Oakland, MD Real Estate Search

Oakland, MD Homes between $500,000 and $600,000 for Sale

Oakland, MD, offers a diverse and vibrant real estate market, particularly for homes priced between $500,000 and $600,000. Nestled in the scenic beauty of the Allegheny Mountains, this charming small town attracts homebuyers seeking a serene lifestyle with access to outdoor recreational activities such as hiking, fishing, and boating on Deep Creek Lake. Properties in this price range often feature spacious interiors, modern amenities, and expansive yards, making them ideal for families and those looking for a peaceful retreat. The community also hosts a variety of local shops, dining options, and cultural attractions, enhancing the appeal of Oakland as both a residential destination and a hub for seasonal activities.

Our website features the best real estate search for homes between $500,000 and $600,000 available in Oakland, MD and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Oakland, MD Homes between $500,000 and $600,000 for Sale

$569,000
3 Beds ⋅ 3 Baths
Fall in love with the perfect blend of comfort, privacy, and outdoor adventure in this beautifully maintained home nestled on 3.67 wooded acres overlooking scenic Meadow Lake. Thoughtfully designed for easy living, this 3-bedroom, 2.5-bath home features an open floor plan where the spacious great room flows seamlessly into a beautifully updated kitchen complete with granite countertops, making it the perfect space for gathering with family and friends. Peaceful lake views can be seen throughout the home. The spacious primary suite features a walk-in closet and a private bath with double vanities and a custom walk-in tile shower. Main-level laundry and an attached two-car garage add everyday convenience, while central air, a propane furnace, and a cozy wood-burning fireplace insert provide year-round comfort. The expansive unfinished basement offers endless possibilities for additional living space, a recreation room, workshop, or home gym. Step outside to enjoy the tranquility of nature from the front and back covered porches. The community offers a beautiful private lake perfect for kayaking, fishing, swimming, relaxing by the beach and 3 community docks. Additional amenities include private walking trails, and a storage shed that provides even more space for tools and outdoor equipment and the impressive 32' x 12' RV pavilion complete with 50 AMP, water and sewer hookups.  Located in the desirable Meadow Lake Estates community, you'll enjoy a peaceful rural setting just minutes from Herrington Manor and Swallow Falls State Parks. As an added bonus, the community borders 598 acres of Maryland DNR land fronting the Youghiogheny River, offering endless opportunities for hiking, wildlife watching, and outdoor recreation. Whether you're searching for a full-time residence, a mountain retreat, or the perfect place to embrace the beauty of Western Maryland, this exceptional property is ready to welcome you home. 

355 Markwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$549,900
4 Beds ⋅ 3 Baths
4BR 2.5BA cabin in the woods! Over 12 wooded acres of privacy and seclusion, laced with trails and surrounded by low maintenance land. Centrally located - only a few miles to Deep Creek Lake, town of Oakland or Swallow Falls State Park. Open floor plan with vaulted ceilings, a wood burning stove and high end finishes throughout. Basement is partially finished. Spacious decking and a must-have covered porch to enjoy the outdoors. Perfect as a vacation retreat or a full time residence. Located at the end of a privately maintained road. No vacation rentals permitted.

995 Betts Ln, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$595,000
2 Beds ⋅ 2 Baths
Ultimate lakefront living awaits at Red Run! This stunning 2-3BR, 2BA condo features a second-floor loft and a versatile den easily used as a 3rd bedroom. Enjoy breathtaking lake views from your gorgeous primary suite and private lakeside balcony. Extensively upgraded with a extensively upgraded kitchen boasting granite countertops and soft-close cabinetry, a newly remodeled laundry room with a new water heater and sink, an upgraded electrical panel, and premium cement-backed luxury vinyl plank flooring for ultimate durability. Stunning new shiplap ceilings with recessed lighting illuminate the freshly painted main living spaces, complete with a cozy wood-burning fireplace. Includes an assigned deep-water boat slip, outdoor storage, and access to 11 acres of incredible amenities: a heated pool, tennis courts, playground, kayak racks, and a stone fire pit. Major community updates include a new metal roof and resurfaced courts. Just minutes from downtown Oakland, Garret Cinemas, and shopping! Seller will sell his 2011 Sea Ray 195 with 4.2 L EFI engine for $4500.00 OBO "As=Is " see photos and dock slip

193 Red Run Rd Unit #1-B-3, Oakland

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005
$599,000
5 Beds ⋅ 4 Baths
Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining. Step inside to discover an inviting open-concept floor plan featuring upscale finishes throughout. The heart of the home is the stunning kitchen, complete with sleek cabinetry, solid surface countertops, stainless steel appliances, a large center island, and contemporary lighting that creates a bright and welcoming atmosphere. The adjoining dining and living spaces flow seamlessly together, making gatherings effortless. The home offers five generously sized bedrooms, including a spacious primary suite, along with 3.5 well-appointed bathrooms. The finished basement provides valuable additional living space perfect for a family room, recreation area, home gym, office, or guest accommodations. Outside, enjoy the charm of the covered front porch and the peaceful setting of this established community. The oversized attached one-car garage offers ample room for parking, storage, and outdoor equipment. Located just minutes from downtown Oakland, schools, shopping, dining, and Deep Creek Lake attractions, this exceptional property combines modern living with a highly desirable location.

428 Sam Snead Cir, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$585,000
3 Beds ⋅ 3 Baths
Tucked in the Yellowstone Village community at Deep Creek Lake, “Dan’s Mountain” is a charming log cabin retreat offering the perfect blend of mountain serenity and convenient access to the area’s top attractions. This 3-bedroom, 3-bathroom home comfortably accommodates guests spanning over 3 levels with a bonus enlcosed porch area. Warm wood interiors and a classic cabin feel welcome you inside, where multiple gathering spaces—including a cozy living area and lower-level den—provide room to relax and unwind. A standout feature is the enclosed sunroom with an indoor hot tub and stone fireplace, offering year-round enjoyment in a private setting. Outdoor living is just as inviting, with a spacious yard perfect for entertaining after a day at the lake. Located just minutes from Deep Creek’s most desirable amenities, this home brings you four seasons of enjoyment. Additionally, Yellowstone Village is one of Deep Creek Lakes top producing cabin rental communities.

55 Village Dr Unit #5, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$559,000
5 Beds ⋅ 5 Baths
Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene atmosphere with the ease of low-maintenance living and a welcoming community feel through the HOA. Already an established and successful vacation rental, this property is truly ready to enjoy or generate income from day one. Just minutes from Wisp Resort, Deep Creek Lake State Park, restaurants, shopping, and endless outdoor adventure—this is the lifestyle and investment opportunity you’ve been waiting for!

178 Winding Trail Ln Unit #5B, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$550,000
3 Beds ⋅ 2 Baths
Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 acres for a total of 42.19 acres. The 2-acre parcel is improved by a fully furnished (26’X42’), 3-bedroom, 2-bathroom Ranch style dwelling and a large parking area. The interior offers a spacious living room, and an eat-in kitchen with all appliances, furniture and window AC units. The land is un-zoned forest that borders over 2000 acres of state forest. The 42.19 acres is fully wooded with mature mixed hardwoods ready for harvest and market; the timber alone has an estimated value of $110K to $125K alone. The property overlooks the Youghiogheny River Valley and is 5.3 miles from town center McHenry and Deep Creek Lake.

98 Bear Run Rd, Oakland

Listing courtesy of 1 Real Estate Source LLC. Contact: 3013878300
$575,000
3 Beds ⋅ 2 Baths
With some minor modifications to the unit, it is possible for this condo to be rented as two separate condos (501 two BR and 701 one BR). Lakefront living at it's best can be found in this completely renovated spacious condo. This three-level unit is the perfect place to get away together! With space to come together and space to escape, this unit promises both privacy and togetherness for a memorable Deep Creek Lake experience! The first level has a full kitchen with wine fridge and attached living room with an electric fireplace, queen sleeper sofa, high top table with stools and a breathtaking balcony. Just up the stairs, enjoy the king bed in a loft bedroom that overlooks the living room and towering two-story window facing Deep Creek Lake! Also on this level is another bedroom with a Queen bed that shares a hallway bathroom with luxury finishes and a walk-in shower. On the top level you will enjoy even more space and accommodations. The 7th floor level has an additional hallway entrance for more privacy. Relax in the King bed and look out to your private balcony with gorgeous lake views. This space also features a well appointed luxury bathroom with walk-in shower and double bowl sinks. An additional mini-fridge and Keurig coffee maker provide easy access if you don't want to go downstairs. Up above in the vaulted loft curl up in the Queen size bed and take in panoramic sunrise views from every angle. Head down to the sandy beach to watch the water gently roll along the sandy shore of the resort’s private beachfront. No matter the season, there is plenty to keep you entertained with an on-site indoor pool, game room, fitness center, and more! RAILEY REALTY IS NOT THE CARETAKER OF PROPERTIES LISTED BY IT. DURING INCLEMENT WEATHER CONDITIONS, PROSPECTIVE PURCHASERS AND THEIR AGENTS ASSUME ALL LIABILITY ASSOCIATED WITH OR BY WEATHER AT THE PROPERTY.

20160 Garrett Hwy Unit #F501-701, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$545,000
4 Beds ⋅ 3 Baths
Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a separate living area, cozy gas fireplace, and beautiful hardwood floors. The open floor plan on the main living level with kitchen and dining areas is perfect for family gatherings and entertaining guests. The entry-level laundry with dog wash, a screened porch, and separate office space check all the boxes for your "wish list". Enjoy your outside space with a little over 3 acres, complete with a firepit area and walking trails throughout the property. Two detached garages, one oversized and both finished, are insulated for cars, additional storage, or hobby workshop. The A-frame cottage for kids is perfect for the ultimate in playtime Make an appointment today to tour this one-of-a-kind home in this beautiful "park-like" setting! Special Financing Options Available.

328 Stool Rock Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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