12,226

Homes in ZIP Code 21550

Section Image
    • 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
  • 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
    • 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
  • 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
    • 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
  • 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
    • 46 Kendall Camp Cir, McHenry, MD 21541
      46 Kendall Camp Cir, McHenry, MD 21541
      46 Kendall Camp Cir, McHenry, MD 21541
      /72

      Est $876,294 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,007 Sq Ft

      46 Kendall Camp Cir, McHenry, MD 21541

      46 Kendall Camp Cir, McHenry, MD 21541
  • 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
  • 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
    • 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
  • 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
  • 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
    • 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
  • 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
  • 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
    • 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
  • 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
  • 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 $839,144

    Last Listing Agent Jon Bell Railey Realty, Inc.

    158 Silver Tree 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
  • 16 Lemley Dr, Oakland, MD 21550
    16 Lemley Dr, Oakland, MD 21550
    16 Lemley Dr, Oakland, MD 21550
    /62

    $399,000

    • 4 Beds
    • 2.5 Baths
    • 1,104 Sq Ft

    16 Lemley Dr, Oakland, MD 21550

    Nestled in the serene community of Roman Nose Spa at Deep Creek Lake, this charming contemporary home offers a perfect blend of comfort and style and makes a great basecamp. With 4 beds and 2 1/2 baths and a thoughtfully designed living space, ideal for both relaxation and entertaining. Enjoy breathtaking views of Deep Creek Lake and the surrounding mountains from your backyard, where outdoor

    Andrew Eiswert Railey Realty, Inc.

    16 Lemley Dr, 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
    • 208 Upper Penn Point Dr, Oakland, MD 21550
      208 Upper Penn Point Dr, Oakland, MD 21550
      208 Upper Penn Point Dr, Oakland, MD 21550
      /50

      Est $635,024 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,086 Sq Ft

      208 Upper Penn Point Dr, Oakland, MD 21550

      208 Upper Penn Point Dr, Oakland, MD 21550
  • 105 Mountain Overlook Ct, McHenry, MD 21550
    105 Mountain Overlook Ct, McHenry, MD 21550
    105 Mountain Overlook Ct, McHenry, MD 21550
    /109

    $759,000

    • 3 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    105 Mountain Overlook Ct, McHenry, MD 21550

    Luxury Mountaintop Ski Chalet with scenic Deep Creek Lake Access for year-round enjoyment. Just minutes from Wisp's ski slopes and ASCI Whitewater, this fantastic location is ideal for exciting summer adventures and winter skiing with effortless connections to the Ski Lodge, Wisp's easy-access mountaintop parking area, lift tickets, on-site community amenities, and everything you need.

    Steven Ritchie Railey Realty, Inc.

    105 Mountain Overlook Ct, McHenry, 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
    • 8081 Oakland Sang Run Rd, Oakland, MD 21550
      8081 Oakland Sang Run Rd, Oakland, MD 21550
      8081 Oakland Sang Run Rd, Oakland, MD 21550
      /30

      Est $388,757 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,867 Sq Ft

      8081 Oakland Sang Run Rd, Oakland, MD 21550

      8081 Oakland Sang Run Rd, Oakland, MD 21550
  • 439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    439 Paradise Heights, Oakland, MD 21550
    /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
  • 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 $155,222

    Last Listing Agent Jon Bell Railey Realty, Inc.

    15 D St, Oakland, MD 21550
    • 175 Whitetail Ct Unit 36, Oakland, MD 21550
      175 Whitetail Ct Unit 36, Oakland, MD 21550
      175 Whitetail Ct Unit 36, Oakland, MD 21550
      /32

      Est $427,500 Not Listed For Sale

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

      175 Whitetail Ct Unit 36, Oakland, MD 21550

      175 Whitetail Ct Unit 36, Oakland, MD 21550
  • 35 Blue Mountain View, McHenry, MD 21541
    35 Blue Mountain View, McHenry, MD 21541
    35 Blue Mountain View, McHenry, MD 21541
    /52

    $849,900 Under Contract

    • 5 Beds
    • 4.5 Baths
    • 2,832 Sq Ft

    35 Blue Mountain View, McHenry, MD 21541

    Looking for a place to slow down and relax? Finished in 2022, This 5-bedroom, 4.5-bath log home, has everything you need! Tucked inside the Lodestone Golf Course, "Blue Mountain Cabin" blends rustic charm with modern comfort. Inside, the open floorplan stitches the home together seamlessly. Hardwood floors, tongue and groove, and exposed timber accents run throughout. The great room features a

    Michael Fenton Railey Realty, Inc.

    35 Blue Mountain View, McHenry, MD 21541
  • 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

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    58 Glendale Woods Rd, Oakland, MD 21550
    • 6 Cedar Ln, Oakland, MD 21550
      6 Cedar Ln, Oakland, MD 21550
      6 Cedar Ln, Oakland, MD 21550
      /12

      Est $94,780 Not Listed For Sale

      6 Cedar Ln, Oakland, MD 21550

      6 Cedar Ln, Oakland, MD 21550
  • 3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    3084 Lake Shore Dr, Oakland, MD 21550
    /71

    $599,900 Pending

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

    3084 Lake Shore Dr, Oakland, MD 21550

    Cozy Retreat on Lake Shore Drive! This 4-bed, 3-bath cottage was built for relaxation, entertainment, and making memories. The open-concept living area keeps everyone connected, while the expansive deck and hot tub allow you to take the fun outside. Upstairs, the primary suite steals the show! A personal fireplace with a wall of glass to let in the light and soak in the views. Three more bedrooms

    Jon Bell Railey Realty, Inc.

    3084 Lake Shore 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
    • 450 Deer Run Rd, Piney Mtn, MD 21550
      450 Deer Run Rd, Piney Mtn, MD 21550
      450 Deer Run Rd, Piney Mtn, MD 21550
      /11

      Est $104,829 Not Listed For Sale

      450 Deer Run Rd, Piney Mtn, MD 21550

      450 Deer Run Rd, Piney Mtn, MD 21550
  • 336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    336 Paradise Heights, Oakland, MD 21550
    /94

    $1,499,000

    • 5 Beds
    • 3 Baths
    • 2,826 Sq Ft

    336 Paradise Heights, Oakland, MD 21550

    Architecturally unique, private and spacious lakefront home with a perfect central location! Step into a home that blends striking architectural design with the best of lake living. The living room showcases a dramatic wall of glass and a floor-to-ceiling stone fireplace, while a large glass-walled rec room on the lower level offers another light-filled space to relax or entertain. This

    Susan Bell Railey Realty, Inc.

    336 Paradise Heights, 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
    • 0 Overlook Dr, Oakland, MD 21550
      0 Overlook Dr, Oakland, MD 21550
      0 Overlook Dr, Oakland, MD 21550
      /13

      Not Listed For Sale

      0 Overlook Dr, Oakland, MD 21550

      0 Overlook Dr, Oakland, MD 21550

Showing Results 81 - 120, Page 3 of 18

Maryland Garrett County Oakland 21550

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