50

Oakland, MD Homes for Sale under $500,000

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  • 0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    0 5 Acres Lake Shore Dr, Oakland, MD 21550
    /3

    $250,000

    • Land
    • 5 Acres
    • $50,000 per Acre

    0 5 Acres Lake Shore Dr, Oakland, MD 21550

    5.0 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 5 Acres Lake Shore Dr, Oakland, MD 21550
  • 127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    127 S Oakhall Dr, Oakland, MD 21550
    /57

    $265,000

    $34K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,913 Sq Ft

    127 S Oakhall Dr, Oakland, MD 21550

    Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakland, MD. Inviting curb appeal with stone exterior and mature landscaping sets the tone. Step inside to a bright and spacious main level featuring gleaming hardwood floors, a large eat-in kitchen with ample cabinetry, and an open living area perfect for gatherings. Enjoy three main-level bedrooms and a full

    Agent Photo

    Nick Fratz-Orr

    Railey Realty, Inc.

    127 S Oakhall Dr, Oakland, MD 21550
  • 157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
    /29

    $294,000

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 550 Sq Ft

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550

    Nestled in the charming Traders Landing community, this delightful end-of-row townhouse offers a perfect blend of comfort and convenience with one of the best unobstructed views of the lake in Traders Landing. This villa-style home features two cozy bedrooms and a full bathroom, ideal for relaxation and unwinding after a long day. The inviting living space is enhanced by a warm wood-burning

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    157 Jeffrey Ln Unit 21B, Oakland, MD 21550
  • 0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
    /5

    $250,000

    • Land
    • 6.89 Acres
    • $36,284 per Acre

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550

    6.89 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to all area parks and amenities.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 6 89 Acres -Woodlands Hill Dr Dr Unit MDGA2011974, Oakland, MD 21550
  • 0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
    /3

    $200,000

    • Land
    • 3.15 Acres
    • $63,492 per Acre

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550

    3.15 unrestricted acres in the heart of Deep Creek Lake area, only 1/4 mile away from the lake. Ready to build your dream home with seclusion and privacy, close to area parks and amenities. No HOA.

    Agent Photo

    Brian Homberg

    Taylor-Made Deep Creek Real Estate, LLC

    0 3 15 Acres Woodlands Hill Dr Unit MDGA2012042, Oakland, MD 21550
  • 20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    20160 Garrett Hwy Unit H706, Oakland, MD 21550
    /27

    $309,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    20160 Garrett Hwy Unit H706, Oakland, MD 21550

    Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a vacation retreat, year-round getaway, or

    Agent Photo

    James Matthews

    Taylor-Made Deep Creek Real Estate, LLC

    20160 Garrett Hwy Unit H706, Oakland, MD 21550
  • 1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    1167 Tall Oaks Dr, Oakland, MD 21550
    /61

    $369,000

    $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    1167 Tall Oaks Dr, Oakland, MD 21550

    Log cabin on 11 private acres. Located in the gated Timbers on the Yough community. The community features shared access to the Youghiogheny River. Home features include spacious covered deck, newly installed walkway, exterior fire pit, breakfast bar, and pellet stove. Heart pine floors on main floor and stairs, reclaimed from RJ Reynolds tobacco factory built around 1900! The primary bath offers

    Kellyann Green Railey Realty, Inc.

    1167 Tall Oaks Dr, 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
    /65

    $464,900

    • 3 Beds
    • 3.5 Baths
    • 1,838 Sq Ft

    256 Jeffrey Ln Unit 28, Oakland, MD 21550

    Looking for a beautifully updated condo at Deep Creek Lake? Welcome to 256 Jeffrey Lane #28, a spacious 3-bedroom, 3.5-bath condo in the desirable Traders Landing community. Enjoy filtered lake views from this well-appointed home, conveniently located just across the street from the water and only minutes from Wisp Resort, restaurants, shopping, marinas, and other area attractions. With a

    Larry Smith Railey Realty, Inc.

    256 Jeffrey Ln Unit 28, Oakland, MD 21550
  • 163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    163 Mitchell Dr, Oakland, MD 21550
    /60

    $289,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    163 Mitchell Dr, Oakland, MD 21550

    Nestled in the charming Mitchell Manor community, this delightful split-level home offers a perfect blend of comfort and style. With 2,242 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. There is also a walk-in closet/dressing room to die for! Step inside to discover an

    Andrew Eiswert Railey Realty, Inc.

    163 Mitchell Dr, Oakland, MD 21550
  • 2448 Birchwood Dr, Oakland, MD 21550
    2448 Birchwood Dr, Oakland, MD 21550
    2448 Birchwood Dr, Oakland, MD 21550
    /75

    $325,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 3,352 Sq Ft

    2448 Birchwood Dr, Oakland, MD 21550

    Tucked within the sought-after Yough Mountain Resort community, this beautifully remodeled 4-bedroom, 2-bath mountain retreat blends rustic charm with thoughtful modern updates. Warm wood finishes, high ceilings, and inviting gathering spaces create a cozy lodge-style atmosphere, while upgrades throughout add comfort and convenience. The home features two full kitchens with granite countertops,

    Jon Bell Railey Realty, Inc.

    2448 Birchwood Dr, Oakland, MD 21550
  • 126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    126 Leo Friend Rd, Oakland, MD 21550
    /50

    $499,900

    $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,235 Sq Ft

    126 Leo Friend Rd, Oakland, MD 21550

    Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits

    Jon Bell Railey Realty, Inc.

    126 Leo Friend Rd, Oakland, MD 21550
  • 13 Laurel Brook Dr, Oakland, MD 21550
    13 Laurel Brook Dr, Oakland, MD 21550
    13 Laurel Brook Dr, Oakland, MD 21550
    /42

    $259,500

    $15K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    13 Laurel Brook Dr, Oakland, MD 21550

    Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile from Deep Creek Lake. Offering low maintenance and a pleasant setting, the property works well for full and part time ownership. The unit offers recent upgrades and Includes 2 parking spaces along with public water, sewer and weekly trash pickup. Shown by appointment only.

    Bill Weissgerber Railey Realty, Inc.

    13 Laurel Brook Dr, Oakland, MD 21550
  • 610 Harvey Winters Dr, Oakland, MD 21550
    610 Harvey Winters Dr, Oakland, MD 21550
    610 Harvey Winters Dr, Oakland, MD 21550
    /38

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft

    610 Harvey Winters Dr, Oakland, MD 21550

    3BR, 2BA home near Broadford Lake & Southern Middle school. Setup perfectly for one-level living with room to expand in the full, unfinished basement. Comfy living room, eat-in kitchen, separate laundry room and recent bathroom remodel. Central location to hospital, shopping and town businesses. Spacious, level back yard offers plenty of sunshine. 2 car attached garage with only a few small steps

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    610 Harvey Winters Dr, Oakland, MD 21550
  • 615 E Oak St, Oakland, MD 21550
    615 E Oak St, Oakland, MD 21550
    615 E Oak St, Oakland, MD 21550
    /60

    $365,000

    • 5 Beds
    • 3 Baths
    • 2,652 Sq Ft

    615 E Oak St, Oakland, MD 21550

    PRIME INVESTMENT OPPURTUNITY! Recently renovated (including plumbing and electric) in 2025, this triplex is a rare opportunity in the heart of downtown Oakland, MD. With three separate units, you'll have the potential for three streams of rental income from one property. Buyer could live in one unit and rent the other units out to help offset mortgage costs! Whether you're a seasoned investor or

    Lucas Muenchow Railey Realty, Inc.

    615 E Oak St, Oakland, MD 21550
  • 106 G St, Oakland, MD 21550
    106 G St, Oakland, MD 21550
    106 G St, Oakland, MD 21550
    /47

    $249,000

    • 4 Beds
    • 1 Bath
    • 1,432 Sq Ft

    106 G St, Oakland, MD 21550

    Step back in time with this charming 1900 home located in the heart of historic Mountain Lake Park. Offering 4 bedrooms, 1 bath, and 1,432 square feet, this property sits on two lots totaling 0.27 acres and is ready for its next chapter. Rich in character, the home features original woodwork, hardwood floors beneath the carpet, two fireplaces, spacious rooms, and a wraparound covered porch

    Kelsey Meyers Railey Realty, Inc.

    106 G St, Oakland, MD 21550
  • 141 Montana Ln, Oakland, MD 21550
    141 Montana Ln, Oakland, MD 21550
    141 Montana Ln, Oakland, MD 21550
    /57

    $219,000

    • 1 Bed
    • 1.5 Baths
    • 912 Sq Ft

    141 Montana Ln, Oakland, MD 21550

    Nestled on nearly 3 acres across two parcels, this chalet-style home offers a rare opportunity to create your retreat just minutes from the lake. Renovate the existing structure, or start fresh and build the lake-area retreat or cabin you’ve always imagined. The level, wooded setting provides privacy, peace, and plenty of room to expand, garden, or simply enjoy nature. With well and septic

    Larry Smith Railey Realty, Inc.

    141 Montana Ln, Oakland, MD 21550
  • 321 Deer Park Hotel Rd, Oakland, MD 21550
    321 Deer Park Hotel Rd, Oakland, MD 21550
    321 Deer Park Hotel Rd, Oakland, MD 21550
    /47

    $399,900

    • 3 Beds
    • 2 Baths
    • 2,476 Sq Ft

    321 Deer Park Hotel Rd, Oakland, MD 21550

    Double lots! Lot 4 & 5 of Hunting Ridge Estates will be sold together to bring up a total of .96 acre on your 2476 sqft. of finished living space home awaits you including your finished basement. Metal Roof is only 4 years old. Windows and doors are only 6 years old. Location, location...Welcome to 321 Deer Park Hotel Rd. where your mountain retreat will be just outside the city limits with only

    Pamela Debnam Houwzer, LLC

    321 Deer Park Hotel Rd, Oakland, MD 21550
  • 511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    511 Main St, Oakland, MD 21550
    /10

    $350,000

    • 5 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    511 Main St, Oakland, MD 21550

    The property offered for sale is 32.20 acres located on the southwest & northwest corners of Maryland Highway, State Route 135 at Main Street & Sand Flat Road, Deer Park. The Single Family Residence built in 1920 has 5 bedrooms, 1 full bathroom and 1 half bathroom. The residence is being sold "As Is". The residence is prime for renovation; the parcel may have commercial potential. The current

    Dan (Sussan) Duggan 1 Real Estate Source LLC

    511 Main St, Oakland, MD 21550
  • 123 B St, Oakland, MD 21550
    123 B St, Oakland, MD 21550
    123 B St, Oakland, MD 21550
    /6

    $219,900

    $70K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,386 Sq Ft

    123 B St, Oakland, MD 21550

    This property is an REO and is being sold in "As Is" condition. 2Bd/2Ba rancher with a 1-car garage, rear deck, and storage shed in the backyard on .27 acres.Recently painted, new flooring, and light fixtures throughout the house. Remodeled kitchen with new appliances. Both bathrooms have been updated.

    Gina Gargeu Century 21 Downtown

    123 B St, Oakland, MD 21550
  • 206 Mayhew Inn Rd, Oakland, MD 21550
    206 Mayhew Inn Rd, Oakland, MD 21550
    206 Mayhew Inn Rd, Oakland, MD 21550
    /31

    $224,900

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft

    206 Mayhew Inn Rd, Oakland, MD 21550

    Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate

    Jay Quinn Taylor-Made Deep Creek Real Estate, LLC

    206 Mayhew Inn Rd, Oakland, MD 21550
  • 565 Glendale Rd Unit 125, Oakland, MD 21550
    565 Glendale Rd Unit 125, Oakland, MD 21550
    565 Glendale Rd Unit 125, Oakland, MD 21550
    /55

    $329,900

    • 1 Bed
    • 1 Bath
    • 496 Sq Ft

    565 Glendale Rd Unit 125, Oakland, MD 21550

    Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks,

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 125, Oakland, MD 21550
  • 26 Green Brier Rd, Oakland, MD 21550
    26 Green Brier Rd, Oakland, MD 21550
    26 Green Brier Rd, Oakland, MD 21550
    /19

    $295,000

    • Land
    • 8.48 Acres
    • $34,788 per Acre

    26 Green Brier Rd, Oakland, MD 21550

    8.48± acres offering excellent commercial or residential potential. Property features an existing well and septic system, with easy access and outstanding visibility. Conveniently located just minutes from the Oakland city limits outside of Zoning Districts. Ideal opportunity for development or investment.

    Rich Orr Railey Realty, Inc.

    26 Green Brier Rd, Oakland, MD 21550
  • 112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    112 E Pennington St, Oakland, MD 21550
    /63

    $350,000

    • 5 Beds
    • 3 Baths
    • 2,165 Sq Ft

    112 E Pennington St, Oakland, MD 21550

    Completely rebuilt and beautifully renovated 5 bedroom 3 bathroom home! Welcome to this stunning 5-bedroom, 3-bathroom home that has been completely transformed from top to bottom with exceptional craftsmanship and modern finishes. Offering the charm of a classic home with the peace of mind of virtually all-new construction, this property is truly move-in ready. Major updates include a new

    Sheila Howell Lake Homes Realty, LLC

    112 E Pennington St, Oakland, MD 21550
  • 552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    552 Black Oak Dr, Oakland, MD 21550
    /46

    $349,000

    $10K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    552 Black Oak Dr, Oakland, MD 21550

    Looking for a vacation spot or main living, Check out this nicely remolded home in a gated community. 3 bedrooms, 1 1/2 bathrooms, main level laundry room. Great rustic touches . Detached Garage with pellet stove. Yough Mountain Resort is the ultimate mountain escape! Nestled in a quiet, secluded area, this beautifully updated retreat offers modern comfort in a rustic Access to over 50 miles of

    Connie Leprevost Long & Foster Real Estate, Inc.

    552 Black Oak Dr, Oakland, MD 21550
  • 531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    531 Glendale Rd Unit B302, Oakland, MD 21550
    /29

    $339,900

    $29K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    531 Glendale Rd Unit B302, Oakland, MD 21550

    Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath unit in Silver Tree Suites—one of the largest units in the complex! This beautifully designed unit features an open floorplan centered around a cozy fireplace, perfect for relaxing after a day on the lake. A generous loft area creates a distinct separation between living and sleeping spaces, offering

    Larry Smith Railey Realty, Inc.

    531 Glendale Rd Unit B302, Oakland, MD 21550
  • 511 Hilltop Rd, Oakland, MD 21550
    511 Hilltop Rd, Oakland, MD 21550
    511 Hilltop Rd, Oakland, MD 21550
    /51

    $424,900

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft

    511 Hilltop Rd, Oakland, MD 21550

    Tucked away on a quiet cul-de-sac in the desirable Royal Charlotte community, this stunning 4-bedroom, 3-bathroom home is the kind of property you'll fall in love with the moment you arrive. Surrounded by the beauty and tranquility of the mountains and accessed by county-maintained roads, this impeccably maintained home showcases pride of ownership throughout. From the expansive Trex decking that

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    511 Hilltop Rd, Oakland, MD 21550
  • 5 Laurel Brook Dr, Oakland, MD 21550
    5 Laurel Brook Dr, Oakland, MD 21550
    5 Laurel Brook Dr, Oakland, MD 21550
    /29

    $269,900

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    5 Laurel Brook Dr, Oakland, MD 21550

    Major renovations on this 2BR, 2BA Laurel brook two level townhome! Updates include new flooring, paint, fixtures, countertops, bathrooms and furnishings. One of the best dollar for dollar values still available at Deep Creek Lake and located within one mile of shopping, dining, entertainment, marinas and more! Enjoy a park-like setting with mature trees, common areas for relaxing or picnics and

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    5 Laurel Brook Dr, Oakland, MD 21550
  • 565 Glendale Rd Unit 303B, Oakland, MD 21550
    565 Glendale Rd Unit 303B, Oakland, MD 21550
    565 Glendale Rd Unit 303B, Oakland, MD 21550
    /34

    $399,900

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    565 Glendale Rd Unit 303B, Oakland, MD 21550

    Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added

    Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    565 Glendale Rd Unit 303B, Oakland, MD 21550
  • 565 Glendale Rd Unit 306, Oakland, MD 21550
    565 Glendale Rd Unit 306, Oakland, MD 21550
    565 Glendale Rd Unit 306, Oakland, MD 21550
    /32

    $249,900

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    565 Glendale Rd Unit 306, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this beautifully appointed studio loft at Silver Tree Suites—one of the lake’s most sought-after locations! Offering two separate sleeping areas, a kitchenette, gas fireplace, and private balcony, this unit is designed for comfort and easy getaway living. Tastefully updated with new carpet and flooring, as well as kitchen and bathroom

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 306, Oakland, MD 21550
  • 1499 Foster Rd, Oakland, MD 21550
    1499 Foster Rd, Oakland, MD 21550
    1499 Foster Rd, Oakland, MD 21550
    /64

    $375,000

    $40K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,234 Sq Ft

    1499 Foster Rd, Oakland, MD 21550

    Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 private wooded acres in the heart of Garrett County. Ideally located just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and downtown Oakland, this turnkey property offers the perfect balance of privacy, recreation, and modern comfort. Originally built as a raised ranch, the home has

    Kelsey Meyers Railey Realty, Inc.

    1499 Foster Rd, Oakland, MD 21550
  • 321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    321 N 3rd St, Oakland, MD 21550
    /48

    $365,000

    $35K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or

    Christina Ford CENTURY 21 New Millennium

    321 N 3rd St, Oakland, MD 21550
  • 102 N 3rd St, Oakland, MD 21550
    102 N 3rd St, Oakland, MD 21550
    102 N 3rd St, Oakland, MD 21550
    /43

    $259,900

    • 3 Beds
    • 2 Baths
    • 1,998 Sq Ft

    102 N 3rd St, Oakland, MD 21550

    Very well maintained 3Br-2BA traditional style home in Oakland with huge 24X24 deck, paved driveway and one car detached garage. Home features almost 2000 square feet of living area, stainless steel appliances, and updated bathrooms. Great place to watch the Autumn Glory parade from you covered front porch. Hot water radiant heat with natural gas being the heat source. Newer replacement windows,

    Kevin Liller Railey Realty, Inc.

    102 N 3rd St, Oakland, MD 21550
  • 718 Boy Scout Crosscut Rd, Oakland, MD 21550
    718 Boy Scout Crosscut Rd, Oakland, MD 21550
    718 Boy Scout Crosscut Rd, Oakland, MD 21550
    /58

    $459,900

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft

    718 Boy Scout Crosscut Rd, Oakland, MD 21550

    Assumable 2.75% VA loan may be available...contact listing agent for details. If peace and privacy are on your must-have list, this one delivers! Picture this: you pull into the driveway and the trees close in around you on three sides, like the forest itself is standing guard. Over an acre of land, and somehow it stays flat and usable instead of the steep terrain so common in this area. This is

    Jeremy Cunningham Railey Realty, Inc.

    718 Boy Scout Crosscut Rd, Oakland, MD 21550
  • 181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
    /25

    $249,900

    • 2 Beds
    • 1 Bath
    • 670 Sq Ft

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550

    Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during

    Larry Smith Railey Realty, Inc.

    181 Jeffrey Ln Unit 23-A, Oakland, MD 21550
  • 560 Glendale Rd, Oakland, MD 21550
    560 Glendale Rd, Oakland, MD 21550
    560 Glendale Rd, Oakland, MD 21550
    /24

    $398,000

    $21K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    560 Glendale Rd, Oakland, MD 21550

    Charming vintage Deep Creek Lake log cabin ideally located in the heart of Deep Creek Lake just minutes from area amenities. Full of character and thoughtfully restored, this established rental property is being sold completely furnished and turnkey. Enjoy filtered lake views from the inviting covered front porch, then unwind in the hot tub or gather around the fire pit after a day on the lake.

    Lauren McCann Railey Realty, Inc.

    560 Glendale Rd, Oakland, MD 21550
  • 210 F St, Oakland, MD 21550
    210 F St, Oakland, MD 21550
    210 F St, Oakland, MD 21550
    /52

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft

    210 F St, Oakland, MD 21550

    Welcome to 210 F St! This well-maintained 3-bedroom, 1-bath home offers a functional two-level floor plan with a partially finished basement, providing flexible living and storage space. Recent improvements, including a new roof and replacement windows, add value and peace of mind. Enjoy outdoor living from the covered front porch, covered back porch, or spacious rear deck overlooking the

    Zach Wesolowski Railey Realty, Inc.

    210 F St, Oakland, MD 21550
  • 961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    961 Cedar Ln, Oakland, MD 21550
    /56

    $299,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    961 Cedar Ln, Oakland, MD 21550
  • 931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    931 Black Oak Dr, Oakland, MD 21550
    /53

    $329,999

    $29K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 990 Sq Ft

    931 Black Oak Dr, Oakland, MD 21550

    Very motivated sellers!!!Escape to Your Profitable Mountain Sanctuary: The Yough Mountain CabinUnveiling the Ultimate Turnkey Retreat & High-Performing InvestmentNestled in the breathtaking heart of the exclusive Yough Mountain Resort, this stunning 3-bedroom cabin offers the perfect harmony of rustic soul and modern investment savvy. Whether you are looking for a private family getaway

    ANGELA BOSLEY Taylor-Made Deep Creek Real Estate, LLC

    931 Black Oak Dr, Oakland, MD 21550
  • 62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    62 Wild Turkey Ct, Oakland, MD 21550
    /30

    $249,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    62 Wild Turkey Ct, Oakland, MD 21550

    Current new home construction project underway, but Builder not going to complete at this time due too busy. So, ready for who may wish to complete project themselves or have completed by others, or current Builder may consider completing for Buyer. Current structure is a custom engineered modular home. This is not a completed or intended by Builder to be completed house project at this time .

    Chip Smith 1 Real Estate Source LLC

    62 Wild Turkey Ct, Oakland, MD 21550
  • 315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    315 Coolidge Ave, Oakland, MD 21550
    /53

    $269,500

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    315 Coolidge Ave, Oakland, MD 21550

    Well maintained brick rancher located in the heart of Oakland. This home offers a large kitchen open to the living room with a built-in fireplace, separate dining room, and new carpet through out. The basement is very clean, offering a clean slate for whatever you would like to do. The rear covered porch, deck and fenced in yard makes a great space to enjoy family and friends. The location is

    Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    315 Coolidge Ave, Oakland, MD 21550

Showing Results 1 - 40, Page 1 of 2

Maryland Garrett County

Real Estate & Homes in Oakland, MD under $500,000

Home Prices in Oakland, MD

The median home sale price in Oakland, MD is $405,000, up 1% year-over-year. Homes in Oakland sell in 98 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$405,000
Median Single Family Sale Price
$405,000
Median Townhouse Sale Price
$462,450
Median 2 Bedroom Sale Price
$285,000
Median 1 Bedroom Sale Price
$221,950
Average Price Per Sq Ft
$273
Number of Homes for Sale
65
Last 12 months Home Sales
142
Months of Supply
5.50
Median List Price
$422,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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