Oakland, MD Homes for Sale under $500,000

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  /13

  $425,000

  • 3 Beds
  • 3.5 Baths
  • 1,596 Sq Ft

  104 Pine Top Trail, Oakland, MD 21550

  Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acreage is right next to the Common Grounds and gives you immediate river access.

  laura Flynn 1 Real Estate Source LLC

  104 Pine Top Trail, Oakland, MD 21550
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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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  /32

  $304,000

  $25K 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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  /43

  $475,000

  • 4 Beds
  • 3.5 Baths
  • 1,492 Sq Ft

  333 Sloan Tract Rd, Oakland, MD 21550

  Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home has three levels of living space, hardwood flooring and a nice fireplace. The lower level is totally finished with walk-out access. There are multiple covered porches plus a hot tub that are great outdoor spaces to enjoy year round. This home feels very secluded but is just minutes to Deep Creek Lake and Wisp

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

  333 Sloan Tract 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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  /46

  $285,500

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft

  1737 King Wildesen Rd, Oakland, MD 21550

  Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland. This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP)

  Justin Liller Railey Realty, Inc.

  1737 King Wildesen Rd, 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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  /37

  $279,000

  • 3 Beds
  • 1.5 Baths
  • 1,148 Sq Ft

  277 Cheeks Ln, Oakland, MD 21550

  Tucked away on a private lane and surrounded by the beauty of the woods, this charming 3-bedroom, 1 full bath and 1 half bath log home offers the perfect mountain retreat on 2 peaceful acres in Garrett County. Ideally located just minutes from Swallow Falls State Park, Muddy Creek Falls, and the Youghiogheny River, this cozy cabin is a dream destination for outdoor enthusiasts seeking hiking,

  Mike Kennedy Railey Realty, Inc.

  277 Cheeks Ln, Oakland, MD 21550
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  /8

  $280,000

  • Land
  • 36.72 Acres
  • $7,625 per Acre

  3257 George Washington Hwy, Oakland, MD 21550

  Discover approximately 36.72 acres of beautiful 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. Located within a 30-minute drive of Deep Creek Lake and Wisp Resort, as well as sought-after West Virginia

  Justin Liller Railey Realty, Inc.

  3257 George Washington Hwy, Oakland, MD 21550
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  /42

  $279,900

  $20K 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 after a

  Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

  400 Bear Dr E, Oakland, MD 21550
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  /2

  $369,000

  • Land
  • 20,473 Sq Ft
  • $785,106 per Acre

  8946 Oakland Sang Run Rd, Oakland, MD 21550

  There are 3 adjacent parcels included with this sale :Tax ID - 1206034144, 1206020860, 1206007082 All parcels together are 8 acres WARNING: 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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