10,739

Oakland, MD Homes

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    • /62

      Est $526,116 Not Listed For Sale

      189 Maple Del Ln, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 2,260 Sq Ft
      • Built 2003
      189 Maple Del Ln, Oakland, MD 21550

      Last Sold Summary

      • 13% Above List Price
      • $206/SF
      • 87 Days On Market

      Last Sold Price $465,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /123

    $545,000

    • 4 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    328 Stool Rock Rd, Oakland, MD 21550

    Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a separate

    Kathy Gibson Railey Realty, Inc.

    328 Stool Rock Rd, Oakland, MD 21550
  • /16

    $100,000 Sold May 02, 2025

    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550

    • Land
    • 2.4 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 433 Days On Market

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

    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    • /32

      Not Listed For Sale

      319 Basswood Way Unit LOT 21, Oakland, MD 21550

      • 4 Beds
      • 3 Baths
      • 2,784 Sq Ft
      • Built 2007
      319 Basswood Way Unit LOT 21, Oakland, MD 21550

      Last Sold Summary

      • $237/SF
      • 15 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /147

    $5,150,000 Coming Soon

    • 8 Beds
    • 8.5 Baths
    • 10,300 Sq Ft

    1010 Holy Cross Dr, Oakland, MD 21550

    ICONIC. A design masterpiece of stone and timber — a true Rex Anderson build that reflects the seamless merging of inspiration and architecture. Warm, and undeniably welcoming, this home stands as a statement of craftsmanship and vision. Discover a breathtaking blend of contemporary luxury and timeless timber frame construction, perfectly positioned for privacy within the prestigious Reserve at

    Rachel Bruch Railey Realty, Inc.

    1010 Holy Cross Dr, Oakland, MD 21550
  • /44

    $140,000 Sold Jul 08, 2025

    15 D St, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,680 Sq Ft
    • Built 1953

    Last Sold Summary

    • $83/SF
    • 86 Days On Market

    Current Estimated Value $157,559

    Last Listing Agent Jon Bell Railey Realty, Inc.

    15 D St, Oakland, MD 21550
    • /61

      Est $611,482 Not Listed For Sale

      48 Skippers Estates Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,454 Sq Ft
      • Built 1984
      48 Skippers Estates Dr, Oakland, MD 21550

      Last Sold Summary

      • 11% Above List Price
      • $378/SF
      • 160 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /79

    $749,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    130 Timberloft Cir Unit 14, Oakland, MD 21550

    Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, 3 bath home offers breathtaking lake and mountain views year round. Designed with an open floor plan, this home is perfect for entertaining. Enjoy the stunning scenery from the spacious main-level deck, or relax in the screened-in lower level porch. A cozy fireplace on both levels adds warmth and charm,

    Nicole Jackson Railey Realty, Inc.

    130 Timberloft Cir Unit 14, Oakland, MD 21550
  • /63

    $711,000 Sold Oct 15, 2025

    58 Glendale Woods Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,556 Sq Ft
    • Built 2006

    Last Sold Summary

    • $278/SF
    • 5 Days On Market

    Current Estimated Value $736,050

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    58 Glendale Woods Rd, Oakland, MD 21550
    • /80

      Est $917,988 Not Listed For Sale

      33 Black Bear Ct, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,976 Sq Ft
      • Built 1989
      33 Black Bear Ct, Oakland, MD 21550

      Last Sold Summary

      • 7% Above List Price
      • $287/SF
      • 88 Days On Market

      Last Sold Price $855,000

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /50

    $529,900

    • 4 Beds
    • 3 Baths
    • 2,235 Sq Ft

    126 Leo Friend Rd, Oakland, MD 21550

    Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits

    Jon Bell Railey Realty, Inc.

    126 Leo Friend Rd, Oakland, MD 21550
  • /14

    $80,000 Sold Sep 26, 2025

    0 Coolidge Ave, Oakland, MD 21550

    • Land
    • 0.46 Acre
    • $173,913 per Acre

    Last Sold Summary

    • 76 Days On Market

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

    0 Coolidge Ave, Oakland, MD 21550
    • /62

      Est $179,860 Not Listed For Sale

      36 Cherokee Ln, Oakland, MD 21550

      • 2 Beds
      • 1.5 Baths
      • 864 Sq Ft
      • Built 1976
      36 Cherokee Ln, Oakland, MD 21550

      Last Sold Summary

      • 28% Above List Price
      • $162/SF
      • 67 Days On Market

      Last Sold Price $140,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /81

    $399,900

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft

    3930 Mayhew Inn Rd, Oakland, MD 21550

    2 for 1 on 2 .3 +/- acres! Remodeled 2BR 2BA cottage with auxiliary building that has an oversized garage, multiple workshop areas and 1BR 1BA apartment on the second level. New Maryland legislation, Accessory Dwelling Units Act of 2025, will allow expanded access to use the apartment above the garage in a more meaningful manner. Cabin boasts high end finishes and open living space with a cozy

    Jay Ferguson Taylor Made Deep Creek Real Estate

    3930 Mayhew Inn Rd, Oakland, MD 21550
  • /35

    $405,000 Sold Dec 22, 2025

    45 Village Dr Unit 4, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • Built 2004

    Last Sold Summary

    • $370/SF
    • 173 Days On Market

    Current Estimated Value $407,972

    Last Listing Agent Ana Dubin RE/MAX Realty Group

    45 Village Dr Unit 4, Oakland, MD 21550
    • /68

      Est $753,882 Not Listed For Sale

      3365 Mayhew Inn Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 3,158 Sq Ft
      • Built 2007
      3365 Mayhew Inn Rd, Oakland, MD 21550

      Last Sold Summary

      • 24% Above List Price
      • $193/SF
      • 4 Days On Market

      Last Sold Price $610,000

      Last Listing Agent Kellyann Green Railey Realty, Inc.

  • /17

    $449,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    654 N Bradley Ln, Oakland, MD 21550

    NEW CONSTRUCTION from Lyv Homes! 3BR/2BA, 1464sf contemporary style home fronting on the 13th hole of the Oakland golf course. This property combines MAJESTIC scenic views with modern design, elite finishes and outdoor living. Key features include multiple wood-burning fireplaces (inside + out), Andersen windows, commercial-grade LVP flooring throughout, gourmet kitchen with soft-close cabinets

    Jay Ferguson Taylor Made Deep Creek Real Estate

    654 N Bradley Ln, Oakland, MD 21550
  • /36

    $326,000 Sold Oct 10, 2025

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1997

    Last Sold Summary

    • $272/SF
    • 42 Days On Market

    Current Estimated Value $332,558

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    • /25

      Not Listed For Sale

      135 Tarn Dr, Oakland, MD 21550

      135 Tarn Dr, Oakland, MD 21550

      Last Sold Summary

      • 41 Days On Market

      Last Sold Price $80,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /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
  • /2

    $20,000 Sold Jun 26, 2025

    Lots 22 & 23 Black Oak Ln, Oakland, MD 21550

    • Land
    • 0.47 Acre
    • $42,553 per Acre

    Last Sold Summary

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

    Lots 22 & 23 Black Oak Ln, Oakland, MD 21550
    • /49

      Est $871,005 Not Listed For Sale

      17 Old Chestnut Dr, Oakland, MD 21550

      • 3 Beds
      • 1 Bath
      • 966 Sq Ft
      • Built 1940
      17 Old Chestnut Dr, Oakland, MD 21550

      Last Sold Summary

      • 12% Above List Price
      • $802/SF
      • 93 Days On Market

      Last Sold Price $775,000

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /67

    $749,000

    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    With a new price you don't want to miss this chance! Beautifully maintained 5 bedroom 5 bathroom lake area chalet. Beautifully landscaped and situated on 4 +/- acres with partial views of the south side of Deep Creek Lake. Recently Professionally appraised for $868,000! This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished

    Dan Shockey Taylor Made Deep Creek Real Estate

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • /69

    $1,535,000 Sold Jan 07, 2026

    272 McComas Beach Terrace, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,448 Sq Ft
    • Built 2005

    Last Sold Summary

    • $627/SF
    • 49 Days On Market

    Current Estimated Value $1,544,908

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    272 McComas Beach Terrace, Oakland, MD 21550
    • /10

      Est $39,000 Not Listed For Sale

      503 Southern Pines Dr, Oakland, MD 21550

      503 Southern Pines Dr, Oakland, MD 21550

      Last Sold Summary

      • 2% Below List Price
      • 68 Days On Market

      Last Sold Price $40,000

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

  • /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

    164 Grandview Dr, Oakland, MD 21550
  • /20

    $80,000 Sold Jun 30, 2025

    81 Timber Ln, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 1,860 Sq Ft
    • Built 1965

    Last Sold Summary

    • $43/SF
    • 5 Days On Market

    Current Estimated Value $90,466

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    81 Timber Ln, Oakland, MD 21550
    • /32

      Est $146,000 Not Listed For Sale

      15 Fawn Dr, Oakland, MD 21550

      15 Fawn Dr, Oakland, MD 21550

      Last Sold Summary

      • 2,439% Above List Price
      • 325 Days On Market

      Last Sold Price $5,750

      Last Listing Agent Mike Fenton Railey Realty, Inc.

  • /29

    $369,000

    • 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
  • /21

    $155,000 Sold May 22, 2025

    3821 Underwood Rd, Oakland, MD 21550

    • 4 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1964

    Last Sold Summary

    • $126/SF
    • 10 Days On Market

    Current Estimated Value $165,417

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    3821 Underwood Rd, Oakland, MD 21550
    • /11

      Not Listed For Sale

      18 Autumn Way, Oakland, MD 21550

      18 Autumn Way, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

      Last Sold Price $20,000

      Last Listing Agent Kathy Gibson Railey Realty, Inc.

  • /68

    $1,199,990 Pending

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

    444 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to 444 Woodlands Hill Ln, in Oakland, MD. Nestled in the private community of The View, this custom home offers stunning lake views in a serene, private setting. Centrally located less than 4 miles from Wisp while backing up to hundreds of acres of untouched forest, this property truly offers the best that Deep Creek Lake has to offer. This luxury home has been impeccably maintained as a

    Corbin Griffith Compass

    444 Woodlands Hill Ln, Oakland, MD 21550
  • /33

    $425,000 Sold Dec 19, 2025

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 0 Days On Market

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    • /4

      Not Listed For Sale

      9.3 +/- Acres Upperman Rd, Oakland, MD 21550

      9.3 +/- Acres Upperman Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

      Last Sold Price $140,000

      Last Listing Agent Russell Bounds Railey Realty, Inc.

  • /50

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,250 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 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 detached garage. Property

    Brian Covell BERKSHIRE HATHAWAY HOMESERVICES TOUCHDOWN HOME PROS REALTY

    609 Southern Pines Dr, Oakland, MD 21550
  • /81

    $700,000 Sold Feb 26, 2026

    329 Lemley Dr, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,632 Sq Ft
    • Built 2004

    Last Sold Summary

    • $266/SF
    • 112 Days On Market

    Current Estimated Value $717,388

    Last Listing Agent Jon Bell Railey Realty, Inc.

    329 Lemley Dr, Oakland, MD 21550
    • /52

      Not Listed For Sale

      3094 Cranesville Rd, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 1,490 Sq Ft
      • Built 1938
      3094 Cranesville Rd, Oakland, MD 21550

      Last Sold Summary

      • $321/SF
      • 0 Days On Market

      Last Sold Price $479,000

      Last Listing Agent Russell Bounds Railey Realty, Inc.

  • /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
  • /18

    $19,500 Sold Sep 04, 2025

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550

    • Land
    • 1.48 Acres
    • $13,176 per Acre

    Last Sold Summary

    • 348 Days On Market

    Last Listing Agent Brady Harden Coldwell Banker Premier

    0 Sanders Ln Unit MDGA2007602, Oakland, MD 21550
    • /40

      Not Listed For Sale

      510 Palmer Ln, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 1,922 Sq Ft
      • Built 2024
      510 Palmer Ln, Oakland, MD 21550

      Last Sold Summary

      • $192/SF
      • 0 Days On Market

      Last Sold Price $369,000

      Last Listing Agent Jay Ferguson Taylor Made Deep Creek Real Estate

Showing Results 81 - 120, Page 3 of 18

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