Oakland Real Estate

Oakland Real Estate

Welcome to Oakland, Maryland—a hidden gem nestled in the picturesque Garrett County, where the beauty of nature meets the charm of small-town living. This quaint town, situated near the stunning Deep Creek Lake, is a haven for outdoor enthusiasts and those seeking a serene lifestyle away from the hustle and bustle of city life.

Oakland boasts a rich history, with its roots dating back to the late 18th century. Stroll through the town and you'll find beautifully preserved Victorian architecture that tells the story of its past. The community is tight-knit and welcoming, making it an ideal place for families and individuals looking to connect with their neighbors.

Nature lovers will find themselves in paradise here, with an abundance of recreational activities at their doorstep. From hiking and biking trails to fishing and boating on Deep Creek Lake, there's no shortage of adventure. In the winter months, nearby ski resorts offer thrilling slopes for skiing and snowboarding, ensuring that Oakland is a year-round destination for outdoor fun.

Additionally, Oakland hosts a variety of local events and festivals that celebrate its vibrant culture and community spirit. Enjoy farmers' markets, art shows, and seasonal celebrations that bring residents together and showcase the town's unique character.

With its stunning scenery, rich history, and warm community atmosphere, Oakland, Maryland, is not just a place to live—it's a place to thrive. Whether you're looking to buy your first home or seeking a peaceful retreat, Oakland offers the perfect backdrop for your next chapter. Come experience the charm of this enchanting town and discover why so many have chosen to call Oakland home!

Newest Listings in Oakland

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

2 Beds ⋅ 1 Baths

A rare opportunity to own a completely renovated farmhouse-style home in Oakland! Offering 6.25 premium acres of gradually sloped land with several apple trees, open field areas and incredible views facing southeast from the top of the property. Inside, you'll be greeted with an oversized mudroom/office space, renovated kitchen, hardwood floors, tile shower and comfort from the recently added HVAC system. The lower level is a full basement with laundry space, plenty of storage, lighting, pellet stove and an attached 1-car garage. Other recent improvements include new roof in 2021, new deck in 2021, new garage roof in 2023, new basement windows in 2023, new HVAC 2021. An additional 2-car garage is insulated with lighting and a wood stove. An oversize shed offers plenty of storage for the toys. At the top of the property, you'll be greeted with incredible views accompanied by a 5 bedroom perc site for a future homesite. Homes in this condition with acreage are difficult to find and do not last long on the market. If you would like to schedule a private tour, please reach out while the opportunity is still available!

1158 Kings Run Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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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