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    206 Properties
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    206 Properties Available In 21550

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    MD >21550 >
    Market Insights
    • 175 ROMAN RIDGE RD #15, Oakland, MD 21550
      4 Beds5 Baths3,192 SqFt
      1/55 55
      Open 6/15 11AM-2PM

      $575,000

      175 ROMAN RIDGE RD #15, Oakland, MD 21550

      MLS# MDGA2009508

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
    • 17 DRIFTWOOD LN, Oakland, MD 21550
      3 Beds2 Baths1,092 SqFt
      1/3 3
      New

      $379,000

      17 DRIFTWOOD LN, Oakland, MD 21550

      MLS# MDGA2009650

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 237 GLENDALE RD, Oakland, MD 21550
      7 Beds6 Baths3,735 SqFt
      1/100 100
      New

      $2,159,000

      237 GLENDALE RD, Oakland, MD 21550

      MLS# MDGA2009792

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 1100 S BLAKESLEE RD, Oakland, MD 21550
      5 Beds6 Baths6,572 SqFt
      1/127 127
      Under Contract

      $2,775,000

      1100 S BLAKESLEE RD, Oakland, MD 21550

      MLS# MDGA2009688

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 333 SLOAN TRACT RD, Oakland, MD 21550
      4 Beds4 Baths1,492 SqFt
      1/40 40
      New

      $475,000

      333 SLOAN TRACT RD, Oakland, MD 21550

      MLS# MDGA2009836

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
    • 1681 SHADY DELL RD, Oakland, MD 21550
      3 Beds1 Bath960 SqFt
      1/31 31
      New

      $189,000

      1681 SHADY DELL RD, Oakland, MD 21550

      MLS# MDGA2009834

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
    • 408 SHENANDOAH, Loch Lynn Heights, MD 21550
      2 Beds1 Bath960 SqFt
      1/43 43
      New

      $105,000

      408 SHENANDOAH, Loch Lynn Heights, MD 21550

      MLS# MDGA2009810

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 609 SOUTHERN PINES DR, Oakland, MD 21550
      4 Beds3 Baths2,030 SqFt
      1/57 57
      New

      $460,000

      609 SOUTHERN PINES DR, Oakland, MD 21550

      MLS# MDGA2009816

      Listed by BHHS Touchdown Home Pros Realty

      Bright MLS (BMLS)
    • 285 WINDING TRAIL LN #10A, Oakland, MD 21550
      5 Beds5 Baths3,300 SqFt
      1/50 50
      New

      $589,000

      285 WINDING TRAIL LN #10A, Oakland, MD 21550

      MLS# MDGA2009744

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 320 COOLIDGE AVE, Oakland, MD 21550
      2 Beds1 Bath720 SqFt
      1/28 28
      New

      $139,000

      320 COOLIDGE AVE, Oakland, MD 21550

      MLS# MDGA2009796

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 62 MIDDLETON RD, Oakland, MD 21550
      3 Beds3 Baths2,397 SqFt
      1/67 67
      New

      $849,900

      62 MIDDLETON RD, Oakland, MD 21550

      MLS# MDGA2009756

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 5914 MARYLAND HWY, Oakland, MD 21550
      4 Beds2 Baths1,775 SqFt
      1/38 38
      Under Contract

      $139,000

      5914 MARYLAND HWY, Oakland, MD 21550

      MLS# MDGA2009752

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
    • 590 S BLAKESLEE RD, Oakland, MD 21550
      4 Beds4 Baths3,071 SqFt
      1/64 64
      Active

      $1,249,000

      590 S BLAKESLEE RD, Oakland, MD 21550

      MLS# MDGA2009738

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
    • 612 HARVEY WINTERS DR, Oakland, MD 21550
      4 Beds3 Baths2,473 SqFt
      1/70 70
      Under Contract

      $475,000

      612 HARVEY WINTERS DR, Oakland, MD 21550

      MLS# MDGA2009746

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 501 CHRISTOPHERS WAY, Oakland, MD 21550
      3 Beds2 Baths1,617 SqFt
      1/39 39
      Active

      $259,000

      501 CHRISTOPHERS WAY, Oakland, MD 21550

      MLS# MDGA2009724

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
    • 531 S 3RD ST, Oakland, MD 21550
      5 Beds3 Baths2,477 SqFt
      1/56 56
      Price Dropped by $6K

      $348,000

      531 S 3RD ST, Oakland, MD 21550

      MLS# MDGA2009682

      Listed by Charis Realty Group

      Bright MLS (BMLS)
    • 413 D ST, Oakland, MD 21550
      4 Beds2 Baths1,760 SqFt
      1/32 32
      Active

      $279,900

      413 D ST, Oakland, MD 21550

      MLS# MDGA2009720

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
    • 4 LAUREL BROOK DR #4, Oakland, MD 21550
      2 Beds2 Baths
      1/22 22
      Active

      $235,000

      4 LAUREL BROOK DR #4, Oakland, MD 21550

      MLS# MDGA2009716

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
    • 101 SUNSET DR, Oakland, MD 21550
      3 Beds3 Baths3,024 SqFt
      3D
      Pending

      $499,000

      101 SUNSET DR, Oakland, MD 21550

      MLS# MDGA2009668

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 2571 SHADY DELL RD, Oakland, MD 21550
      2 Beds2 Baths1,678 SqFt
      1/18 18
      Active

      $299,900

      2571 SHADY DELL RD, Oakland, MD 21550

      MLS# MDGA2009710

      Listed by Garrett Land Sales, PC

      Bright MLS (BMLS)
    • 45 VILLAGE DR #4, Oakland, MD 21550
      2 Beds2 Baths1,096 SqFt
      1/35 35
      Active

      $450,000

      45 VILLAGE DR #4, Oakland, MD 21550

      MLS# MDGA2009698

      Listed by RE/MAX Realty Group

      Bright MLS (BMLS)
    • 4012 MARYLAND HWY, Oakland, MD 21550
      3 Beds1 Bath1,824 SqFt
      1/55 55
      Active

      $299,900

      4012 MARYLAND HWY, Oakland, MD 21550

      MLS# MDGA2009634

      Listed by Railey Realty, Inc.

      Bright MLS (BMLS)
    • 81 TIMBER LN, Oakland, MD 21550
      4 Beds2 Baths1,860 SqFt
      1/20 20
      Pending

      $125,000

      81 TIMBER LN, Oakland, MD 21550

      MLS# MDGA2009696

      Listed by Lake Homes Realty, LLC

      Bright MLS (BMLS)
    • 600 HOPE AVE, Oakland, MD 21550
      3 Beds3 Baths2,480 SqFt
      1/44 44
      Active

      $249,900

      600 HOPE AVE, Oakland, MD 21550

      MLS# MDGA2009596

      Listed by Taylor Made Deep Creek Vacations & Sales

      Bright MLS (BMLS)
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    Olson Realty

    Nick Padilla RS- RS-0024607

    +1(302) 535-7785 nick@delawarerealty.net

    614 N DuPont Highway Suite 300, Dover, DE, 19901

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        Home
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        1. All Listings
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        3. Sold Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        About
        1. About Us
        2. Contact Us
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        Market Snapshot
    Olson Realty

    Nick Padilla RS- RS-0024607

    +1(302) 535-7785 nick@delawarerealty.net

    614 N DuPont Highway Suite 300, Dover, DE, 19901

    Get My App

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.