Oakland Homes for Sale

Oakland Homes for Sale

Welcome to Oakland, Maryland—a charming town nestled in the heart of Garrett County, where the beauty of nature meets the warmth of community. Known for its picturesque landscapes and vibrant local culture, Oakland serves as a gateway to adventure, making it a perfect place to call home.

Surrounded by the stunning peaks of the Appalachian Mountains and the serene waters of Deep Creek Lake, Oakland offers an abundance of outdoor activities year-round. Whether you enjoy hiking the scenic trails, boating on the lake, or skiing in the winter, there’s something for everyone to enjoy. The town itself boasts a rich history, with quaint shops, delightful eateries, and a friendly atmosphere that welcomes newcomers and long-time residents alike.

For those looking to find their dream home in this idyllic setting, Oakland has an array of homes for sale that cater to various lifestyles and budgets. From charming historic houses that reflect the town's heritage to modern family homes nestled in tranquil neighborhoods, there’s a perfect spot for everyone. Many properties offer breathtaking views, spacious yards, and easy access to local amenities and outdoor recreational areas.

Investing in a home in Oakland means not just finding a place to live, but embracing a lifestyle filled with adventure, community, and natural beauty. Explore our listings today and discover the perfect home that aligns with your dreams and aspirations in this enchanting Maryland town!

Newest Oakland Homes for Sale

696 Mayhew Inn Rd, Oakland
$259,000
1 Beds ⋅ 1 Baths
Escape to your own private retreat in the woods! Tucked away on 10.52 wooded acres just off Mayhew Inn Road, this charming rustic cabin offers seclusion, natural beauty, and convenience. Surrounded by towering trees and peaceful woodland, the property features a cozy 1-bedroom, 1-bath cabin, a spacious two-car garage with an apartment above, and a large storage shed for all your outdoor equipment, tools, and toys. Whether you're looking for a hunting getaway, a weekend escape, or a blank canvas to create your own off-grid oasis, this property is full of possibilities. Multiple heating sources and two water sources, including a well and gravity spring-fed supply, add to its versatility and rustic appeal. Enjoy the peace and privacy of your own wooded acreage while remaining just a short drive from Deep Creek Lake, Oakland, and McHenry. Spend your days exploring the outdoors and your evenings unwinding in the quiet of the woods. A rare opportunity to make your vision of mountain living a reality.

696 Mayhew Inn Rd, Oakland

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

1194 Lake Shore Dr, Oakland
$729,900
4 Beds ⋅ 4 Baths
Your Deep Creek Lake escape is ready. This classic log home sits on 1.04 private, wooded acres off Lake Shore Drive, so you get mountain quiet with the lake, marinas, dining and Wisp Resort just minutes away. It has 4 bedrooms and 4 full plus 1 half baths, and the newly finished lower level adds a bedroom, a full bath, and flexible living space. Use it as a guest suite, a game room, or extra sleeping space for a growing vacation-rental plan. Upstairs, warm wood interiors and an open main living area deliver the true cabin feel. A rare bonus at the lake: the detached two-car garage has room for boats, jet skis, ATVs and snow gear. Above it, a nearly finished upper level is ready for your finishing touches as a studio, office, game room or guest loft. A huge driveway gives you plenty of parking for family, guests and trailers. Spend summers boating and swimming, fall on the scenic drives, winters skiing and tubing at Wisp, and every season at Deep Creek Lake State Park and Swallow Falls. Second home, family retreat, or investment: this one checks every box.

1194 Lake Shore Dr, Oakland

Listing courtesy of CENTURY 21 New Millennium. 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:

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:

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:

2296 Lake Shore Dr, Oakland
$909,000
4 Beds ⋅ 3 Baths
Very well maintained 4BR-2.5BA home on 1.001 acres with additional lakefront lot containing .0150 acres and 61.64' of lakefront with Type A dock. This home features several living areas and attached 2 car garage. Living room with wood burning fireplace. Lake views from the home and incredible waterfront on the lakefront lot. Architecturally appealing home with a mountain runoff stream running right under the home. Front lakeside deck and wonderful rear deck with plenty of room for a hot tub. Whole house GENERAC generator with two propane tanks that supply the propane that are owned by the seller. Central location close to Wisp, ASCI, and Lodestone Golf Course. 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.

2296 Lake Shore Dr, 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:

1038 S Blakeslee Rd, Oakland
$2,100,000
5 Beds ⋅ 6 Baths
Get ready to relax & enjoy Deep Creek Lake at your 5 BR 5 Bath home offering a wooded level setting with the lake and dock slip right out in front of you. Located in the area's premiere community, Blakeslee, you'll appreciate the inviting open floor plan featuring two living areas, 5 suites with direct bath access, direct access to a large deck, covered porch or relax in the comfy screened porch. The outdoor area also offers a fire pit and room for outdoor games. Beautifully and tastefully decorated, the atmosphere within and without is perfect regardless of season. The home has had over 30 meaningful updates including bathroom remodels and major mechanical improvements allowing you the opportunity to spend more time relaxing and less time making updates and repairs. The Blakeslee offers the best amenity package on the lake including an indoor pool and community center along with multiple tennis, pickleball courts, a multi use play field, tot lot and more, community trash center, storage area and over 100 common area acres with trails to enjoy. The 5 mile private road system is safe and perfect for walking and biking. The property also currently provides revenue potential and is known as Unsalted Memories.

1038 S Blakeslee Rd, Oakland

Listing courtesy of Railey Realty, Inc.. 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:

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