10,549

Oakland, MD Homes

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  • /15

    $75,000

    Sold Apr 10, 2026

    60 Gorman St, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft
    • Built 1920

    Last Sold Summary

    • $50/SF
    • 126 Days On Market

    Current Estimated Value $77,794

    Last Listing Agent Jennifer Jackson Charis Realty Group

    60 Gorman St, Oakland, MD 21550
    • /131

      Est $2,217,093

      Not Listed For Sale

      1746 Stockslager Rd, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 4,713 Sq Ft
      • Built 1983
      1746 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      • 131 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /21

    $160,000

    • Land
    • 10.1 Acres
    • $15,842 per Acre

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550

    Over 10 acres ready for developing off Dennett Rd. and Oakland Ave. Can be subdivided or could be large parcel to build your dream home, privacy off main streets with 3 separate entrances connecting to town roads. Engineered drawings for subdivision with grading permit in place at time of survey, is available and will be transferred with sale. (Potential up to 20 lots) Public sewar & water can be

    Julie Mead The KW Collective

    0 Dennett Rd 10 Acres To Oakland Ave Unit MDGA2011252, Oakland, MD 21550
  • /35

    $235,000

    Sold Oct 08, 2025

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft
    • Built 1990

    Last Sold Summary

    • $356/SF
    • 11 Days On Market

    Current Estimated Value $246,367

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

    36 Jeffrey Ln Unit 6B, Oakland, MD 21550
    • /64

      Est $1,342,975

      Not Listed For Sale

      441 Paradise Heights, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,548 Sq Ft
      • Built 2002
      441 Paradise Heights, Oakland, MD 21550

      Last Sold Summary

      • 148 Days On Market

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

  • /58

    $234,000

    $15K PRICE DROP Under Contract
    • 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
  • /93

    $785,000

    Sold Jun 01, 2026

    1001 Sutter Ln, Oakland, MD 21550

    • 5 Beds
    • 6 Baths
    • 6,550 Sq Ft
    • Built 2000

    Last Sold Summary

    • $120/SF
    • 172 Days On Market

    Current Estimated Value $776,860

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1001 Sutter Ln, Oakland, MD 21550
    • /32

      Est $1,647,569

      Not Listed For Sale

      2353 Boy Scout Rd, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 3,096 Sq Ft
      • Built 1940
      2353 Boy Scout Rd, Oakland, MD 21550

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /63

    $350,000

    • 5 Beds
    • 3 Baths
    • 2,165 Sq Ft

    112 E Pennington St, Oakland, MD 21550

    Completely rebuilt and beautifully renovated 5 bedroom 3 bathroom home! Welcome to this stunning 5-bedroom, 3-bathroom home that has been completely transformed from top to bottom with exceptional craftsmanship and modern finishes. Offering the charm of a classic home with the peace of mind of virtually all-new construction, this property is truly move-in ready. Major updates include a new

    Sheila Howell Lake Homes Realty, LLC

    112 E Pennington St, Oakland, MD 21550
  • /17

    $18,000

    Sold Nov 14, 2025

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550

    • Land
    • 42,688 Sq Ft
    • $18,367 per Acre

    Last Sold Summary

    • 17 Days On Market

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

    Lots 59 & 60 Cedar Ln, Oakland, MD 21550
    • /27

      Est $197,044

      Not Listed For Sale

      32 Rockville Ct, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,056 Sq Ft
      • Built 2008
      32 Rockville Ct, Oakland, MD 21550

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Michelle Haran Corner House Realty

  • /21

    $599,000

    • Land
    • 97.57 Acres
    • $6,139 per Acre

    97 acres Lot C Garrett Rd, Oakland, MD 21550

    Lot C – 97.57 Acres barn & ponds. | Oakland, Maryland. Discover 97.57 breathtaking acres just 10 minutes from Deep Creek Lake. This exceptional property offers a rare combination of natural beauty, privacy, and convenience, making it an ideal setting for a private estate, recreational retreat, or investment opportunity. The landscape is highlighted by two natural spring-fed and creek-fed ponds,

    Rich Orr Railey Realty, Inc.

    97 acres Lot C Garrett Rd, Oakland, MD 21550
  • /34

    $459,000

    Sold Nov 25, 2025

    50 Village Dr Unit 7, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 2006

    Last Sold Summary

    • $455/SF
    • 17 Days On Market

    Current Estimated Value $425,107

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    50 Village Dr Unit 7, Oakland, MD 21550
    • /48

      Est $301,737

      Not Listed For Sale

      314 Allegheny Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 1,750 Sq Ft
      • Built 2007
      314 Allegheny Dr, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

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

  • /26

    $699,000

    • 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
  • /50

    $559,250

    Sold Sep 02, 2025

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2008

    Last Sold Summary

    • $169/SF
    • 62 Days On Market

    Current Estimated Value $568,437

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    285 Winding Trail Ln Unit 10A, Oakland, MD 21550
    • /87

      Est $430,946

      Not Listed For Sale

      2702 Mayhew Inn Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1982
      2702 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Debbie Rogers Charis Realty Group

  • /118

    $2,699,000

    Under Contract
    • 6 Beds
    • 6.5 Baths
    • 3,442 Sq Ft

    1342 Stockslager Rd, Oakland, MD 21550

    Experience unparalleled lakefront living in this meticulously maintained 6 bedroom en suite home! Designed with an open concept plan to maximize abundant natural light and effortless transition through the kitchen, living and dining areas. Beautiful cathedral ceilings enhance the floor to ceiling native stone fireplace. Your living areas flow out to the expansive outdoor decking and a comfortable

    Kathy Gibson Railey Realty, Inc.

    1342 Stockslager Rd, Oakland, MD 21550
  • /13

    $155,000

    Sold Jan 08, 2026

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550

    • Land
    • 31,363 Sq Ft
    • $215,278 per Acre

    Last Sold Summary

    • 16 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
    • /42

      Est $174,036

      Not Listed For Sale

      112 B St, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1972
      112 B St, Oakland, MD 21550

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Thomas Long Railey Realty, Inc.

  • /17

    $12,500

    $7K PRICE DROP
    • Land
    • 21,344 Sq Ft
    • $25,510 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
  • /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 $572,671

    Last Listing Agent Andrew Orr The KW Collective

    710 Hunters Ridge Dr, Oakland, MD 21550
    • /64

      Est $178,106

      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

      Last Listing Agent Melissa Long Railey Realty, Inc.

  • /53

    $912,000

    $38K PRICE DROP
    • 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
  • /32

    $114,000

    Sold Jul 31, 2026

    5151 Hutton Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $111/SF
    • 53 Days On Market

    Current Estimated Value $115,858

    Last Listing Agent Mark Van Tyne Julian Agency Real Estate

    5151 Hutton Rd, Oakland, MD 21550
    • /42

      Est $232,529

      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

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

  • /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
  • /20

    $200,000

    Sold Feb 06, 2026

    123 Mountainview Ct, Oakland, MD 21550

    • Land
    • 1.69 Acres
    • $118,343 per Acre

    Last Sold Summary

    • 72 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    123 Mountainview Ct, Oakland, MD 21550
    • /74

      Est $645,908

      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

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /35

    $189,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 2,008 Sq Ft

    206 W Liberty St, Oakland, MD 21550

    Welcome to this charming 2 bedroom, 1 bath home in the heart of Oakland, offering endless potential and plenty of character. Step inside to an inviting open floor plan that creates a bright, spacious feel and allows for a comfortable flow between the living and kitchen areas. The large covered front porch provides the perfect spot to enjoy your morning coffee, relax after a long day, or take in

    Nicole Jackson Railey Realty, Inc.

    206 W Liberty St, Oakland, MD 21550
  • /51

    $660,000

    Sold Jan 30, 2026

    155 Basswood Way, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 268 Days On Market

    Current Estimated Value $661,053

    Last Listing Agent Mike Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
    • /62

      Est $327,360

      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

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /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
  • /37

    $250,000

    Sold Dec 31, 2025

    511 E Green St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft
    • Built 1924

    Last Sold Summary

    • $133/SF
    • 176 Days On Market

    Current Estimated Value $250,919

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

    511 E Green St, Oakland, MD 21550
    • /38

      Est $285,112

      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

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

  • /29

    $185,000

    $10K PRICE DROP Under Contract
    • 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
  • /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

    Current Estimated Value $609,271

    Last Listing Agent Rich Orr Railey Realty, Inc.

    2719 Broadford Rd, Oakland, MD 21550
    • /57

      Est $317,565

      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

      Last Listing Agent Daniel Toth EXP Realty, LLC

  • /68

    $191,409

    $74K 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
  • /29

    $185,000

    Sold Jan 23, 2026

    141 Truesdale Rd, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft
    • Built 1988

    Last Sold Summary

    • $101/SF
    • 4 Days On Market

    Current Estimated Value $226,048

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

    141 Truesdale Rd, Oakland, MD 21550

Showing Results 281 - 320, Page 8 of 18

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