Oakland Homes under $500,000

Oakland Homes under $500,000

Welcome to Oakland, Maryland – a hidden gem nestled in the heart of Garrett County! This charming town is surrounded by breathtaking natural beauty, making it an ideal destination for those seeking a serene lifestyle without sacrificing modern conveniences. With its picturesque lakes, lush forests, and stunning mountain views, Oakland offers an abundance of outdoor activities, from boating and fishing on Deep Creek Lake to hiking the scenic trails of the nearby Appalachian Mountains.

As a vibrant community, Oakland boasts a rich history and a warm, welcoming atmosphere. Residents enjoy a variety of local shops, delightful eateries, and cultural attractions, including the historic Oakland B&O Railroad Station and the picturesque Garrett County Courthouse. The annual events, such as the Oakland Heritage Festival, bring the community together, celebrating the unique spirit of this lovely town.

For homebuyers seeking affordability without compromising on quality, Oakland is an excellent choice. The real estate market here features a variety of charming homes priced under $500,000. Whether you’re looking for a cozy cottage, a spacious family home, or a delightful getaway retreat, you’ll find an array of options that cater to diverse tastes and budgets.

With its blend of small-town charm and access to outdoor adventures, Oakland, Maryland, presents an inviting opportunity for homeownership. Come explore this enchanting town and discover your dream home amidst the beauty of Garrett County!

Newest Oakland Homes under $500,000

5423 Gorman Rd, Oakland
$225,000
1 Baths
Currently configured and listed as a small commercial store, this versatile property offers exciting potential for conversion to a residential use, subject to applicable approvals and the addition of a required sprinkler system. Enjoy beautiful mountain views and a convenient location just minutes from downtown Oakland, offering easy access to shopping, dining, entertainment, and local amenities. A unique opportunity for an owner-user, investor, or buyer looking to create a residence in a desirable and convenient location. Bring your vision and explore the possibilities!

5423 Gorman Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

503 E Alder St, Oakland
$155,000
4 Beds ⋅ 2 Baths
Large historic home with lots of unique features in the construction design. Quarter acre, corner lot with lots of outdoor space and a one car detached garage. Home has four upper level bedrooms, a main level and upper level bath.

503 E Alder St, Oakland

Listing courtesy of Homes & Land Real Estate. Contact:

2092 Gorman Rd, Oakland
$349,000
4 Beds ⋅ 2 Baths
Welcome to this spacious raised ranch offering incredible views, abundant living space, and room to grow! The main level features three bedrooms, including a private primary suite with an attached bath complete with a soaking tub, separate shower, private toilet area, and walk-in closet. The inviting kitchen boasts hardwood floors and a pantry, with two separate living areas just off the kitchen, plus a separate dining room for easy entertaining. A convenient main-level laundry and mudroom add functionality, while the paneling throughout adds a warm, classic feel. Step outside onto the covered front deck that wraps around the side of the home and offers incredible views, making it the perfect spot to enjoy your morning coffee or unwind while taking in the scenery. The lower level adds even more living space with a fourth bedroom, game room, additional finished space, and an additional bathroom that is already in place and ready for the final touches, plus additional unfinished space to make your own. An oversized two-car garage provides plenty of room for vehicles, storage, and hobbies. With beautiful surroundings, multiple living areas, a spacious lower level, and breathtaking views from the covered deck, this is a home you won’t want to miss!

2092 Gorman Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

216 N 12th St, Oakland
$285,000
3 Beds ⋅ 2 Baths
"RANCHER WITH IN GROUND POOL" Well maintained Cedar Siding Rancher on large level lot with 3 bedrooms, 1 1/2 baths, beautiful hardwood floors on main level, Living room with wood burning brick fireplace, Large eat-in-kitchen/ dining area, with door that leads to deck overlooking in ground pool! Fenced yard and huge shed/pool storage, lower level finished great room for family entertaining with cozy wood stove which will be great for chilly days. New roof, hot water heater, cedar just stained/sealed, Professional pictures to follow ....

216 N 12th St, Oakland

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

210 Seneca Ave, Oakland
$229,000
3 Beds ⋅ 1 Baths
Excellent opportunity for first time home buyers or anyone looking for an easy to manage home. This charming ranch-style home offers a perfect blend of comfort and functionality. The floor plan seamlessly connects the combination kitchen and dining area, ideal for gatherings. The kitchen boasts stainless steel appliances, including a double oven and built-in microwave, making meal prep a delight. Cozy up in the inviting living space, perfect for relaxing evenings. The home features three well-appointed bedrooms, including an entry-level option for convenience. Enjoy the look of newly installed luxury vinyl plank throughout. Outside, the level lot and fenced in yard provides ample space for outdoor activities, complemented by a covered side porch and an outbuilding for extra storage. With a driveway for easy parking and a welcoming atmosphere, this home is ready to embrace new memories. Experience the warmth and charm that awaits in this delightful property! Call Today to schedule a showing.

210 Seneca Ave, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

425 E Alder St, Oakland
$449,000
Rare opportunity to own a beautifully remodeled multifamily duplex in the heart of downtown Oakland! Situated on a desirable corner lot and conveniently located near Garrett Regional Medical Center, downtown shopping, dining, and local amenities, this property offers an exceptional combination of location, versatility, and investment potential. Both units have been fully remodeled with upgraded kitchens, beautifully updated bathrooms, and new flooring throughout, providing modern finishes while maintaining the character and functionality of the home. One side features 3 bedrooms and 2.5 bathrooms, while the other offers 3 bedrooms and 2 bathrooms, making this an ideal property for an investor seeking a strong multifamily opportunity or an owner-occupant looking to live in one unit while generating rental income from the other. Multifamily properties in downtown Oakland are a rare find, and opportunities like this don't come along often. Whether you're expanding your investment portfolio or looking for a property that can help offset your living expenses, this duplex deserves your attention. Truly a must-see!

425 E Alder St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

127 Jeffrey Ln Unit 4, Oakland
$279,000
2 Beds ⋅ 1 Baths
Roman Ridge is the perfect location for your Deep Creek retreat! This unit has been very well taken care of and conveys fully furnished for immediate enjoyment! Main floor bedroom with full bath and upper level loft bedroom provide great resting space for family and friends. The inviting living area is complete with a warm wood-burning fireplace, perfect for those cool Garrett County evenings! Excellently maintained with new appliances to include stove, refrigerator and hot water heater. Enjoy outdoor entertaining with wonderful lake and mountain views from the expanded deck! Take a look now at Roman Ridge!

127 Jeffrey Ln Unit 4, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

565 Glendale Rd Unit 316, Oakland
$279,000
2 Beds ⋅ 1 Baths
Deep Creek Lake living, without the upkeep. This Silver Tree Suites unit features two beds, an oversized loft, plus a kitchenette, gas fireplace, and private balcony. That's paired with resort-style on-site amenities: a marina, fitness room, sauna, and expansive lakefront deck, all just steps from your door. Dutch's at Silver Tree is directly adjoining along with the Harbor Bar, and Wisp Resort, state parks, and year-round recreation are minutes away. Already an active vacation rental, so the income starts the day you close. Call for more details or to schedule your private tour today!

565 Glendale Rd Unit 316, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

1959 Birchwood Dr, Oakland
$235,000
2 Beds ⋅ 2 Baths
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, while stainless steel appliances and recent updates make the home easy to enjoy. Recent improvements include laminate flooring, added washer and dryer hookups, a water filtration system, a vapor barrier installed in the crawlspace, a new gravel circular driveway, and a new shed for additional storage. Outside, enjoy the covered front porch, rear deck, and balcony off the bedroom, all surrounded by the privacy and beauty of the mountains. Yough Mountain Resort offers 50+ miles of ATV, snowmobile, and hiking trails, as well as fishing, hunting areas, and numerous community amenities. If you're looking for a cabin with privacy, updates, and plenty of outdoor recreation right at your doorstep, this one is ready to enjoy! Call today!

1959 Birchwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

607 Pin Oak Cir, Oakland
$499,000
5 Beds ⋅ 4 Baths
Immaculate from top to bottom, this exceptional five-bedroom home offers three levels of beautifully maintained living space, making it an ideal choice for a primary residence. Thoughtfully designed for comfortable everyday living, the home provides plenty of room to gather, relax, and spread out. A stunning fireplace creates a warm and inviting focal point, while the attached two-car garage adds convenience and storage. Above the garage, an unfinished room offers exciting potential for additional storage, an office, guest quarters, or additional living space. The downstairs family room offers expansive square footage for cozy gatherings. Numerous recent upgrades, including a new roof, high-efficiency mini-split units, and an upgraded energy-efficient boiler and hot water system, provide added peace of mind. The beautiful screened-in back porch is perfect for enjoying morning coffee, relaxing in the evening, or entertaining guests. Tucked away in a wonderful, private Oakland neighborhood, this home offers peaceful residential living while remaining conveniently close to Deep Creek Lake, Wisp Resort, and area amenities. A truly special property that checks all the boxes!

607 Pin Oak Cir, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

139 S Oakhall Dr, Oakland
$229,000
3 Beds ⋅ 2 Baths
Location, location, location! Enjoy easy living in this one-level raised rancher featuring 3 bedrooms and 1.5 baths, with all bedrooms conveniently located on the main level. Beautiful hardwood floors add warmth, while the covered front porch and side covered deck offer inviting spaces to relax and enjoy the peaceful surroundings. The fenced-in backyard provides plenty of outdoor space for pets, play, or entertaining. The full basement is ready for your finishing touches and offers additional potential, while the attached one-car lower-level garage provides convenient parking or extra storage. Recent updates include a new roof and a full WaterGuard system installed along the interior basement foundation. Located in a peaceful neighborhood close to schools, the hospital, and shopping, this home offers comfort, convenience, and plenty of opportunity to make it your own. Call today to schedule your showing!

139 S Oakhall Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

586 Bray School Rd, Oakland
$289,000
4 Beds ⋅ 2 Baths
Spacious one level home, 4 BR with den, living room, extra office off Main BR, large back yard with huge deck. Very large main bedroom with bath and extra room (could be nursery, extra BR or office) . 2 Full baths, 2 fireplaces, Laundry and perfect location for privacy, yet close to all things fun in the Deep Creek Lake area. One mile from Deep Creek Lake, 2 miles from Swallow Falls State Park. Begin sold "AS IS" recent updates, - new Patio door to deck, new flooring in in Kitchen/dinning.

586 Bray School Rd, Oakland

Listing courtesy of The KW Collective. Contact:

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