10,714

Oakland, MD Homes

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  • 126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    /50

    $529,900

    • 4 Beds
    • 3 Baths
    • 2,235 Sq Ft

    126 Leo Friend Rd, Oakland, MD 21550

    Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits

    Jon Bell Railey Realty, Inc.

    126 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
    • 3365 Mayhew Inn Rd, Oakland, MD 21550
      3365 Mayhew Inn Rd, Oakland, MD 21550
      3365 Mayhew Inn Rd, Oakland, MD 21550
      /68

      Est $740,981 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,158 Sq Ft

      3365 Mayhew Inn Rd, Oakland, MD 21550

      3365 Mayhew Inn Rd, Oakland, MD 21550
  • 0 Crosby Dr Unit 64/65, Oakland, MD 21550
    0 Crosby Dr Unit 64/65, Oakland, MD 21550
    0 Crosby Dr Unit 64/65, Oakland, MD 21550
    /55

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft

    0 Crosby Dr Unit 64/65, Oakland, MD 21550

    TO BE BUILT on lots 64 & 65 Country Club Acres - 3BR, 2BA new construction with full walkout basement & attached 2 car garage fronting on hole #13 of the Oakland golf course. Impressive views from .61+/- acres of land, rare privacy and modern floor plan. 1,986 sf of finished living space on the first floor and 1,986 sq ft unfinished basement will have a full bath rough-in and can be finished

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Crosby Dr Unit 64/65, Oakland, MD 21550
  • 931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    /56

    $329,000 Sold Jan 14, 2025

    931 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Built 2007

    Last Sold Summary

    • $299/SF
    • 170 Days On Market

    Current Estimated Value $341,163

    Last Listing Agent Sean Sober Taylor Made Deep Creek Vacations & Sales

    931 Black Oak Dr, Oakland, MD 21550
    • 135 Tarn Dr, Oakland, MD 21550
      135 Tarn Dr, Oakland, MD 21550
      135 Tarn Dr, Oakland, MD 21550
      /25

      Not Listed For Sale

      135 Tarn Dr, Oakland, MD 21550

      135 Tarn Dr, Oakland, MD 21550
  • 0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550
    /6

    $119,000

    • Land
    • 3.1 Acres
    • $38,387 per Acre

    0 Lot 29 Briarwood Ln Unit MDGA2008894, Oakland, MD 21550

    This is the building site you've been waiting for! Lot 29 is located in a subdivision called the View, and it lives up to the name! Offering a generous 3.10 Acres with possible lake views this attractive location is close to lake amenities while giving a sense of privacy. Call today for more information!

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    0 Lot 29 Briarwood Ln Unit MDGA2008894, 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
    • 17 Old Chestnut Dr, Oakland, MD 21550
      17 Old Chestnut Dr, Oakland, MD 21550
      17 Old Chestnut Dr, Oakland, MD 21550
      /49

      Est $904,442 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 966 Sq Ft

      17 Old Chestnut Dr, Oakland, MD 21550

      17 Old Chestnut Dr, Oakland, MD 21550
  • 565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    565 Glendale Rd Unit 106B, Oakland, MD 21550
    /27

    $239,900

    • 1 Bed
    • 1 Bath

    565 Glendale Rd Unit 106B, Oakland, MD 21550

    Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs in a gas fireplace, full bath with tub/shower, and a tidy kitchenette with microwave, dishwasher, and full fridge. Balcony doors open to Deep Creek air and filtered lake scenes. Community perks include sauna, gym, game room and more. Sold turn-key, fully furnished. Ductless units for heat and A/C. Monthly

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 106B, 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 $1,683,702

    Last Listing Agent Jon Bell Railey Realty, Inc.

    2353 Boy Scout Rd, Oakland, MD 21550
    • 503 Southern Pines Dr, Oakland, MD 21550
      503 Southern Pines Dr, Oakland, MD 21550
      503 Southern Pines Dr, Oakland, MD 21550
      /10

      Est $123,333 Not Listed For Sale

      503 Southern Pines Dr, Oakland, MD 21550

      503 Southern Pines Dr, Oakland, MD 21550
  • 1570 Garrett Rd, Oakland, MD 21550
    1570 Garrett Rd, Oakland, MD 21550
    1570 Garrett Rd, Oakland, MD 21550
    /27

    $245,000

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft

    1570 Garrett Rd, Oakland, MD 21550

    Located between Oakland and Deep Creek Lake, this log ranch is situated on 14.82 acres, including a stream, pond, barn and outbuildings with many possibilities to include potential subdivision configurations. The log home needs some TLC and updates; it is being sold as part of an estate. Some items of personal property remain in the house and on grounds. Those items are being removed. More photos

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    1570 Garrett Rd, 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
    • 15 Fawn Dr, Oakland, MD 21550
      15 Fawn Dr, Oakland, MD 21550
      15 Fawn Dr, Oakland, MD 21550
      /32

      Est $156,000 Not Listed For Sale

      15 Fawn Dr, Oakland, MD 21550

      15 Fawn Dr, Oakland, MD 21550
  • 102 Roanoke Ave, Oakland, MD 21550
    102 Roanoke Ave, Oakland, MD 21550
    102 Roanoke Ave, Oakland, MD 21550
    /7

    $130,000

    • 4 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    102 Roanoke Ave, Oakland, MD 21550

    4-bedroom, 1.5-bath home located on a spacious corner lot in Loch Lynn. This two-story property features generous living space and several recent updates, including a new furnace, roof, windows, and stove. A newer deck offers additional outdoor enjoyment. The home is conveniently located near the Loch Lynn soccer fields and just a few minutes from downtown Oakland. Solid structure with great

    Heather Homberg Taylor Made Deep Creek Vacations & Sales

    102 Roanoke Ave, Oakland, MD 21550
  • 1322 Black Oak Dr, Oakland, MD 21550
    1322 Black Oak Dr, Oakland, MD 21550
    1322 Black Oak Dr, Oakland, MD 21550
    /72

    $240,000 Sold Dec 27, 2024

    1322 Black Oak Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 2,058 Sq Ft
    • Built 1974

    Last Sold Summary

    • $117/SF
    • 459 Days On Market

    Current Estimated Value $262,259

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

    1322 Black Oak Dr, 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
  • 62 Crosby Dr, Oakland, MD 21550
    62 Crosby Dr, Oakland, MD 21550
    62 Crosby Dr, Oakland, MD 21550
    /5

    $37,500 Pending

    • Land
    • 0.63 Acre
    • $59,524 per Acre

    62 Crosby Dr, Oakland, MD 21550

    Beautiful building lot in Country Club Acres. Lot 62 and 63 combine for a total 0.629-acre lot and backs up to the Oakland Golf course. Conveniently located close to schools, shopping, restaurants and more. Call today for more info!

    Jon Bell Railey Realty, Inc.

    62 Crosby Dr, 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 $440,954

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

    426 Pergin Farm Rd, Oakland, MD 21550
    • 20476 Garrett Hwy, Oakland, MD 21550
      20476 Garrett Hwy, Oakland, MD 21550
      20476 Garrett Hwy, Oakland, MD 21550
      /82

      Est $1,302,197 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
  • 809 N St, Oakland, MD 21550
    809 N St, Oakland, MD 21550
    809 N St, Oakland, MD 21550
    /19

    $65,000

    • 792 Sq Ft

    809 N St, Oakland, MD 21550

    This home needs TLC with the possibility to rebuild on existing foundation if you want to rehab. Buyer to confirm with the county and the town of Mt. Lake Park for rebuilding stipulations. Being sold "As Is". Caution: Entering this property is at your own discretion and responsibility.RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. PROSPECTIVE PURCHASERS AND THEIR

    Kathy Gibson Railey Realty, Inc.

    809 N St, 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 $277,867

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood 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
  • Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550
    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550
    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550
    /11

    $23,000

    • Land
    • 0.12 Acre
    • $191,667 per Acre

    Lot 55 Gallatin Dr Unit 55, Oakland, MD 21550

    Gallatin Woods is a unique log home community located on Lakeshore Drive in the innermost part of Deep Creek Lake. Each owner may build within the building cylinder indicated on the plat and have exclusive use of the parking area and the additional land that immediately surrounds the home site. All other land within the community is condominiumized to keep the area wooded and carefree. Owners

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    Lot 55 Gallatin Dr Unit 55, 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 $238,303

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    502 E Oak St, 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 $336,214 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
  • 47 Ridgewood Dr, Oakland, MD 21550
    47 Ridgewood Dr, Oakland, MD 21550
    47 Ridgewood Dr, Oakland, MD 21550
    /29

    $219,900

    • Land
    • 1.1 Acres
    • $199,909 per Acre

    47 Ridgewood Dr, Oakland, MD 21550

    Prime Lake Access Lot in Mountainside – Perfect for Your Dream Home! Nestled on a one-acre wooded lot in the sought-after Mountainside community, this homesite offers breathtaking views of Deep Creek Lake and the ideal slope for a walk-out basement. Enjoy the best of four-season living with easy access to community lake privileges, state parks, restaurants, and WISP Resort. Plus, take advantage

    Michael Fenton Railey Realty, Inc.

    47 Ridgewood Dr, 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 $727,914

    Last Listing Agent Charlene Deremer Coldwell Banker Home Town Realty

    116 Wanderer Ln Unit F5, Oakland, MD 21550
    • 1200 Mountainview Dr, Oakland, MD 21550
      1200 Mountainview Dr, Oakland, MD 21550
      1200 Mountainview Dr, Oakland, MD 21550
      /64

      Est $1,747,244 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
  • 9 Timber Falls Rd, Oakland, MD 21550
    9 Timber Falls Rd, Oakland, MD 21550
    9 Timber Falls Rd, Oakland, MD 21550
    /25

    $34,000

    • Land
    • 6.9 Acres
    • $4,928 per Acre

    9 Timber Falls Rd, Oakland, MD 21550

    Buildable wooded lot on Backbone Ridge—approved for a 4-bedroom traditional septic system. Perfectly positioned between Canaan Valley and Deep Creek Lake, this property offers prime access to four-season adventure: hunting, hiking, skiing, and ATV riding. Minutes from Blackwater Falls, Whitegrass XC Ski Center, and the vibrant mountain towns of Thomas and Davis

    Jesse Shimrock Railey Realty, Inc.

    9 Timber Falls Rd, 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

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

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550
    • 19868 Garrett Hwy, Oakland, MD 21550
      19868 Garrett Hwy, Oakland, MD 21550
      19868 Garrett Hwy, Oakland, MD 21550
      /29

      Est $1,825,312 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 3,860 Sq Ft

      19868 Garrett Hwy, Oakland, MD 21550

      19868 Garrett Hwy, Oakland, MD 21550
  • 0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550
    /3

    $135,000

    • Land
    • 1 Acre
    • $135,000 per Acre

    0 Paradise Heights Rd Unit MDGA2007090, Oakland, MD 21550

    Centrally located 1-acre lake access homesite with a dock slip! This property has endless possibilities to build, and depending on where you decide to position your new home, there could be potential for lake views. Offering public sewer and no HOA fees. The only decision left to be made is what style home you will build. Just minutes to the DCL State Park, several restaurants, convenience store,

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 Paradise Heights Rd Unit MDGA2007090, 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 $377,662

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

    5154 Maryland Hwy, Oakland, MD 21550
    • 35 Weber Ct, Oakland, MD 21550
      35 Weber Ct, Oakland, MD 21550
      35 Weber Ct, Oakland, MD 21550
      /21

      Est $281,879 Not Listed For Sale

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

      35 Weber Ct, Oakland, MD 21550

      35 Weber Ct, Oakland, MD 21550
  • 0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
    /2

    $149,000

    • Land
    • 1 Acre
    • $149,000 per Acre

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550

    Wooded lot with spectacular views of Paradise Point area of lake. Great privacy. Sewer tap available

    John Zorzit Eagle Commercial Realty

    0 Paradise Point Rd Unit MDGA2003916, Oakland, MD 21550
  • 62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    62 Middleton Rd, Oakland, MD 21550
    /67

    $760,000 Sold Nov 14, 2025

    62 Middleton Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1993

    Last Sold Summary

    • $317/SF
    • 113 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Middleton Rd, 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 $3,284,741 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
  • 939 Glendale Rd Unit 19, Oakland, MD 21550
    939 Glendale Rd Unit 19, Oakland, MD 21550
    939 Glendale Rd Unit 19, Oakland, MD 21550
    /27

    $765,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft

    939 Glendale Rd Unit 19, Oakland, MD 21550

    SEE DOCUMENTS FOR 07/2025 TAX STATEMENT--$1,533 annual assessment for HOA reserves. $1,500 Annual fee to Bill's Marine for assumable boat-strip lease. $4,500 Annual condo fees. Condo Association responsible for roof, building exterior maintenance, lawn maintenance, snow removal, replacement of deck, porch and front door. Water is included in the condo fees. Sewer fees are not included and average

    Rick Davis Richard A. Davis & Associates

    939 Glendale Rd Unit 19, Oakland, MD 21550

Showing Results 121 - 160, Page 4 of 18

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