12,296

Homes in ZIP Code 21550

Section Image
    • /91

      Est $301,813

      Not Listed For Sale

      106 H St, Oakland, MD 21550

      • 7 Beds
      • 3 Baths
      • 2,934 Sq Ft
      • Built 1900
      106 H St, Oakland, MD 21550

      Last Sold Summary

      • 1,050 Days On Market

  • /6

    $98,000

    $22K PRICE DROP
    • Land
    • 24,829 Sq Ft
    • $171,930 per Acre

    LOT 27 Biltmore Ridge Trail, McHenry, MD 21541

    Welcome to Lot 27, an exceptional homesite in one of the area's most prestigious mountaintop golf course communities. Here, the golf course is literally in your backyard, offering unbeatable views and direct access to one of Deep Creek’s premier destinations—Lodestone Golf Course. Set against a backdrop of panoramic mountain scenery, this lot is the perfect place to bring your dream home to life.

    Anet Harris Taylor-Made Deep Creek Real Estate, LLC

    LOT 27 Biltmore Ridge Trail, McHenry, MD 21541
  • /17

    $118,800

    Sold Jun 16, 2026

    1995 Bethlehem Rd, Oakland, MD 21550

    • Land
    • 7.33 Acres
    • $16,207 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Lana Roby The KW Collective

    1995 Bethlehem Rd, Oakland, MD 21550
    • /63

      Est $2,564,598

      Not Listed For Sale

      25 Old Chestnut Dr, Oakland, MD 21550

      • 9 Beds
      • 9 Baths
      • 5,362 Sq Ft
      • Built 2003
      25 Old Chestnut Dr, Oakland, MD 21550

      Last Sold Summary

      • 270 Days On Market

  • /78

    $689,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 2,670 Sq Ft

    276 Sundance Way, Mc Henry, MD 21541

    276 Sundance Way – a 3BR, 3.5BA Mountaineer Log Home built in 2018, set along Hole 6 of Lodestone Golf Course with a private, wooded backyard. The main level features an open kitchen, dining, and living area centered around a large island, along with a primary bedroom, laundry room, and half bath off the entry. Upstairs offers a large loft, two spacious bedrooms, and a full bathroom, giving

    Kelsey Meyers Railey Realty, Inc.

    276 Sundance Way, Mc Henry, MD 21541
  • /10

    $55,000

    Sold May 25, 2026

    114 C St, Oakland, MD 21550

    • 768 Sq Ft
    • Built 1999

    Last Sold Summary

    • 8% Below List Price
    • $72/SF
    • 60 Days On Market

    Current Estimated Value $59,602

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    114 C St, Oakland, MD 21550
    • /65

      Est $237,479

      Not Listed For Sale

      6663 Gorman Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,982 Sq Ft
      • Built 1978
      6663 Gorman Rd, Oakland, MD 21550

      Last Sold Summary

      • 113 Days On Market

  • /32

    $249,900

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    565 Glendale Rd Unit 306, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this beautifully appointed studio loft at Silver Tree Suites—one of the lake’s most sought-after locations! Offering two separate sleeping areas, a kitchenette, gas fireplace, and private balcony, this unit is designed for comfort and easy getaway living. Tastefully updated with new carpet and flooring, as well as kitchen and bathroom

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 306, Oakland, MD 21550
  • /37

    $365,900

    Sold Mar 23, 2026

    17979 Garrett Hwy, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $381/SF
    • 9 Days On Market

    Current Estimated Value $363,153

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    17979 Garrett Hwy, Oakland, MD 21550
    • /83

      Est $349,837

      Not Listed For Sale

      10 Sunset Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,167 Sq Ft
      • Built 1979
      10 Sunset Dr, Oakland, MD 21550

      Last Sold Summary

      • 53 Days On Market

  • /43

    $220,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    1256 Boiling Spring Rd, Oakland, MD 21550

    Spacious home nestled in a beautifully wooded area in Deer Park! This 3 bedroom, 2 bath home has a primary suite, main floor laundry, and tons of storage space in the basement. The fenced in backyard allows for privacy and enjoying the outdoors. Let your imagination go wild with all the unfinished space in the basement that you can transform into additional living space. Brand new mini-split

    Angie House Railey Realty, Inc.

    1256 Boiling Spring Rd, Oakland, MD 21550
  • /86

    $1,100,000

    Sold Aug 27, 2025

    216 Tarn Dr, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft
    • Built 2020

    Last Sold Summary

    • $231/SF
    • 122 Days On Market

    Current Estimated Value $1,248,275

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

    216 Tarn Dr, Oakland, MD 21550
    • /32

      Est $225,536

      Not Listed For Sale

      601 E Oak St, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 1,744 Sq Ft
      • Built 1922
      601 E Oak St, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • /85

    $1,029,900

    • 5 Beds
    • 4.5 Baths
    • 3,670 Sq Ft

    178 Fern Loop, McHenry, MD 21541

    Luxury golf-front living atop Wisp Resort! Situated along the 12th fairway of the prestigious Lodestone Golf Course, this 5-bedroom, 4.5-bath mountain retreat offers over 5,000 square feet of beautifully designed living space. Soaring wood-clad ceilings, expansive windows, and a floor-to-ceiling stone fireplace create a warm and inviting atmosphere throughout the open-concept main living area.

    Jon Bell Railey Realty, Inc.

    178 Fern Loop, McHenry, MD 21541
  • /38

    $265,000

    Sold Dec 30, 2025

    968 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2012

    Last Sold Summary

    • $148/SF
    • 25 Days On Market

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    968 Hutton Rd, Oakland, MD 21550
    • /78

      Est $296,147

      Not Listed For Sale

      3416 Wilson Corona Rd, Oakland, MD 21550

      • 4 Beds
      • 1.5 Baths
      • 1,936 Sq Ft
      • Built 1973
      3416 Wilson Corona Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /64

    $415,000

    • 4 Beds
    • 2 Baths
    • 2,234 Sq Ft

    1499 Foster Rd, Oakland, MD 21550

    Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 private wooded acres in the heart of Garrett County. Ideally located just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and downtown Oakland, this turnkey property offers the perfect balance of privacy, recreation, and modern comfort. Originally built as a raised ranch, the home has

    Kelsey Meyers Railey Realty, Inc.

    1499 Foster Rd, Oakland, MD 21550
  • /21

    $295,000

    Sold Dec 23, 2025

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 752 Sq Ft
    • Built 1997

    Last Sold Summary

    • $392/SF
    • 21 Days On Market

    Current Estimated Value $297,068

    Last Listing Agent James Matthews Taylor-Made Deep Creek Real Estate, LLC

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    • /47

      Est $547,788

      Not Listed For Sale

      38 Traders Ln, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 2,582 Sq Ft
      • Built 2003
      38 Traders Ln, Oakland, MD 21550

      Last Sold Summary

      • 22 Days On Market

  • /30

    $75,000

    $15K PRICE DROP
    • Land
    • 25,700 Sq Ft
    • $127,119 per Acre

    48 Fern Loop Dr, Sang Run, MD 21541

    Ready to Build on Lot #48 in the desirable peaceful community "Sandy Shores Heights". Enjoy all four seasons golfing at The Lodestone Golf Course, boating on Deep Creek Lake, fish or paddle the Yough River, hike/mountain bike/x-country in Fork Run and ski/golf Wisp Resort-all just minutes from your home. Complete infrastructure system in place with utilities to site to include public water &

    Kathy Gibson Railey Realty, Inc.

    48 Fern Loop Dr, Sang Run, MD 21541
  • /50

    $567,500

    Sold Mar 13, 2026

    189 Red Run Rd Unit 1C2, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $473/SF
    • 227 Days On Market

    Current Estimated Value $545,073

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    189 Red Run Rd Unit 1C2, Oakland, MD 21550
    • /82

      Est $2,388,223

      Not Listed For Sale

      1983 Lake Shore Dr, Oakland, MD 21550

      • 5 Beds
      • 6.5 Baths
      • 4,074 Sq Ft
      • Built 2000
      1983 Lake Shore Dr, Oakland, MD 21550

      Last Sold Summary

      • 236 Days On Market

  • /62

    $735,000

    Under Contract
    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    Check out this beautifully built and maintained 5 bedroom 5 bathroom lake area chalet style home. Located on the Southern side of the lake, near the headwaters of Deep Creek. The namesake stream that feeds into the nearby lake. This property offers it's new owners a tremendous amount of room for storage and entertaining and three levels of finished living space. The top floor is designed as an

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    1875 Pysell Crosscut Rd, Oakland, MD 21550
  • /67

    $1,542,000

    Sold Nov 13, 2025

    1567 Pergin Farm Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 3,200 Sq Ft
    • Built 2002

    Last Sold Summary

    • $482/SF
    • 15 Days On Market

    Current Estimated Value $1,485,782

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1567 Pergin Farm Rd, Oakland, MD 21550
    • /76

      Est $983,217

      Not Listed For Sale

      1865 Paradise Point Rd, Oakland, MD 21550

      • 6 Beds
      • 3.5 Baths
      • 2,158 Sq Ft
      • Built 2005
      1865 Paradise Point Rd, Oakland, MD 21550

      Last Sold Summary

      • 0 Days On Market

  • /48

    $375,000

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or

    Christina Ford CENTURY 21 New Millennium

    321 N 3rd St, Oakland, MD 21550
  • /10

    $59,000

    Sold Jun 26, 2025

    Lot 9 Pheasant Run, Oakland, MD 21550

    • Land
    • 6.22 Acres
    • $9,486 per Acre

    Last Sold Summary

    • 15 Days On Market

    Last Listing Agent Zach Wesolowski Railey Realty, Inc.

    Lot 9 Pheasant Run, Oakland, MD 21550
    • /39

      Est $202,940

      Not Listed For Sale

      227 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,232 Sq Ft
      • Built 1910
      227 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 44 Days On Market

  • /20

    $150,000

    New Construction $49K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths

    3395 Fingerboard Rd, Oakland, MD 21550

    6+ acre homestead with a 4BR, 2BA home currently under construction. Sellers plans have changed and they will not be finishing the house. The structure is under roof, mostly framed-in with building materials on site that will convey with the sale. A new well has been drilled and septic permit is approved for 4BRs. Located just outside of town limits, this parcel has impressive mountain views and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    3395 Fingerboard Rd, Oakland, MD 21550
  • /50

    $295,000

    Sold May 20, 2026

    163 Crestview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,416 Sq Ft
    • Built 1997

    Last Sold Summary

    • $208/SF
    • 275 Days On Market

    Current Estimated Value $307,945

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

    163 Crestview Dr, Oakland, MD 21550
    • /61

      Est $808,480

      Not Listed For Sale

      889 Paradise Ridge Rd, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,004 Sq Ft
      • Built 2004
      889 Paradise Ridge Rd, Oakland, MD 21550

      Last Sold Summary

      • 30 Days On Market

  • /9

    $98,800

    • Land
    • 18,730 Sq Ft
    • $229,767 per Acre

    Lot 42 Biltmore Ridge Trail, Mc Henry, MD 21541

    Get ready to tee off on the golf lovers' mountaintop dream, Biltmore at Lodestone, the award winning Hale Irwin designed premium golf course of the area, ranked by Golf Week as the #2 Public Golf Course in MD. Own one or two of the best priced golf course front lots, right on the cart path (see the listing for adjacent Lot 43). Be protected though from those pesky slices by a picturesque wooded

    Lana Roby The KW Collective

    Lot 42 Biltmore Ridge Trail, Mc Henry, MD 21541
  • /65

    $537,000

    Sold Feb 27, 2026

    77 Meadow Ct, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft
    • Built 2006

    Last Sold Summary

    • $220/SF
    • 100 Days On Market

    Current Estimated Value $567,490

    Last Listing Agent Jon Bell Railey Realty, Inc.

    77 Meadow Ct, Oakland, MD 21550
    • /84

      Est $307,654

      Not Listed For Sale

      255 Foster Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,272 Sq Ft
      • Built 1962
      255 Foster Rd, Oakland, MD 21550

      Last Sold Summary

      • 11 Days On Market

  • /50

    $1,200,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft

    209 Black Angus Dr, Oakland, MD 21550

    Beautiful and peaceful describes this 2 bedroom 2 bath retreat. Situated on 200' of prime lakefront this property is tucked away at the end of a gently sloping lane. The inviting setting includes a tennis/sport court with potential for pickle ball and just about any other outdoor activity you can think of. The property qualifies for a private type A dock and is located in a non-vacation rental

    Bill Weissgerber Railey Realty, Inc.

    209 Black Angus Dr, Oakland, MD 21550
  • /60

    $505,000

    Sold Nov 14, 2025

    36 Ridgewood Dr, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 1,713 Sq Ft
    • Built 2000

    Last Sold Summary

    • $295/SF
    • 228 Days On Market

    Current Estimated Value $509,270

    Last Listing Agent Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
    • /64

      Est $223,558

      Not Listed For Sale

      324 W Liberty St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,725 Sq Ft
      • Built 1900
      324 W Liberty St, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

  • /18

    $4,000

    Under Contract
    • Land
    • 20,473 Sq Ft
    • $8,511 per Acre

    Lot 36 Fox Tail Rd, Oakland, MD 21550

    Discover your mountain escape in Yough Mountain Resort, a gated recreational community in the scenic mountains of Western Maryland, just a short drive to Deep Creek Lake. This amenity-rich community is designed for outdoor enthusiasts, offering ATV and snowmobile trails, Yough River access, nearby state parks, hunting opportunities, plus a playground and pavilion area for gathering.This

    Shannon McWilliams Taylor-Made Deep Creek Real Estate, LLC

    Lot 36 Fox Tail Rd, Oakland, MD 21550
  • /24

    $85,000

    Sold Oct 03, 2025

    1101 Wheeling Ave, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft
    • Built 1950

    Last Sold Summary

    • $49/SF
    • 25 Days On Market

    Current Estimated Value $161,407

    Last Listing Agent Tanavia Greer Long & Foster Real Estate, Inc.

    1101 Wheeling Ave, Oakland, MD 21550
    • /83

      Est $1,196,805

      Not Listed For Sale

      2675 Stockslager Rd, Oakland, MD 21550

      • 4 Beds
      • 4.5 Baths
      • 3,024 Sq Ft
      • Built 2003
      2675 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

Showing Results 441 - 480, Page 12 of 18

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