183 total properties
Did you mean the neighborhood Oakland?
View 1740 Old Crellin Road Oakland, MD MLS# MDGA2011680
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1 of 28
$335,000
3

Beds

3.0

Baths

2,288

Sq.Ft.

1740 Old Crellin Road

Oakland, MD

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Courtesy of THE KW COLLECTIVE
View 827 Penn Point Road Oakland, MD MLS# MDGA2011664
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1 of 64
$1,400,000
5

Beds

3.1

Baths

2,832

Sq.Ft.

827 Penn Point Road

Oakland, MD

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Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
View Sanders Lane Oakland, MD MLS# MDGA2011678
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Save Sanders Lane Oakland, MD MLS# MDGA2011678
1 of 46
$150,000
Studio

Beds

0.0

Baths

Sanders Lane

Oakland, MD

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Courtesy of RAILEY REALTY, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View Bethlehem Road Oakland, MD MLS# MDGA2011660
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Save Bethlehem Road Oakland, MD MLS# MDGA2011660
1 of 14
$249,900
Studio

Beds

0.0

Baths

Bethlehem Road

Oakland, MD

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Courtesy of HAWKINS REAL ESTATE COMPANY
View 39 Leo Friend Road Oakland, MD MLS# MDGA2011668
    Save 39 Leo Friend Road Oakland, MD MLS# MDGA2011668
    1 of 59
    $875,000
    3

    Beds

    3.1

    Baths

    3,897

    Sq.Ft.

    39 Leo Friend Road

    Oakland, MD

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    Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
    View 53 Meadow Court Oakland, MD MLS# MDGA2011658
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    1 of 82
    $824,900
    4

    Beds

    4.2

    Baths

    3,630

    Sq.Ft.

    53 Meadow Court

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 170 Cherrywood Drive Oakland, MD MLS# MDGA2011178
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    Save 170 Cherrywood Drive Oakland, MD MLS# MDGA2011178
    1 of 67
    $699,000
    5

    Beds

    3.0

    Baths

    2,560

    Sq.Ft.

    170 Cherrywood Drive

    Oakland, MD

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    Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
    View Lot 24 Eastview Place Oakland, MD MLS# MDGA2011556
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    Save Lot 24 Eastview Place Oakland, MD MLS# MDGA2011556
    1 of 21
    $49,000
    Studio

    Beds

    0.0

    Baths

    Lot 24 Eastview Place

    Oakland, MD

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    Courtesy of RAILEY REALTY, INC.
    View 34 Hooppole Court # B-1 Oakland, MD MLS# MDGA2011646
      Save 34 Hooppole Court # B-1 Oakland, MD MLS# MDGA2011646
      1 of 36
      $829,000
      3

      Beds

      2.0

      Baths

      1,355

      Sq.Ft.

      34 Hooppole Court # B-1

      Oakland, MD

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      Courtesy of RAILEY REALTY, INC.
      View Lot 233 Cumberland Oakland, MD MLS# MDGA2011636
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      Save Lot 233 Cumberland Oakland, MD MLS# MDGA2011636
      1 of 8
      $35,000
      Studio

      Beds

      0.0

      Baths

      Lot 233 Cumberland

      Oakland, MD

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      Courtesy of LAKE HOMES REALTY, LLC
      View 1204 Alexander Lane Oakland, MD MLS# MDGA2011628
        Save 1204 Alexander Lane Oakland, MD MLS# MDGA2011628
        1 of 64
        $399,900
        3

        Beds

        2.0

        Baths

        2,266

        Sq.Ft.

        1204 Alexander Lane

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View Lot 40 Fawn Drive Oakland, MD MLS# MDGA2011608
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        1 of 18
        $3,500
        Studio

        Beds

        0.0

        Baths

        Lot 40 Fawn Drive

        Oakland, MD

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        Courtesy of TAYLOR MADE DEEP CREEK REAL ESTATE
        View 2411 Lake Shore Drive Oakland, MD MLS# MDGA2011610
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        Save 2411 Lake Shore Drive Oakland, MD MLS# MDGA2011610
        1 of 69
        $2,390,000
        5

        Beds

        4.0

        Baths

        3,463

        Sq.Ft.

        2411 Lake Shore Drive

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View TBD Betts Lane Oakland, MD MLS# MDGA2011574
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        Save TBD Betts Lane Oakland, MD MLS# MDGA2011574
        1 of 1
        $49,900
        Studio

        Beds

        0.0

        Baths

        TBD Betts Lane

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View Lots 37 & 38 Fir Tree Drive Oakland, MD MLS# MDGA2011526
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        Save Lots 37 & 38 Fir Tree Drive Oakland, MD MLS# MDGA2011526
        1 of 30
        $19,900
        Studio

        Beds

        0.0

        Baths

        Lots 37 & 38 Fir Tree Drive

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 660 Glendale Road Oakland, MD MLS# MDGA2011188
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        Save 660 Glendale Road Oakland, MD MLS# MDGA2011188
        1 of 62
        $1,300,000
        5

        Beds

        3.0

        Baths

        2,592

        Sq.Ft.

        660 Glendale Road

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 8956 Oakland Sang Run Road Oakland, MD MLS# MDGA2011566
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        Save 8956 Oakland Sang Run Road Oakland, MD MLS# MDGA2011566
        1 of 67
        $265,000
        3

        Beds

        2.0

        Baths

        1,064

        Sq.Ft.

        8956 Oakland Sang Run Road

        Oakland, MD

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        Courtesy of TAYLOR PROPERTIES
        View 565 Glendale Road # 306 Oakland, MD MLS# MDGA2011544
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        Save 565 Glendale Road # 306 Oakland, MD MLS# MDGA2011544
        1 of 32
        $249,900
        2

        Beds

        1.0

        Baths

        772

        Sq.Ft.

        565 Glendale Road # 306

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 132 &132A Tarn Drive Oakland, MD MLS# MDGA2011528
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        Save 132 &132A Tarn Drive Oakland, MD MLS# MDGA2011528
        1 of 28
        $160,000
        Studio

        Beds

        0.0

        Baths

        132 &132A Tarn Drive

        Oakland, MD

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        Courtesy of RAILEY REALTY, INC.
        View 2332 Paradise Point Road Oakland, MD MLS# MDGA2011510
          Save 2332 Paradise Point Road Oakland, MD MLS# MDGA2011510
          1 of 74
          $1,399,000
          3

          Beds

          2.0

          Baths

          2,064

          Sq.Ft.

          2332 Paradise Point Road

          Oakland, MD

          Bright
          Courtesy of RAILEY REALTY, INC.

          About Oakland

          Listings in Oakland, MD

          183

          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 - 100K44
          $100K - 200K20
          $200K - 300K33
          $300K - 400K20
          $400K - 500K8
          $500K - 600K9
          $600K - 700K10
          $700K - 800K7
          $800K - 900K7
          $900K - 1M3
          $1M - Max22

          Homes for Sale by Type in Oakland, MD

          Property TypeCount
          Single Family81
          Townhouse2
          Condo22
          Commercial14
          Rental6
          Lots and Land64
          Condo/Town/CoOp0
          CoOp0
          Multi Family0
          Mobile Home0
          Farms0

          (Data as of 4/24/2026)

          Find Properties in Oakland, MD

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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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