201 total properties
Did you mean the neighborhood Oakland?
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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    View 251 Robinwood Drive Oakland, MD MLS# MDGA2012378
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    1 of 62
    $775,000
    5

    Beds

    4.1

    Baths

    4,284

    Sq.Ft.

    251 Robinwood Drive

    Oakland, MD

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    View Robinwood Drive # 9 Oakland, MD MLS# MDGA2012380
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    1 of 6
    $175,000
    Studio

    Beds

    0.0

    Baths

    Robinwood Drive # 9

    Oakland, MD

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    The time to sell is now! THE TIME TO SELL IS NOW!
    View 37 Skippers Point Road Oakland, MD MLS# MDGA2012292
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    Save 37 Skippers Point Road Oakland, MD MLS# MDGA2012292
    1 of 49
    $875,000
    4

    Beds

    3.0

    Baths

    2,280

    Sq.Ft.

    37 Skippers Point Road

    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

    Beds

    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

    Beds

    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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    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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      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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        View 112 E Pennington Street Oakland, MD MLS# MDGA2012308
          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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          View 101 Sobriety Way Oakland, MD MLS# MDGA2012278
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          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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          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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            View 97 acres Lot C Garrett Road Oakland, MD MLS# MDGA2012260
              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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              View 104 Roman Ridge Road # 21 Oakland, MD MLS# MDGA2012268
                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

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                View 17240 Garrett Highway Oakland, MD MLS# MDGA2012252
                  Save 17240 Garrett Highway Oakland, MD MLS# MDGA2012252
                  1 of 104
                  $948,000
                  6

                  Beds

                  4.1

                  Baths

                  5,547

                  Sq.Ft.

                  17240 Garrett Highway

                  Oakland, MD

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                  View 256 Jeffrey Lane # 28 Oakland, MD MLS# MDGA2012248
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                  Save 256 Jeffrey Lane # 28 Oakland, MD MLS# MDGA2012248
                  1 of 65
                  $464,900
                  3

                  Beds

                  3.1

                  Baths

                  1,838

                  Sq.Ft.

                  256 Jeffrey Lane # 28

                  Oakland, MD

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                  View 102 N 3Rd Street Oakland, MD MLS# MDGA2012246
                    Save 102 N 3Rd Street Oakland, MD MLS# MDGA2012246
                    1 of 43
                    $259,900
                    3

                    Beds

                    2.0

                    Baths

                    1,998

                    Sq.Ft.

                    102 N 3Rd Street

                    Oakland, MD

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                    View 941 Mountainview Drive Oakland, MD MLS# MDGA2012196
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                    Save 941 Mountainview Drive Oakland, MD MLS# MDGA2012196
                    1 of 71
                    $737,500
                    4

                    Beds

                    3.1

                    Baths

                    4,377

                    Sq.Ft.

                    941 Mountainview Drive

                    Oakland, MD

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                    View 943 Paradise Heights Oakland, MD MLS# MDGA2012214
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                    Save 943 Paradise Heights Oakland, MD MLS# MDGA2012214
                    1 of 62
                    $765,000
                    5

                    Beds

                    3.0

                    Baths

                    2,200

                    Sq.Ft.

                    943 Paradise Heights

                    Oakland, MD

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                    About Oakland

                    Listings in Oakland, MD

                    204

                    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 - 800K15
                    $800K - 900K4
                    $900K - 1M4
                    $1M - Max21

                    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 8/4/2026)

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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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