264

Recently Sold 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

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    1764 Underwood Rd, Oakland, MD 21550
  • 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

    Last Listing Agent Roberta McNamara RE/MAX Results

    969 Hoyes Run Rd, Oakland, MD 21550
  • 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

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    36 Jeffrey Ln Unit 6A, Oakland, MD 21550
  • 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 Vacations & Sales

    501 Christophers Way, Oakland, MD 21550
  • 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

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    1136 Black Oak Dr, Oakland, MD 21550
  • 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 $211,466

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    2571 Shady Dell Rd, Oakland, MD 21550
  • 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

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    128 Big Bass Dr, Oakland, MD 21550
  • 93 Skippers Point Rd, Oakland, MD 21550
    93 Skippers Point Rd, Oakland, MD 21550
    93 Skippers Point Rd, Oakland, MD 21550
    /64

    $1,950,000 Sold Dec 27, 2024

    93 Skippers Point Rd, Oakland, MD 21550

    • 5 Beds
    • 7 Baths
    • 3,300 Sq Ft
    • Built 2022

    Last Sold Summary

    • $591/SF
    • 20 Days On Market

    Current Estimated Value $2,113,594

    Last Listing Agent Lucas Muenchow Railey Realty, Inc.

    93 Skippers Point Rd, Oakland, MD 21550
  • 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

    Last Listing Agent Jennifer Jackson Charis Realty Group

    531 S 3rd St, Oakland, MD 21550
  • 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 $196,959

    Last Listing Agent Steve DuBrueler Coldwell Banker Premier

    405 Sunnyside Rd, Oakland, MD 21550
  • 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 $320,222

    Last Listing Agent Tyler Burch Burch Real Estate Group, LLC

    707 Sunshine Dr, Oakland, MD 21550
  • 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 $1,750,161

    Last Listing Agent Kelsey Meyers Railey Realty, Inc.

    1484 Paradise Point Rd, Oakland, MD 21550
  • 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 $505,329

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    462 Skippers Point Rd, Oakland, MD 21550
  • 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 $228,060

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

    600 Hope Ave, Oakland, MD 21550
  • 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

    Last Listing Agent Jeremy McDonough Mr. Lister Realty

    473 Cumberland Rd, Oakland, MD 21550
  • 180 Winding Trail Ln Unit 5A, Oakland, MD 21550
    180 Winding Trail Ln Unit 5A, Oakland, MD 21550
    180 Winding Trail Ln Unit 5A, Oakland, MD 21550
    /69

    $535,000 Sold Mar 21, 2025

    180 Winding Trail Ln Unit 5A, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,000 Sq Ft
    • Built 2006

    Last Sold Summary

    • $178/SF
    • 277 Days On Market

    Current Estimated Value $539,417

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

    180 Winding Trail Ln Unit 5A, Oakland, MD 21550
  • 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
  • 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
  • 247 Sloan Tract Rd, Oakland, MD 21550
    247 Sloan Tract Rd, Oakland, MD 21550
    247 Sloan Tract Rd, Oakland, MD 21550
    /49

    $461,000 Sold Feb 14, 2025

    247 Sloan Tract Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 2004

    Last Sold Summary

    • $356/SF
    • 3 Days On Market

    Current Estimated Value $481,981

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    247 Sloan Tract Rd, Oakland, MD 21550
  • 604 Harvey Winters Dr, Oakland, MD 21550
    604 Harvey Winters Dr, Oakland, MD 21550
    604 Harvey Winters Dr, Oakland, MD 21550
    /121

    $685,000 Sold Jan 31, 2025

    604 Harvey Winters Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,982 Sq Ft
    • Built 1988

    Last Sold Summary

    • $172/SF
    • 48 Days On Market

    Current Estimated Value $697,297

    Last Listing Agent Justin Liller Railey Realty, Inc.

    604 Harvey Winters Dr, Oakland, MD 21550
  • 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

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
  • 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 $576,677

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    8 Winding Trail Ln Unit 1, Oakland, MD 21550
  • 353 Basswood Way Unit 24, Oakland, MD 21550
    353 Basswood Way Unit 24, Oakland, MD 21550
    353 Basswood Way Unit 24, Oakland, MD 21550
    /64

    $695,000 Sold Oct 09, 2025

    353 Basswood Way Unit 24, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,664 Sq Ft
    • Built 2005

    Last Sold Summary

    • $261/SF
    • 14 Days On Market

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    353 Basswood Way Unit 24, Oakland, MD 21550
  • 1006 Lake Shore Dr, Oakland, MD 21550
    1006 Lake Shore Dr, Oakland, MD 21550
    1006 Lake Shore Dr, Oakland, MD 21550
    /61

    $650,000 Sold Aug 21, 2025

    1006 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 1,935 Sq Ft
    • Built 1993

    Last Sold Summary

    • $336/SF
    • 27 Days On Market

    Current Estimated Value $653,440

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1006 Lake Shore Dr, Oakland, MD 21550
  • 601 Hope Ave, Oakland, MD 21550
    601 Hope Ave, Oakland, MD 21550
    601 Hope Ave, Oakland, MD 21550
    /38

    $398,350 Sold May 07, 2025

    601 Hope Ave, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,142 Sq Ft
    • Built 2025

    Last Sold Summary

    • $186/SF
    • 0 Days On Market

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

    601 Hope Ave, Oakland, MD 21550
  • 215 N 10th St, Oakland, MD 21550
    215 N 10th St, Oakland, MD 21550
    215 N 10th St, Oakland, MD 21550
    /48

    $279,000 Sold Sep 25, 2025

    215 N 10th St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,518 Sq Ft
    • Built 1973

    Last Sold Summary

    • 3% Below List Price
    • $184/SF
    • 6 Days On Market

    Last Listing Agent ADAM MURRAY BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    215 N 10th St, Oakland, MD 21550
  • 0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    /22

    $25,000 Sold Jun 27, 2025

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550

    • Land
    • 1.05 Acres
    • $23,810 per Acre

    Last Sold Summary

    • 84 Days On Market

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

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
  • 245 Santa fe Trail, Oakland, MD 21550
    245 Santa fe Trail, Oakland, MD 21550
    245 Santa fe Trail, Oakland, MD 21550
    /40

    $615,000 Sold Jul 07, 2025

    245 Santa fe Trail, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft
    • Built 2003

    Last Sold Summary

    • $270/SF
    • 51 Days On Market

    Current Estimated Value $600,934

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

    245 Santa fe Trail, Oakland, MD 21550
  • 2045 Swallow Falls Rd, Oakland, MD 21550
    2045 Swallow Falls Rd, Oakland, MD 21550
    2045 Swallow Falls Rd, Oakland, MD 21550
    /79

    $910,000 Sold Sep 25, 2025

    2045 Swallow Falls Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 5,416 Sq Ft
    • Built 2023

    Last Sold Summary

    • $168/SF
    • 82 Days On Market

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

    2045 Swallow Falls Rd, Oakland, MD 21550
  • 307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
    /43

    $587,500 Sold Aug 22, 2025

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2019

    Last Sold Summary

    • $178/SF
    • 9 Days On Market

    Current Estimated Value $582,385

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    307 Winding Trail Ln Unit 12B, Oakland, MD 21550
  • 112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    /4

    $73,900 Sold May 12, 2025

    112 E Pennington St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,380 Sq Ft
    • Built 1916

    Last Sold Summary

    • $54/SF
    • 1 Day On Market

    Current Estimated Value $109,228

    Last Listing Agent Robert Custer Custer Realty & Auction

    112 E Pennington St, Oakland, MD 21550
  • 815 L St, Oakland, MD 21550
    815 L St, Oakland, MD 21550
    815 L St, Oakland, MD 21550
    /17

    $15,000 Sold Jul 09, 2025

    815 L St, Oakland, MD 21550

    • Land
    • 0.28 Acre
    • $53,571 per Acre

    Last Sold Summary

    • 1 Day On Market

    Current Estimated Value $94,477

    Last Listing Agent Lauren McCann Railey Realty, Inc.

    815 L St, Oakland, MD 21550
  • 0 E Reese St, Oakland, MD 21550
    0 E Reese St, Oakland, MD 21550
    0 E Reese St, Oakland, MD 21550
    /4

    $12,000 Sold Sep 25, 2025

    0 E Reese St, Oakland, MD 21550

    • Land
    • 0.25 Acre
    • $48,000 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Thomas Long Railey Realty, Inc.

    0 E Reese St, Oakland, MD 21550
  • 805 Hunters Ridge Dr, Oakland, MD 21550
    805 Hunters Ridge Dr, Oakland, MD 21550
    805 Hunters Ridge Dr, Oakland, MD 21550
    /63

    $689,000 Sold Mar 18, 2025

    805 Hunters Ridge Dr, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 3,756 Sq Ft
    • Built 2010

    Last Sold Summary

    • $183/SF

    Current Estimated Value $696,058

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

    805 Hunters Ridge Dr, Oakland, MD 21550
  • 445 Dennett Rd, Oakland, MD 21550
    445 Dennett Rd, Oakland, MD 21550
    445 Dennett Rd, Oakland, MD 21550
    /62

    $305,000 Sold Nov 07, 2025

    445 Dennett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,410 Sq Ft
    • Built 1955

    Last Sold Summary

    • $216/SF
    • 5 Days On Market

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    445 Dennett Rd, Oakland, MD 21550
  • 1385 Mountainview Dr, Oakland, MD 21550
    1385 Mountainview Dr, Oakland, MD 21550
    1385 Mountainview Dr, Oakland, MD 21550
    /54

    $595,000 Sold Apr 30, 2025

    1385 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft
    • Built 2000

    Last Sold Summary

    • $224/SF
    • 26 Days On Market

    Current Estimated Value $609,360

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1385 Mountainview Dr, Oakland, MD 21550
  • 335 Mountainview Dr, Oakland, MD 21550
    335 Mountainview Dr, Oakland, MD 21550
    335 Mountainview Dr, Oakland, MD 21550
    /81

    $749,000 Sold Dec 31, 2024

    335 Mountainview Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,142 Sq Ft
    • Built 2001

    Last Sold Summary

    • $238/SF
    • 29 Days On Market

    Current Estimated Value $788,356

    Last Listing Agent Larry Smith Railey Realty, Inc.

    335 Mountainview Dr, Oakland, MD 21550
  • 648 S 3rd St, Oakland, MD 21550
    648 S 3rd St, Oakland, MD 21550
    648 S 3rd St, Oakland, MD 21550
    /61

    $275,000 Sold Sep 05, 2025

    648 S 3rd St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1940

    Last Sold Summary

    • $185/SF
    • 3 Days On Market

    Current Estimated Value $282,287

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    648 S 3rd St, Oakland, MD 21550
  • 35 Tenderfoot Rd, Oakland, MD 21550
    35 Tenderfoot Rd, Oakland, MD 21550
    35 Tenderfoot Rd, Oakland, MD 21550
    /51

    $425,000 Sold Dec 27, 2024

    35 Tenderfoot Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1999

    Last Sold Summary

    • $328/SF
    • 168 Days On Market

    Current Estimated Value $457,884

    Last Listing Agent Sandy Bello Taylor Made Deep Creek Vacations & Sales

    35 Tenderfoot Rd, Oakland, MD 21550
  • 1746 Stockslager Rd, Oakland, MD 21550
    1746 Stockslager Rd, Oakland, MD 21550
    1746 Stockslager Rd, Oakland, MD 21550
    /131

    $2,250,000 Sold Mar 31, 2025

    1746 Stockslager Rd, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 4,713 Sq Ft
    • Built 1983

    Last Sold Summary

    • $477/SF
    • 131 Days On Market

    Current Estimated Value $2,348,109

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1746 Stockslager Rd, Oakland, MD 21550

Showing Results 161 - 200, Page 5 of 7

Maryland Garrett County Oakland

Recently Sold Real Estate & Homes in Oakland, MD

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