12,257

Homes in ZIP Code 21550

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  • /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 $176,388

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

    107 E Mason St, Oakland, MD 21550
    • /48

      Not Listed For Sale

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

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 1972
      20160 Garrett Hwy Unit 502/702, Oakland, MD 21550

      Last Sold Summary

      • $314/SF
      • 9 Days On Market

      Last Sold Price $534,000

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • /16

    $40,000

    • Land
    • 0.6 Acre
    • $66,667 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
  • /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 $290,471

    Last Listing Agent Thomas Long Railey Realty, Inc.

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

      Est $598,358 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

      • 1% Above List Price
      • $180/SF
      • 529 Days On Market

      Last Sold Price $595,000

      Last Listing Agent Rachel Bruch Railey Realty, Inc.

  • /21

    $22,500

    • Land
    • 0.58 Acre
    • $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
  • /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 $1,935,297

    Last Listing Agent Jay Quinn Taylor Made Deep Creek Real Estate

    228 Paradise Heights, Oakland, MD 21550
    • /24

      Est $171,521 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

  • /14

    $165,000

    • Land
    • 0.42 Acre
    • $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
  • /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 $375,718

    Last Listing Agent Adam Belasco Keller Williams Capital Properties

    366 Glendale Rd, Oakland, MD 21550
    • /72

      Est $800,472 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

      • 3% Above List Price
      • $258/SF
      • 48 Days On Market

      Last Sold Price $775,000

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /31

    $130,000

    • Land
    • 2.1 Acres
    • $61,905 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
  • /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
    • /45

      Est $1,251,074 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

      • 4% Below List Price
      • $526/SF
      • 13 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Russell Bounds Railey Realty, Inc.

  • /60

    $285,000

    • 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
  • /2

    $20,000 Sold Mar 03, 2026

    0 N Hammond St, Oakland, MD 21550

    • Land
    • 0.48 Acre
    • $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

    0 N Hammond St, Oakland, MD 21550
    • /76

      Est $839,989 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

      • 8% Above List Price
      • $274/SF
      • 59 Days On Market

      Last Sold Price $775,000

      Last Listing Agent Rich Orr Railey Realty, Inc.

  • /36

    $64,900

    • Land
    • 0.63 Acre
    • $103,016 per Acre

    Lot 29 Greenbrier Dr, Sang Run, MD 21541

    Lot 29 is in the exclusive Greenbrier community at the Lodestone Golf course along the fairway of the 8th hole. The location is perfect to provide some peace and quiet and still be with in minutes of the Wisp Resort activities. Snow skiing, Mountain Biking, Whitewater rafting park, summer concerts, Mountain coaster, Ropes course, Snow tubing park. Also just minutes to Deep Creek Lake and Fork Run

    Agent Photo

    Dale Carpenter

    Railey Realty, Inc.

    (240) 226-3870

    Lot 29 Greenbrier Dr, Sang Run, MD 21541
  • /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 $246,555

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

    157 Jeffrey Ln Unit 21A, Oakland, MD 21550
    • /63

      Est $604,311 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.

  • /37

    $275,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 875 Sq Ft

    127 Jeffrey Ln Unit 18C, Oakland, MD 21550

    Welcome to 127 Jeffrey Lane 18C! Centrally located at Deep Creek Lake, this unit offers convenience year round to restaurants, skiing, golf courses, Deep Creek Lake and even one of the areas most desired coffee shops just a few hundred feet away. Enjoy northeastern exposure for great sunrises overlooking the lake. The main level offers a kitchen, living room with wood burning fireplace, 2

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (301) 591-6157

    127 Jeffrey Ln Unit 18C, 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

    1714 Mayhew Inn Rd, Oakland, MD 21550
    • /47

      Est $409,053 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

      • 20% Above List Price
      • $280/SF
      • 82 Days On Market

      Last Sold Price $340,000

      Last Listing Agent Lana Roby The KW Collective

  • /18

    $44,900

    • Land
    • 6.12 Acres
    • $7,337 per Acre

    Lot 6 Hoye Crest Rd, Oakland, MD 21550

    Opportunity to own over 6 acres on Backbone Mountain adjoining the Highest Point in Maryland! This lot will offer some of the best views from Maryland's highest point with western exposure. Approved perc and electric to site, ready for you to build your dream home! Residential community. No camping, no hunting. Call today to schedule a time too see this remarkable property!

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    (240) 652-2465

    Lot 6 Hoye Crest Rd, 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 $231,434

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

    1570 Garrett Rd, Oakland, MD 21550
    • /50

      Est $600,632 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

      • 46% Above List Price
      • $197/SF
      • 5 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Andrew Eiswert Railey Realty, Inc.

  • /28

    $299,000

    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550

    Nestled in the charming Traders Landing community, this delightful end-of-row townhouse offers a perfect blend of comfort and convenience with one of the best unobstructed views of the lake in Traders Landing. This villa-style home features two cozy bedrooms and a full bathroom, ideal for relaxation and unwinding after a long day. The inviting living space is enhanced by a warm wood-burning

    Agent Photo

    James Matthews

    Taylor Made Deep Creek Real Estate

    (240) 883-5848

    157 Jeffrey Ln Unit 21B, 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 $591,732

    Last Listing Agent Sheila Howell Lake Homes Realty, LLC

    939 Glendale Rd, Oakland, MD 21550
    • /69

      Est $540,682 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

      • 1% Above List Price
      • $178/SF
      • 277 Days On Market

      Last Sold Price $535,000

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

  • /37

    $125,000

    • Land
    • 0.49 Acre
    • $255,102 per Acre

    Lot 21 Green Jacket Ct, Mc Henry, MD 21541

    Beautiful 1/2 acre LEVEL lot in the Lodestone Village subdivision, minutes from everything there is to love at Deep Creek Lake sitting on a quiet 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 award-winning championship

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 875-4952

    Lot 21 Green Jacket Ct, Mc Henry, MD 21541
  • /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 $176,306

    Last Listing Agent Brody Monahan Lake Homes Realty, LLC

    306 Shady Acre Ln, Oakland, MD 21550
    • /30

      Est $387,657 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

      • 27% 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

  • /50

    $125,000

    • Land
    • 0.54 Acre
    • $231,481 per Acre

    Lot 20 Green Jacket Ct, Mc Henry, MD 21541

    Beautiful 1/2 acre LEVEL lot in the Lodestone Village subdivision, 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 award-winning championship Lodestone

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (240) 875-5080

    Lot 20 Green Jacket Ct, Mc Henry, MD 21541
  • /5

    $34,500 Sold Jan 15, 2026

    62 Crosby Dr, Oakland, MD 21550

    • Land
    • 0.63 Acre
    • $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
    • /12

      Est $86,118 Not Listed For Sale

      6 Cedar Ln, Oakland, MD 21550

      6 Cedar Ln, Oakland, MD 21550

      Last Sold Summary

      • 761% Above List Price
      • 171 Days On Market

      Last Sold Price $10,000

      Last Listing Agent Mike Kennedy 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
  • /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 $103,399 Not Listed For Sale

      450 Deer Run Rd, Piney Mtn, MD 21550

      450 Deer Run Rd, Piney Mtn, MD 21550

      Last Sold Summary

      • 3% Above List Price
      • 257 Days On Market

      Last Sold Price $100,000

      Last Listing Agent laura Flynn 1 Real Estate Source LLC

  • /110

    $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, easy-access mountaintop ski parking, lift tickets, on-site community amenities, and everything you need. Exceptional

    Nina Beitzel Railey Realty, Inc.

    105 Mountain Overlook Ct, McHenry, 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 $1,170,202

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

    590 S Blakeslee Rd, Oakland, MD 21550

Showing Results 41 - 80, Page 2 of 18

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