159 total properties
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View 19530 Garrett Highway Oakland, MD MLS# MDGA2010798
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Save 19530 Garrett Highway Oakland, MD MLS# MDGA2010798
1 of 25
$2,500,000
7,200

Sq.Ft.

19530 Garrett Highway

Oakland, MD

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Courtesy of RAILEY REALTY, INC.
View 467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164
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Save 467 Paradise Ridge Road Oakland, MD MLS# MDGA2011164
1 of 55
$799,900
4

Beds

3.1

Baths

3,780

Sq.Ft.

467 Paradise Ridge Road

Oakland, MD

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Courtesy of RAILEY REALTY, INC.
View 157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174
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Save 157 Jeffrey Lane # 21B Oakland, MD MLS# MDGA2011174
1 of 28
$299,000
2

Beds

1.0

Baths

550

Sq.Ft.

157 Jeffrey Lane # 21B

Oakland, MD

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Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
The time to sell is now! THE TIME TO SELL IS NOW!
View 74 Parks Road Oakland, MD MLS# MDGA2011172
    Save 74 Parks Road Oakland, MD MLS# MDGA2011172
    1 of 1
    $69,900
    3

    Beds

    1.0

    Baths

    792

    Sq.Ft.

    74 Parks Road

    Oakland, MD

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    Courtesy of REAL BROKER, LLC
    View Lot 36 Fox Tail Rd Oakland, MD MLS# MDGA2011162
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    Save Lot 36 Fox Tail Rd Oakland, MD MLS# MDGA2011162
    1 of 18
    $4,000
    Studio

    Beds

    0.0

    Baths

    Lot 36 Fox Tail Rd

    Oakland, MD

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    Courtesy of THE KW COLLECTIVE
    View 815 Chadderton School Road Oakland, MD MLS# MDGA2011092
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    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 130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146
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    Save 130 Timberloft Circle # 14 Oakland, MD MLS# MDGA2011146
    1 of 79
    $749,000
    3

    Beds

    3.0

    Baths

    1,900

    Sq.Ft.

    130 Timberloft Circle # 14

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 17979 Garrett Highway Oakland, MD MLS# MDGA2011102
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    Save 17979 Garrett Highway Oakland, MD MLS# MDGA2011102
    1 of 37
    $359,900
    2

    Beds

    1.1

    Baths

    960

    Sq.Ft.

    17979 Garrett Highway

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 52 Dam View Drive Oakland, MD MLS# MDGA2011104
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    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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    Courtesy of RAILEY REALTY, INC.
    View 565 Glendale Road # A312 Oakland, MD MLS# MDGA2011076
      Save 565 Glendale Road # A312 Oakland, MD MLS# MDGA2011076
      1 of 48
      $229,000
      1

      Beds

      1.0

      Baths

      785

      Sq.Ft.

      565 Glendale Road # A312

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      View 2173 King Wildesen Road Oakland, MD MLS# MDGA2011098
      • New Construction
      Save 2173 King Wildesen Road Oakland, MD MLS# MDGA2011098
      1 of 11
      $375,000
      3

      Beds

      2.0

      Baths

      2173 King Wildesen Road

      Oakland, MD

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      Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
      View Laurel Run Oakland, MD MLS# MDGA2011122
        Save Laurel Run Oakland, MD MLS# MDGA2011122
        1 of 1
        $200,000
        Studio

        Beds

        0.0

        Baths

        Laurel Run

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 231 Santa Fe Trail Oakland, MD MLS# MDGA2011082
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        Save 231 Santa Fe Trail Oakland, MD MLS# MDGA2011082
        1 of 37
        $629,000
        4

        Beds

        3.0

        Baths

        2,280

        Sq.Ft.

        231 Santa Fe Trail

        Oakland, MD

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        Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
        View 506 Roanoke Avenue Oakland, MD MLS# MDGA2011066
          Save 506 Roanoke Avenue Oakland, MD MLS# MDGA2011066
          1 of 65
          $179,000
          3

          Beds

          1.0

          Baths

          1,350

          Sq.Ft.

          506 Roanoke Avenue

          Oakland, MD

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          View 401 Dave Turney Street Oakland, MD MLS# MDGA2011080
            Save 401 Dave Turney Street Oakland, MD MLS# MDGA2011080
            1 of 2
            $439,000
            5,328

            Sq.Ft.

            401 Dave Turney Street

            Oakland, MD

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            Courtesy of JASON MITCHELL GROUP
            View 127 S Oakhall Drive Oakland, MD MLS# MDGA2011068
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            Save 127 S Oakhall Drive Oakland, MD MLS# MDGA2011068
            1 of 60
            $299,000
            4

            Beds

            2.0

            Baths

            1,913

            Sq.Ft.

            127 S Oakhall Drive

            Oakland, MD

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            Courtesy of RAILEY REALTY, INC.
            View 702 Sunshine Drive Oakland, MD MLS# MDGA2011074
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            Save 702 Sunshine Drive Oakland, MD MLS# MDGA2011074
            1 of 55
            $265,000
            3

            Beds

            2.0

            Baths

            1,848

            Sq.Ft.

            702 Sunshine Drive

            Oakland, MD

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            Courtesy of RAILEY REALTY, INC.
            View 130 Mystic Creek Trail # 1B Oakland, MD MLS# MDGA2011072
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            Save 130 Mystic Creek Trail # 1B Oakland, MD MLS# MDGA2011072
            1 of 71
            $639,000
            5

            Beds

            4.1

            Baths

            2,200

            Sq.Ft.

            130 Mystic Creek Trail # 1B

            Oakland, MD

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            View 175 Roman Ridge Road # 15 Oakland, MD MLS# MDGA2011062
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            Save 175 Roman Ridge Road # 15 Oakland, MD MLS# MDGA2011062
            1 of 53
            $519,000
            4

            Beds

            4.1

            Baths

            3,192

            Sq.Ft.

            175 Roman Ridge Road # 15

            Oakland, MD

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            View 127 Jeffrey Lane # 18C Oakland, MD MLS# MDGA2011056
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            Save 127 Jeffrey Lane # 18C Oakland, MD MLS# MDGA2011056
            1 of 40
            $275,000
            3

            Beds

            2.0

            Baths

            875

            Sq.Ft.

            127 Jeffrey Lane # 18C

            Oakland, MD

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            Courtesy of RAILEY REALTY, INC.

            About Oakland

            Listings in Oakland, MD

            156

            Estimated median home price

            $292,450
            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 - 100K36
            $100K - 200K22
            $200K - 300K25
            $300K - 400K13
            $400K - 500K8
            $500K - 600K10
            $600K - 700K9
            $700K - 800K7
            $800K - 900K5
            $900K - 1M3
            $1M - Max18

            Homes for Sale by Type in Oakland, MD

            Property TypeCount
            Single Family65
            Townhouse2
            Condo21
            Commercial12
            Rental4
            Lots and Land56
            Condo/Town/CoOp0
            CoOp0
            Multi Family0
            Mobile Home0
            Farms0

            (Data as of 2/20/2026)

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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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