12,296

Homes in ZIP Code 21550

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  • /18

    $4,000

    Under Contract
    • Land
    • 20,473 Sq Ft
    • $8,511 per Acre

    Lot 36 Fox Tail Rd, Oakland, MD 21550

    Discover your mountain escape in Yough Mountain Resort, a gated recreational community in the scenic mountains of Western Maryland, just a short drive to Deep Creek Lake. This amenity-rich community is designed for outdoor enthusiasts, offering ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering.This

    Shannon McWilliams Taylor-Made Deep Creek Real Estate, LLC

    Lot 36 Fox Tail Rd, Oakland, MD 21550
  • /24

    $110,000

    Sold Sep 26, 2025

    110 W Pennington St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1946

    Last Sold Summary

    • $143/SF
    • 12 Days On Market

    Current Estimated Value $115,976

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

    110 W Pennington St, Oakland, MD 21550
    • /83

      Est $1,196,805

      Not Listed For Sale

      2675 Stockslager Rd, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 3,024 Sq Ft
      • Built 2003
      2675 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

  • /44

    $145,000

    Under Contract
    • 1 Bed
    • 1 Bath
    • 1,728 Sq Ft

    1099 Table Rock Rd, Oakland, MD 21550

    Nestled in the scenic countryside of Southern Garrett County, on 5+ acre property along North Fork Sand Run, this two-level home provides a solid foundation for renovation or customization, making it ideal for a full-time residence or mountain getaway. In addition to the home, the property features a large detached garage perfect for vehicles, equipment, hobbies, or workshop space, along with a

    Rich Orr Railey Realty, Inc.

    1099 Table Rock Rd, Oakland, MD 21550
  • /50

    $425,000

    Sold Jun 03, 2026

    609 Southern Pines Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,250 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $189/SF
    • 295 Days On Market

    Current Estimated Value $427,509

    Last Listing Agent Brian Covell BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    609 Southern Pines Dr, Oakland, MD 21550
    • /75

      Est $715,210

      Not Listed For Sale

      630 Paradise Ridge Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,044 Sq Ft
      • Built 1997
      630 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /115

    $2,350,000

    • 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 Real Estate, LLC

    2725 Stockslager Rd, Oakland, MD 21550
  • /45

    $150,000

    Sold Aug 14, 2025

    414 D St, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1950

    Last Sold Summary

    • $160/SF
    • 4 Days On Market

    Current Estimated Value $147,993

    Last Listing Agent Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    414 D St, Oakland, MD 21550
    • /4

      Est $106,113

      Not Listed For Sale

      111 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,528 Sq Ft
      • Built 1914
      111 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 10 Days On Market

  • /87

    $1,149,000

    • 6 Beds
    • 6.5 Baths
    • 3,233 Sq Ft

    220 Biltmore View, Mc Henry, MD 21541

    Luxury mountain retreat in the heart of Deep Creek Lake! “Ski Time to Tee Time” is a spacious 6-bedroom, 6.5-bath home offering the perfect blend of rustic elegance and modern comfort, ideally located near Wisp Resort, Lodestone Golf Course, and Deep Creek Lake. Inside, soaring cathedral ceilings with exposed wood beams and a stunning fireplace anchors the expansive open living area, creating a

    Kelsey Meyers Railey Realty, Inc.

    220 Biltmore View, Mc Henry, MD 21541
  • /13

    $50,000

    Sold Feb 06, 2026

    72 Chimney Rock Ln, Mc Henry, MD 21541

    • Land
    • 24,829 Sq Ft
    • $87,719 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 2 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    72 Chimney Rock Ln, Mc Henry, MD 21541
    • /25

      Est $1,097,118

      Not Listed For Sale

      378 Lower Penn Point Dr, Oakland, MD 21550

      • 4 Beds
      • 1 Bath
      • 1,114 Sq Ft
      • Built 1950
      378 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /5

    $27,500

    • Land
    • 0 Sq Ft

    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
  • /48

    $525,000

    Sold Jul 11, 2025

    3554 Lake Shore Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1993

    Last Sold Summary

    • $405/SF
    • 232 Days On Market

    Current Estimated Value $522,143

    Last Listing Agent Robert Krop Keller Williams Realty Centre

    3554 Lake Shore Dr, Oakland, MD 21550
    • /89

      Est $1,657,590

      Not Listed For Sale

      1019 Lake Shore Dr, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 2,605 Sq Ft
      • Built 1962
      1019 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

  • /25

    $259,900

    • 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
  • /22

    $185,000

    Sold May 22, 2026

    1307 Broadford Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $195/SF
    • 46 Days On Market

    Current Estimated Value $204,024

    Last Listing Agent Bill Kenny Keller Williams Realty Centre

    1307 Broadford Rd, Oakland, MD 21550
    • /65

      Est $152,722

      Not Listed For Sale

      94 Tannery Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,108 Sq Ft
      • Built 1900
      94 Tannery Rd, Oakland, MD 21550

      Last Sold Summary

      • 63 Days On Market

  • /38

    $799,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,929 Sq Ft

    62 Middleton Rd, Oakland, MD 21550

    Lake Access with a Dock Slip located in the highly desirable Blakeslee community. This 3-bedroom, 2.5-bath mountain retreat offers the perfect mix of comfort, style, and Deep Creek Lake living. An open, inviting layout give the home a refreshed, updated feel, while the sun-filled four-season room quickly becomes the standout space of the home. A stunning pass-through stone fireplace anchors the

    Jon Bell Railey Realty, Inc.

    62 Middleton Rd, Oakland, MD 21550
  • /5

    $44,000

    Sold Aug 11, 2025

    142 Matthew Rd, Oakland, MD 21550

    • Land
    • 1.83 Acres
    • $24,044 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    142 Matthew Rd, Oakland, MD 21550
    • /66

      Est $192,358

      Not Listed For Sale

      1606 Wheeling Ave, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,502 Sq Ft
      • Built 1976
      1606 Wheeling Ave, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /71

    $999,000

    $50K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 2,730 Sq Ft

    137 Paradise Gardens Rd, Oakland, MD 21550

    Remodeled 4BR/2BA lakefront A-frame with two deep water dock slips! Impressive renovation from top to bottom, this home has everything you are seeking in a vacation home AND a huge, fenced in yard surrounded by massive trees, fire pit and storage building. Features include a massive stone fireplace (wood burning), hot tub with lake views, large kitchen with island, custom tile showers & bathrooms

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    137 Paradise Gardens Rd, Oakland, MD 21550
  • /48

    $229,000

    Sold Dec 15, 2025

    104 G St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • Built 1900

    Last Sold Summary

    • $142/SF
    • 26 Days On Market

    Current Estimated Value $221,485

    Last Listing Agent Julie Mead The KW Collective

    104 G St, Oakland, MD 21550
    • /24

      Est $224,560

      Not Listed For Sale

      123 Spruce St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,392 Sq Ft
      • Built 1990
      123 Spruce St, Oakland, MD 21550

      Last Sold Summary

      • 7 Days On Market

  • /24

    $419,000

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    560 Glendale Rd, Oakland, MD 21550

    Charming vintage Deep Creek Lake log cabin ideally located in the heart of Deep Creek Lake just minutes from area amenities. Full of character and thoughtfully restored, this established rental property is being sold completely furnished and turnkey. Enjoy filtered lake views from the inviting covered front porch, then unwind in the hot tub or gather around the fire pit after a day on the lake.

    Lauren McCann Railey Realty, Inc.

    560 Glendale Rd, Oakland, MD 21550
  • /22

    $38,000

    Sold Jun 16, 2026

    422 Maple Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Built 1940

    Last Sold Summary

    • 37% Below List Price
    • $24/SF
    • 34 Days On Market

    Current Estimated Value $63,515

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    422 Maple Ave, Oakland, MD 21550
    • /69

      Est $842,449

      Not Listed For Sale

      79 Hummingbird Ct, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,800 Sq Ft
      • Built 1999
      79 Hummingbird Ct, Oakland, MD 21550

      Last Sold Summary

      • 59 Days On Market

  • /52

    $399,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,780 Sq Ft

    2254 Garrett Rd, Oakland, MD 21550

    Situated on an expansive and private 17 acres of property this Southern Garrett county home offers its new owners the unique opportunity of space and privacy all while being close to town and additional amenities. A private paved driveway leads you to an extensively updated and lovingly maintained home that has a spacious feeling 3 bedrooms and 2 full bathrooms on the main floor. A full basement

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    2254 Garrett Rd, Oakland, MD 21550
  • /20

    $195,000

    Sold Nov 12, 2025

    210 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft
    • Built 1996

    Last Sold Summary

    • $162/SF
    • 2 Days On Market

    Current Estimated Value $191,817

    Last Listing Agent Andrew Orr The KW Collective

    210 Seneca Ave, Oakland, MD 21550
    • /86

      Est $803,510

      Not Listed For Sale

      105 Meadow Ct, Oakland, MD 21550

      • 4 Beds
      • 6 Baths
      • 3,192 Sq Ft
      • Built 2004
      105 Meadow Ct, Oakland, MD 21550

      Last Sold Summary

      • 47 Days On Market

  • /12

    $39,000

    • Land
    • 1.02 Acres
    • $38,235 per Acre

    Lot 14 Warnick Way, Oakland, MD 21550

    Enjoy scenic mountain views from this 1.02 acre mostly wooded homesite. This property offers a peaceful setting with convenient access off Spring Glade Road and is ideally located between Oakland and Deep Creek Lake. No HOA and mobile homes are not permitted, helping maintain the character of the area. Do not miss this great opportunity to build your getaway or full time residence. Contact me

    Nicole Jackson Railey Realty, Inc.

    Lot 14 Warnick Way, Oakland, MD 21550
  • /40

    $560,000

    Sold Jun 20, 2025

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2009

    Last Sold Summary

    • $170/SF
    • 52 Days On Market

    Current Estimated Value $550,493

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

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    • /59

      Est $413,317

      Not Listed For Sale

      57 Allegro Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,524 Sq Ft
      • Built 2004
      57 Allegro Ln, Oakland, MD 21550

      Last Sold Summary

      • 67 Days On Market

  • /24

    $18,000

    • Land
    • 26,136 Sq Ft
    • $30,000 per Acre

    22 Elm Dr, Oakland, MD 21550

    Build your dream getaway in the gated community of Youghiogheny Mountain Resort! This flat 0.60-acre lot offers an ideal setting for easy building. Perfect for a full-time home or weekend retreat. Enjoy miles of ATV trails, hunting, and fishing, all while being just minutes from Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Approved for a sand mound septic system and located within

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    22 Elm Dr, Oakland, MD 21550
  • /32

    $232,500

    Sold Jul 10, 2025

    114 Waterwheel Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1965

    Last Sold Summary

    • $242/SF
    • 138 Days On Market

    Current Estimated Value $229,328

    Last Listing Agent Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    114 Waterwheel Rd, Oakland, MD 21550
    • /73

      Est $613,209

      Not Listed For Sale

      491 Edens Ridge Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 3,318 Sq Ft
      • Built 2003
      491 Edens Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

  • /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
  • /33

    $130,000

    Sold May 22, 2026

    565 Glendale Rd Unit 210-A, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 382 Sq Ft
    • Built 2006

    Last Sold Summary

    • 26% Below List Price
    • $340/SF
    • 225 Days On Market

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

    565 Glendale Rd Unit 210-A, Oakland, MD 21550
    • /49

      Est $360,476

      Not Listed For Sale

      19398 Garrett Hwy, Oakland, MD 21550

      • 5 Beds
      • 2 Baths
      • 2,414 Sq Ft
      • Built 1940
      19398 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 168 Days On Market

  • /50

    $339,000

    • 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 Real Estate, LLC

    961 Cedar Ln, Oakland, MD 21550

Showing Results 481 - 520, Page 13 of 18

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