Oakland Homes under $400,000

Oakland Homes under $400,000

Welcome to Oakland, Maryland, a hidden gem nestled in the heart of Garrett County! This charming town offers a perfect blend of natural beauty and small-town charm, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle. Surrounded by stunning mountains, lush forests, and pristine lakes, Oakland is a haven for outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply soaking in the breathtaking views, this community has something for everyone.

One of the most appealing aspects of Oakland is its diverse real estate market, particularly for those seeking homes under $400,000. Here, you can find a variety of options that cater to different tastes and lifestyles. From cozy cottages to spacious family homes, Oakland offers affordable properties that don’t compromise on comfort or style. Imagine waking up to the serene sounds of nature, with easy access to local amenities, schools, and parks—all within a friendly, welcoming community.

The town is also rich in history and culture, with charming shops, delightful cafés, and seasonal festivals that bring residents together. Oakland's close-knit community vibe makes it easy to forge lasting friendships and create wonderful memories.

If you’re looking for a place to call home that offers both affordability and a picturesque setting, Oakland, MD, is the perfect choice. Explore the available homes under $400,000 and discover the lifestyle you’ve always dreamed of in this enchanting town!

Newest Oakland Homes under $400,000

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:

216 N 12th St, Oakland
$265,000
3 Beds ⋅ 2 Baths
"RANCHER WITH IN GROUND POOL" REDUCED!! 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! AND NEW DRIVEWAY 10/2026 COST WAS $8K - Come take a look!

216 N 12th St, Oakland

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

615 E Oak St, Oakland
$365,000
5 Beds ⋅ 3 Baths
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 just getting started, this turnkey property offers updated finishes, strong income potential, and a prime location just steps from shops, restaurants, and everything downtown has to offer. Top floor is 1-bedroom and 1-bathroom. Middle floor is 2-bedroom and 1-bathroom. Bottom floor is 2-bedroom, 1-bathroom and has a laundry hookup. Contact me today with any questions or to schedule a time to tour the property!

615 E Oak St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

102 N 3rd St, Oakland
$259,900
3 Beds ⋅ 2 Baths
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, roof replaced recently and as an added bonus this home features a whole house generator back-up. Convenient to all town activities, schools, and the hospital. 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.

102 N 3rd St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

321 N 3rd St, Oakland
$350,000
5 Beds ⋅ 2 Baths
Aww shucks - the sellers have reduced the price!! 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 flexible multi-generational use. Inside, you’ll find a welcoming living room with custom built-in cabinetry, a separate formal dining room, hardwood floors, and two cozy fireplaces that add warmth and character throughout the home. The bright and inviting sunroom provides the perfect place to relax year-round with abundant natural light and additional living space for entertaining or quiet mornings at home. Outdoor living is just as impressive with a large, fully fenced rear yard, rear deck ideal for entertaining, plenty of parking, a one-car garage, and an oversized 28x12 shed offering exceptional storage or workshop space. Additional updates include replacement windows and an HVAC system approximately 6 years old for added peace of mind. Conveniently located within walking distance to town, hospital and medical offices, pharmacy, dining, and banking, this home combines space, comfort, and accessibility in one exceptional property.

321 N 3rd St, Oakland

Listing courtesy of CENTURY 21 New Millennium. Contact:

206 Mayhew Inn Rd, Oakland
$224,900
1 Beds ⋅ 1 Baths
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 entrances for the garage and living space, this property offers built-in flexibility for income potential or multi-purpose use. Plus, the location is minutes to lake activities and downtown Oakland. Don't miss out on the chance to own this versatile gem. Schedule a showing today!

206 Mayhew Inn Rd, Oakland

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

315 Coolidge Ave, Oakland
$264,500
3 Beds ⋅ 2 Baths
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 just minutes to grocery stores, schools, shopping and restaurants. This home won't last long, call today to preview!

315 Coolidge Ave, Oakland

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

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