239

Recently Sold Oakland, MD Homes

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  • 1100 S Blakeslee Rd, Oakland, MD 21550
    1100 S Blakeslee Rd, Oakland, MD 21550
    1100 S Blakeslee Rd, Oakland, MD 21550
    /127

    $2,550,000 Sold Aug 01, 2025

    • 6,572 Sq Ft
    • $388/SF
    • 0 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 1998

    1100 S Blakeslee Rd, Oakland, MD 21550

    A spectacular Deep Creek Lake offering! Here is your rare opportunity to experience the best in lake living at the Blakeslee, Deep Creek Lake's most complete development. Located on the desirable southwest portion of the lake, the level wooded lakefront lot faces directly across the lake to the yacht club and offers opportunities to view spectacular sailboat races. from your private

    Bill Weissgerber Railey Realty, Inc.

    1100 S Blakeslee Rd, Oakland, MD 21550
  • 20160 Garrett Hwy Unit H712, Oakland, MD 21550
    20160 Garrett Hwy Unit H712, Oakland, MD 21550
    20160 Garrett Hwy Unit H712, Oakland, MD 21550
    /28

    $339,000 Sold Aug 01, 2025

    • 450 Sq Ft
    • $753/SF
    • 124 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1972

    20160 Garrett Hwy Unit H712, Oakland, MD 21550

    Welcome to this stunning Will-O-The-Wisp Loft Unit that has beenfully remodeled to offer the perfect blend of modern luxury and breathtaking views of Deep Creek Lake. This unit offers an unparalleled living experience of convenience and location. Every detail has been carefully crafted, from high-end finishes making this home truly one-of-a-kind. The open-concept living space is bathed in

    Larry Smith Railey Realty, Inc.

    20160 Garrett Hwy Unit H712, Oakland, MD 21550
  • 10 Laurel Brook Dr, Oakland, MD 21550
    10 Laurel Brook Dr, Oakland, MD 21550
    10 Laurel Brook Dr, Oakland, MD 21550
    /39

    $210,000 Sold Aug 01, 2025

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

    10 Laurel Brook Dr, Oakland, MD 21550

    Welcome to 10 Laurel Brook Drive! Experience lake area living with leisure and low maintenance condo lifestyle! This condo offers 2 bedrooms and 2 full bathrooms and is just minutes from all of Deep Creek Lake's amenities. Only about 15 minutes to the town of Oakland. This could make a great second home or primary residence.

    Michael Cumerlato Jason Mitchell Group

    10 Laurel Brook Dr, Oakland, MD 21550
  • 500 Seneca Ave, Oakland, MD 21550
    500 Seneca Ave, Oakland, MD 21550
    500 Seneca Ave, Oakland, MD 21550
    /13

    $62,000 Sold Aug 01, 2025

    • 1,284 Sq Ft
    • $48/SF
    • 577 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1940

    500 Seneca Ave, Oakland, MD 21550

    A little TLC and this bungalow would make a nice first home or investment property. Corner lot in residential neighborhood, close to Loch Lynn Town Park and Athletic Fields. Convenient one floor living space also includes appliances, hot tub, two sheds, and back deck.

    Paul Macy Garrett Land Sales, PC

    500 Seneca Ave, Oakland, MD 21550
  • 4012 Maryland Hwy, Oakland, MD 21550
    4012 Maryland Hwy, Oakland, MD 21550
    4012 Maryland Hwy, Oakland, MD 21550
    /55

    $280,000 Sold Jul 31, 2025

    • 1,824 Sq Ft
    • $154/SF
    • 32 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1968

    4012 Maryland Hwy, Oakland, MD 21550

    Tucked back off the beaten path with room to breathe - this solid split-level sits on nearly an acre just 8 minutes from Oakland and 12 from Deep Creek Lake. Meticulously cared for with strong bones and classic charm. Detached garage for tools or toys. Large driveway with plenty of off-street parking. Private back patio surrounded by trees. Roomy half bath with space to convert. 2nd Living area

    Michael Fenton Railey Realty, Inc.

    4012 Maryland Hwy, Oakland, MD 21550
  • 707 Sunshine Dr, Oakland, MD 21550
    707 Sunshine Dr, Oakland, MD 21550
    707 Sunshine Dr, Oakland, MD 21550
    /68

    $310,000 Sold Jul 31, 2025

    • 2,052 Sq Ft
    • $151/SF
    • 94 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2004

    707 Sunshine Dr, Oakland, MD 21550

    Expansive 3 bedroom 2 bathroom rancher on a full walkout basement! All 3 bedrooms are large with walk in closets. Master suite features his and her walk in closets, linen closet in the bathroom, double vanities, soaking tub and standup shower. Huge kitchen with pantry. Two car garage with laundry/mudroom into the home. Expansive back deck overlooking the pond! The walk out basement is ready to be

    Tyler Burch Burch Real Estate Group, LLC

    707 Sunshine Dr, Oakland, MD 21550
  • 1484 Paradise Point Rd, Oakland, MD 21550
    1484 Paradise Point Rd, Oakland, MD 21550
    1484 Paradise Point Rd, Oakland, MD 21550
    /47

    $1,762,500 Sold Jul 29, 2025

    • 3,360 Sq Ft
    • $525/SF
    • 16 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2022

    1484 Paradise Point Rd, Oakland, MD 21550

    "In the Groove" is a newly constructed, high-end lakefront home offering 5 bedrooms, 4.5 bathrooms, and over 3,300 square feet of finished living space on a level lakefront lot in a quiet no-wake cove of Deep Creek Lake. This property features 85 ft of lakefront, a Type A dock with a jet ski port included, no HOA, and a high-grade automatic fire sprinkler system with a dedicated control panel for

    Kelsey Meyers Railey Realty, Inc.

    1484 Paradise Point Rd, Oakland, MD 21550
  • 5154 Maryland Hwy, Oakland, MD 21550
    5154 Maryland Hwy, Oakland, MD 21550
    5154 Maryland Hwy, Oakland, MD 21550
    /65

    $375,000 Sold Jul 29, 2025

    • 2,860 Sq Ft
    • $131/SF
    • 23 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1980

    5154 Maryland Hwy, Oakland, MD 21550

    Welcome to this lovely home in the country setting with endless opportunity. This 5 bedroom/ 2 bathroom home has an incredible layout with plenty of space for entertaining guest inside and out. Located just outside of Oakland and situated on 2.30acres. The covered wrap around porch is great spot to relax or grill out with family and friends throughout the year. The main level features large

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    5154 Maryland Hwy, Oakland, MD 21550
  • 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
  • 29 Sloan Tract Rd, Oakland, MD 21550
    29 Sloan Tract Rd, Oakland, MD 21550
    29 Sloan Tract Rd, 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
  • 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
  • 1714 Mayhew Inn Rd, Oakland, MD 21550
    1714 Mayhew Inn Rd, Oakland, MD 21550
    1714 Mayhew Inn Rd, Oakland, MD 21550
    /23

    $119,000 Sold Jul 18, 2025

    • Land
    • 8 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
  • 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
  • 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
  • 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
  • 15 D St, Oakland, MD 21550
    15 D St, Oakland, MD 21550
    15 D St, Oakland, MD 21550
    /44

    $140,000 Sold Jul 08, 2025

    • 1,680 Sq Ft
    • $83/SF
    • 86 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1953

    15 D St, Oakland, MD 21550

    Solid bones with room to grow. This two-bedroom, one-and-a-half-bath home sits in a quiet spot in Mountain Lake Park, offering a fenced front and back yard for privacy, pets, or play. A detached garage adds extra storage or a workshop. Conveniently located near Downtown Oakland and just 20 minutes from McHenry, it’s a prime spot with potential. Whether you're looking for a starter home or a

    Jon Bell Railey Realty, Inc.

    15 D St, 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
  • 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 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
  • 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
  • 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

Showing Results 1 - 40, Page 1 of 6

Maryland Garrett County Oakland

Recently Sold Real Estate & Homes in Oakland, MD

Frequently Asked Questions Why Live in Oakland

What is the average home price in Oakland, MD?
Homes for sale in Oakland, MD have an average home price of $831,546.
What is the average time to sell a house in Oakland, MD?
The houses for sale in Oakland, MD spend an average of 120 days on the market.
What is the number of active homes for sale in Oakland, MD?
There are 39 active homes for sale in Oakland, MD.
How many homes have sold over the last 12 months in Oakland, MD?
61 homes have sold in Oakland, MD over the last 12 months.
Learn more about living in Oakland

Home Trends in Oakland, MD

On average, homes in Oakland, MD sell after 120 days on the market compared to the national average of 70 days. The median sale price for homes in Oakland, MD over the last 12 months is $465,000, down 15% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$465,000
Median Single Family Sale Price
$592,500
Median Townhouse Sale Price
$369,900
Median 2 Bedroom Sale Price
$440,000
Median 1 Bedroom Sale Price
$270,000
Average Price Per Sq Ft
$385
Number of Homes for Sale
39
Last 12 months Home Sales
61
Months of Supply
7.70
Median List Price
$527,250
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-15%
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