147

Recently Sold Oakland Homes

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  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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 #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
  • 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
  • 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
  • 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
  • 5459 Hutton Rd, Oakland, MD 21550
    5459 Hutton Rd, Oakland, MD 21550
    5459 Hutton Rd, Oakland, MD 21550
    /40

    $171,000 Sold May 30, 2025

    • 2,000 Sq Ft
    • $86/SF
    • 113 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1940

    5459 Hutton Rd, Oakland, MD 21550

    Endless Potential! This diamond in the rough is ready for your vision and creativity. A fantastic opportunity to make this home truly your own. Bring your tools and imagination---this home is waiting for a makeover. Great Investment property! It was used as a Duplex, home needs work but offers a great value for the right buyer. Newer furnace, newer windows installed throughout. Hardwood floors,

    Debra Beitzel Long & Foster Real Estate, Inc.

    5459 Hutton Rd, Oakland, MD 21550
  • 36 Lehman Ln, Oakland, MD 21550
    36 Lehman Ln, Oakland, MD 21550
    36 Lehman Ln, Oakland, MD 21550
    /16

    $25,000 Sold May 27, 2025

    • Land
    • 0.00 Acre
    • 10 Days On Market

    36 Lehman Ln, Oakland, MD 21550

    Lot ready for building available in the beautiful Gallatin Woods community, located just minutes to all Deep Creek Lake area amenities! This gorgeous forested development offers the perfect area for a secluded mountain lake-house feel. While the condominium association maintains ownership of the land, Lot 36 is the perfect buildable lot for a single-family home with 8 beautiful pre-approved house

    Kellyann Green Railey Realty, Inc.

    36 Lehman Ln, Oakland, MD 21550
  • 234 Maple Del Ln, Oakland, MD 21550
    234 Maple Del Ln, Oakland, MD 21550
    234 Maple Del Ln, Oakland, MD 21550
    /51

    $435,000 Sold May 27, 2025

    • 2,750 Sq Ft
    • $158/SF
    • 306 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1995

    234 Maple Del Ln, Oakland, MD 21550

    3/4 BR, 3BA well-built & cared for home, 2700sf+/- in Maple Del, a private community in the Red Run area of Deep Creek Lake. Natural boulders lace the property; tall mature maples, oaks & pines offer plenty of shade but still ample lawn for outdoor activities. Surrounded by ferns, chirping birds and peace & quiet that's rare this close to the lake. You will love the cozy covered porch! Inside,

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    234 Maple Del Ln, Oakland, MD 21550
  • 3821 Underwood Rd, Oakland, MD 21550
    3821 Underwood Rd, Oakland, MD 21550
    3821 Underwood Rd, Oakland, MD 21550
    /21

    $155,000 Sold May 22, 2025

    • 1,232 Sq Ft
    • $126/SF
    • 10 Days On Market
    • 4 Beds
    • 1 Bath
    • Built 1964

    3821 Underwood Rd, Oakland, MD 21550

    An excellent financial opportunity close to Oakland. This 3 bedroom, 1 bathroom ranch can be a great starter home for a young family or a flip. It has good bones and all utilities are in working order. It has a metal roof, vinyl windows and good vinyl siding. The interior needs remodeling; some sweat equity will go a long way for the next owner.

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    3821 Underwood Rd, Oakland, MD 21550
  • 655 Bray School Rd, Oakland, MD 21550
    655 Bray School Rd, Oakland, MD 21550
    655 Bray School Rd, Oakland, MD 21550
    /67

    $259,000 Sold May 14, 2025

    • 960 Sq Ft
    • $270/SF
    • 4 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1984

    655 Bray School Rd, Oakland, MD 21550

    This cozy 2-bedroom, 1-bath home is full of charm and nestled in a peaceful, wooded setting among the pines. A front deck welcomes you inside to a warm living room with a gas fireplace, perfect for those cool mountain evenings. Just off the living room is a flexible space—ideal for a home office, reading nook, or cozy sitting area. An open spacious kitchen with new stove completes the living area

    Susan Bell Railey Realty, Inc.

    655 Bray School Rd, Oakland, MD 21550
  • 107 E Mason St, Oakland, MD 21550
    107 E Mason St, Oakland, MD 21550
    107 E Mason St, Oakland, MD 21550
    /24

    $27,500 Sold May 14, 2025

    • 2,256 Sq Ft
    • $12/SF
    • 18 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1914

    107 E Mason St, Oakland, MD 21550

    Just outside of town this home is easy access to most amenities and just minutes from freshwater lake and snow skiing. Offers a nostalgic feel of days gone by in this simple kitchen . Check it out today and make it your own home sweet home.

    Kathleen Miller Better Homes & Gardens Real Estate Old Line Group

    107 E Mason St, Oakland, MD 21550
  • 112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    /4

    $73,900 Sold May 12, 2025

    • 1,380 Sq Ft
    • $54/SF
    • 1 Day On Market
    • 3 Beds
    • 1 Bath
    • Built 1916

    112 E Pennington St, Oakland, MD 21550

    3 bedroom 2 story dwelling on quiet city street. enclosed porch front & rear. 2 car Detached garage. Estate property

    Robert Custer Custer Realty & Auction

    112 E Pennington St, Oakland, MD 21550
  • 249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    249 Marys Ln, Oakland, MD 21550
    /67

    $855,000 Sold May 12, 2025

    • 2,874 Sq Ft
    • $297/SF
    • 7 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2017

    249 Marys Ln, Oakland, MD 21550

    **Epic Lake Views. Prime Location.** This rustic-modern log home, built in 2018, delivers the best of Deep Creek living with high-end finishes and jaw-dropping views. Inside, vaulted ceilings soar over an open floor plan, anchored by a stunning stacked stone fireplace. The heart of the home? A top-of-the-line kitchen with premium upgrades and hardwood finishes throughout. With 5 bedrooms, 3.5

    Jon Bell Railey Realty, Inc.

    249 Marys Ln, Oakland, MD 21550
  • 158 Silver Tree Ln, Oakland, MD 21550
    158 Silver Tree Ln, Oakland, MD 21550
    158 Silver Tree Ln, Oakland, MD 21550
    /49

    $790,000 Sold May 09, 2025

    • 2,250 Sq Ft
    • $351/SF
    • 79 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2003

    158 Silver Tree Ln, Oakland, MD 21550

    Luxurious Lake Access Craftsman at Silver Tree Landing – This 5 Bedroom, 4.5 Bath home features crisp and clean modern finishes, an updated kitchen with stainless appliances and stone countertops, a spacious deck with a hot tub, and scenic views of Deep Creek Lake. Vaulted ceilings in the main living area with plenty of glass to let in the light and the views. There is a massive loft upstairs

    Jon Bell Railey Realty, Inc.

    158 Silver Tree Ln, Oakland, MD 21550
  • 601 Hope Ave, Oakland, MD 21550
    601 Hope Ave, Oakland, MD 21550
    601 Hope Ave, Oakland, MD 21550
    /38

    $398,350 Sold May 07, 2025

    • 2,142 Sq Ft
    • $186/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    601 Hope Ave, Oakland, MD 21550

    BRAND NEW CONSTRUCTION! 3BR/2.5BA home in Country Club Acres, near Oakland golf course! 2,142sf and roughly .79 acres of land (lots 45 & 46 combined). Modern design offering plenty of natural light, open living and elite finishes. Features include Andersen windows & slider, custom tile bathrooms, stone fireplace, gourmet kitchen, Kraftmaid cabinets, granite counters and an incredibly energy

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    601 Hope Ave, Oakland, MD 21550
  • 1385 Mountainview Dr, Oakland, MD 21550
    1385 Mountainview Dr, Oakland, MD 21550
    1385 Mountainview Dr, Oakland, MD 21550
    /54

    $595,000 Sold Apr 30, 2025

    • 2,660 Sq Ft
    • $224/SF
    • 26 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2000

    1385 Mountainview Dr, Oakland, MD 21550

    Nestled in a serene wooded neighborhood, this stunning water-access chalet offers the perfect blend of rustic charm and modern comfort. Spanning three levels and over 2600 sq ft of finished space, the home boasts an inviting open-concept living space with a striking stone fireplace, perfect for cozy evenings. The main floor features a well-appointed kitchen, a spacious dining area, and large

    Nina Beitzel Railey Realty, Inc.

    1385 Mountainview Dr, Oakland, MD 21550
  • 142 Lemley Dr Unit I, Oakland, MD 21550
    142 Lemley Dr Unit I, Oakland, MD 21550
    142 Lemley Dr Unit I, Oakland, MD 21550
    /26

    $400,000 Sold Apr 21, 2025

    • 146 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    142 Lemley Dr Unit I, Oakland, MD 21550

    3 Bedroom 2 Bath ranch style property with gorgeous lake, ski slope and mountain views AND a deeded dock slip. Conveniently located close to all area amenities. Park like setting with lots of open space. Surrounded by walking trails. Most furnishings convey. No association height restrictions for rebuild on this unit as well but the properties located n front of this cottage are restricted in

    Andrew Eiswert Railey Realty, Inc.

    142 Lemley Dr Unit I, Oakland, MD 21550
  • 20241 Garrett Hwy Unit 5, Oakland, MD 21550
    20241 Garrett Hwy Unit 5, Oakland, MD 21550
    20241 Garrett Hwy Unit 5, Oakland, MD 21550
    /47

    $407,000 Sold Apr 18, 2025

    • 2,330 Sq Ft
    • $175/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1989

    20241 Garrett Hwy Unit 5, Oakland, MD 21550

    Located right in the heart of Deep Creek Lake, this stunning 3-level condo offers the perfect blend of luxury and comfort with breathtaking water views! Boasting 3 spacious bedrooms and 2.5 baths, this home features an open-concept main floor with an eat in kitchen, cozy living area, separate dining space, breakfast nook, and large windows that flood the space with natural light. The main level

    Nina Beitzel Railey Realty, Inc.

    20241 Garrett Hwy Unit 5, Oakland, MD 21550
  • 11 Laurel Brook Dr, Oakland, MD 21550
    11 Laurel Brook Dr, Oakland, MD 21550
    11 Laurel Brook Dr, Oakland, MD 21550
    /26

    $237,500 Sold Apr 15, 2025

    • 157 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1989

    11 Laurel Brook Dr, Oakland, MD 21550

    Check out this immaculately cared for 2 Bedroom, 2 Bathroom townhome in the Laurel Brook community. This townhome is the larger floorplan construction, meaning additional space and comfort over other townhomes in the community. Close to all the amenities of Deep Creek with recently updated bathrooms, kitchen, newer stainless steel appliances, and flooring. Furnishings convey to the new owner for

    Dan Shockey Taylor Made Deep Creek Vacations & Sales

    11 Laurel Brook Dr, Oakland, MD 21550
  • 0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
    /3

    $13,000 Sold Apr 14, 2025

    • Land
    • 2.00 Acres
    • $6,500 per Acre
    • 35 Days On Market

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550

    2 acres off Hutton Rd

    Julie Mead The KW Collective

    0 Hutton Rd Unit MDGA2008936, Oakland, MD 21550
  • 223 Old Crellin Rd, Oakland, MD 21550
    223 Old Crellin Rd, Oakland, MD 21550
    223 Old Crellin Rd, Oakland, MD 21550
    /6

    $180,000 Sold Apr 11, 2025

    • 980 Sq Ft
    • $184/SF
    • 67 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1986

    223 Old Crellin Rd, Oakland, MD 21550

    You wont want to miss this opportunity! Stunning view from every direction of mountains, farm and forest and not to mention , views of the Youch River! The possibilities and views are endless with offering two homes in As-Is condition. This Listing is for 223 Old Crellin rd with on 11.12 acres and a 1986, 980 sq ft single wide trailer on a foundation and 207 Old Crellin rd on 1 acre with a 1400

    Garrett Shingler Realty One Group Generations

    223 Old Crellin Rd, Oakland, MD 21550
  • 17 Laurel Brook Dr, Oakland, MD 21550
    17 Laurel Brook Dr, Oakland, MD 21550
    17 Laurel Brook Dr, Oakland, MD 21550
    /21

    $275,000 Sold Apr 11, 2025

    • 1,840 Sq Ft
    • $149/SF
    • 171 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1991

    17 Laurel Brook Dr, Oakland, MD 21550

    Step into this newly remodeled three level townhome located a 1/4 mile from Deep Creek Lake, 10 minutes from Wisp Ski Resort and centrally located to dining and shopping. This unit would make a great second home with excellent short term rental potential. There are two bedrooms and one bath on the upper level, an all open concept on the entry level to include kitchen, dining and living. There is

    Michael Cumerlato Jason Mitchell Group

    17 Laurel Brook Dr, Oakland, MD 21550
  • 8 Winding Trail Ln Unit 1, Oakland, MD 21550
    8 Winding Trail Ln Unit 1, Oakland, MD 21550
    8 Winding Trail Ln Unit 1, Oakland, MD 21550
    /66

    $575,000 Sold Apr 04, 2025

    • 3,300 Sq Ft
    • $174/SF
    • 174 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2006

    8 Winding Trail Ln Unit 1, Oakland, MD 21550

    Introducing a perfect blend of luxury and convenience, this exquisite 5BR, 3-level vacation home in Timberlake Village at Deep Creek Lake offers a host of features designed for modern living and outdoor enjoyment. Whether you are seeking a wonderful home to create memories or an investment opportunity in the vacation rental market, this property delivers on all fronts! Enjoy your private

    Mike Kennedy Railey Realty, Inc.

    8 Winding Trail Ln Unit 1, Oakland, MD 21550
  • 1489 Mountainview Dr, Oakland, MD 21550
    1489 Mountainview Dr, Oakland, MD 21550
    1489 Mountainview Dr, Oakland, MD 21550
    /80

    $696,000 Sold Apr 02, 2025

    • 3,066 Sq Ft
    • $227/SF
    • 170 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2001

    1489 Mountainview Dr, Oakland, MD 21550

    Discover your retreat in this spacious 5-bedroom, 3-bath home nestled in the highly sought-after Mountainside community. Located just a stone's throw from a range of lake activities, this residence offers both tranquility and convenience in a picturesque setting. With over 3,000 square feet of thoughtfully designed living space, this home accommodates both relaxation and entertaining with ease.

    Larry Smith Railey Realty, Inc.

    1489 Mountainview Dr, Oakland, MD 21550
  • 20160 Garrett Hwy Unit F503, Oakland, MD 21550
    20160 Garrett Hwy Unit F503, Oakland, MD 21550
    20160 Garrett Hwy Unit F503, Oakland, MD 21550
    /68

    $540,000 Sold Mar 31, 2025

    • 1,700 Sq Ft
    • $318/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1972

    20160 Garrett Hwy Unit F503, Oakland, MD 21550

    Rare opportunity to own a completely renovated double unit at Will O The Wisp at Deep Creek Lake! Unit 503F extends from the 5th level up to the 7th level penthouse offering 3 bedrooms and 2 full bathrooms. The upper level bedroom is a penthouse suite offering two beds overlooking the lake and its own full bath. Enjoy eastern exposure with incredible sunrises overlooking the lake. Will O The Wisp

    Nick Fratz-Orr Railey Realty, Inc.

    20160 Garrett Hwy Unit F503, Oakland, MD 21550

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