12,257

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 $421,286

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    15 Village Dr Unit 1, Oakland, MD 21550
    • /36

      Est $609,251 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

      • 6% Above List Price
      • $546/SF
      • 5 Days On Market

      Last Sold Price $575,000

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

  • /10

    $59,900 Under Contract

    • 768 Sq Ft

    114 C St, Oakland, MD 21550

    24x32 garage with heat (propane tank needed), electric service and finished at a very high level inside with metal ceilings, drywall and slab concrete floor. This level lot has both public water & sewer hookups, and can be used as-is or improved upon. Verify with town of Mountain Lake Park for costs to connect to water/sewer and any specifics on how the property would transition to a buildable

    Jay Ferguson Taylor Made Deep Creek Real Estate

    114 C St, 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 $461,416

    Last Listing Agent Larry Smith Railey Realty, Inc.

    783 Mountainview Dr, Oakland, MD 21550
    • /125

      Est $2,244,258 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

      • 8% Below List Price
      • $534/SF
      • 3 Days On Market

      Last Sold Price $2,450,000

      Last Listing Agent Jon Bell 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
  • /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 $374,506

    Last Listing Agent Tim Macauley Taylor Made Deep Creek Real Estate

    20160 Garrett Hwy Unit G509, Oakland, MD 21550
    • /65

      Est $3,934,340 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

  • /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
  • /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
    • /56

      Est $393,903 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

      • 11% Above List Price
      • $217/SF
      • 24 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /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
  • /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
    • /65

      Est $155,350 Not Listed For Sale

      620 E Green St, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,668 Sq Ft
      • Built 1922
      620 E Green St, Oakland, MD 21550

      Last Sold Summary

      • 55% Above List Price
      • $60/SF
      • 81 Days On Market

      Last Sold Price $100,000

      Last Listing Agent Nick Fratz-Orr 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
  • /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 $350,904

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

    465 King Wildesen Rd, Oakland, MD 21550
    • /76

      Est $213,654 Not Listed For Sale

      501 G St, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,520 Sq Ft
      • Built 1979
      501 G St, Oakland, MD 21550

      Last Sold Summary

      • 7% Above List Price
      • $79/SF

      Last Sold Price $200,000

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /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
  • /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
    • /35

      Est $365,315 Not Listed For Sale

      107 Pleasant Hill Cir, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,384 Sq Ft
      • Built 1989
      107 Pleasant Hill Cir, Oakland, MD 21550

      Last Sold Summary

      • 30% Above List Price
      • $117/SF

      Last Sold Price $280,000

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /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
  • /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
    • /6

      Est $663,791 Not Listed For Sale

      20488 Garrett Hwy, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft
      • Built 1946
      20488 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 3% Above List Price
      • $766/SF
      • 125 Days On Market

      Last Sold Price $643,500

      Last Listing Agent Michael Cumerlato Jason Mitchell Group

  • /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
  • /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
    • /85

      Est $1,838,797 Not Listed For Sale

      739 Glendale Rd, Oakland, MD 21550

      • 6 Beds
      • 6.5 Baths
      • 4,160 Sq Ft
      • Built 2003
      739 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 13% Above List Price
      • $393/SF
      • 90 Days On Market

      Last Sold Price $1,634,000

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

  • /22

    $60,000

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

    422 Maple Ave, Oakland, MD 21550

    Investor opportunity in a highly desirable location! This property has been gutted and is ready for your vision. A rare chance to renovate and customize to your exact specifications. Ideal for resale, rental investment, or personal use. Ideally located near Loch Lynn Heights Wetland Trails, soccer complex, and community park. Great potential for the right buyer. RAILEY REALTY IS NOT THE CARETAKER

    Nicole Jackson Railey Realty, Inc.

    422 Maple Ave, 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
    • /73

      Est $244,035 Not Listed For Sale

      723 E Alder St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1950
      723 E Alder St, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $122/SF

      Last Sold Price $215,000

      Last Listing Agent Jesse Shimrock 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
  • /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 $124,269

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    204 E St, Oakland, MD 21550
    • /130

      Est $1,139,013 Not Listed For Sale

      943 S Blakeslee Rd, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft
      • Built 1990
      943 S Blakeslee Rd, Oakland, MD 21550

      Last Sold Summary

      • 14% Above List Price
      • $292/SF
      • 4 Days On Market

      Last Sold Price $999,900

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /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
  • /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 $1,023,872

    Last Listing Agent Edward Bass EXP Realty, LLC

    635 Biltmore Ridge Trail, Mc Henry, MD 21541
    • /88

      Est $395,927 Not Listed For Sale

      223 N 2nd St, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,120 Sq Ft
      • Built 1920
      223 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 2% Above List Price
      • $125/SF
      • 109 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Sean Sober Taylor Made Deep Creek Real Estate

  • /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
  • /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 $275,521

    Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Real Estate

    403 O St, Oakland, MD 21550
    • /54

      Est $2,486,848 Not Listed For Sale

      375 Glendale Rd, Oakland, MD 21550

      • 8 Beds
      • 6.5 Baths
      • 5,638 Sq Ft
      • Built 2001
      375 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 8% Above List Price
      • $408/SF
      • 134 Days On Market

      Last Sold Price $2,300,000

      Last Listing Agent Mike Kennedy 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
  • /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 $735,079

    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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