakland, MD

          205

          Estimated median home price

          $299,000
          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 - 200K26
          $200K - 300K33
          $300K - 400K27
          $400K - 500K8
          $500K - 600K12
          $600K - 700K9
          $700K - 800K16
          $800K - 900K4
          $900K - 1M4
          $1M - Max21

          Homes for Sale by Type in Oakland, MD

          Property TypeCount
          Single Family94
          Townhouse1
          Condo27
          Commercial9
          Rental6
          Lots and Land74
          Condo/Town/CoOp0
          CoOp0
          Multi Family0
          Mobile Home0
          Farms0

          (Data as of 8/3/2026)

          Find Properties in Oakland, MD

          Oakland, MD Information

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          Information deemed reliable but not guaranteed.

          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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          Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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