Oakland Homes under $400,000

Oakland Homes under $400,000

Welcome to Oakland, Maryland – a hidden gem nestled in the picturesque Garrett County! Known for its stunning natural beauty, Oakland is a charming town that offers a perfect blend of small-town warmth and outdoor adventure. With its serene lakes, lush forests, and rolling hills, Oakland is an ideal destination for nature lovers and those seeking a peaceful lifestyle.

One of the standout features of Oakland is its affordability, especially when it comes to homeownership. Here, you can find a variety of homes under $400,000, making it an excellent opportunity for first-time buyers, families, and retirees alike. Whether you're looking for a cozy cottage, a spacious family home, or a charming bungalow, Oakland has something to suit every taste and budget.

The local community is vibrant and welcoming, with a rich history that dates back to the 1800s. Residents enjoy a variety of local amenities, including quaint shops, delicious dining options, and community events that foster a strong sense of belonging. The nearby Deep Creek Lake offers year-round recreational activities, from boating and fishing in the summer to skiing and snowboarding in the winter.

With its affordable housing options and breathtaking surroundings, Oakland, Maryland, is not just a place to live—it's a place to thrive. Explore the possibilities of calling this enchanting town your home, and discover the perfect balance of comfort, adventure, and community. Your dream home awaits in Oakland!

Newest Oakland Homes under $400,000

5979 Cranesville Rd, Oakland
$339,000
5 Beds ⋅ 4 Baths
Stunning 1900 farmhouse situated on 7.82 acres, offering incredible mountain views, a spacious yard, and a beautiful setting adjacent to Nature Conservancy land.. The home features vinyl siding, a shingle roof, and a wraparound deck perfect for enjoying the surrounding scenery. Inside, you'll find five bedrooms, a welcoming entryway and mudroom, main-level laundry, and a spacious layout with three bedrooms on the main level, including a larger primary bedroom and one bedroom with an attached bathroom. The main bathroom features a double-sink vanity, while the upper level offers two additional bedrooms, including one with an attached bathroom featuring both a shower and bathtub. An electric heat pump with central air conditioning provides year-round comfort. The property also includes an impressive 30x50 detached garage with electricity and overhead doors at both the front and rear, offering plenty of space for vehicles, equipment, hobbies, or a workshop. With its acreage, breathtaking mountain views, and generous outdoor space this property offers a unique opportunity to enjoy the charm and possibilities of country living. A separate trailer on the property offers potential for a guest house or additional living space, with work needed to bring it to its full potential. The property is conveniently located just minutes from Deep Creek Lake and the town of Oakland, offering easy access to local shopping, dining, recreation, and year-round outdoor activities. Call today!

5979 Cranesville Rd, Oakland

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

565 Glendale Rd Unit 208, Oakland
$178,000
1 Beds ⋅ 1 Baths
Discover the perfect blend of comfort, convenience and resort-style amenities with this one bedroom, one bath condo at Silver Tree Suites. The balcony is adorned with morning sun to enjoy some coffee or tea. This unit is ideally located on the second floor with close proximity to the elevator and stairs. Enjoy the inviting common areas featuring two peaceful sitting spaces with beautiful lake views. The majestic stone fireplace adds warmth and character. Additional amenities include a fitness center, sauna, game room, laundry facility and meeting spaces. Enjoy the added convenience of Dutch's Resturaunt year round and the Harbor Bar and Marina during the summer. Condo dues include public water, sewer, trash, hot water, propane, water heater and maintenance, snow removal, and grounds upkeep, all helping simplify ownership. Ideally situated near all that Deep Creek Lake has to offer, you'll have easy access to boating, skiing, hiking and the areas many year round attractions. Whether you're looking for an investment opportunity or a relaxing weekend retreat to call your own, this Silver Tree Suites Condo offers an excellent opportunity to enjoy the best of Deep Creek Lake living!

565 Glendale Rd Unit 208, Oakland

Listing courtesy of The Goodfellow Agency. Contact:

16 E Pennington St E, Oakland
$189,900
3 Beds ⋅ 3 Baths
Welcome to 16 E. Pennington Street! This charming two-story home in the heart of downtown Oakland offers plenty of space, character, and an opportunity to make it your own, all at an affordable price! Just a short drive to Deep Creek Lake and priced to sell! Spacious colonial offering over 1,550 square feet, this home features three spacious bedrooms, two full bathrooms, and a convenient main-level half bath. The inviting front porch is a great place to relax, while the covered rear porch and deck provide additional space to enjoy the outdoors. Inside, you'll find a comfortable living room, a separate dining room with plenty of room to gather, and a spacious kitchen featuring oak cabinetry, a gas stove, and room for a large table. A generous laundry area, convenient half bath, and additional storage complete the main level. Upstairs, the primary bedroom offers great natural light and a spacious closet. Two additional generously sized bedrooms and two full bathrooms provide flexibility for family, guests, or a home office. The home underwent a full renovation in 2003 and offers additional improvements such as updated trex front porch steps and an insulated crawl space. Natural gas heat, public utilities, and no HOA add to the appeal. Situated on a nearly quarter-acre lot with off-street parking, this property offers the charm of an older home with plenty of room to personalize. Conveniently located in Oakland with access to local shopping, dining, and everyday amenities, it's a wonderful opportunity for a primary residence or investment property. Don't miss your chance to make this Oakland home your own!

16 E Pennington St E, Oakland

Listing courtesy of The KW Collective. Contact:

74 Parks Rd, Oakland
$59,900
3 Beds ⋅ 1 Baths
**Investor Special with Mountain & Water Views** Opportunity is knocking at 74 Parks Road in Oakland, Maryland, positioned just steps from the West Virginia line and surrounded by some of the most sought-after recreation in the region. Enjoy peaceful views of Snowy Creek right from the front yard and take advantage of being just minutes from Deep Creek Lake, Alpine Lake Resort, and Herrington Manor State Park — offering year-round activities including boating, fishing, hiking, skiing, and more. Whether you're looking to create a full-time residence, mountain getaway, or short-term vacation rental. If you've been searching for a project property in a high-demand recreational area with creek views and proximity to multiple lakes and state parks — this is your chance to build equity in one of Western Maryland’s most scenic settings. Bring your builder or contractor and your creativity — the possibilities are endless!

74 Parks Rd, Oakland

Listing courtesy of Real Broker, LLC. Contact:

1050 Christopher Way, Oakland
$269,900
2 Beds ⋅ 2 Baths
Discover your private mountain retreat at 1050 Christophers Way, situated on 13 acres spanning three separate parcels in the Backbone Ridge community. Showcasing breathtaking panoramic mountain views, this inviting home features warm wood accents, vaulted ceilings, a spacious loft, and a modern kitchen with stainless steel appliances. The walkout lower level offers additional living space, while the expansive deck provides the perfect setting to enjoy the spectacular scenery and peaceful surroundings. Additional features include an electric heat pump and water treatment system. Offering exceptional privacy, incredible views, and endless opportunities to enjoy the outdoors, this property is ideal as a full-time residence or personal getaway. Experience mountain living at its finest... Call today for details!

1050 Christopher Way, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

459 Santa Fe Trl, Oakland
$299,000
3 Beds ⋅ 2 Baths
Set at the end of a cul-de-sac in the conveniently located Roman Nose Spa community, this three-bedroom, two-bath prefab has a private, wooded setting and seasonal views of Deep Creek Lake! With no through traffic and close to the lake, Wisp Resort, restaurants, recreation, and other amenities, it offers potential as a primary residence, weekend getaway, or vacation rental. All three bedrooms are on the main level. The primary bedroom has its own bath with a jetted tub and walk-in shower, while the other two bedrooms share a second full bath. The home also features an open living area, a large kitchen with skylights, a breakfast area, and a separate dining area. The unfinished basement is currently accessed from outside. There is space to add a staircase from the main level, and the basement could be finished for additional living space. The home needs work and is being sold as-is. The annual road maintenance fee is $300 and covers snow plowing and other maintenance.

459 Santa Fe Trl, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

228 N 4th St, Oakland
$295,000
3 Beds ⋅ 2 Baths
Exquisite 3/4BR, 2BA Craftsman-style residence has been incredibly well maintained and lovingly cared for. Impressive kitchen remodel, hardwood floors, gas fireplace and multiple heat/cooling options. Home shows well - very clean and well-kept and a sensible floorplan. Full basement with overflow sleeping area and storage options. The kitchen is equipped with updated countertops & appliances. Cozy front porch and large rear deck with a spacious yard area (double lot) plus a storage shed. Fantastic location, close proximity to downtown Oakland, directly across the street from the hospital and close to pharmacies, dining options and shopping. Oakland offers a vibrant community atmosphere, with access to local parks, schools, and recreational areas. Conveys with most furnishings.

228 N 4th St, Oakland

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

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
This is a Homepath property. 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
$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:

210 Seneca Ave, Oakland
$225,000
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:

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