293

Recently Sold Homes in 21550

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  • 1681 Shady Dell Rd, Oakland, MD 21550
    1681 Shady Dell Rd, Oakland, MD 21550
    1681 Shady Dell Rd, 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
  • 300 Santa fe Trail, Oakland, MD 21550
    300 Santa fe Trail, Oakland, MD 21550
    300 Santa fe Trail, 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
  • 600 Hope Ave, Oakland, MD 21550
    600 Hope Ave, Oakland, MD 21550
    600 Hope Ave, 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
  • 206 N 10th St, Oakland, MD 21550
    206 N 10th St, Oakland, MD 21550
    206 N 10th St, 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
  • 408 Shenandoah Ave, Oakland, MD 21550
    408 Shenandoah Ave, Oakland, MD 21550
    408 Shenandoah Ave, 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
  • 101 Sunset Dr, Oakland, MD 21550
    101 Sunset Dr, Oakland, MD 21550
    101 Sunset Dr, Oakland, MD 21550
    /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
  • 5914 Maryland Hwy, Oakland, MD 21550
    5914 Maryland Hwy, Oakland, MD 21550
    5914 Maryland Hwy, 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
  • 0 Boston Post Rd Unit MDGA2009736, 14, West Oakland, MD 21550
    0 Boston Post Rd Unit MDGA2009736, 14, West Oakland, MD 21550
    0 Boston Post Rd Unit MDGA2009736, 14, West 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
  • 422 Underwood Rd, Oakland, MD 21550
    422 Underwood Rd, Oakland, MD 21550
    422 Underwood Rd, Oakland, 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
  • 3554 Lake Shore Dr, Oakland, MD 21550
    3554 Lake Shore Dr, Oakland, MD 21550
    3554 Lake Shore Dr, Oakland, MD 21550
    /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
  • Lot 42 Winding Estates Dr, Mc Henry, MD 21550
    Lot 42 Winding Estates Dr, Mc Henry, MD 21550
    Lot 42 Winding Estates Dr, Mc Henry, MD 21550
    /12

    $75,000 Sold Jul 10, 2025

    • Land
    • 1.10 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
  • 114 Waterwheel Rd, Oakland, MD 21550
    114 Waterwheel Rd, Oakland, MD 21550
    114 Waterwheel Rd, Oakland, MD 21550
    /32

    $232,500 Sold Jul 10, 2025

    • 960 Sq Ft
    • $242/SF
    • 138 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1965

    114 Waterwheel Rd, Oakland, MD 21550

    Welcome to Willow Cottage, a charming 3-bedroom, 1-bath home nestled near Deep Creek Lake, MD. Surrounded by lush gardens and shaded by a beautiful willow tree, this inviting home is filled with natural light, featuring original hardwood floors and unique custom touches throughout. The newly renovated kitchen boasts brand-new cabinets, countertops, appliances, and flooring, while the updated

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    114 Waterwheel Rd, Oakland, MD 21550
  • 815 L St, Oakland, MD 21550
    815 L St, Oakland, MD 21550
    815 L St, Oakland, MD 21550
    /17

    $15,000 Sold Jul 09, 2025

    • Land
    • 0.28 Acre
    • $53,571 per Acre
    • 1 Day On Market

    815 L St, Oakland, MD 21550

    This vacant lot at 815 L Street in Mountain Lake Park, Maryland, offers a unique opportunity to build in a historic and community-focused setting. This parcel is situated within town limits and is zoned for residential use. Public water and sewer connections are available, though prospective buyers should verify utility details with the town and county. The property is subject to the Mtn Lake

    Lauren McCann Railey Realty, Inc.

    815 L St, Oakland, MD 21550
  • 636 Paradise Heights, Oakland, MD 21550
    636 Paradise Heights, Oakland, MD 21550
    636 Paradise Heights, Oakland, MD 21550
    /46

    $1,120,000 Sold Jul 08, 2025

    • 2,028 Sq Ft
    • $552/SF
    • 11 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1986

    636 Paradise Heights, Oakland, MD 21550

    Lakefront Stone Cottage Retreat at Deep Creek Lake! Welcome to your dream lakefront escape! Nestled in a tranquil cove, this charming 4-bedroom, 2-bathroom stone cottage blends classic charm with modern comforts. Boasting 150 feet of pristine lakefront and a private Type A boat dock, this recently remodeled retreat is perfect for making lasting memories year-round. Step inside to find a

    Mike Kennedy Railey Realty, Inc.

    636 Paradise Heights, Oakland, MD 21550
  • 245 Santa fe Trail, Oakland, MD 21550
    245 Santa fe Trail, Oakland, MD 21550
    245 Santa fe Trail, Oakland, MD 21550
    /40

    $615,000 Sold Jul 07, 2025

    • 2,280 Sq Ft
    • $270/SF
    • 51 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2003

    245 Santa fe Trail, Oakland, MD 21550

    3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, backing to woods & boulders and overlooking Deep Creek Lake! Enjoy an eat-in kitchen, exposed beams and a loft area that the current owners use as a 4th BR with bathroom. Conveys fully furnished. Features include updated flooring, gas fireplace on main level, lower level rec room with pool table and

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    245 Santa fe Trail, Oakland, MD 21550
  • Lot 9 Birchwood Dr, Oakland, MD 21550
    Lot 9 Birchwood Dr, Oakland, MD 21550
    Lot 9 Birchwood Dr, Oakland, MD 21550
    /23

    $18,000 Sold Jul 03, 2025

    • Land
    • 0.80 Acre
    • $22,500 per Acre
    • 5 Days On Market

    Lot 9 Birchwood Dr, Oakland, MD 21550

    Lot 9 Birchwood Drive is a .80 acre wooded lot in the desirable gated community of Youghiogheny Mountain Resort. Approved for an at-grade septic system for up to 4 bedrooms, this is great opportunity to build your future home or vacation retreat. Enjoy access to community amenities including over 50 miles of ATV/snowmobile trails, river access, community center, outdoor pavilion, and much more.

    Nick Fratz-Orr Railey Realty, Inc.

    Lot 9 Birchwood Dr, Oakland, MD 21550
  • 506 Cedar Ln, Oakland, MD 21550
    506 Cedar Ln, Oakland, MD 21550
    506 Cedar Ln, Oakland, MD 21550
    /35

    $285,000 Sold Jul 03, 2025

    • 1,344 Sq Ft
    • $212/SF
    • 16 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1979

    506 Cedar Ln, Oakland, MD 21550

    Tucked away on 1.42 acres across three wooded lots, this recently remodeled 3-bedroom, 2-bath home offers the perfect blend of comfort, character, and privacy. Step onto the expansive front deck, where mornings are made for sipping coffee and soaking in the peaceful surroundings. Inside, you'll find beautiful bamboo floors flowing through the open living, kitchen, and dining spaces—ideal for cozy

    Laura Newhall Taylor Made Deep Creek Vacations & Sales

    506 Cedar Ln, Oakland, MD 21550
  • 30 Snowshoe Ct, McHenry, MD 21541
    30 Snowshoe Ct, McHenry, MD 21541
    30 Snowshoe Ct, McHenry, MD 21541
    /9

    $145,000 Sold Jul 03, 2025

    • Land
    • 0.36 Acre
    • $402,778 per Acre
    • 53 Days On Market

    30 Snowshoe Ct, McHenry, MD 21541

    Can’t find the mountain home you’ve been searching for? Build it your way on this level, wooded .36-acre lot in Highline! Private ski trail access to Wisp Resort. Located near the end of a quiet cul-de-sac, this property offers public water and sewer- ready to build! Perfect for a future vacation rental or your own Deep Creek escape. Surrounded by adventure with skiing, snow tubing, the mountain

    Michael Fenton Railey Realty, Inc.

    30 Snowshoe Ct, McHenry, MD 21541
  • 26 Bright Passage Rd Unit 3C, McHenry, MD 21541
    26 Bright Passage Rd Unit 3C, McHenry, MD 21541
    26 Bright Passage Rd Unit 3C, McHenry, MD 21541
    /92

    $420,000 Sold Jul 03, 2025

    • 2,380 Sq Ft
    • $176/SF
    • 45 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1989

    26 Bright Passage Rd Unit 3C, McHenry, MD 21541

    Tired of choosing between lake days and ski runs? Villages of Wisp offers the best of both worlds! Ski access in the winter. Lake access all summer. Updated top to bottom with newer appliances, fresh carpet, sleek flooring, and modern vanities in all three bathrooms. Ductless AC. A private loft on the third floor adds bonus space without stealing a bedroom. Soak in the mountain lake views from

    Jon Bell Railey Realty, Inc.

    26 Bright Passage Rd Unit 3C, McHenry, MD 21541
  • 116 N 8th St Unit 2, Oakland, MD 21550
    116 N 8th St Unit 2, Oakland, MD 21550
    116 N 8th St Unit 2, Oakland, MD 21550
    /41

    $148,000 Sold Jul 02, 2025

    • 1,494 Sq Ft
    • $99/SF
    • 4 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1940

    116 N 8th St Unit 2, Oakland, MD 21550

    This charming 2-bedroom, 1-bath house offers the perfect blend of comfort and potential. Step inside to find a cozy living space adorned with upgraded carpet and flooring, creating a warm and inviting atmosphere perfect for relaxing or entertaining.One of the standout features of this property is the massive garage, providing ample space for vehicles, storage, or even a workshop. With

    Duane Stein II Keller Williams Realty Centre

    116 N 8th St Unit 2, Oakland, MD 21550
  • 256 Jeffrey Ln Unit 28, Oakland, MD 21550
    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    256 Jeffrey Ln Unit 28, Oakland, MD 21550
    /45

    $435,000 Sold Jul 02, 2025

    • 1,838 Sq Ft
    • $237/SF
    • 626 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2004

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    Looking for an updated condo at Deep Creek Lake? Look no further! 256 Jeffrey Lane #28 is a 3BR/3.5BA condo at Traders Landing offering lake views just across the street from the lake. Centrally located, you can be at most area amenities within minutes from your front door. Northern exposure makes for great all day sun. Recent improvements include renovated kitchen, bathrooms and furnishings.

    Nick Fratz-Orr Railey Realty, Inc.

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
  • 81 Timber Ln, Oakland, MD 21550
    81 Timber Ln, Oakland, MD 21550
    81 Timber Ln, Oakland, MD 21550
    /20

    $80,000 Sold Jun 30, 2025

    • 1,860 Sq Ft
    • $43/SF
    • 5 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1965

    81 Timber Ln, Oakland, MD 21550

    If you’re in the market for an affordable home, this could be the perfect option for you! Located in Crellin, just a few minutes from Oakland, this property features an oversized three-bay garage and an upstairs studio, offering plenty of possibilities. Whether you want to work on cars or create a fantastic woodworking shop, the space is versatile. The four-bedroom home boasts its original oak

    Sheila Howell Lake Homes Realty, LLC

    81 Timber Ln, Oakland, MD 21550
  • 193 Greenbrier Dr, McHenry, MD 21541
    193 Greenbrier Dr, McHenry, MD 21541
    193 Greenbrier Dr, McHenry, MD 21541
    /53

    $1,055,000 Sold Jun 30, 2025

    • 5,712 Sq Ft
    • $185/SF
    • 7 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2019

    193 Greenbrier Dr, McHenry, MD 21541

    Discover high-elevation luxury at this 2019-built masterpiece perched atop Wisp Ski Resort in the sought-after Lodestone Golf Course community of Greenbrier at Deep Creek Lake! Boasting over 5,000 sq ft of finished living space, this impressive 6-bedroom, 5.5-bath home built in 2019 blends upscale comfort with mountain adventure, making it the ultimate four-season retreat or income-generating

    Mike Kennedy Railey Realty, Inc.

    193 Greenbrier Dr, McHenry, MD 21541
  • 0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
    /22

    $25,000 Sold Jun 27, 2025

    • Land
    • 1.05 Acres
    • $23,810 per Acre
    • 84 Days On Market

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550

    5 bedroom perc! Experience a quiet & secluded area of Deep Creek Lake. The Overlook is a lake view and water access community in the southernmost expanse of the lake. Lot 22 is close to the water & shares 21+/- acres of beautiful common area, including a lakeside walking/hiking trail and lakeside gazebo. Teeming with birds and other wildlife, the namesake stream 'Deep Creek' doesn't disappoint!

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    0 Overlook Dr Unit 22 MDGA2009114, Oakland, MD 21550
  • Lot 9 Pheasant Run, Oakland, MD 21550
    Lot 9 Pheasant Run, Oakland, MD 21550
    Lot 9 Pheasant Run, Oakland, MD 21550
    /10

    $59,000 Sold Jun 26, 2025

    • Land
    • 6 Acres
    • $9,486 per Acre
    • 15 Days On Market

    Lot 9 Pheasant Run, Oakland, MD 21550

    Lot 9 Pheasant Run Road is 6.22-acre building lot in the desirable Moss Creek subdivision at Deep Creek Lake. Gently wooded with small, easily clearable brush, this parcel offers stunning mountain views and western exposure—ideal for enjoying breathtaking sunsets. Conveniently located just minutes from Deep Creeks recreational amenities and the shops, dining, and services of Oakland, MD. This

    Zach Wesolowski Railey Realty, Inc.

    Lot 9 Pheasant Run, Oakland, MD 21550
  • 145 Lower Penn Point Dr, Oakland, MD 21550
    145 Lower Penn Point Dr, Oakland, MD 21550
    145 Lower Penn Point Dr, Oakland, MD 21550
    /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
  • Lot #5 Swan Meadow Dr, Oakland, MD 21550
    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    Lot #5 Swan Meadow 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
  • 7 Swan Meadow Dr, Mount Lake Park, MD 21550
    7 Swan Meadow Dr, Mount Lake Park, MD 21550
    7 Swan Meadow Dr, Mount Lake Park, 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
  • p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    p/o parcel 206 G Swauger Rd, Oakland, MD 21550
    /4

    $61,125 Sold Jun 25, 2025

    • Land
    • 7 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
  • 258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    258 Winding Trail Ln Unit 8B, Oakland, MD 21550
    /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
  • 403 O St, Oakland, MD 21550
    403 O St, Oakland, MD 21550
    403 O St, Oakland, MD 21550
    /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
  • Lot 112 Biltmore View, Mc Henry, MD 21541
    Lot 112 Biltmore View, Mc Henry, MD 21541
    Lot 112 Biltmore View, Mc Henry, MD 21541
    /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
  • 202 Deerfield Dr, Oakland, MD 21550
    202 Deerfield Dr, Oakland, MD 21550
    202 Deerfield Dr, Oakland, MD 21550
    /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
  • 19956 Garrett Hwy Unit 2, Oakland, MD 21550
    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    19956 Garrett Hwy Unit 2, Oakland, MD 21550
    /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
  • 13903 Garrett Hwy, Oakland, MD 21550
    13903 Garrett Hwy, Oakland, MD 21550
    13903 Garrett Hwy, 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
  • 116 Wanderer Ln Unit F5, Oakland, MD 21550
    116 Wanderer Ln Unit F5, Oakland, MD 21550
    116 Wanderer Ln Unit F5, Oakland, MD 21550
    /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
  • 415 Mountaintop Rd, Mc Henry, MD 21541
    415 Mountaintop Rd, Mc Henry, MD 21541
    415 Mountaintop Rd, 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
  • 0 Hubbard Rd, Oakland, MD 21550
    0 Hubbard Rd, Oakland, MD 21550
    0 Hubbard Rd, Oakland, MD 21550
    /37

    $290,000 Sold Jun 05, 2025

    • Land
    • 110 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
  • 464 Lake Forest Dr, Oakland, MD 21550
    464 Lake Forest Dr, Oakland, MD 21550
    464 Lake Forest Dr, 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
  • Lot 76 S Blakeslee Rd, Oakland, MD 21550
    Lot 76 S Blakeslee Rd, Oakland, MD 21550
    Lot 76 S Blakeslee Rd, Oakland, MD 21550
    /12

    $380,000 Sold May 30, 2025

    • Land
    • 1.06 Acres
    • $358,491 per Acre
    • 4 Days On Market

    Lot 76 S Blakeslee Rd, Oakland, MD 21550

    If you have been searching for a beautiful homesite in the much sought after Blakeslee community, this is it. This lot is 1.06 acres and has an approved perc, the only hard decision you will have to make it, what style of home. Offering an assigned dock slip, access to an indoor pool, tennis courts, basketball court, soccer field and club house. The location is another plus, while feeling very

    Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    Lot 76 S Blakeslee Rd, Oakland, MD 21550

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