12,226

Homes in ZIP Code 21550

Section Image
  • /42

    $175,000

    • Land
    • 21.46 Acres
    • $8,155 per Acre

    0 Sanders Ln Unit MDGA2009314, Oakland, MD 21550

    Tucked along scenic Sanders Lane just 4 miles from Oakland, MD, this picturesque 21.46-acre pastoral lot offers the perfect blend of open space, gentle rolling fields, and peaceful countryside charm. Surrounded by open spaces, in a sought-after neighborhood, this property is ideal for building your dream estate, hobby farm, or private retreat. Enjoy wide-open skies, room to roam, and the serenity

    Susan Bell Railey Realty, Inc.

    0 Sanders Ln Unit MDGA2009314, 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 $547,019

    Last Listing Agent Andrew Orr The KW Collective

    710 Hunters Ridge Dr, Oakland, MD 21550
    • /38

      Est $445,270 Not Listed For Sale

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

      29 Crescent Ln, Oakland, MD 21550

      29 Crescent Ln, Oakland, MD 21550
  • /15

    $175,000

    • Land
    • 1.6 Acres
    • $109,375 per Acre

    1 Lowes Dr, Oakland, MD 21550

    Lot #1. is 1.6 Acre Cleared Commercial Site in Lowe's Subdivision. Public Utilities and Natural gas to the site. Paved street access and High Traffic Zone. Plat available.

    Rich Orr Railey Realty, Inc.

    1 Lowes Dr, 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 $263,805

    Last Listing Agent Susan Bell Railey Realty, Inc.

    655 Bray School Rd, Oakland, MD 21550
    • /56

      Est $686,367 Not Listed For Sale

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

      148 Wanderer Ln, Oakland, MD 21550

      148 Wanderer Ln, Oakland, MD 21550
  • /58

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    127 Paradise Heights, Oakland, MD 21550

    Beautifully renovated lake access log home located in the centrally located Paradise Cove community. This home offers three levels of living space, an open floorplan and three bedrooms. Recent upgrades in the past five years which include renovated kitchen, granite countertops, upgraded baths and floors, new wrap around deck, some new windows, new appliances, new roof, and new garage doors and

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    127 Paradise Heights, Oakland, MD 21550
  • /78

    $760,000 Sold Sep 15, 2025

    61 Par Way, Mc Henry, MD 21541

    • 4 Beds
    • 3.5 Baths
    • 2,218 Sq Ft
    • Built 2021

    Last Sold Summary

    • $343/SF
    • 5 Days On Market

    Current Estimated Value $767,858

    Last Listing Agent Elizabeth Ware Railey Realty, Inc.

    61 Par Way, Mc Henry, MD 21541
    • /82

      Est $1,712,790 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
  • /11

    $88,900

    • Land
    • 0.59 Acre
    • $150,678 per Acre

    48 Fern Loop Dr, Sang Run, MD 21541

    Ready to Build with public water and public sewer Homesite Lot #48 in the desirable peaceful community "Sandy Shores Heights". Enjoy all "Four Seasons" golfing at The Lodestone Golf Course, boating on Deep Creek Lake, fish or paddle the Yough River, hike/mountain bike/xcountry in Fork Run and ski/golf Wisp Resort-all just minutes from your home. Live the dream-Call today!

    Kathy Gibson Railey Realty, Inc.

    48 Fern Loop Dr, Sang Run, MD 21541
  • /7

    $389,000 Sold Jan 24, 2025

    1517 Upperman Rd, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 530 Sq Ft
    • Built 2024

    Last Sold Summary

    • $734/SF
    • 0 Days On Market

    Current Estimated Value $396,505

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1517 Upperman Rd, Oakland, MD 21550
    • /29

      Est $182,974 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
  • /5

    $195,000

    • Land
    • 0.61 Acre
    • $319,672 per Acre

    Lot 16 Biltmore Ridge Trail, McHenry, MD

    VIEWS*VIEWS along the Loadstone Golf course in the desired community of Biltmore. Lot 16 is ready for. your dream mountain getaway. Enjoy all the amenities that living at Deep Creek Lake and Wisp mountain affords you. Centrally located to all shopping, dining and only 15 minutes from RT. 68, this a great location for the family compound capitalize on the profitable rental market.

    Michael Cumerlato Jason Mitchell Group

    Lot 16 Biltmore Ridge Trail, McHenry, MD
  • /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
    • /33

      Est $474,894 Not Listed For Sale

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

      1012 Hemlock Cir, Oakland, MD 21550

      1012 Hemlock Cir, Oakland, MD 21550
  • /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
  • /134

    $1,375,000 Sold Jun 09, 2025

    415 Mountaintop Rd, Mc Henry, MD 21541

    • 5 Beds
    • 7 Baths
    • 5,404 Sq Ft
    • Built 2021

    Last Sold Summary

    • $254/SF
    • 52 Days On Market

    Current Estimated Value $1,407,473

    Last Listing Agent Jon Bell Railey Realty, Inc.

    415 Mountaintop Rd, Mc Henry, MD 21541
    • /52

      Est $253,072 Not Listed For Sale

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

      1865 Garrett Rd, Oakland, MD 21550

      1865 Garrett Rd, Oakland, MD 21550
  • /38

    $269,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    968 Hutton Rd, Oakland, MD 21550

    3/4BR, 2BA on 1.52 private acres in Crellin school district! Well-kept doublewide on permanent foundation with covered front porch and an addition w/ storage underneath (sun room, office, 4/BR), boasting nearly 1800sf. Features include a wood burning fireplace, multiple heat sources, some handicap features, open kitchen, newer appliances, beamed ceilings, beefed up roof for snow load, and vaulted

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    968 Hutton Rd, Oakland, MD 21550
  • /40

    $410,000 Sold Feb 28, 2025

    341 Doe Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 2024

    Last Sold Summary

    • $237/SF
    • 189 Days On Market

    Current Estimated Value $412,777

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    341 Doe Dr, Oakland, MD 21550
    • /91

      Est $1,357,077 Not Listed For Sale

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

      153 Mallard Loop, Oakland, MD 21550

      153 Mallard Loop, Oakland, MD 21550
  • /50

    $589,000

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

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

    2+BR, 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
  • /37

    $715,000 Sold Jan 30, 2025

    278 Basswood Way Unit 19, Oakland, MD 21550

    • 5 Beds
    • 4 Baths
    • 3,084 Sq Ft
    • Built 2005

    Last Sold Summary

    • $232/SF
    • 87 Days On Market

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

    278 Basswood Way Unit 19, Oakland, MD 21550
    • /70

      Est $1,769,694 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
  • /102

    $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 Vacations & Sales

    2725 Stockslager Rd, Oakland, MD 21550
  • /2

    $25,000 Sold Apr 24, 2025

    Lot 24 Laurel Dr, Oakland, MD 21550

    • Land
    • 0.58 Acre
    • $43,103 per Acre

    Last Sold Summary

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

    Lot 24 Laurel Dr, Oakland, MD 21550
    • /71

      Est $697,426 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
  • /33

    $919,000

    • 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
  • /98

    $590,000 Sold Oct 10, 2025

    2719 Broadford Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 4,253 Sq Ft
    • Built 1984

    Last Sold Summary

    • $139/SF
    • 168 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
    • /41

      Est $369,972 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft

      139 Hunters Dr, Oakland, MD 21550

      139 Hunters Dr, 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
  • /74

    $862,500 Sold Jan 07, 2025

    96 Bobcat Hill Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 3,263 Sq Ft
    • Built 2018

    Last Sold Summary

    • $264/SF
    • 101 Days On Market

    Current Estimated Value $915,552

    Last Listing Agent Kim Palmer Marquee Properties, Inc.

    96 Bobcat Hill Ln, Oakland, MD 21550
    • /83

      Est $2,316,559 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 2,363 Sq Ft

      320 Lake Forest Dr, Oakland, MD 21550

      320 Lake Forest Dr, Oakland, MD 21550
  • /13

    $52,900 Pending

    • Land
    • 0.57 Acre
    • $92,807 per Acre

    72 Chimney Rock Ln, Mc Henry, MD 21541

    Wooded building lot in the gated Biltmore community. Over half an acre of private level land. Public water and public sewer hookups available. Easy build site with recorded plat. Off the beaten path but still minutes from Wisp Ski Resort, Lodestone Golf Course, and Deep Creek Lake. HOA covers road maintenance and snow removal for year-round easy access. If you’re looking to buy and build your

    Jon Bell Railey Realty, Inc.

    72 Chimney Rock Ln, Mc Henry, MD 21541
  • /47

    $405,000 Sold Aug 08, 2025

    343 Maple Del Ln, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,404 Sq Ft
    • Built 1993

    Last Sold Summary

    • $288/SF
    • 3 Days On Market

    Current Estimated Value $399,329

    Last Listing Agent Julie Mead The KW Collective

    343 Maple Del Ln, Oakland, MD 21550
    • /85

      Est $1,510,268 Not Listed For Sale

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

      757 Marsh Hill Rd, Mc Henry, MD 21541

      757 Marsh Hill Rd, Mc Henry, MD 21541
  • /25

    $269,900

    • 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
  • /88

    $1,145,000 Sold Apr 29, 2025

    324 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,820 Sq Ft
    • Built 2004

    Last Sold Summary

    • $300/SF
    • 7 Days On Market

    Current Estimated Value $1,156,066

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

    324 Penn Cove Rd, Oakland, MD 21550
    • /95

      Est $548,009 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,268 Sq Ft

      204 Farm View Ln, Oakland, MD 21550

      204 Farm View Ln, Oakland, MD 21550
  • /59

    $440,000

    • 4 Beds
    • 2.5 Baths
    • 2,030 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 traditional-style 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

    Brian Covell BHHS Touchdown Home Pros Realty

    609 Southern Pines Dr, Oakland, MD 21550

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