10,731

Oakland, MD Homes

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    • 6 Cedar Ln, Oakland, MD 21550
      6 Cedar Ln, Oakland, MD 21550
      6 Cedar Ln, Oakland, MD 21550
      /12

      Est $94,737 Not Listed For Sale

      6 Cedar Ln, Oakland, MD 21550

      6 Cedar Ln, Oakland, MD 21550
  • 328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    328 Stool Rock Rd, Oakland, MD 21550
    /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
  • 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
    • 149 Gobbler Run Rd, Oakland, MD 21550
      149 Gobbler Run Rd, Oakland, MD 21550
      149 Gobbler Run Rd, Oakland, MD 21550
      /15

      Est $37,129 Not Listed For Sale

      149 Gobbler Run Rd, Oakland, MD 21550

      149 Gobbler Run Rd, Oakland, MD 21550
  • 329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    329 Lemley Dr, Oakland, MD 21550
    /81

    $750,000 Pending

    • 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
  • 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

    Current Estimated Value $1,131,451

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

    590 S Blakeslee Rd, Oakland, MD 21550
    • 1506 Broadford Rd, Oakland, MD 21550
      1506 Broadford Rd, Oakland, MD 21550
      1506 Broadford Rd, Oakland, MD 21550
      /98

      Est $490,216 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,048 Sq Ft

      1506 Broadford Rd, Oakland, MD 21550

      1506 Broadford Rd, 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
  • 9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    /4

    $140,000 Sold Mar 17, 2025

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

    • Land
    • 9.2 Acres
    • $15,217 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    9.3 +/- Acres Upperman Rd, Oakland, MD 21550
    • 812 Winter Place, Oakland, MD 21550
      812 Winter Place, Oakland, MD 21550
      812 Winter Place, Oakland, MD 21550
      /4

      Est $40,094 Not Listed For Sale

      812 Winter Place, Oakland, MD 21550

      812 Winter Place, 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 Under Contract

    • 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
  • 158 Silver Tree Ln, Oakland, MD 21550
    158 Silver Tree Ln, Oakland, MD 21550
    158 Silver Tree Ln, Oakland, MD 21550
    /49

    $790,000 Sold May 09, 2025

    158 Silver Tree Ln, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 2,250 Sq Ft
    • Built 2003

    Last Sold Summary

    • $351/SF
    • 79 Days On Market

    Current Estimated Value $871,491

    Last Listing Agent Jon Bell Railey Realty, Inc.

    158 Silver Tree Ln, Oakland, MD 21550
    • 51 Stag Run, Oakland, MD 21550
      51 Stag Run, Oakland, MD 21550
      51 Stag Run, Oakland, MD 21550
      /26

      Not Listed For Sale

      51 Stag Run, Oakland, MD 21550

      51 Stag Run, 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
  • 20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    /39

    $450,000 Sold Nov 10, 2025

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1972

    Last Sold Summary

    • $340/SF
    • 179 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit D308/408, Oakland, MD 21550
    • 94 Lehman Ln Unit 31, Oakland, MD 21550
      94 Lehman Ln Unit 31, Oakland, MD 21550
      94 Lehman Ln Unit 31, Oakland, MD 21550
      /39

      Est $701,977 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,340 Sq Ft

      94 Lehman Ln Unit 31, Oakland, MD 21550

      94 Lehman Ln Unit 31, 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
  • 0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    0 Maryland Hwy Unit MDGA2006436, Oakland, MD 21550
    0 Maryland Hwy Unit MDGA2006436, 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
    • 189 Maple Del Ln, Oakland, MD 21550
      189 Maple Del Ln, Oakland, MD 21550
      189 Maple Del Ln, Oakland, MD 21550
      /62

      Est $539,097 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,260 Sq Ft

      189 Maple Del Ln, Oakland, MD 21550

      189 Maple Del Ln, 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
  • 15 D St, Oakland, MD 21550
    15 D St, Oakland, MD 21550
    15 D St, 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 $155,429

    Last Listing Agent Jon Bell Railey Realty, Inc.

    15 D St, Oakland, MD 21550
    • 319 Basswood Way Unit LOT 21, Oakland, MD 21550
      319 Basswood Way Unit LOT 21, Oakland, MD 21550
      319 Basswood Way Unit LOT 21, Oakland, MD 21550
      /32

      Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,784 Sq Ft

      319 Basswood Way Unit LOT 21, Oakland, MD 21550

      319 Basswood Way Unit LOT 21, Oakland, MD 21550
  • 1019 Lake Shore Dr, Oakland, MD 21550
    1019 Lake Shore Dr, Oakland, MD 21550
    1019 Lake Shore Dr, Oakland, MD 21550
    /75

    $1,749,000

    • 4 Beds
    • 4.5 Baths
    • 2,605 Sq Ft

    1019 Lake Shore Dr, Oakland, MD 21550

    Tucked among the trees, Blue Spruce offers a perfect blend of modern comfort and serene natural beauty. This recently remodeled 4-bedroom, 4 and a half bathroom home invites you to relax, recharge, and reconnect with nature. With each bedroom offering an ensuite bathroom plus a half bath near the kitchen, this home was designed for comfort. Step inside to discover thoughtful updates throughout,

    Rachel Bruch Railey Realty, Inc.

    1019 Lake Shore Dr, Oakland, MD 21550
  • 58 Glendale Woods Rd, Oakland, MD 21550
    58 Glendale Woods Rd, Oakland, MD 21550
    58 Glendale Woods Rd, 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 $715,521

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    58 Glendale Woods Rd, Oakland, MD 21550
    • 48 Skippers Estates Dr, Oakland, MD 21550
      48 Skippers Estates Dr, Oakland, MD 21550
      48 Skippers Estates Dr, Oakland, MD 21550
      /61

      Est $615,853 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,454 Sq Ft

      48 Skippers Estates Dr, Oakland, MD 21550

      48 Skippers Estates 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 Pending

    • 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
  • 0 Coolidge Ave, Oakland, MD 21550
    0 Coolidge Ave, Oakland, MD 21550
    0 Coolidge Ave, 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 Vacations & Sales

    0 Coolidge Ave, Oakland, MD 21550
    • 36 Cherokee Ln, Oakland, MD 21550
      36 Cherokee Ln, Oakland, MD 21550
      36 Cherokee Ln, Oakland, MD 21550
      /62

      Est $210,595 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 864 Sq Ft

      36 Cherokee Ln, Oakland, MD 21550

      36 Cherokee Ln, 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
  • 45 Village Dr Unit 4, Oakland, MD 21550
    45 Village Dr Unit 4, Oakland, MD 21550
    45 Village Dr Unit 4, 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

    Last Listing Agent Ana Dubin RE/MAX Realty Group

    45 Village Dr Unit 4, Oakland, MD 21550
    • 3365 Mayhew Inn Rd, Oakland, MD 21550
      3365 Mayhew Inn Rd, Oakland, MD 21550
      3365 Mayhew Inn Rd, Oakland, MD 21550
      /68

      Est $749,043 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,158 Sq Ft

      3365 Mayhew Inn Rd, Oakland, MD 21550

      3365 Mayhew Inn Rd, Oakland, MD 21550
  • 126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    /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
  • 135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    135 Jeffrey Ln Unit 19D, 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 $328,341

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

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

      Not Listed For Sale

      135 Tarn Dr, Oakland, MD 21550

      135 Tarn Dr, Oakland, MD 21550
  • 1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    1875 Pysell Crosscut Rd, Oakland, MD 21550
    /67

    $769,000

    • 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 Vacations & Sales

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • Lots 22 & 23 Black Oak Ln, Oakland, MD 21550
    Lots 22 & 23 Black Oak Ln, 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
    • 17 Old Chestnut Dr, Oakland, MD 21550
      17 Old Chestnut Dr, Oakland, MD 21550
      17 Old Chestnut Dr, Oakland, MD 21550
      /49

      Est $926,918 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 966 Sq Ft

      17 Old Chestnut Dr, Oakland, MD 21550

      17 Old Chestnut Dr, Oakland, MD 21550
  • 531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    /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
  • 272 McComas Beach Terrace, Oakland, MD 21550
    272 McComas Beach Terrace, Oakland, MD 21550
    272 McComas Beach Terrace, 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

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    272 McComas Beach Terrace, Oakland, MD 21550
    • 503 Southern Pines Dr, Oakland, MD 21550
      503 Southern Pines Dr, Oakland, MD 21550
      503 Southern Pines Dr, Oakland, MD 21550
      /10

      Est $133,000 Not Listed For Sale

      503 Southern Pines Dr, Oakland, MD 21550

      503 Southern Pines Dr, Oakland, MD 21550

Showing Results 81 - 120, Page 3 of 18

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