10,714

Oakland, MD Homes

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  • Lot 5A Valley Rd, Oakland, MD 21550
    Lot 5A Valley Rd, Oakland, MD 21550
    Lot 5A Valley Rd, Oakland, MD 21550
    /14

    $17,000 Sold Dec 18, 2025

    Lot 5A Valley Rd, Oakland, MD 21550

    • Land
    • 2.45 Acres
    • $6,939 per Acre

    Last Sold Summary

    • 1,047 Days On Market

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

    Lot 5A Valley Rd, Oakland, MD 21550
    • 7 Cherrywood Dr, Oakland, MD 21550
      7 Cherrywood Dr, Oakland, MD 21550
      7 Cherrywood Dr, Oakland, MD 21550
      /3

      Not Listed For Sale

      7 Cherrywood Dr, Oakland, MD 21550

      7 Cherrywood Dr, Oakland, MD 21550
  • 1118 Lake Shore Dr, Oakland, MD 21550
    1118 Lake Shore Dr, Oakland, MD 21550
    1118 Lake Shore Dr, Oakland, MD 21550
    /101

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,446 Sq Ft

    1118 Lake Shore Dr, Oakland, MD 21550

    Escape to Serenity: Your Dream Log Home Awaits! Nestled in the heart of a picturesque lake and mountain area, this charming log home offers the perfect blend of rustic charm and modern touches. With cathedral wood ceilings and a cozy gas fireplace, the spacious living area invites you to relax and soak in the warmth and beauty of your surroundings. The living area steps out to a large covered

    Susan Bell Railey Realty, Inc.

    1118 Lake Shore Dr, Oakland, MD 21550
  • 107 E Mason St, Oakland, MD 21550
    107 E Mason St, Oakland, MD 21550
    107 E Mason St, Oakland, MD 21550
    /24

    $27,500 Sold May 14, 2025

    107 E Mason St, Oakland, MD 21550

    • 4 Beds
    • 1.5 Baths
    • 2,256 Sq Ft
    • Built 1914

    Last Sold Summary

    • $12/SF
    • 18 Days On Market

    Current Estimated Value $167,299

    Last Listing Agent Kathleen Miller Better Homes & Gardens Real Estate Old Line Group

    107 E Mason St, Oakland, MD 21550
    • 409 San Francisco St, Oakland, MD 21550
      409 San Francisco St, Oakland, MD 21550
      409 San Francisco St, Oakland, MD 21550
      /21

      Est $103,775 Not Listed For Sale

      409 San Francisco St, Oakland, MD 21550

      409 San Francisco St, Oakland, MD 21550
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /117

    $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
  • 29 Sloan Tract Rd, Oakland, MD 21550
    29 Sloan Tract Rd, Oakland, MD 21550
    29 Sloan Tract Rd, Oakland, MD 21550
    /32

    $260,000 Sold Jul 21, 2025

    29 Sloan Tract Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1983

    Last Sold Summary

    • $271/SF
    • 98 Days On Market

    Current Estimated Value $281,137

    Last Listing Agent Thomas Long Railey Realty, Inc.

    29 Sloan Tract Rd, Oakland, MD 21550
    • 128 Tarn Dr, Oakland, MD 21550
      128 Tarn Dr, Oakland, MD 21550
      128 Tarn Dr, Oakland, MD 21550
      /16

      Not Listed For Sale

      128 Tarn Dr, Oakland, MD 21550

      128 Tarn Dr, Oakland, MD 21550
  • 272 McComas Beach Terrace, Oakland, MD 21550
    272 McComas Beach Terrace, Oakland, MD 21550
    272 McComas Beach Terrace, Oakland, MD 21550
    /69

    $1,589,000 Pending

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

    272 McComas Beach Terrace, Oakland, MD 21550

    Wake up to a light mist rising over Deep Creek Lake and enjoy level lakefront living with your own private dock at the top of Red Run Cove. This stunning Katahdin Cedar Log Home sits on a quiet cul-de-sac, surrounded by mature trees that create a peaceful canopy. Relax on the expansive TimberTech back deck or unwind in the hot tub on the rear stone patio—all with incredible waterfront views.

    Russell Bounds Railey Realty, Inc.

    272 McComas Beach Terrace, Oakland, MD 21550
  • 228 Paradise Heights, Oakland, MD 21550
    228 Paradise Heights, Oakland, MD 21550
    228 Paradise Heights, Oakland, MD 21550
    /82

    $1,900,000 Sold May 16, 2025

    228 Paradise Heights, Oakland, MD 21550

    • 4 Beds
    • 4.5 Baths
    • 2,249 Sq Ft
    • Built 1989

    Last Sold Summary

    • $845/SF
    • 5 Days On Market

    Current Estimated Value $1,888,632

    Last Listing Agent Jay Quinn Taylor Made Deep Creek Vacations & Sales

    228 Paradise Heights, Oakland, MD 21550
    • 1 Overlook Ridge Dr SE, Oakland, MD 21550
      1 Overlook Ridge Dr SE, Oakland, MD 21550
      1 Overlook Ridge Dr SE, Oakland, MD 21550
      /22

      Not Listed For Sale

      • 4 Beds

      1 Overlook Ridge Dr SE, Oakland, MD 21550

      1 Overlook Ridge Dr SE, Oakland, MD 21550
  • 329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    /81

    $750,000

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

    329 Lemley Dr, Oakland, MD 21550

    Lake View Chalet at Deep Creek Lake – This 4 Bedroom 3.5 Bath Mountain Home is privately seated on 1.72 acres of wooded land and features vaulted ceilings, an oversized loft, 2 gas fireplaces, and seasonal views of Deep Creek Lake! Open layout with hardwood floors and custom built-in bookshelves. Walk-out basement with 2nd living space and a pool table. Two stories of outdoor living with upper

    Jon Bell Railey Realty, Inc.

    329 Lemley Dr, Oakland, MD 21550
  • 366 Glendale Rd, Oakland, MD 21550
    366 Glendale Rd, Oakland, MD 21550
    366 Glendale Rd, Oakland, MD 21550
    /29

    $369,900 Sold Oct 17, 2025

    366 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1997

    Last Sold Summary

    • $266/SF
    • 152 Days On Market

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
    • 20160 Garrett Hwy Unit 502/702, Oakland, MD 21550
      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550
      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550
      /48

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550

      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550
  • 47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    47 Holy Cross Cir, Oakland, MD 21550
    /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
  • 1014 Madison St, Oakland, MD 21550
    1014 Madison St, Oakland, MD 21550
    1014 Madison St, Oakland, MD 21550
    /69

    $450,000 Sold Feb 26, 2025

    1014 Madison St, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,016 Sq Ft
    • Built 1988

    Last Sold Summary

    • $149/SF
    • 21 Days On Market

    Current Estimated Value $463,086

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1014 Madison St, Oakland, MD 21550
    • 305 Winding Trail Ln Unit 12A, Oakland, MD 21550
      305 Winding Trail Ln Unit 12A, Oakland, MD 21550
      305 Winding Trail Ln Unit 12A, Oakland, MD 21550
      /64

      Est $603,326 Not Listed For Sale

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

      305 Winding Trail Ln Unit 12A, Oakland, MD 21550

      305 Winding Trail Ln Unit 12A, Oakland, MD 21550
  • 180 Paradise Ridge Rd, Oakland, MD 21550
    180 Paradise Ridge Rd, Oakland, MD 21550
    180 Paradise Ridge Rd, Oakland, MD 21550
    /98

    $425,000

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

    180 Paradise Ridge Rd, Oakland, MD 21550

    Discover your perfect Deep Creek Lake getaway in the desirable Ridge at Paradise Point community, where breathtaking lake views and incredible amenities await! This charming entry level vacation home offers exclusive access to one of the most stunning shared lakefront areas, featuring a level shoreline, picnic pavilion, ample parking, and easy entry for kayaks, canoes, swimming, and

    Justin Liller Railey Realty, Inc.

    180 Paradise Ridge Rd, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    /20

    $237,000 Sold Oct 30, 2025

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550

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

    Last Sold Summary

    • $359/SF
    • 19 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    • 77 Racoon Dr, Oakland, MD 21550
      77 Racoon Dr, Oakland, MD 21550
      77 Racoon Dr, Oakland, MD 21550
      /24

      Est $185,259 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft

      77 Racoon Dr, Oakland, MD 21550

      77 Racoon Dr, Oakland, MD 21550
  • 433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    433 San Francisco St, Oakland, MD 21550
    /66

    $599,900

    • 6 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    433 San Francisco St, Oakland, MD 21550

    Fully renovated, fully loaded, and fully ready to be your Deep Creek Lake getaway! This 6-bedroom mountain retreat is packed with upgrades—New flooring, new septic, new hot tub, and a sleek modern kitchen with concrete counters, soft-close cabinets, and stainless steel appliances. One wood-burning fireplace for the cozy nights, one propane for the lazy mornings. Two and a half bathrooms, all

    Jon Bell Railey Realty, Inc.

    433 San Francisco St, Oakland, MD 21550
  • 297 Paradise Point Rd, Oakland, MD 21550
    297 Paradise Point Rd, Oakland, MD 21550
    297 Paradise Point Rd, Oakland, MD 21550
    /41

    $315,000 Sold Feb 14, 2025

    297 Paradise Point Rd, Oakland, MD 21550

    • 3 Beds
    • 4 Baths
    • 3,024 Sq Ft
    • Built 2005

    Last Sold Summary

    • $104/SF
    • 210 Days On Market

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    297 Paradise Point Rd, Oakland, MD 21550
    • 232 Jeffrey Ln Unit 33, Oakland, MD 21550
      232 Jeffrey Ln Unit 33, Oakland, MD 21550
      232 Jeffrey Ln Unit 33, Oakland, MD 21550
      /48

      Est $413,289 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,480 Sq Ft

      232 Jeffrey Ln Unit 33, Oakland, MD 21550

      232 Jeffrey Ln Unit 33, Oakland, MD 21550
  • 56 Bee Tree Ln, Oakland, MD 21550
    56 Bee Tree Ln, Oakland, MD 21550
    56 Bee Tree Ln, Oakland, MD 21550
    /139

    $2,845,000

    • 6 Beds
    • 7.5 Baths
    • 5,100 Sq Ft

    56 Bee Tree Ln, Oakland, MD 21550

    Unmatched EXCEPTIONAL Lakefront Living – 6 Bedrooms | 7.5 Baths | Tucked Among the Pines Discover a rare opportunity to own a true lakefront, lakeview gem—this 5,400 sq ft, 6-bedroom, 7.5-bath home that is nestled among tall pines on an exceptional lot that sits unusually close to the water’s edge. With peaceful views across a quiet cove and expansive open-water vistas from the oversized covered

    Susan Bell Railey Realty, Inc.

    56 Bee Tree Ln, Oakland, MD 21550
  • 1714 Mayhew Inn Rd, Oakland, MD 21550
    1714 Mayhew Inn Rd, Oakland, MD 21550
    1714 Mayhew Inn Rd, Oakland, MD 21550
    /23

    $119,000 Sold Jul 18, 2025

    1714 Mayhew Inn Rd, Oakland, MD 21550

    • Land
    • 7.5 Acres
    • $15,867 per Acre

    Last Sold Summary

    • 56 Days On Market

    Current Estimated Value $127,546

    Last Listing Agent Brian Homberg Taylor Made Deep Creek Vacations & Sales

    1714 Mayhew Inn Rd, Oakland, MD 21550
    • 157 Jeffrey Ln Unit 21B, Oakland, MD 21550
      157 Jeffrey Ln Unit 21B, Oakland, MD 21550
      157 Jeffrey Ln Unit 21B, Oakland, MD 21550
      /46

      Est $317,282 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 550 Sq Ft

      157 Jeffrey Ln Unit 21B, Oakland, MD 21550

      157 Jeffrey Ln Unit 21B, Oakland, MD 21550
  • 1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    1001 Sutter Ln, Oakland, MD 21550
    /93

    $829,000

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

    1001 Sutter Ln, Oakland, MD 21550

    Discover the ultimate mountain–lake getaway in this stunning 5BR Southern-style home on a private 2.4-acre wooded lot bordering Broadford Lake recreational area! Located just minutes from Deep Creek Lake and Wisp Resort, this magnificent property offers over 6,500 sq ft. and delivers unforgettable space, luxury, and privacy. Step inside to soaring cathedral ceilings, skylights, oak floors, and a

    Nina Beitzel Railey Realty, Inc.

    1001 Sutter Ln, Oakland, MD 21550
  • 939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    939 Glendale Rd, Oakland, MD 21550
    /44

    $589,000 Sold Sep 08, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft
    • Built 1995

    Last Sold Summary

    • $574/SF
    • 62 Days On Market

    Current Estimated Value $588,703

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
    • 20230 Garrett Hwy, Oakland, MD 21550
      20230 Garrett Hwy, Oakland, MD 21550
      20230 Garrett Hwy, Oakland, MD 21550
      /45

      Est $1,270,678 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,470 Sq Ft

      20230 Garrett Hwy, Oakland, MD 21550

      20230 Garrett Hwy, Oakland, MD 21550
  • 155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    155 Basswood Way, Oakland, MD 21550
    /51

    $674,900

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

    155 Basswood Way, Oakland, MD 21550

    Tucked just off Lakeshore Drive, this log home nails that luxury treehouse feel. Wrapped in fresh stain (09/24) and packed with updates - "Time Is On My Side" is dialed in for comfort. Five bedrooms, three baths, including a main-level primary. Inside, modern meets rustic with a sleek kitchen, new propane fireplace, and fresh paint throughout. The lower level offers a second living area, pool

    Michael Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
  • 306 Shady Acre Ln, Oakland, MD 21550
    306 Shady Acre Ln, Oakland, MD 21550
    306 Shady Acre Ln, Oakland, MD 21550
    /27

    $165,000 Sold Oct 30, 2025

    306 Shady Acre Ln, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1972

    Last Sold Summary

    • $72/SF
    • 2 Days On Market

    Last Listing Agent Brody Monahan Lake Homes Realty, LLC

    306 Shady Acre Ln, Oakland, MD 21550
    • 1368 Mountainview Dr, Oakland, MD 21550
      1368 Mountainview Dr, Oakland, MD 21550
      1368 Mountainview Dr, Oakland, MD 21550
      /76

      Est $835,504 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,830 Sq Ft

      1368 Mountainview Dr, Oakland, MD 21550

      1368 Mountainview Dr, Oakland, MD 21550
  • 340 Grandview Dr, Oakland, MD 21550
    340 Grandview Dr, Oakland, MD 21550
    340 Grandview Dr, Oakland, MD 21550
    /87

    $949,900

    • 6 Beds
    • 4 Baths
    • 2,536 Sq Ft

    340 Grandview Dr, Oakland, MD 21550

    Lake Access property overlooking Cherry Creek Cove in the coveted Mountainside community, at 2,536 square feet, this fully furnished retreat pairs modern comfort with timeless mountain style. Freshly updated from top to bottom, with a new roof and deck staining, every detail feels dialed in. A wall of glass and open layout connects bright gathering spaces with panoramic lake views that steal the

    Jon Bell Railey Realty, Inc.

    340 Grandview Dr, Oakland, MD 21550
  • 12 Laurel Ct, Oakland, MD 21550
    12 Laurel Ct, Oakland, MD 21550
    /2

    $55,000 Sold Feb 03, 2025

    12 Laurel Ct, Oakland, MD 21550

    • Land
    • 0.72 Acre
    • $76,389 per Acre

    Last Sold Summary

    • 44% Below List Price
    • 1,251 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    12 Laurel Ct, Oakland, MD 21550
    • 265 Winding Trail Ln Unit 9A, Oakland, MD 21550
      265 Winding Trail Ln Unit 9A, Oakland, MD 21550
      265 Winding Trail Ln Unit 9A, Oakland, MD 21550
      /63

      Est $650,360 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,200 Sq Ft

      265 Winding Trail Ln Unit 9A, Oakland, MD 21550

      265 Winding Trail Ln Unit 9A, Oakland, MD 21550
  • 220 Woodlands Hill Ln, Oakland, MD 21550
    220 Woodlands Hill Ln, Oakland, MD 21550
    220 Woodlands Hill Ln, Oakland, MD 21550
    /85

    $750,000

    • 5 Beds
    • 3 Baths
    • 2,660 Sq Ft

    220 Woodlands Hill Ln, Oakland, MD 21550

    Discover this spacious 5-bedroom, 3-bath chalet in The View community at Deep Creek Lake, offering three finished levels of comfortable living on over 2 acres of private woods!The foyer greets you with a beautiful built-in for hanging jackets, leave your ski boots on the convenient tile floor and proceed in to the main level, where two-story ceilings paneled in solid oak create an impressive

    Ana Dubin RE/MAX Realty Group

    220 Woodlands Hill Ln, Oakland, MD 21550
  • Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
    /20

    $17,000 Sold Nov 21, 2025

    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550

    • Land
    • 1.08 Acres
    • $15,741 per Acre

    Last Sold Summary

    • 24 Days On Market

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

    Lots 57 & 58 Black Oak Ln, Oakland, MD 21550
    • 300 Big Rock Cabin Rd, Oakland, MD 21550
      300 Big Rock Cabin Rd, Oakland, MD 21550
      300 Big Rock Cabin Rd, Oakland, MD 21550
      /47

      Est $415,551 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft

      300 Big Rock Cabin Rd, Oakland, MD 21550

      300 Big Rock Cabin Rd, Oakland, MD 21550
  • 77 Meadow Ct, Oakland, MD 21550
    77 Meadow Ct, Oakland, MD 21550
    77 Meadow Ct, Oakland, MD 21550
    /65

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft

    77 Meadow Ct, Oakland, MD 21550

    Lake Access Chalet at Deep Creek Lake – Featured on HGTV’s Lakefront Bargain Hunt, this property is quietly tucked away on over half an acre on rolling mountain pasture in the sought after Paradise Ridge community, and pairs rustic comfort with clean, modern lines. Warm wood tones, vaulted ceilings, and a two-story stone fireplace anchor the main level. Open kitchen and dining area flow into a

    Jon Bell Railey Realty, Inc.

    77 Meadow Ct, Oakland, MD 21550
  • 590 S Blakeslee Rd, Oakland, MD 21550
    590 S Blakeslee Rd, Oakland, MD 21550
    590 S Blakeslee Rd, Oakland, MD 21550
    /64

    $1,150,000 Sold Oct 24, 2025

    590 S Blakeslee Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 3,071 Sq Ft
    • Built 2000

    Last Sold Summary

    • $374/SF
    • 102 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    590 S Blakeslee Rd, Oakland, MD 21550

Showing Results 41 - 80, Page 2 of 18

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