12,259

Homes in ZIP Code 21550

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  • /37

    $382,500 Sold Feb 27, 2026

    15 Village Dr Unit 1, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • Built 2004

    Last Sold Summary

    • 408 Days On Market

    Current Estimated Value $420,776

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    15 Village Dr Unit 1, Oakland, MD 21550
    • /132

      Est $3,736,209 Not Listed For Sale

      2524 Stockslager Rd, Oakland, MD 21550

      • 5 Beds
      • 7 Baths
      • 9,134 Sq Ft
      • Built 2006
      2524 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      • 6% Above List Price
      • $387/SF
      • 15 Days On Market

      Last Sold Price $3,537,000

      Last Listing Agent Melissa Goodfellow Railey Realty, Inc.

  • /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
  • /76

    $420,000 Sold Oct 15, 2025

    783 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 1,971 Sq Ft
    • Built 2002

    Last Sold Summary

    • $213/SF
    • 122 Days On Market

    Current Estimated Value $447,386

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
    • /32

      Est $575,912 Not Listed For Sale

      1519 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 2000
      1519 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 16% Above List Price
      • $340/SF
      • 9 Days On Market

      Last Sold Price $495,000

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

  • /18

    $4,000

    • Land
    • 0.47 Acre
    • $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 The KW Collective

    Lot 36 Fox Tail Rd, Oakland, MD 21550
  • /35

    $380,000 Sold Sep 26, 2025

    20160 Garrett Hwy Unit G509, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1974

    Last Sold Summary

    • $594/SF
    • 24 Days On Market

    Current Estimated Value $380,210

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Real Estate

    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    • /21

      Est $496,893 Not Listed For Sale

      471 Clifton Dr, Oakland, MD 21550

      • 5 Beds
      • 2 Baths
      • 3,612 Sq Ft
      • Built 1971
      471 Clifton Dr, Oakland, MD 21550

      Last Sold Summary

      • 31% Above List Price
      • $105/SF
      • 18 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

  • /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

    2725 Stockslager Rd, Oakland, MD 21550
  • /50

    $239,000 Sold Feb 11, 2026

    5202 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,199 Sq Ft
    • Built 1950

    Last Sold Summary

    • $199/SF
    • 149 Days On Market

    Current Estimated Value $233,922

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    5202 Hutton Rd, Oakland, MD 21550
    • /68

      Est $1,314,695 Not Listed For Sale

      1835 Marsh Hill Rd, Mc Henry, MD 21541

      • 4 Beds
      • 4 Baths
      • 3,854 Sq Ft
      • Built 1990
      1835 Marsh Hill Rd, Mc Henry, MD 21541

      Last Sold Summary

      • 10% Above List Price
      • $311/SF
      • 3 Days On Market

      Last Sold Price $1,200,000

      Last Listing Agent Debra Savage Railey Realty, Inc.

  • /33

    $875,000

    • 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
  • /13

    $20,000 Sold Nov 05, 2025

    0 Weber Ct, Oakland, MD 21550

    • Land
    • 0.24 Acre
    • $83,333 per Acre

    Last Sold Summary

    • 10 Days On Market

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    0 Weber Ct, Oakland, MD 21550
    • /81

      Est $697,926 Not Listed For Sale

      43 Robinwood Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 2,921 Sq Ft
      • Built 2005
      43 Robinwood Dr, Oakland, MD 21550

      Last Sold Summary

      • $239/SF
      • 148 Days On Market

      Last Sold Price $699,000

      Last Listing Agent Brian Homberg Taylor Made Deep Creek Real Estate

  • /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
  • /40

    $335,000 Sold May 23, 2025

    465 King Wildesen Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1988

    Last Sold Summary

    • 22% Below List Price
    • $436/SF
    • 123 Days On Market

    Current Estimated Value $330,858

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

    465 King Wildesen Rd, Oakland, MD 21550
    • /16

      Est $75,466 Not Listed For Sale

      36 Preston Ln, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 964 Sq Ft
      • Built 1918
      36 Preston Ln, Oakland, MD 21550

      Last Sold Summary

      • 54% Above List Price
      • $51/SF
      • 1 Day On Market

      Last Sold Price $49,000

      Last Listing Agent Adrianne Thompson Coldwell Banker Premier

  • /50

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,250 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 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 detached garage. Property

    Brian Covell BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    609 Southern Pines Dr, Oakland, MD 21550
  • /58

    $1,100,000 Sold Feb 20, 2026

    515 Winding Estates Dr, McHenry, MD 21541

    • 5 Beds
    • 5.5 Baths
    • 3,594 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $306/SF
    • 20 Days On Market

    Current Estimated Value $1,140,000

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

    515 Winding Estates Dr, McHenry, MD 21541
    • /44

      Est $708,365 Not Listed For Sale

      870 Hunters Ridge Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,896 Sq Ft
      • Built 2007
      870 Hunters Ridge Dr, Oakland, MD 21550

      Last Sold Summary

      • 12% Above List Price
      • $218/SF
      • 5 Days On Market

      Last Sold Price $632,501

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /22

    $207,500

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft

    1307 Broadford Rd, Oakland, MD 21550

    Nestled in the scenic countryside of Oakland, this charming ready to move in 2 bed 1 Bath home offers the perfect blend of privacy, space, and small-town convenience. Situated on a beautiful property along Broadford Road, the home provides peaceful surroundings while remaining just minutes from downtown Oakland, schools, shopping, and plenty of outdoor recreation areas.. Properties in this area

    Bill Kenny Keller Williams Realty Centre

    1307 Broadford Rd, Oakland, MD 21550
  • /20

    $17,000 Sold Oct 29, 2025

    9 & 10 Grouse Run Rd, Oakland, MD 21550

    • Land
    • 0.96 Acre
    • $17,708 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent Brent Housley Railey Realty, Inc.

    9 & 10 Grouse Run Rd, Oakland, MD 21550
    • /81

      Est $802,886 Not Listed For Sale

      335 Mountainview Dr, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,142 Sq Ft
      • Built 2001
      335 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 7% Above List Price
      • $238/SF
      • 29 Days On Market

      Last Sold Price $749,000

      Last Listing Agent Larry Smith Railey Realty, Inc.

  • /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
  • /2

    $8,000 Sold Aug 29, 2025

    0 E Water St, Oakland, MD 21550

    • Land
    • 0.33 Acre
    • $24,242 per Acre

    Last Sold Summary

    • 2 Days On Market

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

    0 E Water St, Oakland, MD 21550
    • /56

      Est $529,411 Not Listed For Sale

      741 Hoyes Run Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft
      • Built 1984
      741 Hoyes Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 6% Above List Price
      • $231/SF
      • 10 Days On Market

      Last Sold Price $500,000

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

  • /5

    $25,000

    • Land
    • 0.34 Acre
    • $73,529 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
  • /2

    $110,000 Sold May 09, 2025

    Lot 22 Winding Estates Dr, Mc Henry, MD 21550

    • Land
    • 1.07 Acres
    • $102,804 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    Lot 22 Winding Estates Dr, Mc Henry, MD 21550
    • /36

      Est $601,330 Not Listed For Sale

      21651 Garrett Hwy, Deer Park, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,053 Sq Ft
      • Built 1960
      21651 Garrett Hwy, Deer Park, MD 21550

      Last Sold Summary

      • 5% Above List Price
      • $546/SF
      • 5 Days On Market

      Last Sold Price $575,000

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

  • /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
  • /37

    $120,000 Sold Dec 04, 2025

    204 E St, Oakland, MD 21550

    • 5 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 1975

    Last Sold Summary

    • $58/SF
    • 1 Day On Market

    Current Estimated Value $122,290

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
    • /125

      Est $2,266,786 Not Listed For Sale

      427 Lake Shore Dr, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 4,584 Sq Ft
      • Built 1987
      427 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 7% Below List Price
      • $534/SF
      • 3 Days On Market

      Last Sold Price $2,450,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /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
  • /64

    $1,010,000 Sold Jan 09, 2026

    635 Biltmore Ridge Trail, Mc Henry, MD 21541

    • 5 Beds
    • 5 Baths
    • 4,437 Sq Ft
    • Built 2024

    Last Sold Summary

    • $228/SF
    • 91 Days On Market

    Current Estimated Value $1,038,965

    Last Listing Agent Edward Bass EXP Realty, LLC

    635 Biltmore Ridge Trail, Mc Henry, MD 21541
    • /65

      Est $3,932,768 Not Listed For Sale

      2276 Paradise Point Rd, Oakland, MD 21550

      • 8 Beds
      • 5.5 Baths
      • 8,453 Sq Ft
      • Built 2006
      2276 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 7% Above List Price
      • $434/SF
      • 0 Days On Market

      Last Sold Price $3,670,000

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

  • /50

    $359,000

    • 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

    961 Cedar Ln, Oakland, MD 21550
  • /47

    $270,000 Sold Jun 20, 2025

    403 O St, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,240 Sq Ft
    • Built 1976

    Last Sold Summary

    • $121/SF
    • 329 Days On Market

    Current Estimated Value $265,504

    Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    403 O St, Oakland, MD 21550
    • /56

      Est $384,112 Not Listed For Sale

      5289 Oakland Sang Run Rd, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,638 Sq Ft
      • Built 2006
      5289 Oakland Sang Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 8% Above List Price
      • $217/SF
      • 24 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /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
  • /80

    $696,000 Sold Apr 02, 2025

    1489 Mountainview Dr, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 3,066 Sq Ft
    • Built 2001

    Last Sold Summary

    • $227/SF
    • 170 Days On Market

    Current Estimated Value $706,364

    Last Listing Agent Larry Smith Railey Realty, Inc.

    1489 Mountainview Dr, Oakland, MD 21550

Showing Results 401 - 440, Page 11 of 18

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