12,216

Homes in ZIP Code 21550

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    • /68

      Est $705,738 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,158 Sq Ft

      3365 Mayhew Inn Rd, Oakland, MD 21550

      3365 Mayhew Inn Rd, Oakland, MD 21550
  • /52

    $767,500

    • 5 Beds
    • 4 Baths
    • 2,364 Sq Ft

    25 Silver Tree Ln, Oakland, MD 21550

    Beautiful lake access retreat located in the Silver Tree Landings community. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any season, while offering views from

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    25 Silver Tree Ln, Oakland, MD 21550
  • /31

    $189,000 Sold Jul 24, 2025

    • 960 Sq Ft
    • $197/SF
    • 2 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1985

    1681 Shady Dell Rd, Oakland, MD 21550

    3 Bedroom Home in Pleasant Valley! Discover the perfect blend of comfort, privacy, and potential with this 3-bedroom, 1-bath home nestled in the heart of Pleasant Valley. Situated on just under an acre and surrounded by mature woods, this property offers the serenity of country living with convenient access to local amenities. Full basement and Multiple heat sources. Schedule a showing today.

    Tim Macauley Taylor Made Deep Creek Vacations & Sales

    1681 Shady Dell Rd, Oakland, MD 21550
    • /25

      Not Listed For Sale

      135 Tarn Dr, Oakland, MD 21550

      135 Tarn Dr, Oakland, MD 21550
  • /51

    $699,900

    • 5 Beds
    • 3 Baths
    • 2,792 Sq Ft

    155 Basswood Way, Oakland, MD 21550

    Tucked just off Lakeshore Drive, this log home nails that luxury treehouse feel. Wrapped in fresh stain (09/24) and packed with updates - "Time Is On My Side" is dialed in for comfort. Five bedrooms, three baths, including a main-level primary. Inside, modern meets rustic with a sleek kitchen, new propane fireplace, and fresh paint throughout. The lower level offers a second living area, pool

    Michael Fenton Railey Realty, Inc.

    155 Basswood Way, Oakland, MD 21550
  • /29

    $431,000 Sold Jul 24, 2025

    • 1,080 Sq Ft
    • $399/SF
    • 102 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1967

    300 Santa fe Trail, Oakland, MD 21550

    Updated Lake-Area A-Frame – Turnkey & Ready to Enjoy! This beautifully upgraded A-frame is the perfect Deep Creek getaway. Freshly painted inside and out, this charming retreat features upscale furnishings and is being sold fully turnkey. Enjoy the open-concept living area with a stunning stone fireplace, a spacious wrap-around deck for outdoor relaxation, and a cozy loft for extra sleeping

    Lauren McCann Railey Realty, Inc.

    300 Santa fe Trail, Oakland, MD 21550
    • /49

      Est $903,455 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 966 Sq Ft

      17 Old Chestnut Dr, Oakland, MD 21550

      17 Old Chestnut Dr, Oakland, MD 21550
  • /60

    $525,000

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

    36 Ridgewood Dr, Oakland, MD 21550

    Looking for the secluded cabin in the woods but want to be close to everything the Lake has to offer? Look no further! This 3 bedroom 3 1/2 bath home offers just that! Located in the established and sought after community of Mountainside, this home is an inviting and place where you can get away from it all. Cozy up to the large stone wood burning fireplace in the living room, open concept

    Larry Smith Railey Realty, Inc.

    36 Ridgewood Dr, Oakland, MD 21550
  • /32

    $260,000 Sold Jul 21, 2025

    • 960 Sq Ft
    • $271/SF
    • 98 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1983

    29 Sloan Tract Rd, Oakland, MD 21550

    Affordable Deep Creek Lake Opportunity – Act Now!Don’t miss this chance to own in the Deep Creek Lake watershed at an unbeatable price! This 3-bedroom, 2-bath home needs some TLC but promises a strong return on investment. Located just off Lake Shore Dr, it features an oversized front deck with filtered lake views—perfect for relaxing or entertaining. The open kitchen/family room layout

    Thomas Long Railey Realty, Inc.

    29 Sloan Tract Rd, Oakland, MD 21550
    • /12

      Est $95,292 Not Listed For Sale

      48 Sandstone Cir, Mc Henry, MD 21541

      48 Sandstone Cir, 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
  • /44

    $225,000 Sold Jul 18, 2025

    • 2,480 Sq Ft
    • $91/SF
    • 21 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1981

    600 Hope Ave, Oakland, MD 21550

    3BR, 2.5BA contemporary home in Country Club Acres, adjacent to Oakland golf course. Abundant natural lighting in a private, wooded setting. Updated metal roof and siding, attached carport. Gorgeous kitchen with updated cabinets and granite countertops; slate, tile and hardwood floors. Some handicap accessible features, including a chairlift from main to upper floor. Lower level storage,

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    600 Hope Ave, Oakland, MD 21550
    • /122

      Not Listed For Sale

      • 7 Beds
      • 5.5 Baths
      • 4,320 Sq Ft

      535 Deep Creek Highlands Rd, McHenry, MD 21550

      535 Deep Creek Highlands Rd, McHenry, 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
  • /103

    $320,000 Sold Jul 18, 2025

    • 2,772 Sq Ft
    • $115/SF
    • 37 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1972

    206 N 10th St, Oakland, MD 21550

    One level living in this duplex that has never been rented as two separate units but could be. Or, with minor modifications it could be one home with two separate living areas. Very well maintained home featuring brick fireplace on one side. Two kitchens, 2 bedrooms on each side with third area that could be another BR on each side. Two separate entrances, two garages. Full basement under 206 and

    Kevin Liller Railey Realty, Inc.

    206 N 10th St, Oakland, MD 21550
    • /13

      Not Listed For Sale

      6 Greenbrier Dr, Mc Henry, MD 21541

      6 Greenbrier Dr, Mc Henry, MD 21541
  • /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
  • /23

    $119,000 Sold Jul 18, 2025

    • Land
    • 7.5 Acres
    • $15,867 per Acre
    • 56 Days On Market

    1714 Mayhew Inn Rd, Oakland, MD 21550

    Beautiful 7.5 Acre wooded lots less than 1/2 mile from Deep Creek Lake. Some home site infrastructure in place from a recently torn down home. Over 400' of road frontage. Minutes away from state parks, Youghiogheny River, ski slopes, hiking and biking trails, kayaking, fishing, boating, golf, restaurants and nostalgic town Oakland.

    Brian Homberg Taylor Made Deep Creek Vacations & Sales

    1714 Mayhew Inn Rd, Oakland, MD 21550
    • /10

      Not Listed For Sale

      74 Chimney Rock Ln, Mc Henry, MD 21541

      74 Chimney Rock Ln, Mc Henry, MD 21541
  • /45

    $1,359,000

    • 6 Beds
    • 4.5 Baths
    • 4,113 Sq Ft

    439 Paradise Heights, Oakland, MD 21550

    Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180 views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive

    Mike Kennedy Railey Realty, Inc.

    439 Paradise Heights, Oakland, MD 21550
  • /43

    $110,000 Sold Jul 16, 2025

    • 960 Sq Ft
    • $115/SF
    • 2 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1950

    408 Shenandoah Ave, Oakland, MD 21550

    This welcoming 2-bedroom home in Loch Lynn has lots of potential. Situated on a quaint lot with a spacious yard, there's plenty of room for gardening, play, or relaxing outdoors. With a little TLC, this home can truly shine—making it ideal for someone looking to personalize a space of their own. Conveniently located just minutes from town and shopping, you'll enjoy both a peaceful setting and

    Rich Orr Railey Realty, Inc.

    408 Shenandoah Ave, Oakland, MD 21550
    • /32

      Est $152,000 Not Listed For Sale

      15 Fawn Dr, Oakland, MD 21550

      15 Fawn Dr, Oakland, MD 21550
  • /78

    $1,399,900

    • 6 Beds
    • 5 Baths
    • 4,227 Sq Ft

    116 Wisp Mountain Rd, Mc Henry, MD 21541

    Luxury Log Home Perched atop Wisp Mountain – This 6 Bed, 5 Bath chalet offers 4227 sq ft, and features three stories of outdoor living space, vaulted ceilings, timber accents, and lots of glass to let in the mountain/lake views! Modern kitchen with stone tops and stainless appliances. Rugged stacked stone fireplace in the great room with a second fireplace on the lower level. Fully finished

    Jon Bell Railey Realty, Inc.

    116 Wisp Mountain Rd, Mc Henry, MD 21541
  • /66

    $499,000 Sold Jul 15, 2025

    • 3,024 Sq Ft
    • $165/SF
    • 11 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    101 Sunset Dr, Oakland, MD 21550

    Private 5.5-Acre Property with Immaculate Home & Subdivision Potential – 9 Lots Included!Enjoy the perfect blend of privacy, space, and convenience with this beautifully maintained home on 5.5 acres, offered with 9 total recorded lots—presenting excellent subdivision or development potential. Ideally located within walking distance to shopping, yet tucked away in a peaceful, natural

    Rich Orr Railey Realty, Inc.

    101 Sunset Dr, Oakland, MD 21550
    • /11

      Not Listed For Sale

      18 Autumn Way, Oakland, MD 21550

      18 Autumn Way, Oakland, MD 21550
  • /93

    $3,489,000

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft

    1931 Lake Shore Dr, Oakland, MD 21550

    Deep Creek Lakes, Sunset Hills, luxury retreat offering majestic mountain & lake views. A unique lakefront property that plays a perfect host to relaxing vacations with family and friends is a low-key lifestyle centered around the outdoors. Vast stretches of glass ensure a sparkling water view is always on hand. Though sleek materials and high-end finishes abound, their low-profile design puts

    Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • /38

    $100,000 Sold Jul 11, 2025

    • 1,775 Sq Ft
    • $56/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1973

    5914 Maryland Hwy, Oakland, MD 21550

    Great opportunity with tons of potential! This home features 4 bedrooms, 2 baths, and offers over 3,500 square feet. With a few renovations and some TLC, this will be an amazing property! A nice sized 1.2 acre lot adds more possibilities of creating an enjoyable outdoor space. The location is wonderful as well, situated near the southern end of Deep Creek Lake and only minutes to Oakland!

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    5914 Maryland Hwy, Oakland, MD 21550
    • /82

      Est $1,290,633 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 2,635 Sq Ft

      20476 Garrett Hwy, Oakland, MD 21550

      20476 Garrett Hwy, Oakland, MD 21550
  • /53

    $1,599,900

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    1674 Paradise Point Rd, Oakland, MD 21550

    Beautifully remodeled lakefront home offering private dock and stunning views of Deep Creek Lake! Located on Paradise Point Rd, this home faces south for abundant natural light. 4 Bedrooms, 2.5 Bathrooms and sold fully furnished providing a gorgeous contemporary aesthetic throughout. Brand-new roof caps the Bright and Open Space with lots of glass to bring in the scenic lake views! Cozy fireplace

    Jon Bell Railey Realty, Inc.

    1674 Paradise Point Rd, Oakland, MD 21550
  • /20

    $240,000 Sold Jul 11, 2025

    • Land
    • 0.36 Acre
    • $666,667 per Acre
    • 6 Days On Market

    0 Boston Post Rd Unit MDGA2009736, 14, West Oakland, MD 21550

    Here’s your chance to own a Dock slip at Deep Creek Lake! Located just off iconic Lake Shore Drive, this rare corner lot offers filtered views of the water and convenient access to your very own dock slip. Public sewer available. Level lot that’s tucked in a quiet pocket just minutes from dining, marinas, and the slopes at Wisp. Whether you're dreaming of a cozy second home, vacation rental, or

    Michael Fenton Railey Realty, Inc.

    0 Boston Post Rd Unit MDGA2009736, 14, West Oakland, MD 21550
    • /47

      Est $320,784 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft

      33 Laurel Brook Dr, Oakland, MD 21550

      33 Laurel Brook Dr, Oakland, MD 21550
  • /84

    $829,000

    • 3 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    105 Mountain Overlook Ct, McHenry, MD 21550

    Discover mountain luxury in this beautifully maintained 3-bedroom, 3.5-bath Mountaintop Chalet near Wisp Resort with scenic Deep Creek Lake access. Exceptional craftsmanship and upscale finishes shine throughout its bright, open layout designed for entertaining. Gather in the cozy living room with stone fireplace, enjoy the comfort of a wonderful family room and versatile loft, and take advantage

    Steven Ritchie Railey Realty, Inc.

    105 Mountain Overlook Ct, McHenry, MD 21550
  • /45

    $195,000 Sold Jul 11, 2025

    • 960 Sq Ft
    • $203/SF
    • 17 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1972

    422 Underwood Rd, Oakland, MD 21550

    Tucked away just outside the town of Oakland, this 3-bedroom, 1-bath home sits on a private, wooded 1-acre lot that offers peace, quiet, and room to breathe. Relax on the large front porch and listen to the gentle sounds of the nearby stream while you watch the world go by. Inside, you'll find a well-maintained space with an unfinished basement that’s full of potential—create a rec room,

    Larry Smith Railey Realty, Inc.

    422 Underwood Rd, Oakland, MD 21550
    • /64

      Est $1,719,136 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 5,926 Sq Ft

      1200 Mountainview Dr, Oakland, MD 21550

      1200 Mountainview Dr, Oakland, MD 21550
  • /123

    $1,600,000

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

    188 Highline Dr, Mc Henry, MD 21541

    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, a freshly painted deck, and a naturally

    Elizabeth Ware Railey Realty, Inc.

    188 Highline Dr, Mc Henry, MD 21541
  • /48

    $525,000 Sold Jul 11, 2025

    • 1,296 Sq Ft
    • $405/SF
    • 232 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1993

    3554 Lake Shore Dr, Oakland, MD 21550

    Discover your perfect getaway in this charming 3-bedroom, 2-bathroom detached home, ideally situated in a sought-after waterfront community just minutes from Wisp Ski Resort. With its serene surroundings and direct water access, this property offers the ultimate blend of relaxation and adventure. Step inside to a bright and welcoming open-concept living space featuring vaulted ceilings . The

    Robert Krop Keller Williams Realty Centre

    3554 Lake Shore Dr, Oakland, MD 21550
    • /29

      Est $1,774,045 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 3,860 Sq Ft

      19868 Garrett Hwy, Oakland, MD 21550

      19868 Garrett Hwy, Oakland, MD 21550
  • /106

    $3,249,000 New Construction

    • 4 Beds
    • 5 Baths
    • 6,036 Sq Ft

    415 Nazelrod Rd, Oakland, MD 21550

    One of Garrett County's most unique and breathtaking mountain estates, this completely custom masterpiece was designed and built with exceptional craftsmanship and attention to detail. The 6000 +/- sq ft custom newly built home is located in the beautiful mountains of Garrett County, Maryland and offers the new owner one-of-a-kind unobstructed panoramic views, serenity, privacy and endless

    Larry Smith Railey Realty, Inc.

    415 Nazelrod Rd, Oakland, MD 21550
  • /12

    $75,000 Sold Jul 10, 2025

    • Land
    • 1.1 Acres
    • $68,182 per Acre
    • 7 Days On Market

    Lot 42 Winding Estates Dr, Mc Henry, MD 21550

    This prime mountaintop square shaped lot offers the perfect blank canvas to start your dream home design! Mature trees border the property, offering a natural buffer and added privacy, while the open areas make it easy to plan your home’s orientation to take full advantage of the scenery. This is a great option for anyone looking to build in a quiet, scenic setting without sacrificing

    Lucas Muenchow Railey Realty, Inc.

    Lot 42 Winding Estates Dr, Mc Henry, MD 21550
    • /21

      Est $296,150 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft

      35 Weber Ct, Oakland, MD 21550

      35 Weber Ct, Oakland, MD 21550

Showing Results 121 - 160, Page 4 of 18

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