10,549

Oakland, MD Homes

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  • /24

    $16,000

    • Land
    • 21,344 Sq Ft
    • $32,653 per Acre

    21 Bear Dr E, Oakland, MD 21550

    Don’t miss this great opportunity in the gated community of Youghiogheny Mountain Resort! This flat 0.49-acre lot offers an easy build site. Perfect for your dream home or weekend escape. Enjoy access to ATV trails, hunting, and fishing, all while being just a short drive to Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Approved for a sand mound septic system and set within a

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    21 Bear Dr E, Oakland, MD 21550
  • /30

    $200,000

    Sold Oct 09, 2025

    929 Dogwood Dr, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1973

    Last Sold Summary

    • $174/SF
    • 15 Days On Market

    Current Estimated Value $223,730

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

    929 Dogwood Dr, Oakland, MD 21550
    • /67

      Est $252,317

      Not Listed For Sale

      218 Weber Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,605 Sq Ft
      • Built 1930
      218 Weber Rd, Oakland, MD 21550

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Kelsey Meyers Railey Realty, Inc.

  • /7

    $22,000

    $8K PRICE DROP
    • Land
    • 4 Acres
    • $5,500 per Acre

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550

    This 4-acre building lot in the Backbone Ridge community offers breathtaking mountain views and a 3-bedroom perc approval — ready for your dream home. Perfectly positioned near Deep Creek Lake, WISP Ski Resort, Canaan Valley, Timberline Ski Resort, and Blackwater Falls State Park, outdoor adventure is just minutes away. Whether you're building a year-round residence or a weekend escape, enjoy the

    Brent Housley Railey Realty, Inc.

    Lot 7 Backbone Ridge Rd, Oakland, MD 21550
  • /110

    $1,650,000

    Sold Jun 18, 2026

    815 Chadderton School Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,619 Sq Ft
    • Built 1989

    Last Sold Summary

    • 13% Below List Price
    • $357/SF
    • 80 Days On Market

    Current Estimated Value $1,736,460

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    815 Chadderton School Rd, Oakland, MD 21550
    • /66

      Est $481,217

      Not Listed For Sale

      101 Sunset Dr, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 3,024 Sq Ft
      • Built 1987
      101 Sunset Dr, Oakland, MD 21550

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /11

    $49,900

    • Land
    • 1.38 Acres
    • $36,159 per Acre

    LOT 6B Betts Ln, Oakland, MD 21550

    This 1.38-acre property offers a private, quiet setting with level ground and easy access from a well maintained road. Located just a short drive from Deep Creek Lake and Oakland, MD, it gives you the feel of being in the country while still being close to town. The lot is surrounded by woods and is a great spot to enjoy nature, with plenty of wildlife in the area. A solid option for a future

    Thomas Long Railey Realty, Inc.

    LOT 6B Betts Ln, Oakland, MD 21550
  • /31

    $745,000

    Sold Sep 02, 2025

    200 Lake Shore Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,559 Sq Ft
    • Built 2025

    Last Sold Summary

    • $291/SF
    • 16 Days On Market

    Current Estimated Value $734,294

    Last Listing Agent Jonathan Minerick Homecoin.com

    200 Lake Shore Dr, Oakland, MD 21550
    • /71

      Est $833,168

      Not Listed For Sale

      589 Mountainview Dr, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 2,665 Sq Ft
      • Built 1993
      589 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 247 Days On Market

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

  • /78

    $1,579,900

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

    2311 Boy Scout Rd, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this private waterfront retreat tucked among mature trees on nearly an acre of land. With over 100 feet of lake frontage, a private Type-A dock, and a gentle distance to deep water, this property offers the kind of shoreline that's increasingly hard to find. Thoughtfully positioned to capture expansive lake views while preserving a sense of

    Jon Bell Railey Realty, Inc.

    2311 Boy Scout 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
    • /100

      Est $419,582

      Not Listed For Sale

      3241 Pleasant Valley Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,496 Sq Ft
      • Built 1972
      3241 Pleasant Valley Rd, Oakland, MD 21550

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /58

    $215,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,440 Sq Ft

    2967 Pysell Crosscut Rd, Oakland, MD 21550

    This charming manufactured home offers a delightful blend of comfort and functionality, perfect for those seeking a cozy retreat. With 1,440 square feet of thoughtfully designed living space, this residence features two bedrooms and full bathroom. Step inside to discover a warm and welcoming interior. The combination dining and living area is perfect for entertaining or enjoying quiet evenings at

    Larry Smith Railey Realty, Inc.

    2967 Pysell Crosscut Rd, Oakland, MD 21550
  • /68

    $1,060,000

    Sold Apr 10, 2026

    444 Woodlands Hill Ln, Oakland, MD 21550

    • 4 Beds
    • 6 Baths
    • 4,744 Sq Ft
    • Built 2007

    Last Sold Summary

    • 12% Below List Price
    • $223/SF
    • 50 Days On Market

    Current Estimated Value $1,144,260

    Last Listing Agent Corbin Griffith Compass

    444 Woodlands Hill Ln, Oakland, MD 21550
    • /61

      Est $273,611

      Not Listed For Sale

      48 Spring Ln, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1977
      48 Spring Ln, Oakland, MD 21550

      Last Sold Summary

      • 67 Days On Market

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

  • /25

    $45,000

    Under Contract
    • Land
    • 2.1 Acres
    • $21,429 per Acre

    14 Yough View Dr, Oakland, MD 21550

    Adventure starts at the Youghiogheny River!Bring your plans and build your dream mountain getaway on this beautiful 2-acre homesite in The Timbers on the Yough, where the outdoors is truly at your doorstep. The property fronts the community river access area, putting you just an easy walk from the Youghiogheny River, a Maryland Blue Ribbon Trout Stream, and all the recreation it offers. Spend

    Rachel Bruch Railey Realty, Inc.

    14 Yough View Dr, Oakland, MD 21550
  • /8

    $99,000

    Sold Jan 30, 2026

    125 N 2nd St, Oakland, MD 21550

    • Land
    • 9,583 Sq Ft
    • $450,000 per Acre

    Last Sold Summary

    • 38 Days On Market

    Current Estimated Value $104,402

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    125 N 2nd St, Oakland, MD 21550
    • /22

      Est $465,874

      Not Listed For Sale

      20917 Garrett Hwy, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 576 Sq Ft
      • Built 1940
      20917 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 262 Days On Market

      Last Listing Agent Eric Crawford Taylor-Made Deep Creek Real Estate, LLC

  • /26

    $219,900

    $70K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,386 Sq Ft

    123 B St, Oakland, MD 21550

    Discover the charm of this delightful ranch-style home nestled in the serene MT Lake Park community. Built in 1993, this well-maintained and recently updated home offers plenty of comfortable living space, featuring 2 spacious bedrooms and 2 full bathrooms, perfect for relaxation and privacy. The inviting layout seamlessly connects the living areas, creating an ideal setting for gatherings or

    Gina Gargeu Century 21 Downtown

    123 B St, 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

    Current Estimated Value $618,560

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    1720 Pysell Crosscut Rd, Oakland, MD 21550
    • /47

      Est $267,889

      Not Listed For Sale

      403 O St, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 2,240 Sq Ft
      • Built 1976
      403 O St, Oakland, MD 21550

      Last Sold Summary

      • 329 Days On Market

      Last Listing Agent ANGELA BOSLEY Taylor-Made Deep Creek Real Estate, LLC

  • /17

    $39,900

    Under Contract
    • Land
    • 20,037 Sq Ft
    • $86,739 per Acre

    504 San Francisco St, Oakland, MD 21550

    This .46 AC lot sits atop Roman Nose Spa and is the perfect place to build your vacation getaway. Prime locale for all activities in the Deep Creek area, whether you are boating, skiing, hiking, biking, whitewater rafting, sightseeing or enjoying our hundreds of acres of wonderful state parks. This property has a well and septic that has been in place since 1975. Both will need to be

    Kathy Gibson Railey Realty, Inc.

    504 San Francisco St, 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
    • /56

      Est $334,102

      Not Listed For Sale

      931 Black Oak Dr, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,100 Sq Ft
      • Built 2007
      931 Black Oak Dr, Oakland, MD 21550

      Last Sold Summary

      • 170 Days On Market

      Last Listing Agent Sean Sober Taylor-Made Deep Creek Real Estate, LLC

  • /39

    $489,900

    • Land
    • 1.5 Acres
    • $326,600 per Acre

    Lot 7 Heron Cove, Oakland, MD 21550

    Bring your vision to life on this beautiful lake access homesite in Heron Cove, conveniently located to many Deep Creek Lake attractions. This property offers the opportunity to build your ideal mountain retreat in a peaceful setting while remaining close to everything the lake has to offer. Enjoy easy access to your boat slip on the main side of Heron Cove via the paved path to the lake (golf

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

    Lot 7 Heron Cove, Oakland, MD 21550
  • /64

    $385,000

    Sold Jun 03, 2026

    1204 Alexander Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,266 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $170/SF
    • 4 Days On Market

    Current Estimated Value $382,812

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1204 Alexander Ln, Oakland, MD 21550
    • /35

      Est $285,912

      Not Listed For Sale

      763 Pysell Crosscut Rd, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,854 Sq Ft
      • Built 1994
      763 Pysell Crosscut Rd, Oakland, MD 21550

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /7

    $119,000

    Under Contract
    • Land
    • 20.33 Acres
    • $5,853 per Acre

    0 Bethlehem Rd, Oakland, MD 21550

    20.33 BEAUTIFUL WOODED ACRES ON TOPOF BACKBONE MOUNTAIN WITH VIEWS IN ALL DIRECTIONS. IDEAL FOR MOUNTAINTOP HOME OR RETREAT. MATURE TIMBER. PRIME RECREATIONAL/HUNTING PROPEPRTY. PERK SCHEDULED

    Robert Custer Custer Realty & Auction

    0 Bethlehem Rd, Oakland, MD 21550
  • /17

    $30,000

    Sold Jul 23, 2026

    815 L St, Oakland, MD 21550

    • Land
    • 12,196 Sq Ft
    • $107,143 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 72 Days On Market

    Current Estimated Value $39,609

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

    815 L St, Oakland, MD 21550
    • /36

      Est $220,343

      Not Listed For Sale

      2607 Maryland Hwy, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,357 Sq Ft
      • Built 1970
      2607 Maryland Hwy, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jarrod Harper Real Broker, LLC

  • /61

    $605,000

    Under Contract
    • 5 Beds
    • 4.5 Baths
    • 2,582 Sq Ft

    104 Roman Ridge Rd Unit 21, Oakland, MD 21550

    Waves & Moguls- Mountain living meets lake lifestyle in this beautifully appointed 5-bedroom, 4.5-bath condominium home. Privately nestled on a quiet hillside cul-de-sac, this fully furnished, turn-key retreat offers three levels of thoughtfully designed living space with two stone fireplaces and views of Deep Creek Lake. The spacious floor plan features two private primary suites, generous guest

    Amy Skipper Railey Realty, Inc.

    104 Roman Ridge Rd Unit 21, Oakland, MD 21550
  • /39

    $405,000

    Sold Jun 15, 2026

    232 Jeffrey Ln Unit 33, Oakland, MD 21550

    • 2 Beds
    • 2.5 Baths
    • 2,960 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Below List Price
    • $137/SF
    • 99 Days On Market

    Current Estimated Value $396,531

    Last Listing Agent Sean Brink Samson Properties

    232 Jeffrey Ln Unit 33, Oakland, MD 21550
    • /43

      Est $287,828

      Not Listed For Sale

      37 Laurel Brook Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft
      • Built 1992
      37 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • /31

    $224,900

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft

    206 Mayhew Inn Rd, Oakland, MD 21550

    Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate

    Jay Quinn Taylor-Made Deep Creek Real Estate, LLC

    206 Mayhew Inn Rd, Oakland, MD 21550
  • /7

    $26,000

    Sold Jun 30, 2026

    0 Hutton Road(2 Acres), Oakland, MD 21550

    • Land
    • 2 Acres
    • $13,000 per Acre

    Last Sold Summary

    • 20 Days On Market

    Last Listing Agent Julie Mead The KW Collective

    0 Hutton Road(2 Acres), Oakland, MD 21550
    • /44

      Est $229,655

      Not Listed For Sale

      405 Sunnyside Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1974
      405 Sunnyside Rd, Oakland, MD 21550

      Last Sold Summary

      • 100 Days On Market

      Last Listing Agent Steve DuBrueler Coldwell Banker Premier

  • /61

    $185,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft

    729 E Oak St, Oakland, MD 21550

    Great, affordable starter home located in Oakland with public water and sewer, one car detached garage, hot water natural gas heat. Two bedroom and full bath on second level and possible third bedroom on main level with 1/2 bath. Cellar basement with mechanicals. Washer and Dryer hookups, washer/dryer convey, are located on the back enclosed porch which has electric baseboard heat. Enclosed front

    Kevin Liller Railey Realty, Inc.

    729 E Oak St, Oakland, MD 21550
  • /139

    $2,625,000

    Sold Mar 31, 2026

    56 Bee Tree Ln, Oakland, MD 21550

    • 6 Beds
    • 7.5 Baths
    • 5,100 Sq Ft
    • Built 2000

    Last Sold Summary

    • $515/SF
    • 305 Days On Market

    Current Estimated Value $2,770,357

    Last Listing Agent Susan Bell Railey Realty, Inc.

    56 Bee Tree Ln, Oakland, MD 21550
    • /37

      Est $236,852

      Not Listed For Sale

      139 S Oakhall Dr, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 2,112 Sq Ft
      • Built 1962
      139 S Oakhall Dr, Oakland, MD 21550

      Last Sold Summary

      • 171 Days On Market

      Last Listing Agent Michaela Green 1 Real Estate Source LLC

  • /55

    $329,900

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft

    565 Glendale Rd Unit 125, Oakland, MD 21550

    Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks,

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550

Showing Results 241 - 280, Page 7 of 18

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