12,296

Homes in ZIP Code 21550

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  • /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 $282,333

    Last Listing Agent Thomas Long Railey Realty, Inc.

    29 Sloan Tract Rd, Oakland, MD 21550
    • /64

      Est $606,086

      Not Listed For Sale

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

      • 5 Beds
      • 4.5 Baths
      • 3,300 Sq Ft
      • Built 2009
      305 Winding Trail Ln Unit 12A, Oakland, MD 21550

      Last Sold Summary

      • 529 Days On Market

  • /99

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    211 High Point Ridge Rd, Oakland, MD 21550

    Once in a lifetime opportunity to own one of Maryland’s most distinctive homes. Built in 2019, this fully custom modern home is located on the highest elevation building lot in the state of Maryland, making it the highest elevation home in the state at over 3300 feet above sea level. Designed to take full advantage of the setting, the property offers incredible panoramic views stretching across

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 443-3345

    211 High Point Ridge 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

    Current Estimated Value $367,864

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
    • /24

      Est $168,646

      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

      • 32 Days On Market

  • /2

    $200,000

    • Land
    • 3.15 Acres
    • $63,492 per Acre

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550

    3.15 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities. No HOA.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 226-3852

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
  • /4

    $250,000

    Sold Feb 05, 2026

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550

    • Land
    • 45.7 Acres
    • $5,470 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 0 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    0 Upperman Rd Unit MDGA2010944, Oakland, MD 21550
    • /72

      Est $832,553

      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

      • 48 Days On Market

  • /23

    $69,000

    • Land
    • 24,829 Sq Ft
    • $121,053 per Acre

    Lot 79 Sundance Way, McHenry, MD 21541

    0.57 acre mountaintop homesite at Deep Creek Lake! Competitively priced and ready to build. This property offers location just minutes from Wisp, ASCI and all of Deep Creek Lake's amenities with a private feel towards the end of the cup-de-sac. Public water and sewer taps are paid, providing several thousand dollars in savings for a purchaser. Electricity is to site. The only thing missing is

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 650-9125

    Lot 79 Sundance Way, McHenry, MD 21541
  • /2

    $20,000

    Sold Mar 03, 2026

    0 N Hammond St, Oakland, MD 21550

    • Land
    • 20,908 Sq Ft
    • $41,667 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 6 Days On Market

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

    0 N Hammond St, Oakland, MD 21550
    • /66

      Est $560,589

      Not Listed For Sale

      8 Winding Trail Ln Unit 1, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 3,300 Sq Ft
      • Built 2006
      8 Winding Trail Ln Unit 1, Oakland, MD 21550

      Last Sold Summary

      • 174 Days On Market

  • /27

    $309,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H706, Oakland, MD 21550

    Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a vacation retreat, year-round getaway, or

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 266-9392

    20160 Garrett Hwy Unit H706, 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

    Current Estimated Value $241,371

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

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    • /45

      Est $1,262,597

      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

      • 13 Days On Market

  • /12

    $105,000

    • Land
    • 29,185 Sq Ft
    • $156,716 per Acre

    110 Sundance Way, Mc Henry, MD 21541

    Whether you're into Boating, Skiing or Golfing all three and so many other amenities are within minutes of this beautiful lot on the ridge of Marsh Mountain overlooking the McHenry cove of Deep Creek Lake. Situated just half a mile from Wisp Resort ski slopes & Ropes course & mountain coaster, snow tubing and White water rafting at one of the few man made white water courses in the United States.

    Agent Photo

    Dale Carpenter

    Railey Realty, Inc.

    (240) 443-3324

    110 Sundance Way, Mc Henry, MD 21541
  • /35

    $165,000

    Sold Jun 15, 2026

    505 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,632 Sq Ft
    • Built 1950

    Last Sold Summary

    • $101/SF
    • 3 Days On Market

    Current Estimated Value $163,334

    Last Listing Agent Justin Liller Railey Realty, Inc.

    505 Shenandoah Ave, Oakland, MD 21550
    • /47

      Est $396,373

      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

      • 82 Days On Market

  • /16

    $35,000

    $15K PRICE DROP
    • Land
    • 26,136 Sq Ft
    • $58,333 per Acre

    Lot 2 Cedar Ln, Oakland, MD 21550

    Cleared, perc approved and ready to build! Lot 2 Cedar Lane sits on a 0.6 acre level lot at the beginning of Cedar Lane which sits close to the community center, tennis courts, pavilion and only a short ride to Muddy Creek and the access to Youghiogheny River! Youghiogheny Mountain Resort offers over 50 miles of trails for riding ATV’s, side by sides, fishing at Muddy Creek and much more! The

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 594-8377

    Lot 2 Cedar Ln, 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

    Last Listing Agent Brian Homberg Taylor-Made Deep Creek Real Estate, LLC

    1714 Mayhew Inn Rd, Oakland, MD 21550
    • /50

      Est $670,628

      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

      • 5 Days On Market

  • /2

    $250,000

    • Land
    • 5 Acres
    • $50,000 per Acre

    0 5 Acres Lake Shore Dr, Oakland, MD 21550

    5.0 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 802-8705

    0 5 Acres Lake Shore Dr, Oakland, MD 21550
  • /27

    $225,000

    Sold Feb 19, 2026

    1570 Garrett Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft
    • Built 1984

    Last Sold Summary

    • $160/SF
    • 122 Days On Market

    Current Estimated Value $232,240

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

    1570 Garrett Rd, Oakland, MD 21550
    • /69

      Est $539,707

      Not Listed For Sale

      180 Winding Trail Ln Unit 5A, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 3,000 Sq Ft
      • Built 2006
      180 Winding Trail Ln Unit 5A, Oakland, MD 21550

      Last Sold Summary

      • 277 Days On Market

  • /21

    $22,500

    • Land
    • 25,264 Sq Ft
    • $38,793 per Acre

    Lot 13 Dogwood Dr, Oakland, MD 21550

    Discover the perfect blend of privacy and potential with these two adjoining lots located in the Youghiogheny Mountain Resort community. Lot 13 Dogwood Drive offers 0.58 wooded acres of mountain serenity. Lot 13 is approved for a sand mound septic system, making it an ideal site for your future mountain cabin or getaway retreat. The community offers gated access, over 50 miles of community roads

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 875-5545

    Lot 13 Dogwood Dr, 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 $581,693

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
    • /30

      Est $382,351

      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

      • 122 Days On Market

  • /56

    $1,200,000

    • 4 Beds
    • 4.5 Baths
    • 2,656 Sq Ft

    122 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to mountain living at its finest. Nestled on 6.89 private acres, 122 Woodlands Hill Lane offers the perfect blend of seclusion, space, and comfort in one of Garrett County’s most desirable settings. This impressive 4-bedroom, 4.5-bath home features approximately 4,000 square feet of living space designed for gathering, relaxing, and enjoying the beauty of Western Maryland. The home sits

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 290-8978

    122 Woodlands Hill 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

    Current Estimated Value $183,521

    Last Listing Agent Brody Monahan Lake Homes Realty, LLC

    306 Shady Acre Ln, Oakland, MD 21550
    • /55

      Est $525,011

      Not Listed For Sale

      180 Roman Ridge Rd Unit 18, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 2,608 Sq Ft
      • Built 2005
      180 Roman Ridge Rd Unit 18, Oakland, MD 21550

      Last Sold Summary

      • 232 Days On Market

  • /14

    $165,000

    • Land
    • 18,295 Sq Ft
    • $392,857 per Acre

    Lot 5 Lodestone Way, Sang Run, MD 21541

    Premium lot on the Lodestone Golf Course tucked away in a private nook with just a handful of homes, just minutes from everything there is to love at Deep Creek Lake, sitting on a cul-de-sac! Bring your own builder and floorplan, or use ours! This lot has public water and sewer hookups! High-speed cable/internet! Propane is available for cooking or heat if you'd like! This lot is adjacent to the

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 872-0656

    Lot 5 Lodestone Way, Sang Run, MD 21541
  • /5

    $34,500

    Sold Jan 15, 2026

    62 Crosby Dr, Oakland, MD 21550

    • Land
    • 27,442 Sq Ft
    • $54,762 per Acre

    Last Sold Summary

    • 73% Above List Price
    • 2,385 Days On Market

    Last Listing Agent Jon Bell Railey Realty, Inc.

    62 Crosby Dr, Oakland, MD 21550
    • /26

      Est $386,690

      Not Listed For Sale

      142 Lemley Dr Unit I, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • Built 1987
      142 Lemley Dr Unit I, Oakland, MD 21550

      Last Sold Summary

      • 146 Days On Market

  • /31

    $124,000

    $6K PRICE DROP
    • Land
    • 2.1 Acres
    • $59,048 per Acre

    Lot 20 Paradise Ridge Rd, Oakland, MD 21550

    Discover the perfect setting for your mountain retreat in the Paradise Ridge community at Deep Creek Lake. This beautiful 2.10 acre wooded lot is tucked away on a quiet cul-de-sac, offering privacy, natural surroundings, and a peaceful atmosphere. The property has already been approved for a conventional septic system, making it an ideal choice for building your dream home or vacation getaway.

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 526-7577

    Lot 20 Paradise Ridge Rd, 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
    • /11

      Est $113,532

      Not Listed For Sale

      450 Deer Run Rd, Piney Mtn, MD 21550

      450 Deer Run Rd, Piney Mtn, MD 21550

      Last Sold Summary

      • 257 Days On Market

  • /57

    $275,000

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,913 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakland, MD. Inviting curb appeal with stone exterior and mature landscaping sets the tone. Step inside to a bright and spacious main level featuring gleaming hardwood floors, a large eat-in kitchen with ample cabinetry, and an open living area perfect for gatherings. Enjoy three main-level bedrooms and a full

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 792-8710

    127 S Oakhall Dr, 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 $1,121,873

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

    590 S Blakeslee Rd, Oakland, MD 21550
    • /15

      Est $91,712

      Not Listed For Sale

      149 Gobbler Run Rd, Oakland, MD 21550

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

      Last Sold Summary

      • 18 Days On Market

  • /5

    $119,000

    • Land
    • 27,878 Sq Ft
    • $185,938 per Acre

    34 Blue Mountain View, McHenry, MD 21541

    Discover the perfect setting for your future mountain retreat in the Biltmore at Lodestone community! Lot 34 Blue Mountain View in McHenry offers a desirable building site located just off the cart path between Hole #5 and Hole #6 of the Lodestone Golf Course close enough to enjoy the golf course lifestyle, but hopefully far enough from anyone’s slice. This homesite provides peaceful mountain

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    (240) 634-9565

    34 Blue Mountain View, McHenry, MD 21541
  • /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 $651,008

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

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

Showing Results 41 - 80, Page 2 of 18

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