10,771

Oakland, MD Homes

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  • /58

    $234,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    1021 E High St, Oakland, MD 21550

    ***BACK ON THE MARKET, don't miss this one a second time! Welcome home to this solid, ranch style home on one of Oakland's most convenient streets. Built in 1954, this 3-bedroom, 2-bath home delivers 1,520 sq ft of comfortable living, plus a partially finished full basement ready for your vision, whether that's a rec room, home office, or extra storage. The metal roof means peace of mind for

    Jeremy Cunningham Railey Realty, Inc.

    1021 E High St, Oakland, MD 21550
  • /28

    $135,000

    Sold Sep 22, 2025

    320 Coolidge Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1900

    Last Sold Summary

    • $188/SF
    • 47 Days On Market

    Current Estimated Value $133,900

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    320 Coolidge Ave, Oakland, MD 21550
    • /64

      Est $177,887

      Not Listed For Sale

      608 I St, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,674 Sq Ft
      • Built 1900
      608 I St, Oakland, MD 21550

      Last Sold Summary

      • 83 Days On Market

  • /19

    $295,000

    • Land
    • 8.48 Acres
    • $34,788 per Acre

    26 Green Brier Rd, Oakland, MD 21550

    8.48± acres offering excellent commercial or residential potential. Property features an existing well and septic system, with easy access and outstanding visibility. Conveniently located just minutes from the Oakland city limits outside of Zoning Districts. Ideal opportunity for development or investment.

    Rich Orr Railey Realty, Inc.

    26 Green Brier Rd, Oakland, MD 21550
  • /74

    $915,000

    Sold Sep 15, 2025

    186 Thornberry Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,347 Sq Ft
    • Built 1992

    Last Sold Summary

    • $390/SF
    • 48 Days On Market

    Current Estimated Value $984,230

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

    186 Thornberry Rd, Oakland, MD 21550
    • /42

      Est $224,054

      Not Listed For Sale

      19 A St, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,920 Sq Ft
      • Built 1973
      19 A St, Oakland, MD 21550

      Last Sold Summary

      • 152 Days On Market

  • /56

    $325,000

    $34K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,563 Sq Ft

    17921 Garrett Hwy, Oakland, MD 21550

    Charming and well-maintained, this 4-bedroom, 1.5-bath traditional home offers the perfect combination of comfort, character, and convenience. Built in 1952 and thoughtfully cared for, the home features beautifully refinished hardwood floors, inviting built-ins, and a cozy living room with a functional wood burner. With over 1,500 square feet of living space, the spacious layout includes an

    Michelle Clark Taylor-Made Deep Creek Real Estate, LLC

    17921 Garrett Hwy, 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 $211,827

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

    929 Dogwood Dr, Oakland, MD 21550
    • /74

      Est $699,347

      Not Listed For Sale

      14 Wanderer Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft
      • Built 1973
      14 Wanderer Ln, Oakland, MD 21550

      Last Sold Summary

      • 1 Day On Market

  • /26

    $699,000

    Under Contract
    • Land
    • 33.93 Acres
    • $20,601 per Acre

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550

    Incredible Development Opportunity! Almost 34 acres of beautiful grounds zoned Residential/Industrial/Professional (RIP). This parcel would make a beautiful site for a single family or condo/townhome subdivision, business park, or industrial complex. Or, build your dream home with over 33 acres of privacy, yet close to schools, hospital, and downtown Oakland shopping. Public Water on site and

    Justin Liller Railey Realty, Inc.

    0 Memorial Dr Unit MDGA2010668, Oakland, MD 21550
  • /70

    $465,000

    Sold Aug 12, 2025

    612 Harvey Winters Dr, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,473 Sq Ft
    • Built 2010

    Last Sold Summary

    • $188/SF
    • 6 Days On Market

    Current Estimated Value $465,328

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    612 Harvey Winters Dr, Oakland, MD 21550
    • /62

      Est $326,932

      Not Listed For Sale

      103 Overlook Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,640 Sq Ft
      • Built 1985
      103 Overlook Dr, Oakland, MD 21550

      Last Sold Summary

      • 63 Days On Market

  • /17

    $19,000

    • Land
    • 21,344 Sq Ft
    • $38,776 per Acre

    6 Cedar Ln, Oakland, MD 21550

    Discover the perfect place to build your mountain getaway, full-time residence, or adventure basecamp. Located within the highly sought-after Yough Mountain Resort community, this property offers access to more than 2,000 acres of private wilderness to explore and enjoy year-round. This land is at the top of the mountain where it is generally quieter. It has been surveyed for a well site and has

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    6 Cedar 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 $752,441

    Last Listing Agent Jonathan Minerick Homecoin.com

    200 Lake Shore Dr, Oakland, MD 21550
    • /38

      Est $286,478

      Not Listed For Sale

      644 Silver Knob Rd, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 1,728 Sq Ft
      • Built 1967
      644 Silver Knob Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

  • /50

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    164 Grandview Dr, Oakland, MD 21550

    Experience mountain living at its finest in this breathtaking mountaintop home overlooking Deep Creek Lake. With sweeping views from almost every room, your hardest decision may be where to sit to enjoy them. Offering three levels of living space, hardwood floors ( which were recently refinished), and some new appliances. The multiple decks are ideal to enjoy family and friends while taking in

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

    164 Grandview Dr, 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
    • /57

      Est $332,215

      Not Listed For Sale

      840 Smouse Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,863 Sq Ft
      • Built 1980
      840 Smouse Rd, Oakland, MD 21550

      Last Sold Summary

      • 17 Days On Market

  • /2

    $64,900

    $5K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    74 Parks Rd, Oakland, MD 21550

    **Investor Special with Mountain & Water Views**Opportunity is knocking at 74 Parks Road in Oakland, Maryland! This 3-bedroom, 1-bath one story is perfectly positioned just steps from the West Virginia line and surrounded by some of the most sought-after recreation in the region.Enjoy peaceful views of Snowy Creek right from the front yard and take advantage of being just minutes from

    Emillie Albrecht Real Broker, LLC

    74 Parks 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 $1,081,707

    Last Listing Agent Corbin Griffith Compass

    444 Woodlands Hill Ln, Oakland, MD 21550
    • /30

      Est $362,442

      Not Listed For Sale

      968 Paradise Heights, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 1993
      968 Paradise Heights, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /43

    $2,499,900

    • 4 Beds
    • 1.5 Baths
    • 2,190 Sq Ft

    83 Bethlehem Rd, Oakland, MD 21550

    Rare opportunity to own 327+/- acres of scenic countryside featuring a mix of open pasture, mature woods, and flowing stream frontage along Block Run. This 4-bedroom, 1.5-bath farmhouse is privately tucked among rolling fields and mountain views, offering endless potential for farming, recreation, hunting, ATV trails, or a private estate. Multiple barns and outbuildings provide ample storage and

    Jon Bell Railey Realty, Inc.

    83 Bethlehem Rd, 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 $99,070

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    125 N 2nd St, Oakland, MD 21550
    • /105

      Est $391,833

      Not Listed For Sale

      1265 Bray School Rd, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1983
      1265 Bray School Rd, Oakland, MD 21550

      Last Sold Summary

      • 66 Days On Market

  • /29

    $195,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,382 Sq Ft

    2918 Oakland Sang Run Rd, Oakland, MD 21550

    This charming 3-bedroom, 1-bathroom ranch-style home in the desirable Oakland Sang Run Rd area near the Youghiogheny River offers a blend of modern upgrades and classic appeal. Recently renovated in 2022, the interior features an open floor plan with luxury vinyl tile flooring, built-ins, and a gourmet kitchen equipped with stainless steel appliances and upgraded countertops. Enjoy the

    Andrew Eiswert Railey Realty, Inc.

    2918 Oakland Sang Run Rd, 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 $540,710

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

    1720 Pysell Crosscut Rd, Oakland, MD 21550
    • /95

      Est $1,524,141

      Not Listed For Sale

      478 Lake Forest Dr, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 2,688 Sq Ft
      • Built 1996
      478 Lake Forest Dr, Oakland, MD 21550

      Last Sold Summary

      • 48 Days On Market

  • /69

    $219,900

    $45K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    8956 Oakland Sang Run Rd, Oakland, MD 21550

    Welcome to The Wise Quack - our cozy cabin in the center of Deep Creek Lake activities...all 4 seasons! If you’re looking for a weekend or holiday retreat, this is it! The Wise Quack is a successful short-term rental with rave reviews. The home has three bedrooms, two full bathrooms, a fully equipped kitchen, laundry room and lots of outdoor living space. There is parking for 6+ cars on the

    Lisa Irving Taylor Properties

    8956 Oakland Sang Run Rd, 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
    • /54

      Est $640,846

      Not Listed For Sale

      1385 Mountainview Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,660 Sq Ft
      • Built 2000
      1385 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 26 Days On Market

  • /7

    $42,000

    • Land
    • 1.05 Acres
    • $40,000 per Acre

    0 Maple Del Ln, Oakland, MD 21550

    Lot 6 Maple Del is a mostly wooded , 1.05 acre lot near the western parts of Deep Creek Lake, Red Run cove and centrally located off Mayhew Inn Rd. There is a small stream running through the property and huge boulders strewn throughout, making it a fantastic setting for a wooded retreat. Incredible location near state parks and Deep Creek Lake area amenities. Public sewer available with sewer

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    0 Maple Del Ln, 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 $394,763

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1204 Alexander Ln, Oakland, MD 21550
    • /17

      Est $128,102

      Not Listed For Sale

      2 E Center St, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1910
      2 E Center St, Oakland, MD 21550

      Last Sold Summary

      • 63 Days On Market

  • /46

    $359,000

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    552 Black Oak Dr, Oakland, MD 21550

    Looking for a vacation spot or main living, Check out this nicely remolded home in a gated community. 3 bedrooms, 1 1/2 bathrooms, main level laundry room. Great rustic touches . Detached Garage with pellet stove. Yough Mountain Resort is the ultimate mountain escape! Nestled in a quiet, secluded area, this beautifully updated retreat offers modern comfort in a rustic Access to over 50 miles of

    Connie Leprevost Long & Foster Real Estate, Inc.

    552 Black Oak Dr, 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 $419,874

    Last Listing Agent Sean Brink Samson Properties

    232 Jeffrey Ln Unit 33, Oakland, MD 21550
    • /38

      Est $392,506

      Not Listed For Sale

      29 Crescent Ln, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,536 Sq Ft
      • Built 2007
      29 Crescent Ln, Oakland, MD 21550

      Last Sold Summary

      • 2 Days On Market

  • /29

    $339,900

    $29K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    531 Glendale Rd Unit B302, Oakland, MD 21550

    Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath unit in Silver Tree Suites—one of the largest units in the complex! This beautifully designed unit features an open floorplan centered around a cozy fireplace, perfect for relaxing after a day on the lake. A generous loft area creates a distinct separation between living and sleeping spaces, offering

    Larry Smith Railey Realty, Inc.

    531 Glendale Rd Unit B302, 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 $2,641,772

    Last Listing Agent Susan Bell Railey Realty, Inc.

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

      Est $672,180

      Not Listed For Sale

      148 Wanderer Ln, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft
      • Built 1970
      148 Wanderer Ln, Oakland, MD 21550

      Last Sold Summary

      • 111 Days On Market

  • /15

    $39,000

    • Land
    • 2.57 Acres
    • $15,175 per Acre

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550

    2 lots (7 & 8) totaling 2.57 acres, on gently sloping wooded area. Nestled between Cannan Valley & Deep Creek Lake, this promises to be a perfect blend of convenience and tranquility. Nature surrounds you - the perfect spot for a cozy cabin! Call agent for more information!

    Julie Mead The KW Collective

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550

Showing Results 241 - 280, Page 7 of 18

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