10,771

Oakland, MD Homes

Section Image
    • /61

      Est $278,034

      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

  • /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
  • /42

    $545,000

    Sold Sep 22, 2025

    793 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,564 Sq Ft
    • Built 1995

    Last Sold Summary

    • $348/SF
    • 23 Days On Market

    Current Estimated Value $569,537

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    793 Mountainview Dr, Oakland, MD 21550
    • /22

      Est $468,977

      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

  • /7

    $24,900

    $5K PRICE DROP
    • Land
    • 4 Acres
    • $6,225 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
  • /13

    $62,000

    Sold Aug 01, 2025

    500 Seneca Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,284 Sq Ft
    • Built 1940

    Last Sold Summary

    • $48/SF
    • 577 Days On Market

    Current Estimated Value $105,288

    Last Listing Agent Paul Macy Garrett Land Sales, PC

    500 Seneca Ave, Oakland, MD 21550
    • /35

      Est $287,458

      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

  • /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
  • /48

    $250,000

    Sold Mar 27, 2026

    702 Sunshine Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2009

    Last Sold Summary

    • 9% Below List Price
    • $135/SF
    • 16 Days On Market

    Current Estimated Value $257,103

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

    702 Sunshine Dr, Oakland, MD 21550
    • /36

      Est $218,986

      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

  • /50

    $325,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft

    29 Woodmont Ln, Oakland, MD 21550

    Immaculate 4-bedroom/3-bath countryside home less than 10 minutes from Oakland. This property has been exceptionally well-maintained — truly move-in ready and prepared for you to make your own memories. A private in-ground pool awaits you out back - perfect for summer entertaining. Enjoy the western exposure and stunning sunsets from your elevated deck. A .86 acre lot provides a great yard and

    Brent Housley Railey Realty, Inc.

    29 Woodmont Ln, Oakland, MD 21550
  • /47

    $202,039

    Sold Jun 08, 2026

    43 Sloan Tract Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,743 Sq Ft
    • Built 1930

    Last Sold Summary

    • 38% Below List Price
    • $116/SF
    • 34 Days On Market

    Current Estimated Value $295,000

    Last Listing Agent Justin Liller Railey Realty, Inc.

    43 Sloan Tract Rd, Oakland, MD 21550
    • /43

      Est $314,588

      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

  • /26

    $425,000

    • Land
    • 1.34 Acres
    • $317,164 per Acre

    LOT 25 Holy Cross Dr, Oakland, MD 21550

    Discover the perfect blend of privacy, prestige, and natural beauty with Lot 25 in The Reserve at Holy Cross—a premier wooded lakefront homesite tucked into a serene private cove on Deep Creek Lake. Boasting 1.34 acres and an impressive 251 feet of lake frontage, this exceptional lot offers the ideal setting to build your dream retreat. Enjoy direct access to the water with up to two boat slips

    Nina Beitzel Railey Realty, Inc.

    LOT 25 Holy Cross Dr, Oakland, MD 21550
  • /74

    $664,500

    Sold Oct 17, 2025

    94 Meadow Ct, Oakland, MD 21550

    • 3 Beds
    • 4 Baths
    • 2,460 Sq Ft
    • Built 1999

    Last Sold Summary

    • $270/SF
    • 54 Days On Market

    Current Estimated Value $658,353

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

    94 Meadow Ct, Oakland, MD 21550
    • /44

      Est $189,652

      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

  • /78

    $1,579,900

    • 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
  • /21

    $115,000

    Sold Nov 03, 2025

    607 K St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1920

    Last Sold Summary

    • $86/SF
    • 213 Days On Market

    Current Estimated Value $113,305

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

    607 K St, Oakland, MD 21550
    • /37

      Est $227,332

      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

  • /58

    $215,000

    • 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
  • /37

    $255,000

    Sold Apr 23, 2026

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 875 Sq Ft
    • Built 1997

    Last Sold Summary

    • 7% Below List Price
    • $291/SF
    • 34 Days On Market

    Current Estimated Value $268,159

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

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550
    • /131

      Est $2,277,962

      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

  • /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
  • /39

    $210,000

    Sold Aug 01, 2025

    10 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 421 Days On Market

    Current Estimated Value $218,642

    Last Listing Agent Michael Cumerlato Jason Mitchell Group

    10 Laurel Brook Dr, Oakland, MD 21550
    • /64

      Est $1,346,688

      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

  • /45

    $149,900

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    115 Woodmont Ln, Oakland, MD 21550

    Set on 1 acre just minutes from town, this 3-bedroom, 1 bath home is full of potential and ready for its next chapter. Whether you're searching for an affordable starter home or your next renovation project, this property offers a solid opportunity to create something special. Features include a spacious screened porch, functional floor plan, and a full basement with ample storage and workspace.

    Mike Fenton Railey Realty, Inc.

    115 Woodmont Ln, Oakland, MD 21550
  • /65

    $150,000

    Sold Mar 26, 2026

    506 Roanoke Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1940

    Last Sold Summary

    • 16% Below List Price
    • $111/SF
    • 4 Days On Market

    Current Estimated Value $156,389

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    506 Roanoke Ave, Oakland, MD 21550
    • /32

      Est $1,702,199

      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

  • /61

    $185,000

    • 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
  • /39

    $262,500

    Sold Feb 05, 2026

    14 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $199/SF
    • 2 Days On Market

    Current Estimated Value $264,532

    Last Listing Agent Larry Smith Railey Realty, Inc.

    14 Laurel Brook Dr, Oakland, MD 21550
    • /27

      Est $186,131

      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

  • /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
  • /41

    $485,000

    Sold Sep 22, 2025

    20160 Garrett Hwy Unit D310, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,379 Sq Ft
    • Built 1975

    Last Sold Summary

    • $352/SF
    • 41 Days On Market

    Last Listing Agent Stephanie Smith Select Premium Properties, Inc

    20160 Garrett Hwy Unit D310, Oakland, MD 21550
    • /48

      Est $308,261

      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

  • /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
  • /11

    $5,000

    Sold Apr 03, 2026

    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550

    • Land
    • 41,817 Sq Ft
    • $5,208 per Acre

    Last Sold Summary

    • 40 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    Lots 34 & 35 Fox Tail Rd, Oakland, MD 21550
    • /87

      Est $448,844

      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

  • /17

    $37,250

    $5K PRICE DROP Pending
    • Land
    • 3.03 Acres
    • $12,294 per Acre

    Lot 1 Cherrywood Dr, Oakland, MD 21550

    ****NOW ONLY $37,250!! Discover the perfect blend of space, privacy, and convenience with this 3.03 acre lot, a short drive from downtown Oakland, Deep Creek Lake, Potomac State Forest and Garrett State Forest! With a 5-bedroom perc on file, this property is ready for your dream home. This beautiful property is located in Cherrywood Ridge Subdivision, with only 7 lots in the community.

    Amy Skipper Railey Realty, Inc.

    Lot 1 Cherrywood Dr, Oakland, MD 21550
  • /69

    $2,217,500

    Sold May 28, 2026

    2411 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 4 Baths
    • 3,463 Sq Ft
    • Built 1979

    Last Sold Summary

    • 7% Below List Price
    • $640/SF
    • 7 Days On Market

    Current Estimated Value $2,356,754

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    2411 Lake Shore Dr, Oakland, MD 21550
    • /42

      Est $169,914

      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

Showing Results 201 - 240, Page 6 of 18

How to Buy a Home How to Finance a Home How to Sell a Home