10,739

Oakland, MD Homes

Section Image
  • 1764 Underwood Rd, Oakland, MD 21550
    1764 Underwood Rd, Oakland, MD 21550
    1764 Underwood Rd, Oakland, MD 21550
    /47

    $285,000 Sold Oct 31, 2025

    1764 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,304 Sq Ft
    • Built 1968

    Last Sold Summary

    • $124/SF
    • 175 Days On Market

    Current Estimated Value $281,513

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    1764 Underwood Rd, Oakland, MD 21550
    • 128 Shaffer Ln, Oakland, MD 21550
      128 Shaffer Ln, Oakland, MD 21550
      128 Shaffer Ln, Oakland, MD 21550
      /27

      Not Listed For Sale

      128 Shaffer Ln, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,040 Sq Ft
      • Built 2001
      128 Shaffer Ln, Oakland, MD 21550

      Last Sold Summary

      • $144/SF
      • 2 Days On Market

      Last Sold Price $150,000

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • 969 Hoyes Run Rd, Oakland, MD 21550
    969 Hoyes Run Rd, Oakland, MD 21550
    969 Hoyes Run Rd, Oakland, MD 21550
    /56

    $697,000 Sold Dec 19, 2025

    969 Hoyes Run Rd, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,614 Sq Ft
    • Built 1998

    Last Sold Summary

    • $193/SF
    • 180 Days On Market

    Current Estimated Value $716,808

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
    • 400 E St, Oakland, MD 21550
      400 E St, Oakland, MD 21550
      400 E St, Oakland, MD 21550
      /74

      Est $169,363 Not Listed For Sale

      400 E St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,880 Sq Ft
      • Built 1900
      400 E St, Oakland, MD 21550

      Last Sold Summary

      • 276% Above List Price
      • $16/SF
      • 98 Days On Market

      Last Sold Price $45,000

      Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

  • 36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    /29

    $225,000 Sold Nov 17, 2025

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 520 Sq Ft
    • Built 1990

    Last Sold Summary

    • $433/SF
    • 26 Days On Market

    Current Estimated Value $230,718

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
    • 67 Fireside Rd, Oakland, MD 21550
      67 Fireside Rd, Oakland, MD 21550
      67 Fireside Rd, Oakland, MD 21550
      /32

      Est $313,761 Not Listed For Sale

      67 Fireside Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1998
      67 Fireside Rd, Oakland, MD 21550

      Last Sold Summary

      • 18% Above List Price
      • $185/SF
      • 4 Days On Market

      Last Sold Price $266,000

      Last Listing Agent Melissa Long Railey Realty, Inc.

  • 501 Christophers Way, Oakland, MD 21550
    501 Christophers Way, Oakland, MD 21550
    501 Christophers Way, Oakland, MD 21550
    /39

    $195,000 Sold Nov 12, 2025

    501 Christophers Way, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • Built 1994

    Last Sold Summary

    • $121/SF
    • 138 Days On Market

    Last Listing Agent Dan Shockey Taylor Made Deep Creek Real Estate

    501 Christophers Way, Oakland, MD 21550
    • 116 S Oakhall Dr, Oakland, MD 21550
      116 S Oakhall Dr, Oakland, MD 21550
      116 S Oakhall Dr, Oakland, MD 21550
      /35

      Est $257,417 Not Listed For Sale

      116 S Oakhall Dr, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1960
      116 S Oakhall Dr, Oakland, MD 21550

      Last Sold Summary

      • 18% Above List Price
      • $217/SF
      • 39 Days On Market

      Last Sold Price $219,000

      Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

  • 1136 Black Oak Dr, Oakland, MD 21550
    1136 Black Oak Dr, Oakland, MD 21550
    1136 Black Oak Dr, Oakland, MD 21550
    /41

    $218,000 Sold Dec 01, 2025

    1136 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1971

    Last Sold Summary

    • $206/SF
    • 7 Days On Market

    Current Estimated Value $224,409

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Real Estate

    1136 Black Oak Dr, Oakland, MD 21550
    • 26 Arrowhead Ln, Oakland, MD 21550
      26 Arrowhead Ln, Oakland, MD 21550
      26 Arrowhead Ln, Oakland, MD 21550
      /42

      Est $684,471 Not Listed For Sale

      26 Arrowhead Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 1988
      26 Arrowhead Ln, Oakland, MD 21550

      Last Sold Summary

      • 1% Above List Price
      • $338/SF
      • 389 Days On Market

      Last Sold Price $675,000

      Last Listing Agent Kellyann Green Railey Realty, Inc.

  • 2571 Shady Dell Rd, Oakland, MD 21550
    2571 Shady Dell Rd, Oakland, MD 21550
    2571 Shady Dell Rd, Oakland, MD 21550
    /18

    $200,000 Sold Sep 15, 2025

    2571 Shady Dell Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1985

    Last Sold Summary

    • $119/SF
    • 62 Days On Market

    Current Estimated Value $222,360

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
    • 419 Seneca Ave, Oakland, MD 21550
      419 Seneca Ave, Oakland, MD 21550
      419 Seneca Ave, Oakland, MD 21550
      /26

      Est $151,874 Not Listed For Sale

      419 Seneca Ave, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,184 Sq Ft
      • Built 1920
      419 Seneca Ave, Oakland, MD 21550

      Last Sold Summary

      • 2% Below List Price
      • $131/SF
      • 46 Days On Market

      Last Sold Price $155,000

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • 128 Big Bass Dr, Oakland, MD 21550
    128 Big Bass Dr, Oakland, MD 21550
    128 Big Bass Dr, Oakland, MD 21550
    /93

    $1,445,000 Sold Nov 14, 2025

    128 Big Bass Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,305 Sq Ft
    • Built 2023

    Last Sold Summary

    • $336/SF
    • 13 Days On Market

    Current Estimated Value $1,447,505

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    128 Big Bass Dr, Oakland, MD 21550
    • 581 Skippers Point Rd, Oakland, MD 21550
      581 Skippers Point Rd, Oakland, MD 21550
      581 Skippers Point Rd, Oakland, MD 21550
      /62

      Est $1,323,196 Not Listed For Sale

      581 Skippers Point Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1977
      581 Skippers Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 9% Below List Price
      • $1,326/SF
      • 3 Days On Market

      Last Sold Price $1,458,600

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • 531 S 3rd St, Oakland, MD 21550
    531 S 3rd St, Oakland, MD 21550
    531 S 3rd St, Oakland, MD 21550
    /56

    $320,000 Sold Nov 05, 2025

    531 S 3rd St, Oakland, MD 21550

    • 5 Beds
    • 2.5 Baths
    • 2,477 Sq Ft
    • Built 1920

    Last Sold Summary

    • $129/SF
    • 118 Days On Market

    Current Estimated Value $318,587

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
    • 233 N 2nd St, Oakland, MD 21550
      233 N 2nd St, Oakland, MD 21550
      233 N 2nd St, Oakland, MD 21550
      /87

      Est $325,900 Not Listed For Sale

      233 N 2nd St, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 2,218 Sq Ft
      • Built 1914
      233 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 9% Above List Price
      • $135/SF
      • 432 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Julie Mead The KW Collective

  • 405 Sunnyside Rd, Oakland, MD 21550
    405 Sunnyside Rd, Oakland, MD 21550
    405 Sunnyside Rd, Oakland, MD 21550
    /44

    $185,000 Sold Apr 14, 2025

    405 Sunnyside Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,184 Sq Ft
    • Built 1974

    Last Sold Summary

    • $85/SF
    • 100 Days On Market

    Current Estimated Value $202,583

    Last Listing Agent Steve DuBrueler Coldwell Banker Premier

    405 Sunnyside Rd, Oakland, MD 21550
    • 503 Tower St, Oakland, MD 21550
      503 Tower St, Oakland, MD 21550
      503 Tower St, Oakland, MD 21550
      /20

      Est $159,595 Not Listed For Sale

      503 Tower St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 856 Sq Ft
      • Built 1939
      503 Tower St, Oakland, MD 21550

      Last Sold Summary

      • 21% Above List Price
      • $154/SF
      • 27 Days On Market

      Last Sold Price $132,000

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • 3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    /71

    $590,000 Sold Jan 16, 2026

    3084 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft
    • Built 1999

    Last Sold Summary

    • $239/SF
    • 305 Days On Market

    Current Estimated Value $613,099

    Last Listing Agent Jon Bell Railey Realty, Inc.

    3084 Lake Shore Dr, Oakland, MD 21550
    • 1094 Eagle Rock Rd, Oakland, MD 21550
      1094 Eagle Rock Rd, Oakland, MD 21550
      1094 Eagle Rock Rd, Oakland, MD 21550
      /76

      Est $638,916 Not Listed For Sale

      1094 Eagle Rock Rd, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,780 Sq Ft
      • Built 2008
      1094 Eagle Rock Rd, Oakland, MD 21550

      Last Sold Summary

      • 19% Above List Price
      • $142/SF
      • 109 Days On Market

      Last Sold Price $538,000

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • 707 Sunshine Dr, Oakland, MD 21550
    707 Sunshine Dr, Oakland, MD 21550
    707 Sunshine Dr, Oakland, MD 21550
    /68

    $310,000 Sold Jul 31, 2025

    707 Sunshine Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,052 Sq Ft
    • Built 2004

    Last Sold Summary

    • $151/SF
    • 94 Days On Market

    Current Estimated Value $323,591

    Last Listing Agent Tyler Burch Burch Real Estate Group, LLC

    707 Sunshine Dr, Oakland, MD 21550
    • 700 N St, Oakland, MD 21550
      700 N St, Oakland, MD 21550
      700 N St, Oakland, MD 21550
      /34

      Est $207,970 Not Listed For Sale

      700 N St, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,724 Sq Ft
      • Built 1973
      700 N St, Oakland, MD 21550

      Last Sold Summary

      • 22% Above List Price
      • $62/SF
      • 57 Days On Market

      Last Sold Price $170,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • 1484 Paradise Point Rd, Oakland, MD 21550
    1484 Paradise Point Rd, Oakland, MD 21550
    1484 Paradise Point Rd, Oakland, MD 21550
    /47

    $1,762,500 Sold Jul 29, 2025

    1484 Paradise Point Rd, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,360 Sq Ft
    • Built 2022

    Last Sold Summary

    • $525/SF
    • 16 Days On Market

    Current Estimated Value $1,808,023

    Last Listing Agent Kelsey Meyers Railey Realty, Inc.

    1484 Paradise Point Rd, Oakland, MD 21550
    • 134 Skippers Ln, Oakland, MD 21550
      134 Skippers Ln, Oakland, MD 21550
      134 Skippers Ln, Oakland, MD 21550
      /46

      Est $346,675 Not Listed For Sale

      134 Skippers Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,497 Sq Ft
      • Built 1990
      134 Skippers Ln, Oakland, MD 21550

      Last Sold Summary

      • 26% Above List Price
      • $184/SF
      • 59 Days On Market

      Last Sold Price $275,000

      Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

  • 462 Skippers Point Rd, Oakland, MD 21550
    462 Skippers Point Rd, Oakland, MD 21550
    462 Skippers Point Rd, Oakland, MD 21550
    /66

    $490,000 Sold Aug 08, 2025

    462 Skippers Point Rd, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1983

    Last Sold Summary

    • $302/SF
    • 51 Days On Market

    Current Estimated Value $533,863

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    462 Skippers Point Rd, Oakland, MD 21550
    • 1634 Shady Dell Rd, Oakland, MD 21550
      1634 Shady Dell Rd, Oakland, MD 21550
      1634 Shady Dell Rd, Oakland, MD 21550
      /48

      Est $230,530 Not Listed For Sale

      1634 Shady Dell Rd, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,176 Sq Ft
      • Built 1950
      1634 Shady Dell Rd, Oakland, MD 21550

      Last Sold Summary

      • 62% Above List Price
      • $121/SF
      • 21 Days On Market

      Last Sold Price $142,000

      Last Listing Agent Michael Nelson Berkshire Hathaway HomeServices Homesale Realty

  • 600 Hope Ave, Oakland, MD 21550
    600 Hope Ave, Oakland, MD 21550
    600 Hope Ave, Oakland, MD 21550
    /44

    $225,000 Sold Jul 18, 2025

    600 Hope Ave, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,480 Sq Ft
    • Built 1981

    Last Sold Summary

    • $91/SF
    • 21 Days On Market

    Current Estimated Value $236,218

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

    600 Hope Ave, Oakland, MD 21550
    • 685 Oakland Dr, Oakland, MD 21550
      685 Oakland Dr, Oakland, MD 21550
      685 Oakland Dr, Oakland, MD 21550
      /51

      Est $249,775 Not Listed For Sale

      685 Oakland Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,378 Sq Ft
      • Built 1975
      685 Oakland Dr, Oakland, MD 21550

      Last Sold Summary

      • 4% Below List Price
      • $189/SF
      • 21 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Anet Harris Taylor Made Deep Creek Real Estate

  • 473 Cumberland Rd, Oakland, MD 21550
    473 Cumberland Rd, Oakland, MD 21550
    473 Cumberland Rd, Oakland, MD 21550
    /35

    $285,000 Sold Nov 13, 2025

    473 Cumberland Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Built 1989

    Last Sold Summary

    • $205/SF
    • 155 Days On Market

    Current Estimated Value $306,224

    Last Listing Agent Jeremy McDonough Mr. Lister Realty

    473 Cumberland Rd, Oakland, MD 21550
    • 615 E High St, Oakland, MD 21550
      615 E High St, Oakland, MD 21550
      615 E High St, Oakland, MD 21550
      /22

      Est $203,331 Not Listed For Sale

      615 E High St, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,180 Sq Ft
      • Built 1920
      615 E High St, Oakland, MD 21550

      Last Sold Summary

      • 56% Above List Price
      • $60/SF
      • 257 Days On Market

      Last Sold Price $130,000

      Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Real Estate

  • 19 Pheasant Run, Oakland, MD 21550
    19 Pheasant Run, Oakland, MD 21550
    19 Pheasant Run, Oakland, MD 21550
    /20

    $55,000 Sold Nov 17, 2025

    19 Pheasant Run, Oakland, MD 21550

    • Land
    • 2.84 Acres
    • $19,366 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    19 Pheasant Run, Oakland, MD 21550
    • 524 Bray School Rd, Oakland, MD 21550
      524 Bray School Rd, Oakland, MD 21550
      524 Bray School Rd, Oakland, MD 21550
      /87

      Est $492,060 Not Listed For Sale

      524 Bray School Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,536 Sq Ft
      • Built 2003
      524 Bray School Rd, Oakland, MD 21550

      Last Sold Summary

      • 4% Above List Price
      • $309/SF
      • 11 Days On Market

      Last Sold Price $474,700

      Last Listing Agent Debra Beitzel Long & Foster

  • 0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    /18

    $160,000 Sold Aug 28, 2025

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550

    • Land
    • 25 Acres
    • $6,400 per Acre

    Last Sold Summary

    • 44 Days On Market

    Last Listing Agent Ally Litten Mountainside Home Realty

    0 Betts Ln Unit MDGA2009850, Oakland, MD 21550
    • 514 M St, Oakland, MD 21550
      514 M St, Oakland, MD 21550
      514 M St, Oakland, MD 21550
      /38

      Est $171,319 Not Listed For Sale

      514 M St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,326 Sq Ft
      • Built 1945
      514 M St, Oakland, MD 21550

      Last Sold Summary

      • 2% Below List Price
      • $132/SF
      • 5 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Sheila Howell Lake Homes Realty, LLC

  • 0 Laurel Run Rd, Oakland, MD 21550
    0 Laurel Run Rd, Oakland, MD 21550
    /2

    $200,000 Sold Feb 27, 2026

    0 Laurel Run Rd, Oakland, MD 21550

    • Land
    • 70 Acres
    • $2,857 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    0 Laurel Run Rd, Oakland, MD 21550
    • 15705 Garrett Hwy, Oakland, MD 21550
      15705 Garrett Hwy, Oakland, MD 21550
      15705 Garrett Hwy, Oakland, MD 21550
      /50

      Est $343,525 Not Listed For Sale

      15705 Garrett Hwy, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,046 Sq Ft
      • Built 1965
      15705 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 25% Above List Price
      • $134/SF
      • 146 Days On Market

      Last Sold Price $275,000

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

  • 1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    1674 Paradise Point Rd, Oakland, MD 21550
    /53

    $1,500,000 Sold Dec 01, 2025

    1674 Paradise Point Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 465 Days On Market

    Current Estimated Value $1,510,630

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
    • 301 Oak St, Oakland, MD 21550
      301 Oak St, Oakland, MD 21550
      301 Oak St, Oakland, MD 21550
      /67

      Est $292,512 Not Listed For Sale

      301 Oak St, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,400 Sq Ft
      • Built 1963
      301 Oak St, Oakland, MD 21550

      Last Sold Summary

      • 6% Above List Price
      • $198/SF
      • 265 Days On Market

      Last Sold Price $277,000

      Last Listing Agent Kathy Gibson Railey Realty, Inc.

  • 8 Winding Trail Ln Unit 1, Oakland, MD 21550
    8 Winding Trail Ln Unit 1, Oakland, MD 21550
    8 Winding Trail Ln Unit 1, Oakland, MD 21550
    /66

    $575,000 Sold Apr 04, 2025

    8 Winding Trail Ln Unit 1, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2006

    Last Sold Summary

    • $174/SF
    • 174 Days On Market

    Current Estimated Value $568,153

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    8 Winding Trail Ln Unit 1, Oakland, MD 21550
    • 106 E 3rd Ave, Oakland, MD 21550
      106 E 3rd Ave, Oakland, MD 21550
      106 E 3rd Ave, Oakland, MD 21550
      /7

      Est $121,460 Not Listed For Sale

      106 E 3rd Ave, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 708 Sq Ft
      • Built 1930
      106 E 3rd Ave, Oakland, MD 21550

      Last Sold Summary

      • 6% Above List Price
      • $162/SF
      • 93 Days On Market

      Last Sold Price $115,000

      Last Listing Agent Robert Custer Custer Realty & Auction

Showing Results 481 - 520, Page 13 of 18

Maryland Garrett County Oakland

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