12,215

Homes in ZIP Code 21550

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  • /71

    $899,900 Sold Jun 26, 2025

    • 2,106 Sq Ft
    • $427/SF
    • 135 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2007

    145 Lower Penn Point Dr, Oakland, MD 21550

    **SPLIT LAKE FRONT** WITH TYPE A DOCK**Discover this stunning chalet-style home located in the coveted Penn Point subdivision at Deep Creek Lake. Luxury vinyl plank flooring through out, fresh paint, all new decking and railings, new pine tongue and groove through-out giving a warm lodge feel. The main floor is open concept, living, dining, kitchen and half bath, the upper level presents 2

    Emillie Albrecht Real Broker, LLC

    145 Lower Penn Point Dr, Oakland, MD 21550
    • /90

      Est $1,589,195 Not Listed For Sale

      • 4 Beds
      • 6 Baths
      • 3,008 Sq Ft

      3037 Shingle Camp Rd, Mc Henry, MD 21541

      3037 Shingle Camp Rd, Mc Henry, MD 21541
  • /71

    $625,000

    • 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
  • /5

    $135,000 Sold Jun 25, 2025

    • Land
    • 10 Acres
    • $13,500 per Acre
    • 0 Days On Market

    Lot #5 Swan Meadow Dr, Oakland, MD 21550

    Lot #5 Swan Meadows situated on 10 acres in the beautiful rolling hills of Pleasant Valley. Perc approved with electric & telephone service. Lot #5 Swan Meadows offers Southern Exposure with Gorgeous views!

    Rich Orr Railey Realty, Inc.

    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    • /39

      Est $559,788 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      193 Red Run Rd Unit 1B1, Oakland, MD 21550

      193 Red Run Rd Unit 1B1, Oakland, MD 21550
  • /101

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,446 Sq Ft

    1118 Lake Shore Dr, Oakland, MD 21550

    Escape to Serenity: Your Dream Log Home Awaits! Nestled in the heart of a picturesque lake and mountain area, this charming log home offers the perfect blend of rustic charm and modern touches. With cathedral wood ceilings and a cozy gas fireplace, the spacious living area invites you to relax and soak in the warmth and beauty of your surroundings. The living area steps out to a large covered

    Susan Bell Railey Realty, Inc.

    1118 Lake Shore Dr, Oakland, MD 21550
  • /4

    $150,000 Sold Jun 25, 2025

    • Land
    • 10 Acres
    • $15,000 per Acre

    7 Swan Meadow Dr, Mount Lake Park, MD 21550

    Lot #7 Swan Meadows situated on 10 acres in the beautiful rolling hills of Pleasant Valley. Perc approved with electric & telephone service. Lot #7 Swan Meadows offers Southern Exposure with Gorgeous views!

    Rich Orr Railey Realty, Inc.

    7 Swan Meadow Dr, Mount Lake Park, MD 21550
    • /38

      Est $542,815 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,300 Sq Ft

      193 Red Run Rd Unit 1A2, Oakland, MD 21550

      193 Red Run Rd Unit 1A2, Oakland, MD 21550
  • /45

    $589,000

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    170 Winding Trail Ln Unit 4B, Oakland, MD 21550

    Spacious home located in the Timberlake Village community. This duplex home offers three levels of living space, granite counter tops, hardwood flooring, propane fireplace and an attached garage. The large kitchen and open floorplan make this an ideal permanent or vacation home. The exterior space is just as pleasing offering a covered front deck and a lower patio, which boasts a hot tub for your

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    170 Winding Trail Ln Unit 4B, Oakland, MD 21550
  • /4

    $61,125 Sold Jun 25, 2025

    • Land
    • 6.75 Acres
    • $9,056 per Acre

    p/o parcel 206 G Swauger Rd, Oakland, MD 21550

    6.75 acres farmland part of parcel 206 G. Swauger Rd. in Pleasant Valley. Survey Pending.

    Rich Orr Railey Realty, Inc.

    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    • /84

      Est $997,229 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,209 Sq Ft

      181 Skippers Point Rd, Oakland, MD 21550

      181 Skippers Point Rd, Oakland, MD 21550
  • /35

    $55,000

    • Land
    • 0.57 Acre
    • $96,491 per Acre

    0 Chimney Rock Ln Unit LotWP001 20577769, Mc Henry, MD 21541

    Welcome to your future homesite! This exceptional 0.57-acre lot is perfectly positioned on level ground, offering a prime location within a private community. Located just a row back from the Lodestone Golf Course, this property provides a picturesque setting for your dream home. Enjoy the tranquility and exclusivity of this private community while being just a short distance from the stunning

    Taylor Nitterhouse Whitetail Properties Real Estate

    0 Chimney Rock Ln Unit LotWP001 20577769, Mc Henry, MD 21541
  • /40

    $560,000 Sold Jun 20, 2025

    • 3,300 Sq Ft
    • $170/SF
    • 52 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2009

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550

    258 Winding Trail Lane is a luxurious duplex home located in the serene yet convenient community of Timberlake Village. The home feels warm and inviting from the moment you enter. Offering 3,300 SF with an open floorplan, three levels of living space, a large kitchen with granite countertops, two stone propane fireplaces, and LVF on the main and lower levels. This home boasts many recent

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    • /61

      Est $274,393 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,008 Sq Ft

      48 Spring Ln, Oakland, MD 21550

      48 Spring Ln, Oakland, MD 21550
  • /16

    $165,000

    • Land
    • 0.51 Acre
    • $323,529 per Acre

    0 Highline Dr Unit 19726892, Mc Henry, MD 21541

    Mountaintop Lot-If you love the mountains, the lake and the snow-take a look at this location and bring your home plans that will take advantage of all these beautiful aspects of Garrett County! .51 AC lot with utilities to site and easy access to Main St. slope! Public water and sewer hook-ups available.Copyright © 2025 Bright MLS. All rights reserved. All information provided by the

    Kathy Gibson

    0 Highline Dr Unit 19726892, Mc Henry, MD 21541
  • /47

    $270,000 Sold Jun 20, 2025

    • 2,240 Sq Ft
    • $121/SF
    • 329 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1976

    403 O St, Oakland, MD 21550

    NEWLY RENOVATED!So excited to be on the market with new carpet, paint , appliances, and roof!!! One-level living with great open views in town! 4 BR, (2 PRIMARY)) and 3 1/2 Baths, NEW outside decks on front & back of home with a large fenced-in yard (back/side). Located on a nice corner lot with lots of privacy. All bedrooms are spacious! Laundry room with plenty of storage. Large kitchen

    ANGELA BOSLEY Taylor Made Deep Creek Vacations & Sales

    403 O St, Oakland, MD 21550
    • /48

      Est $467,201 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,006 Sq Ft

      72 Crabtree Hill, Oakland, MD 21550

      72 Crabtree Hill, Oakland, MD 21550
  • /30

    $500,000

    • Land
    • 102.93 Acres
    • $4,858 per Acre

    0 George Washington Hwy Unit Lot WP001 18623689, Mount Lake Park, MD 21550

    Discover the incredible potential of this expansive 100+ acre property, ideally situated with nearly 1.5 miles of road frontage along George Washington Hwy and Table Rock Rd. The land is subdivided into five parcels, offering versatile options for developers and investors alike. Three of these parcels can be served with public water, enhancing development possibilities. Additionally, two parcels

    Taylor Nitterhouse Whitetail Properties Real Estate

    0 George Washington Hwy Unit Lot WP001 18623689, Mount Lake Park, MD 21550
  • /15

    $82,500 Sold Jun 20, 2025

    • Land
    • 0.64 Acre
    • $128,906 per Acre
    • 751 Days On Market

    Lot 112 Biltmore View, Mc Henry, MD 21541

    Exceptional golf course-fronting homesite located in the Biltmore community at Lodestone! The lot is 0.64 acres and sits directly on the Lodestone golf course at Deep Creek Lake. Minutes to all Wisp Resort and all other amenities at Deep Creek Lake. This gated community is home to many new construction homesites and is ready for your plans to begin being drawn! Public water tap has been paid and

    Nick Fratz-Orr Railey Realty, Inc.

    Lot 112 Biltmore View, Mc Henry, MD 21541
    • /22

      Est $475,990 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 576 Sq Ft

      20917 Garrett Hwy, Oakland, MD 21550

      20917 Garrett Hwy, Oakland, MD 21550
  • /11

    $88,900

    • Land
    • 0.59 Acre
    • $150,678 per Acre

    48 Fern Loop, McHenry, MD 21541

    Ready to Build with public water and public sewer Homesite 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/xcountry in Fork Run and ski/golf Wisp Resort-all just minutes from your home. Live the dream-Call today!Copyright © 2025

    Kathy Gibson

    48 Fern Loop, McHenry, MD 21541
  • /72

    $310,000 Sold Jun 18, 2025

    • 2,720 Sq Ft
    • $114/SF
    • 128 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1987

    202 Deerfield Dr, Oakland, MD 21550

    Come enjoy the mountain views from this well maintained 4 bedroom 3 bath split-level home on just over an acre of wooded privacy with plenty of wildlife outside your door. Freshly painted throughout home and an brand new stove has been installed. Just minutes from the Deep Creek Lake or Oakland area and within a short drive to WV Blackwater Falls and Canaan Valley.

    Sharon Murray Coldwell Banker Home Town Realty

    202 Deerfield Dr, Oakland, MD 21550
    • /35

      Est $240,540 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,854 Sq Ft

      763 Pysell Crosscut Rd, Oakland, MD 21550

      763 Pysell Crosscut Rd, Oakland, MD 21550
  • /11

    $98,000

    • Land
    • 0.6 Acre
    • $163,333 per Acre

    47 Fern Loop Dr, Mc Henry, MD 21541

    Take a look at Lot #47 in Sandy Shores Heights! This 4 season mountaintop location is just minutes to everything fun in the Deep Creek Lake area-Wisp Ski Resort, Lodestone Golf, Fork Run Recreation area and so many incredible state parks for outdoor enjoyment! Public water & sewer hookups available with underground utilities to the site. Level wooded lot to build your dream home and enjoy the

    Kathy Gibson Railey Realty, Inc.

    47 Fern Loop Dr, Mc Henry, MD 21541
  • /57

    $1,200,000 Sold Jun 13, 2025

    • 3,012 Sq Ft
    • $398/SF
    • 5 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2007

    19956 Garrett Hwy Unit 2, Oakland, MD 21550

    Luxury waterfront townhome located in the pristine Creekside community! This home will be sure to check off all the boxes and the lakefront views from almost every room makes it all the more special. Boasting four bedrooms (two of which are en suites), hardwood flooring, granite countertops, and two propane fireplaces. The open concept is inviting and felt from the moment you enter, along with

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    • /36

      Est $239,432 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,357 Sq Ft

      2607 Maryland Hwy, Oakland, MD 21550

      2607 Maryland Hwy, Oakland, MD 21550
  • /33

    $429,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    20160 Garrett Hwy Unit G507, Oakland, MD 21550

    Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep Creek Lake! Offering 2 bedrooms and 1 full bathroom, it captures breathtaking lake views from both levels. The main floor features a functional kitchen and a cozy living area with a wood-burning fireplace—perfect for relaxing after a day on the water. Upstairs, you’ll find two comfortable bedrooms and a full

    Nina Beitzel Railey Realty, Inc.

    20160 Garrett Hwy Unit G507, Oakland, MD 21550
  • /62

    $237,000 Sold Jun 13, 2025

    • 1,536 Sq Ft
    • $154/SF
    • 15 Days On Market
    • 1 Bed
    • 3 Baths
    • Built 1977

    13903 Garrett Hwy, Oakland, MD 21550

    Prime Commercial Opportunity with Rental Apartment & Multiple Uses!Seize this incredible commercial business opportunity in a high-demand location, just minutes from a thriving commercial district. Currently operating as a successful hair salon, this versatile property is perfect for a variety of businesses, including retail, office space, or other service-based ventures.Plus, the included rental

    Rich Orr Railey Realty, Inc.

    13903 Garrett Hwy, Oakland, MD 21550
    • /37

      Est $242,161 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,112 Sq Ft

      139 S Oakhall Dr, Oakland, MD 21550

      139 S Oakhall Dr, Oakland, MD 21550
  • /64

    $1,099,000

    • 5 Beds
    • 5 Baths
    • 4,437 Sq Ft

    635 Biltmore Ridge Trail, Mc Henry, MD 21541

    GOLF COURSE living!! Don’t miss out on this custom-built, log-cabin. This beauty was built in 2024 and comes FULLY FURNISHED. With its proximity to Wisp Ski resort, hiking trails and lakes, this home can be enjoyed in all four seasons making it perfect for a vacation or primary home. There are 5 bedrooms, 5 baths and plenty of space for entertainment and recreation. Don’t forget the hot tub and

    Edward Bass EXP Realty, LLC

    635 Biltmore Ridge Trail, Mc Henry, MD 21541
  • /97

    $732,500 Sold Jun 09, 2025

    • 1,440 Sq Ft
    • $509/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    116 Wanderer Ln Unit F5, Oakland, MD 21550

    Pack your bags and escape to your move in ready condo located at Four Hooppole South, nestled in peaceful mountain Maryland in one of the most coveted coves of Four-Season Deep Creek Lake. Enjoy breathtaking views from the deck of your stunning, lakefront, 3+ bedroom, 2 bath condo or cozy up to the free-standing wood fireplace in your spacious livingroom. Condo boasts many upgrades

    Charlene Deremer Coldwell Banker Home Town Realty

    116 Wanderer Ln Unit F5, Oakland, MD 21550
    • /56

      Est $324,126 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,112 Sq Ft

      47 Mount Pleasant Ln, Oakland, MD 21550

      47 Mount Pleasant Ln, Oakland, MD 21550
  • /35

    $1,399,000

    • 3 Beds
    • 1 Bath
    • 1,568 Sq Ft

    34 Shingle Camp Terrace, Mc Henry, MD 21541

    Cozy lakefront log cabin with private Type A dock! Metal roof ( 3 yrs old), post & beam interior, gas fireplace and impressive lake view sitting area that was built as an addition. Offering 120+ ft of waterfront and the buydown has been purchased & completed. Impressive location on the water with wider lake views and views of the 219 bridge in the distance. Full, unfinished basement offers

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    34 Shingle Camp Terrace, Mc Henry, MD 21541
  • /134

    $1,375,000 Sold Jun 09, 2025

    • 5,404 Sq Ft
    • $254/SF
    • 52 Days On Market
    • 5 Beds
    • 7 Baths
    • Built 2021

    415 Mountaintop Rd, Mc Henry, MD 21541

    Sleek. Spacious. Stunning. "No Black Tie Affair" is more than a house—it’s an experience. Over 5,400 sq ft of modern luxury tucked into Deep Creek Highlands, with access to a lakeside park, hiking trails, outdoor pool, and more. Abundant natural light floods the open-concept design, highlighting quartz counters, a walk-in pantry, and a gas fireplace that anchors the main living space. Five

    Jon Bell Railey Realty, Inc.

    415 Mountaintop Rd, Mc Henry, MD 21541
    • /56

      Est $356,135 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,440 Sq Ft

      407 Bear Dr E, Oakland, MD 21550

      407 Bear Dr E, Oakland, MD 21550
  • /24

    $650,000

    • 4 Beds
    • 4 Baths
    • 2,550 Sq Ft

    66 Paradise Ridge Rd, Oakland, MD 21550

    Welcome to 66 Paradise Ridge Rd, a charming single-familyhome in the picturesque town of Oakland, MD. LAKE ACCESS WITH DEEDED "A" Dock.Built in 1984, this two-story residence offers a spacious layout with 4 bathrooms and 2,550square feet of finished living space. Situated on a generous 21,780-square-foot lot, theproperty provides plenty of room to roam and enjoy the natural

    Joseph Hawkins Hawkins Real Estate Company

    66 Paradise Ridge Rd, Oakland, MD 21550
  • /37

    $290,000 Sold Jun 05, 2025

    • Land
    • 110.17 Acres
    • $2,632 per Acre
    • 43 Days On Market

    0 Hubbard Rd, Oakland, MD 21550

    Nestled in the picturesque southern end of Garrett County, this expansive 110.17-acre property offers a perfect blend of partially wooded areas and mostly open field, providing endless possibilities for your next venture. Whether you're looking to hunt or enjoy recreation, develop a subdivision, or create your dream home with ample land to enjoy, this property has it all.The land is ideal for a

    Justin Liller Railey Realty, Inc.

    0 Hubbard Rd, Oakland, MD 21550
    • /8

      Est $162,667 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft

      282 Longview Ln, Deer Park, MD 21550

      282 Longview Ln, Deer Park, MD 21550
  • /114

    $999,999

    • 5 Beds
    • 5.5 Baths
    • 8,000 Sq Ft

    1720 Pysell Crosscut Rd, Oakland, MD 21550

    'Four Winds' is a Frank Lloyd Wright inspired masterpiece at Deep Creek Lake. Restored & renovated as recently as 2021, this 4/5BR home boasts 8000sf on nearly 5 acres of land. A small part of the home was converted to accommodate a successful medical practice - 2 patient rooms, bathroom & private office - which adds amazing potential to creatively 'work from home' in many professional fields

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    1720 Pysell Crosscut Rd, Oakland, MD 21550
  • /26

    $1,275,000 Sold Jun 02, 2025

    • 2,496 Sq Ft
    • $511/SF
    • 277 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1997

    464 Lake Forest Dr, Oakland, MD 21550

    Truly wonderful lakefront property in the Lake Forest Drive area of Deep Creek Lake with a large deck for taking in the great views of Deep Creek Lake. 70 feet of waterfront, with a private Type A Dock. Nice backyard with a fire pit, a sitting area next to the lake, and plenty of room to entertain. Inside, there are four bedrooms, three full bathrooms, and a half bathroom. There are also three

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    464 Lake Forest Dr, Oakland, MD 21550

Showing Results 201 - 240, Page 6 of 18

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