Oakland, MD Homes for Sale under $500,000

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  /64

  $275,900

  • 4 Beds
  • 2 Baths
  • 1,928 Sq Ft

  449 S 3rd St, Oakland, MD 21550

  Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where historic character meets modern convenience. Situated on a charming lot with mature landscaping and blooming trees, this home offers timeless curb appeal with a welcoming covered front porch perfect for relaxing and enjoying the neighborhood. Inside, you’ll find modern updates throughout while preserving classic

  Justin Liller Railey Realty, Inc.

  449 S 3rd St, Oakland, MD 21550
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  /52

  $399,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  1407 Broadford Rd, Oakland, MD 21550

  Welcome to this beautifully crafted new construction home, where modern comfort meets thoughtful design in an unbeatable location. From the moment you step inside, you'll appreciate the spacious layout, quality finishes, cathedral ceilings, and abundance of natural light throughout. The heart of the home is the spacious kitchen, featuring crisp white cabinetry, warm natural wood butcher-block

  Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

  1407 Broadford Rd, Oakland, MD 21550
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  /25

  $296,500

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  20160 Garrett Hwy Unit 105A, Oakland, MD 21550

  Will O the Wisp unit 105A is a charming one-bedroom, one-bath lakefront condominium. Unit 105A offers convenient first-floor living with ground-level access from a private patio directly to the waters edge, beach area and docks. . The unit features a fully equipped kitchen, comfortable living and dining areas, a cozy fireplace, one queen bed, and a sleeper sofa—accommodating up to three

  Rich Orr Railey Realty, Inc.

  20160 Garrett Hwy Unit 105A, Oakland, MD 21550
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  /32

  $299,900

  $29K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  565 Glendale Rd Unit B206, Oakland, MD 21550

  Charming true 1-bedroom + loft (can be used as 2nd bedroom) condo at Silver Tree Suites, LAKEFRONT living at its finest! This spacious second-floor unit features a private balcony, fully equipped kitchenette, cozy gas fireplace and abundant natural light. Enjoy resort-style amenities including a fitness center, sauna, on-site laundry and game room, plus steps-away fine dining at Dutch’s at Silver

  Carlos Espinoza Jason Mitchell Group

  565 Glendale Rd Unit B206, Oakland, MD 21550
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  /36

  $235,000

  • 2 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  1959 Birchwood Dr, Oakland, MD 21550

  Comfy, cozy, and full of mountain charm! This inviting 2-bedroom, 1.5-bath cabin is nestled on 1.26 private acres within Yough Mountain Resort, offering the perfect setting for a weekend getaway, recreational retreat, or peaceful escape. The open floor plan creates a comfortable gathering space, highlighted by a beautiful stone fireplace with a wood-burning insert that adds warmth and character,

  Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

  1959 Birchwood Dr, Oakland, MD 21550
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  /27

  $259,000

  • Land
  • 42 Acres
  • $6,167 per Acre

  Lot B Loch Deer Rd, Oakland, MD 21550

  42 Acres of un-zoned mostly wooded property located near Oakland and Deep Creek Lake MD. The property offers great opportunities for a variety of uses and also provides great views. Access to the property is off of Garrett Road via Loch Deer Road. The property has been surveyed.

  Bill Weissgerber Railey Realty, Inc.

  Lot B Loch Deer Rd, Oakland, MD 21550
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  /22

  $294,999

  • 2 Beds
  • 1 Bath
  • 2,344 Sq Ft

  135 Jeffrey Ln Unit 19-A, Oakland, MD 21550

  Experience the best of lakeview living in this great condo at Deep Creek Lake. Offering two bedrooms, a fireplace and a lower-level family room for your enjoyment. Wake up to peaceful water views and enjoy ample space for everyday comfort and entertaining. The location is another plus, within walking distance to coffee shop, dining, and shopping. A perfect blend of size, scenery, and value!

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

  135 Jeffrey Ln Unit 19-A, Oakland, MD 21550
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  /49

  $379,500

  • 1 Bed
  • 1 Bath
  • 636 Sq Ft

  20160 Garrett Hwy Unit C307, Oakland, MD 21550

  Experience the best of Deep Creek Lake from this beautifully situated 2-story, 1-bedroom, 1-bath condominium at Will O' The Wisp. Offering 636 square feet of comfortable living space and spectacular lake views, this waterfront retreat is the perfect personal getaway, year-round residence, or vacation rental investment. Enjoy your morning coffee while taking in panoramic views of the water, then

  Justin Liller Railey Realty, Inc.

  20160 Garrett Hwy Unit C307, Oakland, MD 21550
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  /55

  $400,000

  $120K PRICE INCREASE

  • Land
  • 43.72 Acres
  • $9,149 per Acre

  3257 George Washington Hwy, Oakland, MD 21550

  Discover approximately 43.72 acres of beautiful mostly wooded land offering privacy, mountain views, and exceptional convenience. This expansive property provides easy access to both George Washington Highway and Garrett Highway, making travel simple while still feeling tucked away in nature. Set up with a well and septic system, this property is perfect to build your dream home with an already

  Justin Liller Railey Realty, Inc.

  3257 George Washington Hwy, Oakland, MD 21550
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  /40

  $229,900

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  808 N St, Oakland, MD 21550

  Nestled in the charming Oakland subdivision, this delightful traditional-style home, built in 2022, offers a perfect blend of modern comfort and timeless appeal. With 1,008 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy yet functional environment. Step inside to discover a warm and inviting atmosphere, accentuated by luxury vinyl tile flooring

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

  808 N St, Oakland, MD 21550
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  /42

  $249,900

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 560 Sq Ft

  400 Bear Dr E, Oakland, MD 21550

  Tucked away in the scenic beauty of Yough Mountain Resort, this exceptional 2-bedroom, 2-bath log cabin offers the perfect blend of rustic charm and modern comfort. Spanning two stories, this immaculately maintained home has seen thoughtful renovations in recent years, creating a warm and inviting retreat that’s move-in ready.Step inside to discover cozy living spaces ideal for relaxing

  Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

  400 Bear Dr E, Oakland, MD 21550
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  /51

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  181 Glotfelty Dr, Oakland, MD 21550

  Talk about central location! Only minutes to Deep Creek Lake, Wisp Resort and downtown Oakland! This 3 bedroom, 2 bath home sits on a nice-sized 1.29 AC partially wooded lot, at the end of a private, no thru street. Great outdoor living space as well with a covered porch, back deck and large 24x44 detached garage. Many upgrades & improvements by the current owner, to include new HVAC, all new

  Kathy Gibson Railey Realty, Inc.

  181 Glotfelty Dr, Oakland, MD 21550
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  /68

  $460,000

  • 5 Beds
  • 2 Baths
  • 2,860 Sq Ft

  5154 Maryland Hwy, Oakland, MD 21550

  Escape to the tranquility of country living in this spacious 5-bedroom, 2-bath home nestled on over 2 acres and conveniently located just minutes from the recreational opportunities of Deep Creek Lake and the charming town of Oakland, The property offers the perfect combination of peaceful country living and easy access to shopping, dining, and year-round activities. The kitchen has been

  Charlene Deremer Aburn Coldwell Banker Home Town Realty

  5154 Maryland Hwy, Oakland, MD 21550
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  /2

  $305,000

  $64K PRICE DROP

  • Land
  • 20,473 Sq Ft
  • $648,936 per Acre

  8946 Oakland Sang Run Rd, Oakland, MD 21550

  There are 3 adjacent parcels included with this sale :Tax ID - 1206034144, 1206020860, 1206007082All parcels together are 8 acresWARNING: The house on this property is condemned and ready for tear down. Enter at your own risk.

  Joe Zorzit Eagle Commercial Realty

  8946 Oakland Sang Run Rd, Oakland, MD 21550

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