12,259

Homes in ZIP Code 21550

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    • /24

      Est $171,041 Not Listed For Sale

      77 Racoon Dr, Oakland, MD 21550

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1976
      77 Racoon Dr, Oakland, MD 21550

      Last Sold Summary

      • 5% Below List Price
      • $221/SF
      • 32 Days On Market

      Last Sold Price $180,000

      Last Listing Agent Bob Orr 1 Real Estate Source LLC

  • /150

    $3,690,000 Under Contract

    • 6 Beds
    • 5.5 Baths
    • 4,354 Sq Ft

    282 McComas Beach Terrace, Oakland, MD 21550

    Discover The Birch Bower, a rare architect-designed lakefront sanctuary offering 600 feet of private shoreline on Deep Creek Lake. Completed in 2021, this 6-bedroom, 5.5-bath residence exemplifies modern luxury, combining meticulous design, serene natural surroundings, and proven short-term rental performance. Turnkey consideration is available with a compelling offer. This extraordinary

    Morgan Boyer Hunt Country Sotheby's International Realty

    282 McComas Beach Terrace, Oakland, MD 21550
  • /49

    $640,000 Sold Jan 09, 2026

    750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541

    • 3 Beds
    • 3.5 Baths
    • 3,096 Sq Ft
    • Built 2004

    Last Sold Summary

    • $207/SF
    • 38 Days On Market

    Current Estimated Value $662,714

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

    750 Wisp Mountain Rd Unit B, Mc Henry, MD 21541
    • /72

      Est $822,683 Not Listed For Sale

      46 Kendall Camp Cir, McHenry, MD 21541

      • 4 Beds
      • 4 Baths
      • 3,007 Sq Ft
      • Built 2008
      46 Kendall Camp Cir, McHenry, MD 21541

      Last Sold Summary

      • 6% Above List Price
      • $258/SF
      • 48 Days On Market

      Last Sold Price $775,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /61

    $379,000

    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    1167 Tall Oaks Dr, Oakland, MD 21550

    Picture perfect log cabin on 11 private, wooded acres in the gated Timbers on the Yough community featuring Youghiogheny River access. This inviting home features a metal roof, spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. The primary bath offers dual sinks, an oversized soaking tub, dual shower heads and radiant floor heat!Recent updates

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, 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 $836,884

    Last Listing Agent Jon Bell Railey Realty, Inc.

    158 Silver Tree Ln, Oakland, MD 21550
    • /45

      Est $1,221,618 Not Listed For Sale

      20230 Garrett Hwy, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,470 Sq Ft
      • Built 1998
      20230 Garrett Hwy, Oakland, MD 21550

      Last Sold Summary

      • 6% Below List Price
      • $526/SF
      • 13 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Russell Bounds 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
  • /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
    • /76

      Est $807,346 Not Listed For Sale

      1368 Mountainview Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 2,830 Sq Ft
      • Built 1992
      1368 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 4% Above List Price
      • $274/SF
      • 59 Days On Market

      Last Sold Price $775,000

      Last Listing Agent Rich Orr 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
  • /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
    • /63

      Est $605,978 Not Listed For Sale

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

      • 5 Beds
      • 4.5 Baths
      • 4,200 Sq Ft
      • Built 2009
      265 Winding Trail Ln Unit 9A, Oakland, MD 21550

      Last Sold Summary

      • 1% Above List Price
      • $143/SF
      • 12 Days On Market

      Last Sold Price $599,000

      Last Listing Agent Bill Weissgerber Railey Realty, Inc.

  • /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
  • /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 $154,337

    Last Listing Agent Jon Bell Railey Realty, Inc.

    15 D St, Oakland, MD 21550
    • /47

      Est $398,935 Not Listed For Sale

      300 Big Rock Cabin Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft
      • Built 1999
      300 Big Rock Cabin Rd, Oakland, MD 21550

      Last Sold Summary

      • 17% Above List Price
      • $280/SF
      • 82 Days On Market

      Last Sold Price $340,000

      Last Listing Agent Lana Roby The KW Collective

  • /62

    $314,000

    • 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
  • /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
    • /50

      Est $607,133 Not Listed For Sale

      208 Upper Penn Point Dr, Oakland, MD 21550

      • 4 Beds
      • 2 Baths
      • 2,086 Sq Ft
      • Built 1975
      208 Upper Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 48% Above List Price
      • $197/SF
      • 5 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • /141

    $1,590,000

    • 7 Beds
    • 5.5 Baths
    • 5,200 Sq Ft

    188 Highline Dr, Mc Henry, MD 21541

    Ski-In Ski-Out 7/5.5 Views Views Views! Welcome to your dream mountain retreat at Wisp Resort! Rare opportunity to own a ski-in/ski-out access home with dramatic 12-mile lake views from all three floors. New appliance and investment upgrades throughout the home as of July 2025. Your near-zero maintenance DREAM: cedar shakes boasting upwards of 50-years longevity, ultra durable hardy board siding,

    Elizabeth Ware Railey Realty, Inc.

    188 Highline Dr, Mc Henry, MD 21541
  • /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
    • /30

      Est $384,517 Not Listed For Sale

      8081 Oakland Sang Run Rd, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 1,867 Sq Ft
      • Built 1941
      8081 Oakland Sang Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 26% Above List Price
      • $163/SF
      • 122 Days On Market

      Last Sold Price $305,000

      Last Listing Agent ANGELA BOSLEY Taylor Made Deep Creek Real Estate

  • /67

    $799,900 Pending

    • 5 Beds
    • 4.5 Baths
    • 2,964 Sq Ft

    116 Chimney Rock Ln, McHenry, MD 21541

    Tucked inside a gated ridgetop community beside Lodestone Golf, this new-build chalet keeps it clean and classic. Eight-inch logs frame the vaulted living room, anchored by a two-story stone fireplace and wide plank floors. The kitchen cuts sharp with granite, hardwood cabinetry, and stainless appliances. 5 bedrooms, 4.5 baths, and nearly 3,000 square feet stretch across three levels, including a

    Jon Bell Railey Realty, Inc.

    116 Chimney Rock Ln, McHenry, MD 21541
  • /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
    • /32

      Est $440,173 Not Listed For Sale

      175 Whitetail Ct Unit 36, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 2006
      175 Whitetail Ct Unit 36, Oakland, MD 21550

      Last Sold Summary

      • 1% Below List Price
      • $386/SF
      • 6 Days On Market

      Last Sold Price $445,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /73

    $1,599,900 New Construction

    • 6 Beds
    • 6.5 Baths
    • 4,484 Sq Ft

    110 Wisp Adventure Rd, Mc Henry, MD 21541

    Luxury cedar chalet in the heart of Deep Creek Lake. This custom lodge sits beside the ASCI whitewater course, placing you in the center of Garrett county’s year-round outdoor scene and just minutes from local shops and restaurants. The community trail gives direct access to Wisp on one side, and Fork Run’s 550-acre nature preserve on the other. Finished in 2022, the home was crafted for

    Jon Bell Railey Realty, Inc.

    110 Wisp Adventure Rd, Mc Henry, MD 21541
  • /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 $338,300

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Real Estate

    135 Jeffrey Ln Unit 19D, Oakland, MD 21550
    • /12

      Est $91,788 Not Listed For Sale

      6 Cedar Ln, Oakland, MD 21550

      6 Cedar Ln, Oakland, MD 21550

      Last Sold Summary

      • 818% Above List Price
      • 171 Days On Market

      Last Sold Price $10,000

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /66

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 3,566 Sq Ft

    110 Highline Dr, Mc Henry, MD 21541

    Take a look at this awesome chalet style home with stunning lake and mountain views. Featuring 4 bedrooms and 3.5 baths, this home is perfect for entertaining. This ski-in and ski-out property is located in the highly coveted Highline community that sits very close to the Wisp Ski Area and ASCI. Two fireplaces, one in the main level living room and one in the lower level recreation room. Main

    Kevin Liller Railey Realty, Inc.

    110 Highline Dr, Mc Henry, MD 21541
  • /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
    • /11

      Est $103,942 Not Listed For Sale

      450 Deer Run Rd, Piney Mtn, MD 21550

      450 Deer Run Rd, Piney Mtn, MD 21550

      Last Sold Summary

      • 4% Above List Price
      • 257 Days On Market

      Last Sold Price $100,000

      Last Listing Agent laura Flynn 1 Real Estate Source LLC

  • /93

    $799,000

    • 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
  • /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
    • /15

      Est $87,377 Not Listed For Sale

      149 Gobbler Run Rd, Oakland, MD 21550

      • Built 2006
      149 Gobbler Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 157% Above List Price
      • $53/SF
      • 18 Days On Market

      Last Sold Price $34,000

      Last Listing Agent Sherry Nally Berkshire Hathaway HomeServices Homesale Realty

  • /104

    $1,350,000

    • 5 Beds
    • 5.5 Baths
    • 3,696 Sq Ft

    615 Sandy Shores Rd, Mc Henry, MD 21541

    This stunning log home near Wisp Resort offers a luxurious retreat with seasonal views, an indoor pool house and plenty of space for indoor and outdoor living. Five-bedroom, five-and-a-half-bath masterpiece is designed for both relaxation and entertainment. Step inside to discover an open floor plan adorned with exposed beams and rich wood floors. The gourmet kitchen, equipped with high-end

    Kellyann Green Railey Realty, Inc.

    615 Sandy Shores Rd, Mc Henry, MD 21541
  • /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
    • /98

      Est $488,433 Not Listed For Sale

      1506 Broadford Rd, Oakland, MD 21550

      • 5 Beds
      • 3 Baths
      • 2,048 Sq Ft
      • Built 2023
      1506 Broadford Rd, Oakland, MD 21550

      Last Sold Summary

      • 3% Above List Price
      • $232/SF
      • 36 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Justin Liller Railey Realty, Inc.

  • /62

    $379,000

    • 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
  • /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 $160,411

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

    3821 Underwood Rd, Oakland, MD 21550
    • /4

      Est $37,957 Not Listed For Sale

      812 Winter Place, Oakland, MD 21550

      812 Winter Place, Oakland, MD 21550

      Last Sold Summary

      • 5% Below List Price
      • 3 Days On Market

      Last Sold Price $40,000

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

Showing Results 81 - 120, Page 3 of 18

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