10,731

Oakland, MD Homes

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  • 18 Hoye Crest Rd, Oakland, MD 21550
    18 Hoye Crest Rd, Oakland, MD 21550
    18 Hoye Crest Rd, Oakland, MD 21550
    /9

    $25,000 Sold Jan 14, 2026

    18 Hoye Crest Rd, Oakland, MD 21550

    • Land
    • 7.51 Acres
    • $3,329 per Acre

    Last Sold Summary

    • 63 Days On Market

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    18 Hoye Crest Rd, Oakland, MD 21550
    • 1265 Bray School Rd, Oakland, MD 21550
      1265 Bray School Rd, Oakland, MD 21550
      1265 Bray School Rd, Oakland, MD 21550
      /105

      Est $437,720 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft

      1265 Bray School Rd, Oakland, MD 21550

      1265 Bray School Rd, Oakland, MD 21550
  • 189 Red Run Rd Unit 1C2, Oakland, MD 21550
    189 Red Run Rd Unit 1C2, Oakland, MD 21550
    189 Red Run Rd Unit 1C2, Oakland, MD 21550
    /50

    $589,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    189 Red Run Rd Unit 1C2, Oakland, MD 21550

    2/3BR, 2BA waterfront condo at Red Run offering lake views and assigned deep water boat slip! Recently awarded 'top 1% of all homes on Airbnb'! Immaculately maintained, the owners have remodeled the entire unit in the last year. Luxurious and well-appointed with upscale furnishings & contents - conveys essentially TURNKEY. Gorgeous master suite with lake views, spacious bedrooms, wood burning

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    189 Red Run Rd Unit 1C2, Oakland, MD 21550
  • 125 N 2nd St, Oakland, MD 21550
    125 N 2nd St, Oakland, MD 21550
    125 N 2nd St, Oakland, MD 21550
    /8

    $99,000 Sold Jan 30, 2026

    125 N 2nd St, Oakland, MD 21550

    • Land
    • 0.22 Acre
    • $450,000 per Acre

    Last Sold Summary

    • 38 Days On Market

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    125 N 2nd St, Oakland, MD 21550
    • 325 Coolidge Ave, Oakland, MD 21550
      325 Coolidge Ave, Oakland, MD 21550
      325 Coolidge Ave, Oakland, MD 21550
      /29

      Est $170,003 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 834 Sq Ft

      325 Coolidge Ave, Oakland, MD 21550

      325 Coolidge Ave, Oakland, MD 21550
  • 2725 Stockslager Rd, Oakland, MD 21550
    2725 Stockslager Rd, Oakland, MD 21550
    2725 Stockslager Rd, Oakland, MD 21550
    /115

    $2,350,000 Under Contract

    • 5 Beds
    • 6.5 Baths
    • 5,376 Sq Ft

    2725 Stockslager Rd, Oakland, MD 21550

    Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built log home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. This home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled comfort. Nestled on 1.03

    Shelia McCracken Taylor Made Deep Creek Vacations & Sales

    2725 Stockslager Rd, Oakland, MD 21550
  • 1720 Pysell Crosscut Rd, Oakland, MD 21550
    1720 Pysell Crosscut Rd, Oakland, MD 21550
    1720 Pysell Crosscut Rd, Oakland, MD 21550
    /114

    $1,000,000 Sold Feb 05, 2026

    1720 Pysell Crosscut Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 8,000 Sq Ft
    • Built 1976

    Last Sold Summary

    • $125/SF
    • 52 Days On Market

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

    1720 Pysell Crosscut Rd, Oakland, MD 21550
    • 11 Trailside Ct, Oakland, MD 21550
      11 Trailside Ct, Oakland, MD 21550
      11 Trailside Ct, Oakland, MD 21550
      /56

      Est $542,635 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,442 Sq Ft

      11 Trailside Ct, Oakland, MD 21550

      11 Trailside Ct, Oakland, MD 21550
  • Lot 54 Gallatin Spur Rd, Oakland, MD 21550
    Lot 54 Gallatin Spur Rd, Oakland, MD 21550
    Lot 54 Gallatin Spur Rd, Oakland, MD 21550
    /5

    $27,500

    • Land
    • 0 Acre

    Lot 54 Gallatin Spur Rd, Oakland, MD 21550

    Building lot located in the premier subdivision - Gallatin Woods! This beautifully wooded community is located in the heart of the Deep Creek Lake. This is a condominium ownership type in regards to the land itself, but is buildable for a single family home! There are 8 pre-approved building plans designed and engineered by Mountaineer Log Homes that range anywhere from 1571 to 3908 square feet.

    Nina Beitzel Railey Realty, Inc.

    Lot 54 Gallatin Spur Rd, Oakland, MD 21550
  • 3 Edens Ridge Rd, Oakland, MD 21550
    3 Edens Ridge Rd, Oakland, MD 21550
    3 Edens Ridge Rd, Oakland, MD 21550
    /6

    $57,500 Sold Aug 27, 2025

    3 Edens Ridge Rd, Oakland, MD 21550

    • Land
    • 5 Acres
    • $11,500 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    3 Edens Ridge Rd, Oakland, MD 21550
    • 478 Lake Forest Dr, Oakland, MD 21550
      478 Lake Forest Dr, Oakland, MD 21550
      478 Lake Forest Dr, Oakland, MD 21550
      /95

      Est $1,598,141 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 2,688 Sq Ft

      478 Lake Forest Dr, Oakland, MD 21550

      478 Lake Forest Dr, Oakland, MD 21550
  • 13209 Garrett Hwy, Oakland, MD 21550
    13209 Garrett Hwy, Oakland, MD 21550
    13209 Garrett Hwy, Oakland, MD 21550
    /10

    $649,000 Under Contract

    • Land
    • 37.8 Acres
    • $17,169 per Acre

    13209 Garrett Hwy, Oakland, MD 21550

    Access to Public Utilities and Natural Gas within the Town of Oakland Utility systems.Access to Public Utilities and Natural Gas within the Town of Oakland Utility systems. Property has State Highway Entrance completed. New Owner would utilize this access Road to develop property. Recorded plat and Covenants available online.

    Rich Orr Railey Realty, Inc.

    13209 Garrett Hwy, Oakland, MD 21550
  • 215 Lower Penn Point Dr, Oakland, MD 21550
    215 Lower Penn Point Dr, Oakland, MD 21550
    215 Lower Penn Point Dr, Oakland, MD 21550
    /49

    $1,250,000 Sold Apr 11, 2025

    215 Lower Penn Point Dr, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,580 Sq Ft
    • Built 2001

    Last Sold Summary

    • $484/SF
    • 51 Days On Market

    Current Estimated Value $1,223,985

    Last Listing Agent Lauren McCann Railey Realty, Inc.

    215 Lower Penn Point Dr, Oakland, MD 21550
    • 29 Crescent Ln, Oakland, MD 21550
      29 Crescent Ln, Oakland, MD 21550
      29 Crescent Ln, Oakland, MD 21550
      /38

      Est $426,389 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,536 Sq Ft

      29 Crescent Ln, Oakland, MD 21550

      29 Crescent Ln, Oakland, MD 21550
  • 0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
    /5

    $30,000

    • Land
    • 0.34 Acre
    • $88,235 per Acre

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550

    Love Deep Creek Lake living. This 0.34 acre wooded lot sits near the heart of everything that makes the lake special. Launch the boat at nearby marinas, hike and swim at Deep Creek Lake State Park, and enjoy four season adventure at Wisp Resort with skiing, tubing, and mountain rides. Restaurants, shops, and local events are just down the road, while your homesite feels peaceful and private. Do

    Debra Hayne Cummings & Co. Realtors

    0 Santa fe Trail Unit MDGA2010334, Oakland, MD 21550
  • 36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    /35

    $235,000 Sold Oct 08, 2025

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550

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

    Last Sold Summary

    • $356/SF
    • 11 Days On Market

    Current Estimated Value $240,285

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

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    • 148 Wanderer Ln, Oakland, MD 21550
      148 Wanderer Ln, Oakland, MD 21550
      148 Wanderer Ln, Oakland, MD 21550
      /56

      Est $688,050 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft

      148 Wanderer Ln, Oakland, MD 21550

      148 Wanderer Ln, Oakland, MD 21550
  • Lot 14 Warnick Way, Oakland, MD 21550
    Lot 14 Warnick Way, Oakland, MD 21550
    Lot 14 Warnick Way, Oakland, MD 21550
    /3

    $45,900

    • Land
    • 1.02 Acres
    • $45,000 per Acre

    Lot 14 Warnick Way, Oakland, MD 21550

    Enjoy mountain views from this 1.02-acre, mostly wooded lot! No mobile homes permitted. No HOA. Easy access off Spring Glade Rd. Ideally situated between Oakland and Deep Creek Lake. Contact me today for more info!

    Nicole Jackson Railey Realty, Inc.

    Lot 14 Warnick Way, Oakland, MD 21550
  • 20160 Garrett Hwy Unit F503, Oakland, MD 21550
    20160 Garrett Hwy Unit F503, Oakland, MD 21550
    20160 Garrett Hwy Unit F503, Oakland, MD 21550
    /68

    $540,000 Sold Mar 31, 2025

    20160 Garrett Hwy Unit F503, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1972

    Last Sold Summary

    • $318/SF
    • 0 Days On Market

    Current Estimated Value $533,968

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

    20160 Garrett Hwy Unit F503, Oakland, MD 21550
    • 1597 Lake Shore Dr, Oakland, MD 21550
      1597 Lake Shore Dr, Oakland, MD 21550
      1597 Lake Shore Dr, Oakland, MD 21550
      /82

      Est $1,711,731 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 1,904 Sq Ft

      1597 Lake Shore Dr, Oakland, MD 21550

      1597 Lake Shore Dr, Oakland, MD 21550
  • 267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    267 San Francisco St, Oakland, MD 21550
    /30

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    267 San Francisco St, Oakland, MD 21550

    Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake views! So clear you’ll catch the slopes of Wisp in the distance. Includes 3 lots and the privacy is unmatched. This house was torn down to the foundation and a new house was built in 2009. Inside, you’ll find four spacious bedrooms, two and a half baths, and soaring vaulted ceilings and a grand fireplace.

    Bradley West HomeSmart

    267 San Francisco St, Oakland, MD 21550
  • Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    /17

    $18,000 Sold Nov 14, 2025

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550

    • Land
    • 0.98 Acre
    • $18,367 per Acre

    Last Sold Summary

    • 17 Days On Market

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

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    • 216 E Center St, Oakland, MD 21550
      216 E Center St, Oakland, MD 21550
      216 E Center St, Oakland, MD 21550
      /29

      Est $180,574 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,472 Sq Ft

      216 E Center St, Oakland, MD 21550

      216 E Center St, Oakland, MD 21550
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /50

    $379,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    961 Cedar Ln, Oakland, MD 21550
  • 50 Village Dr Unit 7, Oakland, MD 21550
    50 Village Dr Unit 7, Oakland, MD 21550
    50 Village Dr Unit 7, Oakland, MD 21550
    /34

    $459,000 Sold Nov 25, 2025

    50 Village Dr Unit 7, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 2006

    Last Sold Summary

    • $455/SF
    • 17 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    50 Village Dr Unit 7, Oakland, MD 21550
    • 1012 Hemlock Cir, Oakland, MD 21550
      1012 Hemlock Cir, Oakland, MD 21550
      1012 Hemlock Cir, Oakland, MD 21550
      /33

      Est $475,953 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,590 Sq Ft

      1012 Hemlock Cir, Oakland, MD 21550

      1012 Hemlock Cir, Oakland, MD 21550
  • 178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
    /47

    $589,000

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

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550

    Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene

    Nina Beitzel Railey Realty, Inc.

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
  • 285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    /50

    $559,250 Sold Sep 02, 2025

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2008

    Last Sold Summary

    • $169/SF
    • 62 Days On Market

    Current Estimated Value $571,341

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    • 1865 Garrett Rd, Oakland, MD 21550
      1865 Garrett Rd, Oakland, MD 21550
      1865 Garrett Rd, Oakland, MD 21550
      /52

      Est $254,446 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,144 Sq Ft

      1865 Garrett Rd, Oakland, MD 21550

      1865 Garrett Rd, Oakland, MD 21550
  • LOT 181 Santa fe Trail, Oakland, MD 21550
    LOT 181 Santa fe Trail, Oakland, MD 21550
    LOT 181 Santa fe Trail, Oakland, MD 21550
    /12

    $45,000

    • Land
    • 0.34 Acre
    • $132,353 per Acre

    LOT 181 Santa fe Trail, Oakland, MD 21550

    Don't miss the opportunity to own a lake area lot near the one and only Deep Creek Lake. 0.34 acre wooded lot, close to multiple local attractions. Call today! Verify utilities with Garrett County Environmental Department. Being sold subject to successful perc.

    Amy Skipper Railey Realty, Inc.

    LOT 181 Santa fe Trail, Oakland, MD 21550
  • 0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    /13

    $155,000 Sold Jan 08, 2026

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550

    • Land
    • 0.72 Acre
    • $215,278 per Acre

    Last Sold Summary

    • 16 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    • 153 Mallard Loop, Oakland, MD 21550
      153 Mallard Loop, Oakland, MD 21550
      153 Mallard Loop, Oakland, MD 21550
      /91

      Est $1,463,109 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,506 Sq Ft

      153 Mallard Loop, Oakland, MD 21550

      153 Mallard Loop, Oakland, MD 21550
  • 0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
    /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550

    1+ acre building lot. Fairly leveled cleared lot with some distant mountain views. Paved County road frontage with private road/drive access to lot. Approved for private septic and well. Electric on-site. Located approx. 10+ mins from Deep Creek Lake and approx. less than 5 minutes from Oakland. Located within small 8 lot development, "The Homestead".

    Chip Smith 1 Real Estate Source LLC

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
  • 710 Hunters Ridge Dr, Oakland, MD 21550
    710 Hunters Ridge Dr, Oakland, MD 21550
    710 Hunters Ridge Dr, Oakland, MD 21550
    /54

    $550,000 Sold Aug 29, 2025

    710 Hunters Ridge Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 2007

    Last Sold Summary

    • $317/SF
    • 70 Days On Market

    Current Estimated Value $554,860

    Last Listing Agent Andrew Orr The KW Collective

    710 Hunters Ridge Dr, Oakland, MD 21550
    • 22 Duck Cove Rd, Oakland, MD 21550
      22 Duck Cove Rd, Oakland, MD 21550
      22 Duck Cove Rd, Oakland, MD 21550
      /70

      Est $1,753,871 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 1,964 Sq Ft

      22 Duck Cove Rd, Oakland, MD 21550

      22 Duck Cove Rd, Oakland, MD 21550
  • 931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    /53

    $359,000

    • 3 Beds
    • 1 Bath
    • 990 Sq Ft

    931 Black Oak Dr, Oakland, MD 21550

    Escape to Your Profitable Mountain Sanctuary: The Yough Mountain CabinUnveiling the Ultimate Turnkey Retreat & High-Performing InvestmentNestled in the breathtaking heart of the exclusive Yough Mountain Resort, this stunning 3-bedroom cabin offers the perfect harmony of rustic soul and modern investment savvy. Whether you are looking for a private family getaway or a powerful addition to

    ANGELA BOSLEY Taylor Made Deep Creek Vacations & Sales

    931 Black Oak Dr, Oakland, MD 21550
  • 655 Bray School Rd, Oakland, MD 21550
    655 Bray School Rd, Oakland, MD 21550
    655 Bray School Rd, Oakland, MD 21550
    /67

    $259,000 Sold May 14, 2025

    655 Bray School Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1984

    Last Sold Summary

    • $270/SF
    • 4 Days On Market

    Current Estimated Value $259,476

    Last Listing Agent Susan Bell Railey Realty, Inc.

    655 Bray School Rd, Oakland, MD 21550
    • 10 Ortiz Ct, Oakland, MD 21550
      10 Ortiz Ct, Oakland, MD 21550
      10 Ortiz Ct, Oakland, MD 21550
      /71

      Est $757,562 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,440 Sq Ft

      10 Ortiz Ct, Oakland, MD 21550

      10 Ortiz Ct, Oakland, MD 21550
  • Lot 40 W Big Piney Dr, Oakland, MD 21550
    Lot 40 W Big Piney Dr, Oakland, MD 21550
    Lot 40 W Big Piney Dr, Oakland, MD 21550
    /8

    $17,000 Pending

    • Land
    • 0.77 Acre
    • $22,078 per Acre

    Lot 40 W Big Piney Dr, Oakland, MD 21550

    Located in the Youghiogheny Mountain Resort community, this .77ac lot offers the ultimate gateway to peaceful surroundings, beautiful views, and abundant wildlife. Approved for a sand mound sewage system, this lot provides the perfect opportunity to build your future outdoor enthusiast retreat! Enjoy exclusive access to over 50 miles of private roads and trails perfect for ATV and side-by-side

    Elizabeth Broadwater Taylor Made Deep Creek Vacations & Sales

    Lot 40 W Big Piney Dr, Oakland, MD 21550
  • 0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550
    0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550
    0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550
    /13

    $34,500 Sold Feb 12, 2025

    0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550

    • Land
    • 3.18 Acres
    • $10,849 per Acre

    Last Sold Summary

    • 114 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    0 Oakland Sang Run Rd Unit MDGA2008132, Oakland, MD 21550

Showing Results 281 - 320, Page 8 of 18

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