207 total properties
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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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View 52 Dam View Drive Oakland, MD MLS# MDGA2011104
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Save 52 Dam View Drive Oakland, MD MLS# MDGA2011104
1 of 91
$1,074,900
4

Beds

4.2

Baths

3,032

Sq.Ft.

52 Dam View Drive

Oakland, MD

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The time to sell is now! THE TIME TO SELL IS NOW!
View 231 Santa Fe Trail Oakland, MD MLS# MDGA2011082
    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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    View 127 S Oakhall Drive Oakland, MD MLS# MDGA2011068
      Save 127 S Oakhall Drive Oakland, MD MLS# MDGA2011068
      1 of 60
      $275,000
      4

      Beds

      2.0

      Baths

      1,913

      Sq.Ft.

      127 S Oakhall Drive

      Oakland, MD

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      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 26 Green Brier Road Oakland, MD MLS# MDGA2011050
        Save 26 Green Brier Road Oakland, MD MLS# MDGA2011050
        1 of 19
        $295,000
        Studio

        Beds

        0.0

        Baths

        26 Green Brier Road

        Oakland, MD

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        View 26 Green Brier Road Oakland, MD MLS# MDGA2011054
          Save 26 Green Brier Road Oakland, MD MLS# MDGA2011054
          1 of 19
          $295,000

          26 Green Brier Road

          Oakland, MD

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          View 729 E Oak Street Oakland, MD MLS# MDGA2011048
            Save 729 E Oak Street Oakland, MD MLS# MDGA2011048
            1 of 62
            $185,000
            3

            Beds

            1.1

            Baths

            1,170

            Sq.Ft.

            729 E Oak Street

            Oakland, MD

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            View 267 San Francisco Street Oakland, MD MLS# MDGA2011040
              Save 267 San Francisco Street Oakland, MD MLS# MDGA2011040
              1 of 30
              $899,900
              4

              Beds

              2.1

              Baths

              3,278

              Sq.Ft.

              267 San Francisco Street

              Oakland, MD

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              View Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
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              Save Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
              1 of 21
              $975,000
              Studio

              Beds

              0.0

              Baths

              Glendale Rd Lot 12 Alpine Village Subdivision

              Oakland, MD

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              View 232 Jeffrey Lane # 33 Oakland, MD MLS# MDGA2011030
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              Save 232 Jeffrey Lane # 33 Oakland, MD MLS# MDGA2011030
              1 of 39
              $414,999
              2

              Beds

              2.1

              Baths

              2,960

              Sq.Ft.

              232 Jeffrey Lane # 33

              Oakland, MD

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              View 3395 Fingerboard Road Oakland, MD MLS# MDGA2010996
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              1 of 20
              $150,000
              4

              Beds

              2.0

              Baths

              3395 Fingerboard Road

              Oakland, MD

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              View 931 Black Oak Drive Oakland, MD MLS# MDGA2010958
                Save 931 Black Oak Drive Oakland, MD MLS# MDGA2010958
                1 of 53
                $339,999
                3

                Beds

                1.0

                Baths

                990

                Sq.Ft.

                931 Black Oak Drive

                Oakland, MD

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                View 178 Winding Trail Lane # 5B Oakland, MD MLS# MDGA2010960
                  Save 178 Winding Trail Lane # 5B Oakland, MD MLS# MDGA2010960
                  1 of 47
                  $569,000
                  5

                  Beds

                  4.1

                  Baths

                  3,300

                  Sq.Ft.

                  178 Winding Trail Lane # 5B

                  Oakland, MD

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                  View Lot 17 Birchwood Drive Oakland, MD MLS# MDGA2010950
                    Save Lot 17 Birchwood Drive Oakland, MD MLS# MDGA2010950
                    1 of 10
                    $5,000
                    Studio

                    Beds

                    0.0

                    Baths

                    Lot 17 Birchwood Drive

                    Oakland, MD

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                    View 1358 Crellin Underwood Road Oakland, MD MLS# MDGA2010946
                      Save 1358 Crellin Underwood Road Oakland, MD MLS# MDGA2010946
                      1 of 38
                      $79,999
                      2

                      Beds

                      1.0

                      Baths

                      864

                      Sq.Ft.

                      1358 Crellin Underwood Road

                      Oakland, MD

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                      View 5423 Gorman Road Oakland, MD MLS# MDGA2010906
                        Save 5423 Gorman Road Oakland, MD MLS# MDGA2010906
                        1 of 21
                        $275,000
                        720

                        Sq.Ft.

                        5423 Gorman Road

                        Oakland, MD

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                        View 209 Glendale Road Oakland, MD MLS# MDGA2010922
                          Save 209 Glendale Road Oakland, MD MLS# MDGA2010922
                          1 of 89
                          $2,100,000
                          6

                          Beds

                          4.1

                          Baths

                          3,882

                          Sq.Ft.

                          209 Glendale Road

                          Oakland, MD

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                          View Lot 20 Paradise Ridge Road Oakland, MD MLS# MDGA2010926
                            Save Lot 20 Paradise Ridge Road Oakland, MD MLS# MDGA2010926
                            1 of 31
                            $124,000
                            Studio

                            Beds

                            0.0

                            Baths

                            Lot 20 Paradise Ridge Road

                            Oakland, MD

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                            About Oakland

                            Listings in Oakland, MD

                            206

                            Estimated median home price

                            $295,000
                            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 - 100K50
                            $100K - 200K26
                            $200K - 300K29
                            $300K - 400K24
                            $400K - 500K12
                            $500K - 600K7
                            $600K - 700K8
                            $700K - 800K12
                            $800K - 900K6
                            $900K - 1M7
                            $1M - Max25

                            Homes for Sale by Type in Oakland, MD

                            Property TypeCount
                            Single Family93
                            Townhouse2
                            Condo24
                            Commercial15
                            Rental6
                            Lots and Land72
                            Condo/Town/CoOp0
                            CoOp0
                            Multi Family0
                            Mobile Home0
                            Farms0

                            (Data as of 6/13/2026)

                            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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