Oakland Real Estate

Oakland Real Estate

Welcome to Oakland, a charming town nestled in Garrett County, Maryland, USA. Known for its picturesque surroundings and small-town charm, Oakland offers residents a peaceful and close-knit community to call home.

Nature enthusiasts will appreciate Oakland's proximity to outdoor recreational opportunities, including Deep Creek Lake and the surrounding mountains, perfect for hiking, skiing, and boating. The town's four distinct seasons provide a variety of outdoor activities year-round, from vibrant fall foliage to snowy winter wonderlands.

Oakland's historic downtown area boasts a variety of shops, restaurants, and local businesses, making it a hub for community gatherings and events. Residents can enjoy a leisurely stroll through the streets, stopping to browse unique boutiques or grab a bite to eat at a cozy cafe.

Families are drawn to Oakland for its top-rated schools and safe neighborhoods, providing a welcoming environment to raise children. With a strong sense of community pride and involvement, Oakland residents come together to support local schools, businesses, and organizations.

Whether you're seeking a peaceful retreat or a place to put down roots, Oakland offers a quality of life that is truly unmatched. Come discover the beauty and warmth of Oakland, Maryland, and find your perfect place to call home in this idyllic town.

Newest Listings in Oakland

3 Beds ⋅ 4 Baths

Welcome to your ultimate woodland retreat! Nestled in a private, serene setting, this meticulously maintained 3-bedroom, 3.5-bathroom log home perfectly blends rustic charm with modern luxury. Freshly painted throughout and boasting gleaming, well-maintained wide-plank hardwood floors and new carpeting, this property is completely turn-key. The heart of the home is the grand family room, which features soaring open ceilings, an abundance of natural light, and a majestic stone fireplace perfect for cozy evenings. Right off the family room, the newly renovated chef's kitchen comes fully equipped with granite countertops, brand-new appliances, a custom tile backsplash, and a garbage disposal. For ultimate comfort, the main-level primary suite highlights a newly renovated bathroom complete with a luxurious, spa-style walk-in shower, while a secure, large owner's closet with a keypad lock provides peace of mind. Upgraded ductless mini-split heating and cooling systems in all bedrooms and new lighting throughout ensure modern convenience at every turn. Above the main living area, a versatile, spacious open loft overlooks the family room, creating the ideal footprint for a home office, gaming hub, or quiet reading nook. The entertainment continues downstairs in the finished, sun-drenched walkout basement. This massive lower level features a fully equipped wet bar and a large recreation area with plenty of space for a foosball or ping-pong table. An additional private room offers flexible space for a private office or extra sleeping accommodations, while the nearby laundry room comes complete with a radon system and UV light water filtration. The outdoor living spaces are truly unmatched, starting with a gorgeous wraparound porch that includes a peaceful, covered front section outfitted with rocking chairs and a swing. The rear portion of the deck expands your hosting options with a dedicated dining area, a BBQ setup, and a gas-heated pizza oven. Step out from the walkout basement to an expansive patio featuring a relaxing hot tub and a cozy fire pit area surrounded by Adirondack chairs. From here, you can enjoy a completely private, picturesque view of mature trees, neighboring farmland, and beautifully terraced flower beds. This rare private paradise offers the perfect escape without sacrificing modern luxury. Please see ABNB for more photos . Income from Sept 25- Aug 26 amounted to $56k

204 Farm View Ln, Oakland

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005

2 Beds ⋅ 2 Baths

Rare opportunity to own a thoughtfully designed container home in the Deep Creek Lake area! This distinctive 2BR/2BA retreat combines modern comfort with a private wooded setting. The open-concept interior features abundant natural light, a full kitchen, comfortable living space, and large sliders connecting the indoors to the outdoors. Enjoy a private backyard with hot tub, fire pit, and grill, plus additional storage for outdoor gear. Conveniently located near Deep Creek Lake, Wisp Resort, hiking, biking, golf, boating, fishing, state park trails, and local dining. Built with quality, this home features Superior foundation walls, high end finishes and a mountaintop setting that is sure to impress. A truly one-of-a-kind property with excellent appeal as a personal getaway, investment property, or short-term rental.

100 San Francisco St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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: 3013874700

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:

1 Beds ⋅ 1 Baths

Will O the Wisp unit 105A is a charming one-bedroom, one-bath lakefront condominium. Unit 105A offers convenient first-floor living with ground-level access from a private patio directly to the waters edge, beach area and docks. . The unit features a fully equipped kitchen, comfortable living and dining areas, a cozy fireplace, one queen bed, and a sleeper sofa—accommodating up to three adults. Relax at the private patio, spending the day on the sandy beach, or taking advantage of the community’s indoor pool, game room, fitness center, and additional on-site amenities. An ideal lakefront getaway with comfort, convenience, and beautiful waterfront access!

20160 Garett Hwy Unit #105A, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Lot 28 Wild Turkey Lane is an affordable 1-acre corner lot in the private Deerfield Subdivision, conveniently located off Mayhew Inn Road. This homesite is perc approved and ready for you to build your dream home or mountain getaway. Enjoy a peaceful community setting just minutes from Deep Creek Lake, area state parks, shopping, dining, and other local attractions. Recorded survey available.

Wild Turkey Ln Unit #LOT 28, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 2 Baths

Vintage 3BR Lakefront Dome Home with Private Type "A" Dock! & no HOA . Own a piece of Deep Creek charm with this unique 3-bedroom, 2-bath vintage lakefront home w/ 2,034 finished square ft of living area, featuring 100 feet of lake frontage, beautiful sandy shoreline, and a private dock. The eye-catching dome-style architecture sets this property apart, offering a cozy and distinctive retreat. Located just minutes from Wisp Ski & Golf Resort and the ASCI Whitewater Course, it’s perfectly positioned for year-round adventure. Currently an established rental, this home offers both personal enjoyment and income potential. Don’t miss your chance to own a truly special lakefront getaway! Schedule your showing today

2849 Shingle Camp Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Discover this quiet .94 acre lot in the sought-after Yough Mountain Resort community, ideal for a mountain getaway, full-time home, or adventure basecamp. Enjoy access to over 2,000 acres of private wilderness, private hunting and fishing areas, ATV and snowmobile trails, community pavilions, playgrounds, sports courts, and green space, just minutes from Deep Creek Lake and Wisp Resort. A rare chance to own your own piece of one of the area's most desirable communities.

Cedar Ln Unit #LOT 66, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

3 Beds ⋅ 1 Baths

INVESTOR SPECIAL!! GREAT FOR FIX AND FLIP OR HOLD! Property is sold completely as-is with all contents. Buyer to pay all closing,100% TT&Rs. CASH or Hard money only.

102 Roanoke Ave, Oakland

Listing courtesy of Samson Properties. Contact: 7033788810

Tucked among the trees in The Timbers on the Yough, this 2.43-acre homesite offers a peaceful setting with access to some of Garrett County’s best outdoor recreation. Enjoy community access to the Youghiogheny River, along with a pavilion, common area, and hiking trails—all just minutes from Oakland. The wooded lot provides a beautiful natural setting with plenty of space to create your own mountain retreat. Whether you're looking for a quiet weekend escape or a place to build for year-round enjoyment, this property offers the perfect combination of privacy, recreation, and convenience.

Yough View Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 2 Baths

Fall in love with the peaceful setting of this inviting log home nestled in the sought after Pergin Farm community at Deep Creek Lake. Surrounded by trees and tucked away in a quiet setting, this 3 bedroom, 1.5 bath home offers the warmth and character of a true mountain retreat with a layout that feels both comfortable and connected. Step inside through the welcoming mudroom, where the home naturally opens into the kitchen and dining area, creating an easy gathering space that flows into the inviting living room. A bedroom and full bath complete the main level, while two additional bedrooms upstairs provide a private retreat for family or guests. The lower level expands the living space with a spacious family room, bar, half bath, foosball, and shuffleboard, giving everyone a place to relax and have fun after a day at the lake. Outside, enjoy the full length covered front porch, wooded surroundings, patio with hot tub and grill, and firepit made for evenings under the stars. An oversized two car garage with storage above and a detached garage provide plenty of space for vehicles, lake gear, and storage. Whether you are looking for a year round home, a private mountain escape, or an investment opportunity, this property offers the flexibility to make it your own. Currently operating as a vacation rental, it provides the added opportunity for rental income while you enjoy all that Deep Creek Lake has to offer. Call today!

482 Pergin Farm Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

Now available! Build your primary residence or investment home on this rare and oversized 4.91 Acre building lot located in Hunters Ridge Estates. This property offers a wooded and peaceful setting all while being conveniently located around Deep Creek Lake. This particular area is desirable because of the close location to town amenities and shopping in Oakland as well as Deep Creek attractions. Call today for more information!

Lot 4 Hunters Ridge Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700

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