10,714

Oakland, MD Homes

Section Image
  • 31 Mount Airy Ct, Oakland, MD 21550
    31 Mount Airy Ct, Oakland, MD 21550
    31 Mount Airy Ct, Oakland, MD 21550
    /13

    $122,000 Sold Apr 11, 2025

    31 Mount Airy Ct, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 2012

    Last Sold Summary

    • $112/SF
    • 22 Days On Market

    Current Estimated Value $133,150

    Last Listing Agent Katie Cantrell Taylor Made Deep Creek Vacations & Sales

    31 Mount Airy Ct, Oakland, MD 21550
    • 704 Old Crellin Rd, Oakland, MD 21550
      704 Old Crellin Rd, Oakland, MD 21550
      704 Old Crellin Rd, Oakland, MD 21550
      /42

      Est $402,725 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,507 Sq Ft

      704 Old Crellin Rd, Oakland, MD 21550

      704 Old Crellin Rd, Oakland, MD 21550
  • 83 Boston Post Rd, Oakland, MD 21550
    83 Boston Post Rd, Oakland, MD 21550
    83 Boston Post Rd, Oakland, MD 21550
    /41

    $247,500 Sold Oct 03, 2025

    83 Boston Post Rd, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 400 Sq Ft
    • Built 2019

    Last Sold Summary

    • $619/SF
    • 109 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    83 Boston Post Rd, Oakland, MD 21550
    • 912 Snowy Creek Rd, Oakland, MD 21550
      912 Snowy Creek Rd, Oakland, MD 21550
      912 Snowy Creek Rd, Oakland, MD 21550
      /12

      Est $72,974 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,482 Sq Ft

      912 Snowy Creek Rd, Oakland, MD 21550

      912 Snowy Creek Rd, Oakland, MD 21550
  • 2463 Mayhew Inn Rd, Oakland, MD 21550
    2463 Mayhew Inn Rd, Oakland, MD 21550
    2463 Mayhew Inn Rd, Oakland, MD 21550
    /144

    $1,950,000 Sold Nov 25, 2025

    2463 Mayhew Inn Rd, Oakland, MD 21550

    • 6 Beds
    • 5.5 Baths
    • 5,389 Sq Ft
    • Built 1989

    Last Sold Summary

    • $362/SF
    • 329 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    2463 Mayhew Inn Rd, Oakland, MD 21550
    • 920 Mayhew Inn Rd, Oakland, MD 21550
      920 Mayhew Inn Rd, Oakland, MD 21550
      920 Mayhew Inn Rd, Oakland, MD 21550
      /35

      Est $300,411 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,314 Sq Ft

      920 Mayhew Inn Rd, Oakland, MD 21550

      920 Mayhew Inn Rd, Oakland, MD 21550
  • Lots 14 & 17 Mallard Loop, Oakland, MD 21550
    Lots 14 & 17 Mallard Loop, Oakland, MD 21550
    Lots 14 & 17 Mallard Loop, Oakland, MD 21550
    /11

    $79,900 Sold Apr 04, 2025

    Lots 14 & 17 Mallard Loop, Oakland, MD 21550

    • Land
    • 1.07 Acres
    • $74,673 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    Lots 14 & 17 Mallard Loop, Oakland, MD 21550
    • 13873 Garrett Hwy, Oakland, MD 21550
      13873 Garrett Hwy, Oakland, MD 21550
      13873 Garrett Hwy, Oakland, MD 21550
      /24

      Est $230,626 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,472 Sq Ft

      13873 Garrett Hwy, Oakland, MD 21550

      13873 Garrett Hwy, Oakland, MD 21550
  • Lot 1 Betts Ln, Oakland, MD 21550
    Lot 1 Betts Ln, Oakland, MD 21550
    Lot 1 Betts Ln, Oakland, MD 21550
    /13

    $55,000 Sold Feb 07, 2025

    Lot 1 Betts Ln, Oakland, MD 21550

    • Land
    • 8.68 Acres
    • $6,336 per Acre

    Last Sold Summary

    • 157 Days On Market

    Last Listing Agent Amy Skipper Railey Realty, Inc.

    Lot 1 Betts Ln, Oakland, MD 21550
    • 3900 Mayhew Inn Rd, Oakland, MD 21550
      3900 Mayhew Inn Rd, Oakland, MD 21550
      3900 Mayhew Inn Rd, Oakland, MD 21550
      /19

      Est $603,168 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,160 Sq Ft

      3900 Mayhew Inn Rd, Oakland, MD 21550

      3900 Mayhew Inn Rd, Oakland, MD 21550
  • 873 Paradise Heights, Oakland, MD 21550
    873 Paradise Heights, Oakland, MD 21550
    873 Paradise Heights, Oakland, MD 21550
    /77

    $780,000 Sold Dec 11, 2025

    873 Paradise Heights, Oakland, MD 21550

    • 5 Beds
    • 4 Baths
    • 2,934 Sq Ft
    • Built 2017

    Last Sold Summary

    • $266/SF
    • 129 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    873 Paradise Heights, Oakland, MD 21550
    • 198 Crellin Underwood Rd, Oakland, MD 21550
      198 Crellin Underwood Rd, Oakland, MD 21550
      198 Crellin Underwood Rd, Oakland, MD 21550
      /26

      Est $202,113 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,000 Sq Ft

      198 Crellin Underwood Rd, Oakland, MD 21550

      198 Crellin Underwood Rd, Oakland, MD 21550
  • 501 Spruce St, Oakland, MD 21550
    501 Spruce St, Oakland, MD 21550
    501 Spruce St, Oakland, MD 21550
    /42

    $214,900 Sold May 29, 2025

    501 Spruce St, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,176 Sq Ft
    • Built 1978

    Last Sold Summary

    • $183/SF
    • 2 Days On Market

    Current Estimated Value $212,098

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    501 Spruce St, Oakland, MD 21550
    • 479 Underwood Rd, Oakland, MD 21550
      479 Underwood Rd, Oakland, MD 21550
      479 Underwood Rd, Oakland, MD 21550
      /70

      Est $292,000 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,944 Sq Ft

      479 Underwood Rd, Oakland, MD 21550

      479 Underwood Rd, Oakland, MD 21550
  • 116 N 8th St Unit 2, Oakland, MD 21550
    116 N 8th St Unit 2, Oakland, MD 21550
    116 N 8th St Unit 2, Oakland, MD 21550
    /41

    $148,000 Sold Jul 02, 2025

    116 N 8th St Unit 2, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,494 Sq Ft
    • Built 1940

    Last Sold Summary

    • $99/SF
    • 4 Days On Market

    Current Estimated Value $146,609

    Last Listing Agent Duane Stein II Keller Williams Realty Centre

    116 N 8th St Unit 2, Oakland, MD 21550
    • 450 Fern Dr, Oakland, MD 21550
      450 Fern Dr, Oakland, MD 21550
      450 Fern Dr, Oakland, MD 21550
      /36

      Est $300,899 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 861 Sq Ft

      450 Fern Dr, Oakland, MD 21550

      450 Fern Dr, Oakland, MD 21550
  • 118 Roman Ridge Rd, Oakland, MD 21550
    118 Roman Ridge Rd, Oakland, MD 21550
    118 Roman Ridge Rd, Oakland, MD 21550
    /43

    $485,000 Sold Oct 16, 2025

    118 Roman Ridge Rd, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,820 Sq Ft
    • Built 2003

    Last Sold Summary

    • $266/SF
    • 3 Days On Market

    Last Listing Agent Charlotte Savoy The KW Collective

    118 Roman Ridge Rd, Oakland, MD 21550
    • 3432 Fingerboard Rd, Oakland, MD 21550
      3432 Fingerboard Rd, Oakland, MD 21550
      3432 Fingerboard Rd, Oakland, MD 21550
      /58

      Est $336,437 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,120 Sq Ft

      3432 Fingerboard Rd, Oakland, MD 21550

      3432 Fingerboard Rd, Oakland, MD 21550
  • 300 Santa fe Trail, Oakland, MD 21550
    300 Santa fe Trail, Oakland, MD 21550
    300 Santa fe Trail, Oakland, MD 21550
    /29

    $431,000 Sold Jul 24, 2025

    300 Santa fe Trail, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • Built 1967

    Last Sold Summary

    • $399/SF
    • 102 Days On Market

    Current Estimated Value $423,523

    Last Listing Agent Lauren McCann Railey Realty, Inc.

    300 Santa fe Trail, Oakland, MD 21550
    • 377 Fingerboard Rd, Oakland, MD 21550
      377 Fingerboard Rd, Oakland, MD 21550
      377 Fingerboard Rd, Oakland, MD 21550
      /78

      Est $491,149 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,824 Sq Ft

      377 Fingerboard Rd, Oakland, MD 21550

      377 Fingerboard Rd, Oakland, MD 21550
  • 5 Laurel Brook Dr, Oakland, MD 21550
    5 Laurel Brook Dr, Oakland, MD 21550
    5 Laurel Brook Dr, Oakland, MD 21550
    /29

    $187,500 Sold Aug 26, 2025

    5 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1989

    Last Sold Summary

    • $134/SF
    • 304 Days On Market

    Current Estimated Value $206,283

    Last Listing Agent Sherry Nally Berkshire Hathaway HomeServices Homesale Realty

    5 Laurel Brook Dr, Oakland, MD 21550
    • 195 Fingerboard Rd, Oakland, MD 21550
      195 Fingerboard Rd, Oakland, MD 21550
      195 Fingerboard Rd, Oakland, MD 21550
      /67

      Est $191,791 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,613 Sq Ft

      195 Fingerboard Rd, Oakland, MD 21550

      195 Fingerboard Rd, Oakland, MD 21550
    • 3931 Hutton Rd, Oakland, MD 21550
      3931 Hutton Rd, Oakland, MD 21550
      3931 Hutton Rd, Oakland, MD 21550
      /70

      Est $196,533 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,104 Sq Ft

      3931 Hutton Rd, Oakland, MD 21550

      3931 Hutton Rd, Oakland, MD 21550
    • 18071 Garrett Hwy, Oakland, MD 21550
      18071 Garrett Hwy, Oakland, MD 21550
      18071 Garrett Hwy, Oakland, MD 21550
      /32

      Est $304,782 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,122 Sq Ft

      18071 Garrett Hwy, Oakland, MD 21550

      18071 Garrett Hwy, Oakland, MD 21550
    • 115 Crellin St, Oakland, MD 21550
      115 Crellin St, Oakland, MD 21550
      115 Crellin St, Oakland, MD 21550
      /19

      Est $157,136 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      115 Crellin St, Oakland, MD 21550

      115 Crellin St, Oakland, MD 21550
    • 2880 Sand Flat Rd, Oakland, MD 21550
      2880 Sand Flat Rd, Oakland, MD 21550
      2880 Sand Flat Rd, Oakland, MD 21550
      /75

      Est $577,429 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,944 Sq Ft

      2880 Sand Flat Rd, Oakland, MD 21550

      2880 Sand Flat Rd, Oakland, MD 21550
    • 14 Hotel Dr, Oakland, MD 21550
      14 Hotel Dr, Oakland, MD 21550
      14 Hotel Dr, Oakland, MD 21550
      /49

      Est $258,495 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,040 Sq Ft

      14 Hotel Dr, Oakland, MD 21550

      14 Hotel Dr, Oakland, MD 21550
    • 857 Fricks Crossing Rd, Oakland, MD 21550
      857 Fricks Crossing Rd, Oakland, MD 21550
      857 Fricks Crossing Rd, Oakland, MD 21550
      /52

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      857 Fricks Crossing Rd, Oakland, MD 21550

      857 Fricks Crossing Rd, Oakland, MD 21550
    • 97 Shady Ln, Oakland, MD 21550
      97 Shady Ln, Oakland, MD 21550
      97 Shady Ln, Oakland, MD 21550
      /33

      Est $306,768 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,840 Sq Ft

      97 Shady Ln, Oakland, MD 21550

      97 Shady Ln, Oakland, MD 21550
    • 221 Church St, Oakland, MD 21550
      221 Church St, Oakland, MD 21550
      221 Church St, Oakland, MD 21550
      /50

      Est $394,468 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,792 Sq Ft

      221 Church St, Oakland, MD 21550

      221 Church St, Oakland, MD 21550
    • 3694 Broadford Rd, Oakland, MD 21550
      3694 Broadford Rd, Oakland, MD 21550
      3694 Broadford Rd, Oakland, MD 21550
      /41

      Est $256,864 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,976 Sq Ft

      3694 Broadford Rd, Oakland, MD 21550

      3694 Broadford Rd, Oakland, MD 21550
    • 1127 Sand Flat Rd, Oakland, MD 21550
      1127 Sand Flat Rd, Oakland, MD 21550
      1127 Sand Flat Rd, Oakland, MD 21550
      /42

      Est $329,991 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,482 Sq Ft

      1127 Sand Flat Rd, Oakland, MD 21550

      1127 Sand Flat Rd, Oakland, MD 21550
    • 388 Deer Park Hotel Rd, Oakland, MD 21550
      388 Deer Park Hotel Rd, Oakland, MD 21550
      388 Deer Park Hotel Rd, Oakland, MD 21550
      /14

      Est $200,751 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 992 Sq Ft

      388 Deer Park Hotel Rd, Oakland, MD 21550

      388 Deer Park Hotel Rd, Oakland, MD 21550
    • 1082 Sunnyside Rd, Oakland, MD 21550
      1082 Sunnyside Rd, Oakland, MD 21550
      1082 Sunnyside Rd, Oakland, MD 21550
      /42

      Est $222,375 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,112 Sq Ft

      1082 Sunnyside Rd, Oakland, MD 21550

      1082 Sunnyside Rd, Oakland, MD 21550
    • 2189 Table Rock Rd, Oakland, MD 21550
      2189 Table Rock Rd, Oakland, MD 21550
      2189 Table Rock Rd, Oakland, MD 21550
      /39

      Est $250,236 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,656 Sq Ft

      2189 Table Rock Rd, Oakland, MD 21550

      2189 Table Rock Rd, Oakland, MD 21550
    • 131 Circle Four Ln, Oakland, MD 21550
      131 Circle Four Ln, Oakland, MD 21550
      131 Circle Four Ln, Oakland, MD 21550
      /68

      Est $608,811 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,128 Sq Ft

      131 Circle Four Ln, Oakland, MD 21550

      131 Circle Four Ln, Oakland, MD 21550
    • 1021 E High St, Oakland, MD 21550
      1021 E High St, Oakland, MD 21550
      1021 E High St, Oakland, MD 21550
      /76

      Est $259,099 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,876 Sq Ft

      1021 E High St, Oakland, MD 21550

      1021 E High St, Oakland, MD 21550
    • 157 Jasper Riley Rd, Oakland, MD 21550
      157 Jasper Riley Rd, Oakland, MD 21550
      157 Jasper Riley Rd, Oakland, MD 21550
      /84

      Est $352,501 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 4,186 Sq Ft

      157 Jasper Riley Rd, Oakland, MD 21550

      157 Jasper Riley Rd, Oakland, MD 21550
    • 45 Oakland Dr, Oakland, MD 21550
      45 Oakland Dr, Oakland, MD 21550
      45 Oakland Dr, Oakland, MD 21550
      /63

      Est $682,735 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,200 Sq Ft

      45 Oakland Dr, Oakland, MD 21550

      45 Oakland Dr, Oakland, MD 21550
    • 8214 Oakland Sang Run Rd, Oakland, MD 21550
      8214 Oakland Sang Run Rd, Oakland, MD 21550
      8214 Oakland Sang Run Rd, Oakland, MD 21550
      /56

      Est $566,931 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 4,943 Sq Ft

      8214 Oakland Sang Run Rd, Oakland, MD 21550

      8214 Oakland Sang Run Rd, Oakland, MD 21550

Showing Results 641 - 680, Page 17 of 18

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