10,731

Oakland, MD Homes

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  • 444 Woodlands Hill Ln, Oakland, MD 21550
    444 Woodlands Hill Ln, Oakland, MD 21550
    444 Woodlands Hill Ln, Oakland, MD 21550
    /68

    $1,199,990 Pending

    • 4 Beds
    • 6 Baths
    • 4,744 Sq Ft

    444 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to 444 Woodlands Hill Ln, in Oakland, MD. Nestled in the private community of The View, this custom home offers stunning lake views in a serene, private setting. Centrally located less than 4 miles from Wisp while backing up to hundreds of acres of untouched forest, this property truly offers the best that Deep Creek Lake has to offer. This luxury home has been impeccably maintained as a

    Corbin Griffith Compass

    444 Woodlands Hill Ln, Oakland, MD 21550
  • 81 Timber Ln, Oakland, MD 21550
    81 Timber Ln, Oakland, MD 21550
    81 Timber Ln, Oakland, MD 21550
    /20

    $80,000 Sold Jun 30, 2025

    81 Timber Ln, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 1,860 Sq Ft
    • Built 1965

    Last Sold Summary

    • $43/SF
    • 5 Days On Market

    Current Estimated Value $90,553

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    81 Timber Ln, Oakland, MD 21550
    • 15 Fawn Dr, Oakland, MD 21550
      15 Fawn Dr, Oakland, MD 21550
      15 Fawn Dr, Oakland, MD 21550
      /32

      Est $127,500 Not Listed For Sale

      15 Fawn Dr, Oakland, MD 21550

      15 Fawn Dr, Oakland, MD 21550
  • 355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    355 Lonesome Pine Rd, Oakland, MD 21550
    /22

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,584 Sq Ft

    355 Lonesome Pine Rd, Oakland, MD 21550

    Escape to your own private mountain retreat! This contemporary 2-bed, 2-bath home is perfectly situated on approximately 84 acres of pristine land, offering breathtaking views overlooking a picturesque 7-acre field. Expansive windows, high vaulted ceilings and an open layout maximize the stunning scenery, allowing natural light to flood the space. Whether you're seeking a peaceful getaway, an

    Brody Monahan Lake Homes Realty, LLC

    355 Lonesome Pine Rd, Oakland, MD 21550
  • 3821 Underwood Rd, Oakland, MD 21550
    3821 Underwood Rd, Oakland, MD 21550
    3821 Underwood Rd, Oakland, MD 21550
    /21

    $155,000 Sold May 22, 2025

    3821 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1964

    Last Sold Summary

    • $126/SF
    • 10 Days On Market

    Current Estimated Value $164,086

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

    3821 Underwood Rd, Oakland, MD 21550
    • 18 Autumn Way, Oakland, MD 21550
      18 Autumn Way, Oakland, MD 21550
      18 Autumn Way, Oakland, MD 21550
      /11

      Not Listed For Sale

      18 Autumn Way, Oakland, MD 21550

      18 Autumn Way, Oakland, MD 21550
  • 519 Paradise Heights, Oakland, MD 21550
    519 Paradise Heights, Oakland, MD 21550
    519 Paradise Heights, Oakland, MD 21550
    /17

    $765,000

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

    519 Paradise Heights, Oakland, MD 21550

    Secluded 4 bedroom 3 bath log home with lake access and single dock slip located in the heart of Deep Creek Lake Resort Area Full unfinished basement, front covered porch and rear deck. Call Office for particulares.

    Linda Deremer Appalachian Realty

    519 Paradise Heights, Oakland, MD 21550
  • 33 Black Bear Ct, Oakland, MD 21550
    33 Black Bear Ct, Oakland, MD 21550
    33 Black Bear Ct, Oakland, MD 21550
    /80

    $855,000 Sold Mar 13, 2025

    33 Black Bear Ct, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,976 Sq Ft
    • Built 1989

    Last Sold Summary

    • $287/SF
    • 88 Days On Market

    Current Estimated Value $908,654

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    33 Black Bear Ct, Oakland, MD 21550
    • 510 Palmer Ln, Oakland, MD 21550
      510 Palmer Ln, Oakland, MD 21550
      510 Palmer Ln, Oakland, MD 21550
      /40

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,922 Sq Ft

      510 Palmer Ln, Oakland, MD 21550

      510 Palmer Ln, Oakland, MD 21550
  • 39 Leo Friend Rd, Oakland, MD 21550
    39 Leo Friend Rd, Oakland, MD 21550
    39 Leo Friend Rd, Oakland, MD 21550
    /33

    $919,000

    • 3 Beds
    • 3.5 Baths
    • 3,897 Sq Ft

    39 Leo Friend Rd, Oakland, MD 21550

    **In the process of having new pictures taken. To see the pictures on the prior listing, go to MSL listing

    Andrew Orr The KW Collective

    39 Leo Friend Rd, Oakland, MD 21550
  • 0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    /33

    $425,000 Sold Dec 19, 2025

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 0 Days On Market

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

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    • 25 Acres Lot D Bailiff Ln, Oakland, MD 21550
      25 Acres Lot D Bailiff Ln, Oakland, MD 21550
      25 Acres Lot D Bailiff Ln, Oakland, MD 21550
      /7

      Not Listed For Sale

      25 Acres Lot D Bailiff Ln, Oakland, MD 21550

      25 Acres Lot D Bailiff Ln, Oakland, MD 21550
  • 181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    /25

    $269,900

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

    Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during

    Larry Smith Railey Realty, Inc.

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
  • 0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    /18

    $19,500 Sold Sep 04, 2025

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550

    • Land
    • 1.48 Acres
    • $13,176 per Acre

    Last Sold Summary

    • 348 Days On Market

    Last Listing Agent Brady Harden Coldwell Banker Premier

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    • 20476 Garrett Hwy, Oakland, MD 21550
      20476 Garrett Hwy, Oakland, MD 21550
      20476 Garrett Hwy, Oakland, MD 21550
      /82

      Est $1,293,984 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 2,635 Sq Ft

      20476 Garrett Hwy, Oakland, MD 21550

      20476 Garrett Hwy, Oakland, MD 21550
  • 609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    609 Southern Pines Dr, Oakland, MD 21550
    /59

    $440,000

    • 4 Beds
    • 2.5 Baths
    • 2,030 Sq Ft

    609 Southern Pines Dr, Oakland, MD 21550

    Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built traditional-style residence combines comfort, and convenience. Just minutes from Broadford Lake Park, healthcare, shopping, Deep Creek Lake, and Wisp Ski Resort, this peaceful property offers easy access to all the local amenities. Two story stone & cedar, 4BR, 2.5 Bath w/ 2 - car attached garage, & 2 - car

    Brian Covell BHHS Touchdown Home Pros Realty

    609 Southern Pines Dr, Oakland, MD 21550
  • 2353 Boy Scout Rd, Oakland, MD 21550
    2353 Boy Scout Rd, Oakland, MD 21550
    2353 Boy Scout Rd, Oakland, MD 21550
    /32

    $1,699,900 Sold May 23, 2025

    2353 Boy Scout Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 3,096 Sq Ft
    • Built 1940

    Last Sold Summary

    • $549/SF
    • 6 Days On Market

    Current Estimated Value $1,687,617

    Last Listing Agent Jon Bell Railey Realty, Inc.

    2353 Boy Scout Rd, Oakland, MD 21550
    • 0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550
      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550
      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550
      /10

      Not Listed For Sale

      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550

      0 Sandy Beach Ln Unit MDGA2008344, Oakland, MD 21550
  • 565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    565 Glendale Rd Unit 103B, Oakland, MD 21550
    /53

    $260,000

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 103B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites! This inviting one-bedroom layout features a gas fireplace, full bath with tub/shower, and a tidy kitchenette equipped with a microwave, dishwasher, and full-size refrigerator. Balcony doors open to fresh Deep Creek air and filtered lake views, with a private deck that is perfect for relaxing after a day on the water. Enjoy a variety of

    Rachel Bruch Railey Realty, Inc.

    565 Glendale Rd Unit 103B, Oakland, MD 21550
  • Lot 18 Moss Creek Cir, Oakland, MD 21550
    Lot 18 Moss Creek Cir, Oakland, MD 21550
    Lot 18 Moss Creek Cir, Oakland, MD 21550
    /25

    $42,000 Sold Aug 06, 2025

    Lot 18 Moss Creek Cir, Oakland, MD 21550

    • Land
    • 3.61 Acres
    • $11,634 per Acre

    Last Sold Summary

    • 58 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    Lot 18 Moss Creek Cir, Oakland, MD 21550
    • TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550
      TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550
      TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550
      /10

      Not Listed For Sale

      TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550

      TRACT 2: 51.31+/- AC Gorman Rd, Oakland, MD 21550
  • 104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    104 Pine Top Trail, Oakland, MD 21550
    /13

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft

    104 Pine Top Trail, Oakland, MD 21550

    Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acreage is right next to the Common Grounds and gives you immediate river access.

    laura Flynn 1 Real Estate Source LLC

    104 Pine Top Trail, Oakland, MD 21550
  • 426 Pergin Farm Rd, Oakland, MD 21550
    426 Pergin Farm Rd, Oakland, MD 21550
    426 Pergin Farm Rd, Oakland, MD 21550
    /42

    $430,000 Sold Mar 27, 2025

    426 Pergin Farm Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • Built 1985

    Last Sold Summary

    • $269/SF
    • 15 Days On Market

    Current Estimated Value $444,270

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

    426 Pergin Farm Rd, Oakland, MD 21550
    • 33 Laurel Brook Dr, Oakland, MD 21550
      33 Laurel Brook Dr, Oakland, MD 21550
      33 Laurel Brook Dr, Oakland, MD 21550
      /47

      Est $334,401 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft

      33 Laurel Brook Dr, Oakland, MD 21550

      33 Laurel Brook Dr, Oakland, MD 21550
  • 175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
    /53

    $519,000

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550

    Welcome to this 4-bedroom, 4.5-bath stand-alone, multi-level unit in Traders Landing! Offering filtered lake views, ample square footage, oversized bedrooms, and multiple living spaces, this property is ideal for entertaining, large groups, or relaxed mountain-lake living. Enjoy a central Deep Creek location just minutes from Deep Creek Lake, local restaurants, shopping, and Wisp Resort.

    Nina Beitzel Railey Realty, Inc.

    175 Roman Ridge Rd Unit 15, Oakland, MD 21550
  • 290 Crellin Underwood Rd, Oakland, MD 21550
    290 Crellin Underwood Rd, Oakland, MD 21550
    290 Crellin Underwood Rd, Oakland, MD 21550
    /65

    $280,500 Sold Sep 12, 2025

    290 Crellin Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft
    • Built 1982

    Last Sold Summary

    • $127/SF
    • 96 Days On Market

    Current Estimated Value $283,502

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
    • 1200 Mountainview Dr, Oakland, MD 21550
      1200 Mountainview Dr, Oakland, MD 21550
      1200 Mountainview Dr, Oakland, MD 21550
      /64

      Est $1,755,870 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 5,926 Sq Ft

      1200 Mountainview Dr, Oakland, MD 21550

      1200 Mountainview Dr, Oakland, MD 21550
  • 333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    333 Sloan Tract Rd, Oakland, MD 21550
    /43

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 1,492 Sq Ft

    333 Sloan Tract Rd, Oakland, MD 21550

    Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home has three levels of living space, hardwood flooring and a nice fireplace. The lower level is totally finished with walk-out access. There are multiple covered porches plus a hot tub that are great outdoor spaces to enjoy year round. This home feels very secluded but is just minutes to Deep Creek Lake and Wisp

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    333 Sloan Tract Rd, Oakland, MD 21550
  • 502 E Oak St, Oakland, MD 21550
    502 E Oak St, Oakland, MD 21550
    502 E Oak St, Oakland, MD 21550
    /41

    $239,900 Sold Sep 12, 2025

    502 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1956

    Last Sold Summary

    • $143/SF
    • 17 Days On Market

    Current Estimated Value $243,725

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    502 E Oak St, Oakland, MD 21550
    • 35 Weber Ct, Oakland, MD 21550
      35 Weber Ct, Oakland, MD 21550
      35 Weber Ct, Oakland, MD 21550
      /21

      Est $299,449 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft

      35 Weber Ct, Oakland, MD 21550

      35 Weber Ct, Oakland, MD 21550
  • 2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    2 Overlook Ridge Dr S, Oakland, MD 21550
    /11

    $199,900

    • Land
    • 0.11 Acre
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, Oakland, MD 21550
  • 116 Wanderer Ln Unit F5, Oakland, MD 21550
    116 Wanderer Ln Unit F5, Oakland, MD 21550
    116 Wanderer Ln Unit F5, Oakland, MD 21550
    /97

    $732,500 Sold Jun 09, 2025

    116 Wanderer Ln Unit F5, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1975

    Last Sold Summary

    • $509/SF
    • 6 Days On Market

    Current Estimated Value $727,693

    Last Listing Agent Charlene Deremer Coldwell Banker Home Town Realty

    116 Wanderer Ln Unit F5, Oakland, MD 21550
    • 214 McComas Beach Terrace, Oakland, MD 21550
      214 McComas Beach Terrace, Oakland, MD 21550
      214 McComas Beach Terrace, Oakland, MD 21550
      /4

      Est $3,239,913 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 6,890 Sq Ft

      214 McComas Beach Terrace, Oakland, MD 21550

      214 McComas Beach Terrace, Oakland, MD 21550
  • 41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    41 Boyd Paugh Ln, Oakland, MD 21550
    /103

    $2,399,000 Pre-Foreclosure

    • 7 Beds
    • 5 Baths
    • 4,691 Sq Ft

    41 Boyd Paugh Ln, Oakland, MD 21550

    Gorgeous 7 bedroom home with dock slip! This newer construction home sits on a quiet corner of Deep Creek Lake with 200 feet of lake frontage. Located in the beautiful and quiet Heron Cove community and comes with two community lake access points, one with a sandy beach area, tennis courts, and walking trails. The level lot is surrounded by trees and designed for privacy and outdoor enjoyment,

    Rachel Bruch Railey Realty, Inc.

    41 Boyd Paugh Ln, Oakland, MD 21550
  • 131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    /53

    $495,000 Sold Oct 08, 2025

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,422 Sq Ft
    • Built 2004

    Last Sold Summary

    • $204/SF
    • 106 Days On Market

    Current Estimated Value $500,661

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    • 145 Ridgewood Dr, Oakland, MD 21550
      145 Ridgewood Dr, Oakland, MD 21550
      145 Ridgewood Dr, Oakland, MD 21550
      /72

      Est $646,004 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,838 Sq Ft

      145 Ridgewood Dr, Oakland, MD 21550

      145 Ridgewood Dr, Oakland, MD 21550
  • 3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    3898 Underwood Rd, Oakland, MD 21550
    /31

    $1,800,000

    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    One of a kind 4 BR 4 BA brick Home. 5,100 sq. ft. + 3 car garage. Situated on 23.47 elevated acres with unbelievable panoramic views of Pleasant Valley and surrounding farming community. Living area on one level with full unfinished basement. Views from every room. Massive amount of closet space The opportunities are abundant with this property.

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, Oakland, MD 21550
  • 5154 Maryland Hwy, Oakland, MD 21550
    5154 Maryland Hwy, Oakland, MD 21550
    5154 Maryland Hwy, Oakland, MD 21550
    /65

    $375,000 Sold Jul 29, 2025

    5154 Maryland Hwy, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,860 Sq Ft
    • Built 1980

    Last Sold Summary

    • $131/SF
    • 23 Days On Market

    Current Estimated Value $381,261

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

    5154 Maryland Hwy, Oakland, MD 21550
    • 4368 Underwood Rd, Oakland, MD 21550
      4368 Underwood Rd, Oakland, MD 21550
      4368 Underwood Rd, Oakland, MD 21550
      /61

      Est $242,266 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,760 Sq Ft

      4368 Underwood Rd, Oakland, MD 21550

      4368 Underwood Rd, Oakland, MD 21550
  • 697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    697 Monte Vista Rd, Oakland, MD 21550
    /56

    $339,000

    • 5 Beds
    • 3.5 Baths
    • 3,682 Sq Ft

    697 Monte Vista Rd, Oakland, MD 21550

    Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    697 Monte Vista Rd, Oakland, MD 21550

Showing Results 121 - 160, Page 4 of 18

Maryland Garrett County Oakland

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