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

An exceptional opportunity to own 18.87 acres in one of Deep Creek Lake's most desirable locations. Featuring 8 approved perc sites, this lake access property offers outstanding potential for a private estate, luxury mountain retreat, or future subdivision with the possibility of up to 8 homesites. Ideally situated on Boy Scout Road, the property provides the perfect balance of privacy and convenience. Enjoy a peaceful, wooded setting just minutes from Deep Creek Lake, Wisp Resort, state parks, restaurants, shopping, golf, and year-round recreation. Whether you're envisioning an exclusive residential enclave or a legacy investment, this rare offering combines development potential with the natural beauty and tranquility that make Garrett County so sought after. Don't miss this unique opportunity to create something truly special in the heart of Deep Creek Lake.

Boy Scout Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

4 Beds ⋅ 4 Baths

Experience modern mountain living in this brand-new 2026 construction. This beautifully designed 4-bedroom, 4-bath home offers two spacious levels, quality finishes, and plenty of room for family and guests. Open layout with modern kitchen, island bar, and stone fireplace. Stamped concrete patio with covered fireplace and outdoor kitchen. Over half an acre of private wooded mountain-top space complete with fire pit and level usable yard. Andersen Windows and LVP flooring throughout. Ideally situated just minutes from Wisp Resort, Deep Creek Lake, state parks, restaurants, shopping, and year-round recreational attractions, this home provides the perfect blend of comfort, convenience, and adventure. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this new construction is ready to make lasting memories.

15 Byran Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 3 Baths

Fall in love with the perfect blend of comfort, privacy, and outdoor adventure in this beautifully maintained home nestled on 3.67 wooded acres overlooking scenic Meadow Lake. Thoughtfully designed for easy living, this 3-bedroom, 2.5-bath home features an open floor plan where the spacious great room flows seamlessly into a beautifully updated kitchen complete with granite countertops, making it the perfect space for gathering with family and friends. Peaceful lake views can be seen throughout the home. The spacious primary suite features a walk-in closet and a private bath with double vanities and a custom walk-in tile shower. Main-level laundry and an attached two-car garage add everyday convenience, while central air, a propane furnace, and a cozy wood-burning fireplace insert provide year-round comfort. The expansive unfinished basement offers endless possibilities for additional living space, a recreation room, workshop, or home gym. Step outside to enjoy the tranquility of nature from the front and back covered porches. The community offers a beautiful private lake perfect for kayaking, fishing, swimming, relaxing by the beach and 3 community docks. Additional amenities include private walking trails, and a storage shed that provides even more space for tools and outdoor equipment and the impressive 32' x 12' RV pavilion complete with 50 AMP, water and sewer hookups. Located in the desirable Meadow Lake Estates community, you'll enjoy a peaceful rural setting just minutes from Herrington Manor and Swallow Falls State Parks. As an added bonus, the community borders 598 acres of Maryland DNR land fronting the Youghiogheny River, offering endless opportunities for hiking, wildlife watching, and outdoor recreation. Whether you're searching for a full-time residence, a mountain retreat, or the perfect place to embrace the beauty of Western Maryland, this exceptional property is ready to welcome you home.

355 Markwood Dr, Oakland

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

2 Beds ⋅ 1 Baths

Welcome to this charming 2 bedroom, 1 bath home in the heart of Oakland, offering endless potential and plenty of character. Step inside to an inviting open floor plan that creates a bright, spacious feel and allows for a comfortable flow between the living and kitchen areas. The large covered front porch provides the perfect spot to enjoy your morning coffee, relax after a long day, or take in the peaceful surroundings. Whether you're looking for your first home, an investment property, or a property to personalize and make your own, this home offers incredible potential. Located in a highly desirable school district, you'll enjoy the convenience of being just minutes from shopping, dining, recreation, and all the amenities Oakland has to offer. With its charming details, functional layout, and unbeatable location, this property is ready for your vision and personal touch. Don't let this opportunity pass you by. Schedule your showing today!

206 W Liberty St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 1 Baths

Enjoy the charm of country living with the convenience of being in downtown Crellin! Situated on nearly an acre, this inviting 3-bedroom, 1-bath home offers a bright, open layout filled with natural light. The main level features a spacious bedroom surrounded by windows, creating a warm and welcoming retreat. Upstairs, you'll find two additional bedrooms that can easily accommodate family, guests, or be transformed into a home office, playroom, or hobby space. Storage is abundant with an interior pantry, storage room, and dedicated workspace, plus an outdoor shed and detached garage for all your tools, equipment, and recreational gear. The yard is fenced in, beautifully manicured and has a fire pit. An added bonus is the additional lot included with the property at 97 Crellin Street. This parcel already has public water and sewer hookups and was formerly the site of the Crellin Community Center, offering exciting possibilities for future use, expansion, or investment (subject to local zoning and approvals). Whether you're looking for your first home, a peaceful retreat, or a property with room to grow, this unique offering combines comfort, space, and potential in a convenient location. This one won't last! Reach out for a showing today!

40 Sunshine, Oakland

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

Excellent investment opportunity available now! Flat and mostly clear 2.34 acre lot with an existing 65'x25' Steel pole building outside of zoning restrictions! With access to public utilities and existing infrastructure Possible uses could be storage or layover yard for a contractor, storage units for an investor, car lot, new home build, or any other possibility the new owner can imagine. Call today before this opportunity is gone!

926 Hutton Rd, Oakland

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

5 Beds ⋅ 3 Baths

PRIME INVESTMENT OPPURTUNITY! Recently renovated (including plumbing and electric) in 2025, this triplex is a rare opportunity in the heart of downtown Oakland, MD. With three separate units, you'll have the potential for three streams of rental income from one property. Buyer could live in one unit and rent the other units out to help offset mortgage costs! Whether you're a seasoned investor or just getting started, this turnkey property offers updated finishes, strong income potential, and a prime location just steps from shops, restaurants, and everything downtown has to offer. Top floor is 1-bedroom and 1-bathroom. Middle floor is 2-bedroom and 1-bathroom. Bottom floor is 2-bedroom, 1-bathroom and has a laundry hookup. Contact me today with any questions or to schedule a time to tour the property!

615 E Oak St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 2 Baths

Assumable VA loan at a below-market interest rate may be available...contact listing agent for details. If peace and privacy are on your must-have list, this one delivers! Picture this: you pull into the driveway and the trees close in around you on three sides, like the forest itself is standing guard. Over an acre of land, and somehow it stays flat and usable instead of the steep, awkward terrain so common in this area. This is a lot you can actually walk, garden, and live on. Step onto the front porch and you'll want to grab a seat and forget you were there to see a house. The view stretches out far enough to make your coffee cup last a little longer every morning. In the evenings, the saltwater hot tub (just a few years young) turns this into the kind of backyard people usually only dream about. Inside, the kitchen and main-level bathroom were recently remodeled with an eye for quality over trend, so you get the updates without the "flip house" feel. The ensuite bedroom on the main level is a fantastic one-level living option. Out back, a garage-sized shed and a separate potting shed give you room for tools, toys, or a hobby waiting to happen, and there's a garden plot already established for whoever's ready to put in the work. This isn't a house that's trying to impress you with size. It's a property that's already figured out what matters: privacy, usability, upgrades that make daily life easier. Come see why the setting sells itself.

718 Boy Scout Crosscut Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Build your dream home, or vacation home. This development has 50 miles of private roads and trails perfect for ATV riding, UTVs, dirt bikes, hiking, hunting and outdoor recreation.

Bear Dr E, Oakland

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

4 Beds ⋅ 4 Baths

LAKEFRONT 4BR, 3.5BA log home with over 3300sf and 4.35 acres of privacy! Lovingly maintained property with gorgeous views of the 10 acre lake from almost every room in the house! Peaceful surroundings with towering mature trees and just enough yard space in a very laid back, rural setting near Herrington Manor and Swallow Falls state parks. If that weren't impressive enough, Meadow Lake Estates community is adjacent to 598 acres of DNR / state land fronting on the Youghiogheny River. Set up for one level living - bedroom suite and laundry room on first floor. Features include whole-house generator, wood-burning fireplace, a recently finished basement adding a game room and a fourth bedroom, front and rear decks (trex on back deck), covered porches, fire-pit, wrap-around driveway and a spacious loft that serves as a third living room. Must see to appreciate the solitude of this fantastic home! Furnishings negotiable. Short term rentals are not permitted in this community.

325 Markwood Dr, Oakland

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

4 Beds ⋅ 4 Baths

A rare opportunity to own a lakefront property in the Blakeslee. Located in one of best coves and communities on Deep Creek Lake, the 4 bedroom, 3.5 bath property offers the perfect home and lot package for the best in lakefront living. The 1+ acre wooded property with 150' of premium frontage was the first building site purchased when the development opened . The gently sloping wooded sunset facing lot provides easy access to the lake and dock areas. The current owners have added multiple landscape upgrades including paver stone walkways along with lakeside picnic and fire pit areas. A paved circular driveway provides easy year round access from the street. With lake and summer sunset views from nearly every room, the well designed home offers an open floor plan featuring plenty of window coverage. The main level offers a recently upgraded kitchen and lake facing eating area. A large lake facing great room with fireplace adjoins a cozy family room with its own fireplace and direct deck access. The recently added primary bedroom suite includes a spacious bedroom, luxurious bath, 2 walk in closets and a bonus room currently used as an office. The second floor includes a second primary suite and two spacious bedrooms along with a loft. There is also a lower level with a room that could be a game and or work out area. Many would consider the recently added lakeside covered porch with impressive wood fireplace their favorite spot. It offers direct access to the new deck and primary suite. The property also offers an attached 2 car garage and a detached 24 x 24 garage with plenty of interior height for boat and or tall vehicle storage. Additional upgrades and features includes the addition of a detached 2 car garage, complete deck replacement, whole house generator, replacement and updated HVAC and security systems. The roof shingles have also been recently replaced . Blakeslee is considered by many to be the finest community in the Deep Creek Lake area. The developers believed quality was more important than quantity and designed a community with great amenities and over 100 acres of open space that is restricted from additional development. Blakeslee has also attracted a healthy mixture of full time and vacation owners. The self managed community offers many unique amenities. These amenities include a community center with indoor heated pool, locker rooms, kitchen and decking. Two tennis courts along with a basketball and pickleball courts are well maintained . A multipurpose field is available for outdoor games. A trail system runs through the wooded areas for area residents. Other important features include a storage areas for boats and trailers along with a dedicated trash removal area. It all adds up to a a great opportunity to experience all the benefits that home ownership in the Deep Creek Lake area has to offer. Schedule your showing today as homes for sale in this community typically don't last long.

255 Thornberry Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

4 Beds ⋅ 3 Baths

4BR 2.5BA cabin in the woods! Over 12 wooded acres of privacy and seclusion, laced with trails and surrounded by low maintenance land. Centrally located - only a few miles to Deep Creek Lake, town of Oakland or Swallow Falls State Park. Open floor plan with vaulted ceilings, a wood burning stove and high end finishes throughout. Basement is partially finished. Spacious decking and a must-have covered porch to enjoy the outdoors. Perfect as a vacation retreat or a full time residence. Located at the end of a privately maintained road. No vacation rentals permitted.

995 Betts Ln, Oakland

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

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