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

142 Allan Dr, Oakland
$349,000
Create your woodland retreat near Deep Creek Lake! These two adjoining parcels include approximately 20.9 acres of mature forest, abundant wildlife and moss-covered boulders in a peaceful hillside setting. Enjoy privacy and room to explore, with Wisp Resort and the Deep Creek Lake area’s year-round recreation nearby. The 0.9-acre Holiday Hill lot at 142 Allan Drive has renewed four-bedroom septic approval. The adjoining 20-acre tract is approved for two sewage disposal systems, subject to approval conditions and permitted uses; however, legal access to the rear tract remains unresolved and requires Holiday Hill HOA approval. Acreage and boundaries are approximate; buyers should verify access rights, septic approvals and development potential. Photos have been digitally enhanced for marketing purposes.

142 Allan Dr, Oakland

Listing courtesy of Beycome Brokerage Realty LLC. Contact:

1019 Lake Shore Dr, Oakland
$1,699,000
4 Beds ⋅ 5 Baths
Welcome to Your Dream Retreat at Deep Creek Lake! Discover this stunning, recently remodeled home that perfectly blends modern luxury with the tranquility of nature. Nestled among picturesque blue spruce trees, this 4-bedroom, 4.5-bath residence offers an exceptional getaway for both relaxation and adventure. The open-concept living space is designed for comfort and style. Enjoy a cozy fireplace that sets the perfect ambiance for chilly evenings, making gatherings with family and friends even more special. Step outside to a large deck that provides ample space for outdoor dining and relaxation. Unwind in the hot tub while surrounded by the serene sounds of nature. Take advantage of your very own “Type A” private dock slip, perfect for boating, fishing, and enjoying the stunning lake views and sunsets just steps away from your doorstep. Minutes from Wisp Ski Resort, you’ll have year-round access to outdoor activities and adventures. A variety of restaurants and shops are also nearby, ensuring convenience and fun at your fingertips. Whether you’re looking for a serene family retreat or a smart investment opportunity, this home at Deep Creek Lake delivers everything you need to make unforgettable memories.

1019 Lake Shore Dr, Oakland

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

Warnick Way, Oakland
$34,900
Enjoy the privacy you’ve been looking for with this conveniently located property between Oakland and Deep Creek Lake. With no HOA fees and just one restriction—mobile homes are not permitted—this is a great opportunity to create your ideal getaway or homesite.

Warnick Way, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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:

Fawn Drive, Oakland
$23,000
Discover the perfect setting for your future getaway or full-time home with this beautiful, wooded 0.96-acre lot near the entrance of Youghiogheny Mountain Resort (YMR). Approved for a gravity sewage disposal system and a 3-bedroom single-family dwelling, this property offers a great opportunity to build and enjoy the surrounding natural beauty. YMR features 50+ miles of private roads and trails, a playground, hunting opportunities, and plenty of outdoor recreation. Whether you're looking for a peaceful retreat or a place to enjoy year-round adventures, this property is full of possibilities!

Fawn Drive, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. 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:

Lot 1 Betts, Oakland
$79,000
Enjoy the privacy of a wooded 8.68-acre property in the southern end of Garrett County. Located on Betts Lane, just off Foster Road, this property offers a great opportunity to build a mountain getaway or full-time residence while remaining close to Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and other area attractions. Approved for up to a four bedroom home with a site-plan on file. If you're looking for acreage, privacy, and a convenient location near everything Deep Creek Lake has to offer, call today for for more information!

Lot 1 Betts, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Santa Fe Trl, Oakland
$29,999
Great location building Lot. Close to all lake activities!!!

Santa Fe Trl, Oakland

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

335 Pergin Farm Rd, Oakland
$475,000
3 Beds ⋅ 3 Baths
Enjoy the convenience of one-level living at 335 Pergin Farm Road. This 3-bedroom, 3-bath lake area home features recent interior upgrades that blend its original character with a refreshed feel, including updated flooring, bathrooms, appliances, cabinetry, and countertops. The primary bedroom offers a walk-in closet and tiled shower. Adding to the functional layout is a finished basement that provides additional living and flex space to suit a variety of needs and a full bathroom with a walkout. An attached 2-car garage adds everyday convenience, and the flat, 2.00-acre lot features an expansive grassy yard with plenty of room to enjoy the outdoors. Superior walls ensure a top of the line foundation from the ground up. Conveniently located near Deep Creek Lake, Wisp Resort, and the shops, restaurants, and amenities of Oakland, this property offers a great combination of updated interior features, usable outdoor space, and prime location for full time living or second home enjoyment.

335 Pergin Farm Rd, Oakland

Listing courtesy of Railey Realty, Inc.. 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:

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