Oakland Homes for Sale

Oakland Homes for Sale

Welcome to Oakland, Maryland – a charming town nestled in the heart of Garrett County, where natural beauty meets small-town charm. Known for its stunning lakes, lush forests, and vibrant community, Oakland offers a unique blend of outdoor adventure and serene living. With its picturesque landscapes and friendly atmosphere, this quaint town is the perfect place to call home.

Oakland is surrounded by breathtaking views of Deep Creek Lake, the largest freshwater lake in Maryland, offering a plethora of recreational activities such as boating, fishing, hiking, and skiing in the winter months. The town is steeped in history, with charming architecture and local shops that reflect its rich heritage. Residents enjoy a tight-knit community with a variety of local events, farmers' markets, and festivals that celebrate the area’s culture and traditions.

When it comes to real estate, Oakland has an array of homes for sale that cater to diverse lifestyles and budgets. Whether you’re looking for a cozy cabin by the lake, a charming historic home, or a modern family residence, Oakland has something to offer. The real estate market here is thriving, with properties that provide not only comfort but also the opportunity to embrace a lifestyle surrounded by nature's beauty.

Discover the magic of Oakland, MD, and find your dream home in this idyllic setting. With its welcoming community, stunning landscapes, and a variety of homes for sale, Oakland is not just a place to live; it’s a place to thrive. Come see for yourself why so many are choosing to make Oakland their home!

Newest Oakland Homes for Sale

4 Beds ⋅ 3 Baths

Experience the best of Deep Creek Lake living at this beautifully renovated mountain retreat in the peaceful and desirable Paradise Ridge lake access community. Thoughtfully updated from top to bottom, this home blends modern comfort with the serenity of nature, creating the perfect full-time residence, vacation getaway, or potential vacation rental investment property. One of the property's standout features is its close proximity to one of the most desirable lake access areas on Deep Creek Lake. Enjoy convenient access to the water with limited dock use, offering a more private and relaxing lake experience without the crowds. Featuring a level shoreline, picnic pavilion, ample parking, and easy entry for paddle boards, kayaks, canoes, swimming, and fishing in the quiet no wake zone cove. Nestled in a quiet, wooded setting, you'll appreciate the peaceful surroundings while remaining just minutes from local restaurants, shopping, Wisp Resort, state parks, golf, and all the year-round recreation Deep Creek Lake has to offer. Whether you're spending the day on the lake, enjoying nearby dining, or relaxing in the tranquil setting, 180 Paradise Ridge Road offers the perfect combination of spacious living space, convenience, comfort, and mountain charm. Chill out on the large back deck and patio area or around the campfire. Don't miss this opportunity to own your own slice of Deep Creek paradise. Get your tour scheduled now!

180 Paradise Ridge Rd, Oakland

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

5 Beds ⋅ 4 Baths

Rare opportunity to own a truly exceptional Deep Creek Lake property combining 59 Boyd Paugh Lane along with its separately deeded adjoining waterfront lot, offering approximately 1.45 total acres and 523 feet of combined lake frontage. The custom 5-bedroom, 3.5-bath lakefront home is situated on a beautifully landscaped and wooded 0.88-acre lot with approximately 209 feet of shoreline. Features include a main-level primary suite with dressing area, spacious kitchen and great room, cathedral ceilings, recreation room with built-in bar, screened porch, generous decking, stone patio, finished lower level, two fireplaces, and an attached garage. The adjoining separately deeded 0.57-acre waterfront lot adds approximately 314 feet of shoreline on a quiet point in a protected cove and includes a Type A dock. Together, the properties offer one Type A dock and one deeded dock slip, providing accommodations for up to three powerboats. Public sewer is reported to be available to the adjoining lot. Enjoy exceptional privacy, extensive shoreline, multiple boating options, and a desirable mid-lake location with convenient access to shopping, dining, recreation, and entertainment. The residence and adjoining lot are being offered together as one exceptional Deep Creek Lake package.

59 Boyd Paugh Ln, Oakland

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

5 Beds ⋅ 4 Baths

Welcome to your mountain retreat in the highly sought-after Mountainside community at Deep Creek Lake! This spacious 5-bedroom, 4-bath cedar-sided chalet blends classic mountain charm with the perfect layout for unforgettable lake getaways, family vacations, or a proven investment opportunity. Step inside to soaring walls of glass that frame filtered seasonal views of Deep Creek Lake, filling the open-concept main living area with natural light. The inviting kitchen, dining, and family room create the perfect gathering space, complete with a warm mountain ambiance and seamless access to the expansive full-width deck overlooking the lake. The main level also offers two comfortable bedrooms and a full bath, providing convenient single-level accommodations. Upstairs, you'll find two private primary suites, each featuring generous storage and peaceful spaces to unwind after a day on the lake. The finished lower level is designed for entertainment, offering a spacious family room, game area with three game tables, an additional bedroom, and a full bath—making it ideal for hosting guests of all ages. Outdoor living is just as impressive. Relax in the covered hot tub gazebo while taking in the mountain surroundings, gather around the firepit under the stars, or enjoy friendly competition on your own volleyball court. The expansive deck provides the perfect vantage point for enjoying filtered summer lake views that become even more spectacular as autumn gives way to winter. Mountainside residents enjoy exceptional community amenities, including a fenced three-court tennis and pickleball complex, a large covered pavilion for neighborhood gatherings, and membership to the Mountainside Marina Club. The marina clubhouse offers an inviting lakefront setting with access to Deep Creek Lake, making it easy to spend your days boating, swimming, and enjoying everything the lake lifestyle has to offer. Whether you're searching for a year-round residence, vacation home, or income-producing rental, this beautifully maintained chalet offers the space, amenities, and coveted Deep Creek location you've been waiting for.

18 Mountainside Ct, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

2 Beds ⋅ 2 Baths

Enjoy all the seasons in this beautiful Cape Cod home nestled on a 1-acre private wooded lot close to Oakland and all the attractions Deep Creek Lake has to offer. Whether you are seeking a year-round permanent residence or a private seasonal getaway for summer and winter fun, this property delivers a wonderful setting with an ideal balance of privacy and convenience. The open floor plan allows seamless flow throughout the main living areas. The vaulted ceiling in the living room maximize light and space. Enjoy the main floor primary suite with private access to a full bathroom, complete with a huge bath and a spacious walk-in closet. The upper loft features an open area that overlooks the living room, it can be used as a recreation room or easily function as a third bedroom or extra sleeping space. The one car garage with attached carport affords plenty of space to store your vehicle alongside your seasonal outdoor gear and toys.

18948 Garrett Hwy, Oakland

Listing courtesy of 1 Real Estate Source LLC. Contact: 3013878300

8 Beds ⋅ 10 Baths

Experience exceptional lakefront living in this spectacular eight-bedroom estate designed for unforgettable gatherings and year-round enjoyment. Perfectly positioned on an oversized lakefront lot with 116’ LF, this remarkable home offers easy access to the water via a walking path, and the abundance of windows fill the interior with natural light. At the heart of the home is a magnificent great room with soaring ceilings, creating an impressive space for entertaining family and friends. The gourmet kitchen is a chef's dream, featuring premium finishes, generous prep space, and abundant cabinetry, making it as functional as it is beautiful. Boasting an indoor sparkling pool and sauna right off the lower-level family room, along with a full kitchen and a playroom. Then step outside to your private lakeside retreat, complete with two relaxing hot tubs, a fire pit area, a sports court in the front, and spacious outdoor living areas ideal for dining, entertaining, or simply soaking in the peaceful surroundings. With eight spacious en-suite bedrooms, there is ample room for guests, making this an exceptional primary residence, vacation home, or luxury rental opportunity “The Haven”. Offering the perfect blend of elegance, comfort, and resort-style amenities, this extraordinary waterfront property is a rare opportunity to own the ultimate lakefront lifestyle.

1131 Lake Shore Dr, Oakland

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

5 Beds ⋅ 2 Baths

Escape to the tranquility of country living in this spacious 5-bedroom, 2-bath home nestled on over 2 acres and conveniently located just minutes from the recreational opportunities of Deep Creek Lake and the charming town of Oakland, The property offers the perfect combination of peaceful country living and easy access to shopping, dining, and year-round activities. The kitchen has been thoughtfully updated with new stainless-steel appliances, including a microwave, refrigerator, gas range with oven, and gas wall oven. You'll also appreciate the new stainless-steel farmhouse sink with an updated faucet, and a new InSinkErator garbage disposal. The main floor also offers the convenience of a bedroom, full bathroom, and laundry area complete with a new washer and dryer, making one-level living a possibility. Upstairs, you'll find four generously sized bedrooms and an additional full bathroom, offering plenty of space for family and guests. Additional interior improvements include a new 50-gallon hot water heater, a new attic fan with humidifier, a new well water filtration system, and a newly installed ADT security system for added peace of mind. Recent exterior updates include new outdoor lighting and a new roof including all new sheathing, underlayment (roof wrap), and shingles, providing years of worry-free ownership. If you've been searching for privacy, space, and the beauty of rural living, this property is a must-see!

5154 Maryland Hwy, Oakland

Listing courtesy of Coldwell Banker Home Town Realty. Contact: 125014.lead@leads.leadrouter.com

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

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 2.75% VA loan 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 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 get lost in the surroundings. The view stretches out far enough to make your cup of coffee 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 anyone who wants fresh vegetables all summer long. This is 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:

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