10,771

Oakland, MD Homes

Section Image
    • /61

      Est $578,486

      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

      • 160 Days On Market

  • /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
  • /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 $405,365

    Last Listing Agent Ana Dubin RE/MAX Realty Group

    45 Village Dr Unit 4, Oakland, MD 21550
    • /80

      Est $831,818

      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

      • 88 Days On Market

  • /109

    $6,499,900

    • 8 Beds
    • 8.5 Baths
    • 11,417 Sq Ft

    47 Holy Cross Cir, Oakland, MD 21550

    Luxury lakefront living at its peak. This 11,417 sq ft masterpiece sits on 1.65 acres in The Reserve at Holy Cross with 345 feet of Deep Creek Lake frontage and an engineered DNR-approved sea wall. Crafted in 2016, the home features timber-framed vaulted ceilings, wide-plank hardwood floors, and panoramic lake views from nearly every room. The commercial-grade kitchen anchors the main level with

    Jon Bell Railey Realty, Inc.

    47 Holy Cross Cir, 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 $326,280

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

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    • /62

      Est $180,231

      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

      • 67 Days On Market

  • /60

    $289,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an

    Andrew Eiswert Railey Realty, Inc.

    163 Mitchell Dr, Oakland, MD 21550
  • /2

    $20,000

    Sold Jun 26, 2025

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

    • Land
    • 20,473 Sq Ft
    • $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
    • /12

      Not Listed For Sale

      Lot 76 S Blakeslee Rd, Oakland, MD 21550

      Lot 76 S Blakeslee Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /45

    $1,329,000

    • 6 Beds
    • 4.5 Baths
    • 4,113 Sq Ft

    439 Paradise Heights, Oakland, MD 21550

    Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180 views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive

    Mike Kennedy Railey Realty, Inc.

    439 Paradise Heights, 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 $1,574,731

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    272 McComas Beach Terrace, Oakland, MD 21550
    • /38

      Not Listed For Sale

      601 Hope Ave, Oakland, MD 21550

      • 3 Beds
      • 2.5 Baths
      • 2,142 Sq Ft
      • Built 2025
      601 Hope Ave, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • /69

    $899,900

    • 4 Beds
    • 3.5 Baths
    • 3,185 Sq Ft

    113 Jubb Meadows Ln, Oakland, MD 21550

    Luxury Estate just outside the town of Oakland. This 4-bed, 3.5 bath is situated on 9.72 acres. Offering 4,555 sq ft with vaulted ceilings, open concept living, and a rustic stacked stone fireplace. Modern gourmet kitchen with a large island and granite tops. Hardwood floors and timber frame accents throughout. Attached three-car garage. Full unfinished basement ready to add up to an additional

    Jon Bell Railey Realty, Inc.

    113 Jubb Meadows Ln, 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 $90,791

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    81 Timber Ln, Oakland, MD 21550
    • /10

      Est $162,000

      Not Listed For Sale

      503 Southern Pines Dr, Oakland, MD 21550

      503 Southern Pines Dr, Oakland, MD 21550

      Last Sold Summary

      • 68 Days On Market

  • /69

    $639,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 2,200 Sq Ft

    130 Mystic Creek Trail Unit 1B, Oakland, MD 21550

    Discover refined mountain and lake living in this quality built townhome at Mystic Creek on Deep Creek Lake, nestled in a quiet, serene setting with a truly custom feel. This spacious 5-bedroom, 4.5 bath residence offers an open concept main level ideal for entertaining, featuring hardwood floors throughout the main living area, abundant natural light, and seamless flow between the living,

    Melissa Long Railey Realty, Inc.

    130 Mystic Creek Trail Unit 1B, 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, LLC

    0 Sam Snead Cir Unit 1 MDGA2010358, Oakland, MD 21550
    • /32

      Est $152,500

      Not Listed For Sale

      15 Fawn Dr, Oakland, MD 21550

      15 Fawn Dr, Oakland, MD 21550

      Last Sold Summary

      • 325 Days On Market

  • /72

    $1,689,000

    • 5 Beds
    • 4.5 Baths
    • 3,714 Sq Ft

    670 Woodlands Hill Ln, Oakland, MD 21550

    Experience what may be the most spectacular view in all of Deep Creek Lake! Perched in an extraordinary setting, this exceptional Yellowstone Log Home showcases breathtaking panoramic water views that create a true “top of the world” feel. Designed to capture the scenery from every angle, the main level features an open-concept layout with soaring natural light, a stunning stone fireplace, luxury

    Nina Beitzel Railey Realty, Inc.

    670 Woodlands Hill Ln, 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 $703,332

    Last Listing Agent Jon Bell Railey Realty, Inc.

    329 Lemley Dr, Oakland, MD 21550
    • /11

      Not Listed For Sale

      Lots 14 & 17 Mallard Loop, Oakland, MD 21550

      Lots 14 & 17 Mallard Loop, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /11

    $199,900

    $20K PRICE DROP
    • Land
    • 4,791 Sq Ft
    • $1,817,273 per Acre

    2 Overlook Ridge Dr S, Oakland, MD 21550

    Enjoy the best the lake has to offer from 'Overlook Ridge'! Boasting year-round lake views, yet tucked away in a peaceful and serene community setting. Short drive to the community lake access area for swimming and fishing! Dock Slips may be leased through HOA. Utilities to site and ready to build your perfect four-season Deep Creek getaway. Located just off of Rt. 219, with easy access to all

    Jon Bell Railey Realty, Inc.

    2 Overlook Ridge Dr S, 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
    • /68

      Est $525,958

      Not Listed For Sale

      20160 Garrett Hwy Unit F503, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 1972
      20160 Garrett Hwy Unit F503, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • /38

    $287,500

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    505 Southern Pines Dr, Oakland, MD 21550

    Charming ranch-style home located in the desirable Southern Pines neighborhood. From the moment you enter, you’ll appreciate the warm and inviting feel of the open layout. The main level features three comfortable bedrooms, two full bathrooms, beautiful hardwood flooring, and a seamless kitchen, living, and dining area that creates an ideal space for everyday living and entertaining. The recently

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

    505 Southern Pines Dr, Oakland, MD 21550
  • /25

    $42,000

    Sold Aug 06, 2025

    Lot 18 Moss Creek Cir, Oakland, MD 21550

    • Land
    • 3.61 Acres
    • $11,634 per Acre

    Last Sold Summary

    • 58 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    Lot 18 Moss Creek Cir, Oakland, MD 21550
    • /3

      Not Listed For Sale

      0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550

      0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550

      Last Sold Summary

      • 35 Days On Market

  • /31

    $1,650,000

    • 4 Beds
    • 6 Baths
    • 5,117 Sq Ft

    3898 Underwood Rd, Oakland, MD 21550

    Unique luxury home on 23 acres with 360 degree views of Pleasant Valley. 5,100 + SQ. FT. 4 ensuite bedrooms, 2 additional powder rooms, formal living room/ballroom, informal living room, sunroom, den, pantry and large dine in kitchen. 4 fireplaces. full basement, 3 car attached garage. Whole home generator. Everything in this home is first rate. A must see for the discerning buyer

    Robert Custer Custer Realty & Auction

    3898 Underwood Rd, Oakland, MD 21550
  • /65

    $280,500

    Sold Sep 12, 2025

    290 Crellin Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft
    • Built 1982

    Last Sold Summary

    • $127/SF
    • 96 Days On Market

    Current Estimated Value $277,328

    Last Listing Agent Kevin Liller Railey Realty, Inc.

    290 Crellin Underwood Rd, Oakland, MD 21550
    • /13

      Est $135,549

      Not Listed For Sale

      31 Mount Airy Ct, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft
      • Built 2012
      31 Mount Airy Ct, Oakland, MD 21550

      Last Sold Summary

      • 22 Days On Market

  • /75

    $349,900

    • 4 Beds
    • 2 Baths
    • 3,352 Sq Ft

    2448 Birchwood Dr, Oakland, MD 21550

    Tucked within the sought-after Yough Mountain Resort community, this beautifully remodeled 4-bedroom, 2-bath mountain retreat blends rustic charm with thoughtful modern updates. Warm wood finishes, high ceilings, and inviting gathering spaces create a cozy lodge-style atmosphere, while upgrades throughout add comfort and convenience. The home features two full kitchens with granite countertops,

    Jon Bell Railey Realty, Inc.

    2448 Birchwood Dr, Oakland, MD 21550
  • /25

    $28,000

    Sold Jun 02, 2026

    9 Timber Falls Rd, Oakland, MD 21550

    • Land
    • 6.9 Acres
    • $4,058 per Acre

    Last Sold Summary

    • 220 Days On Market

    Last Listing Agent Jesse Shimrock Railey Realty, Inc.

    9 Timber Falls Rd, 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

  • /21

    $975,000

    $20K PRICE DROP
    • Land
    • 25,264 Sq Ft
    • $1,681,034 per Acre

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550

    RARE OPPURTUNITY! Discover one of the final opportunities to own true lakefront on the iconic Glendale Road! This premier homesite offers approximately 75 feet of pristine Deep Creek Lake frontage in a serene no wake zone, perfect for swimming, kayaking, and peaceful lakeside enjoyment. Zoning in this area is Town Center. This allows for a larger building area within the lot with relaxed

    Lucas Muenchow Railey Realty, Inc.

    0 Glendale Rd Lot 12 Alpine Village Subdivision, Oakland, MD 21550
  • /41

    $239,900

    Sold Sep 12, 2025

    502 E Oak St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1956

    Last Sold Summary

    • $143/SF
    • 17 Days On Market

    Current Estimated Value $236,395

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    502 E Oak St, 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

      • 0 Days On Market

  • /66

    $749,900

    $29K PRICE DROP
    • 5 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    222 Skippers Point Rd, Oakland, MD 21550

    Lake cottage (5 Bedrooms) on large level lot with path to your own private class A dock & 25' of Lakefront, directly across the street. This comfy (one level living) cottage sits on 1.8 level acres with 2 storage garages and mature landscaping. 5BRs, open living, dinning & kitchen area, with lots of sunlight. 1 full & 1-1/2 bath, with 5 Bedrooms! Laundry room located off back of the home. Cute

    Julie Mead The KW Collective

    222 Skippers Point Rd, Oakland, MD 21550
  • /53

    $495,000

    Sold Oct 08, 2025

    131 Rock Ridge Ln Unit 12, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,422 Sq Ft
    • Built 2004

    Last Sold Summary

    • $204/SF
    • 106 Days On Market

    Current Estimated Value $486,360

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

    131 Rock Ridge Ln Unit 12, 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

      • 0 Days On Market

Showing Results 81 - 120, Page 3 of 18

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