Oakland Homes for Sale

Oakland Homes for Sale

Welcome to Oakland, Maryland—a hidden gem nestled in the heart of Garrett County, where charm meets natural beauty. This picturesque town is renowned for its stunning landscapes, serene lakes, and vibrant community spirit. Whether you’re seeking a peaceful retreat or a lively place to call home, Oakland offers a perfect blend of both.

As you explore the charming streets of Oakland, you’ll be captivated by its rich history and warm, welcoming atmosphere. The town is surrounded by the breathtaking beauty of Deep Creek Lake, providing endless opportunities for outdoor activities such as boating, fishing, and hiking. In the winter months, the nearby Wisp Resort transforms the area into a winter wonderland, offering skiing and snowboarding for the adventurous at heart.

When it comes to real estate, Oakland boasts an array of homes for sale that cater to diverse tastes and budgets. From cozy cabins perfect for weekend getaways to elegant family homes with modern amenities, there’s something for everyone. Many properties offer stunning views of the surrounding mountains and lakes, allowing you to enjoy the beauty of nature right from your doorstep.

With a strong sense of community and a variety of local events, Oakland is not just a place to live—it’s a place to thrive. Explore the charming shops, dine at local eateries, and immerse yourself in the vibrant culture that makes Oakland a truly special place to call home. Don’t miss your chance to find your dream home in this enchanting town—discover the homes for sale in Oakland today!

Newest Oakland Homes for Sale

2 Beds ⋅ 2 Baths

Nestled in the charming Oakland subdivision, this delightful traditional-style home, built in 2022, offers a perfect blend of modern comfort and timeless appeal. With 1,008 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy yet functional environment. Step inside to discover a warm and inviting atmosphere, accentuated by luxury vinyl tile flooring that flows seamlessly throughout the home. The floor plan features two bedrooms and two bathrooms, providing convenience and accessibility for all. The heart of the home is the well-appointed open kitchen/dining/living area, equipped with essential appliances including a built-in microwave, electric oven/range, dishwasher, refrigerator, and access to the covered porch. Natural light pours in through the many windows, creating a bright and airy ambiance that enhances the home's inviting feel. The living areas are perfect for relaxation or entertaining, while the main floor laundry/mudroom adds an extra layer of convenience to your daily routine. Step outside to the covered porch where you can unwind with a morning coffee or host evening gatherings under the stars. Parking is a breeze with an attached garage and paved driveway, ensuring you have easy access to your vehicle year-round. The home's excellent condition means you can move in with peace of mind, knowing that everything is ready for you to make it your own. Don't miss the opportunity to make this inviting space your own!

808 N St, Mt Lake Park

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:

5 Beds ⋅ 3 Baths

Price drop!! Close to the hospital and schools. Completely rebuilt and beautifully renovated 5 bedroom 3 bathroom home! Welcome to this stunning 5-bedroom, 3-bathroom home that has been completely transformed from top to bottom with exceptional craftsmanship and modern finishes. Offering the charm of a classic home with the peace of mind of virtually all-new construction, this property is truly move-in ready. Major updates include a new high-efficiency central HVAC system, all-new plumbing, new electrical wiring, and a new gas line. The home also features new exterior and interior wood framing, professionally waterproofed basement, and complete whole-house insulation, providing comfort and energy efficiency year-round. The exterior has been beautifully updated with new wood siding and hardie siding, new energy-efficient windows, new exterior doors, new trim, and a new rear porch, creating outstanding curb appeal and outdoor living space. Inside, you'll find a bright, open layout with new drywall, beautiful hardwood flooring, stylish lighting throughout, and a fully renovated interior. The gorgeous kitchen boasts brand-new appliances, modern cabinetry, and updated finishes, while all three bathrooms have been completely remodeled with contemporary fixtures and finishes. This is a rare opportunity to own a home where nearly every major component has been replaced, offering years of worry-free living. Combining timeless style, modern amenities, and quality construction, this exceptional home is ready for its next owner.

112 E Pennington St, Oakland

Listing courtesy of Lake Homes Realty, LLC. Contact: 8665253466

6 Beds ⋅ 5 Baths

Luxury Living Meets Timeless Country Charm! Perfectly positioned on 10.33 picturesque acres between Oakland and Deep Creek Lake, this exceptional 6-bedroom, 4.5-bath home offers the ideal blend of refined comfort, modern updates, and peaceful privacy. Step inside to discover an inviting open floor plan highlighted by soaring wood ceilings, a dramatic floor-to-ceiling stone fireplace, and expansive windows that fill the home with natural light while showcasing the serene surroundings. The beautifully updated kitchen is designed for gathering, featuring granite countertops, abundant cabinetry, stainless steel appliances, and a spacious island that flows seamlessly into the dining and living areas. With six generously sized bedrooms and four-and-a-half baths, there's room for everyone to relax in comfort. Thoughtful upgrades throughout the home provide a fresh, modern feel while maintaining the warmth and character of this impressive property. Outside, your own private retreat awaits. Spend summer days enjoying the heated in-ground swimming pool, entertain on the expansive rear deck, or simply unwind while taking in the views of the park-like backyard. The sprawling acreage offers plenty of room for recreation, gardening, or simply enjoying the beauty of nature. Completing the property is a 3-car attached garage, offering ample space for vehicles, outdoor gear, and storage. Conveniently located just minutes from Deep Creek Lake, Wisp Resort, restaurants, shopping, and Oakland's historic downtown, this remarkable home delivers the perfect balance of luxury, convenience, and country living. Whether you're searching for a full-time residence or a private retreat near Maryland's premier four-season destination, this extraordinary property is one you won't want to miss. *$5,000 buyer credit for carpeting with accepted offer*

17240 Garrett Hwy, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 2 Baths

Very well maintained 3Br-2BA traditional style home in Oakland with huge 24X24 deck, paved driveway and one car detached garage. Home features almost 2000 square feet of living area, stainless steel appliances, and updated bathrooms. Great place to watch the Autumn Glory parade from you covered front porch. Hot water radiant heat with natural gas being the heat source. Newer replacement windows, roof replaced recently and as an added bonus this home features a whole house generator back-up. Convenient to all town activities, schools, and the hospital. 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.

102 N 3rd St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

5 Beds ⋅ 2 Baths

Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or flexible multi-generational use. Inside, you’ll find a welcoming living room with custom built-in cabinetry, a separate formal dining room, hardwood floors, and two cozy fireplaces that add warmth and character throughout the home. The bright and inviting sunroom provides the perfect place to relax year-round with abundant natural light and additional living space for entertaining or quiet mornings at home. Outdoor living is just as impressive with a large, fully fenced rear yard, rear deck ideal for entertaining, plenty of parking, a one-car garage, and an oversized 28x12 shed offering exceptional storage or workshop space. Additional updates include replacement windows and an HVAC system approximately 6 years old for added peace of mind. Conveniently located within walking distance to town, hospital and medical offices, pharmacy, dining, and banking, this home combines space, comfort, and accessibility in one exceptional property.

321 N 3rd St, Oakland

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005

1 Beds ⋅ 1 Baths

Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath house blends cozy living with endless potential. The upper level offers a cozy living area, a full kitchen, laundry room, bedroom, and full bath. But the real bonus? A spacious 2-car garage with its own entrance. It is perfect for a workshop, extra storage, or even a rental opportunity. With separate entrances for the garage and living space, this property offers built-in flexibility for income potential or multi-purpose use. Plus, the location is minutes to lake activities and downtown Oakland. Don't miss out on the chance to own this versatile gem. Schedule a showing today!

206 Mayhew Inn Rd, Oakland

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

3 Beds ⋅ 2 Baths

Well maintained brick rancher located in the heart of Oakland. This home offers a large kitchen open to the living room with a built-in fireplace, separate dining room, and new carpet through out. The basement is very clean, offering a clean slate for whatever you would like to do. The rear covered porch, deck and fenced in yard makes a great space to enjoy family and friends. The location is just minutes to grocery stores, schools, shopping and restaurants. This home won't last long, call today to preview!

315 Coolidge Ave, Oakland

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

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About Jessie Railey | Third Generation Deep Creek Lake REALTOR®

Third Generation REALTOR® | Deep Creek Lake • Garrett County • Western Maryland For my family, Deep Creek Lake isn't just where we work—it's where our story began. Helping buyers and sellers here isn't just my profession—it's a privilege, and one I don't take for granted. Buying a home at Deep Creek Lake is about more than square footage, lake frontage, or market statistics. It's about finding the place where memories will be made for years to come. Whether you're searching for a luxury lakefront home, a vacation property, an investment opportunity, or your forever home, my goal is to help you make that decision with confidence, honesty, and local knowledge that only comes from a lifetime spent here. A Lifetime at Deep Creek Lake I was born and raised in Garrett County, and Deep Creek Lake has always been home. I learned to ski at Wisp Resort, spent summers on the lake, and now my husband and I are raising our two children in the same community that shaped me. Living here year-round has given me insight that extends well beyond the MLS. I know the neighborhoods, the lakefront communities, the hidden gems, and the small details that help buyers find not just the right property—but the right lifestyle. Real estate isn't just about finding a home. It's about finding the place where your life happens. A Legacy of Service My family's connection to Deep Creek Lake spans more than a century. In the early 1920s, my great-grandfather, C.M. Railey, helped clear the valley before Deep Creek Lake was created. In 1974, my grandparents, Sis and Jim Railey, founded Railey Realty. My father, Jimmy Railey, along with the Railey Realty partners, has helped lead and grow the company into one of the region's most respected real estate firms. Today, I'm proud to continue that tradition as a third-generation REALTOR®, carrying forward the same values of integrity, hard work, and personalized service that have guided my family for generations. Experience Beyond Real Estate Before returning to real estate full-time, I owned and operated Railey Design for more than 15 years. Helping homeowners prepare, furnish, and stage properties taught me how buyers emotionally connect with a home—and how thoughtful presentation can maximize both value and appeal. Today, I combine that design background with strategic marketing, skilled negotiation, and generations of local knowledge to help my clients achieve exceptional results when buying or selling Deep Creek Lake real estate. What You Can Expect Whether you're purchasing your first vacation home, searching for a luxury lakefront property, investing in rental real estate, or selling a home that's been in your family for years, my commitment remains the same. You'll always receive: Honest advice—even when it's not the easiest answer. Responsive communication from start to finish. Local insight you won't find online. Professional marketing and design expertise to showcase your home's full potential. Personalized guidance throughout every step of the buying or selling process. I believe real estate should feel personal—not transactional. Life Outside Real Estate When I'm not working with clients, you'll usually find me enjoying everything that makes Deep Creek Lake such a special place with my family. Boating. Wake surfing. Skiing. Mountain biking. Hiking. Or cheering on our kids at local sporting events. I genuinely love this community, and I'm grateful every day that I get to help others experience it too. Let's Find the Right Place for Your Next Chapter Whether you're buying, selling, investing, or simply exploring your options, I'd love the opportunity to help you navigate the Deep Creek Lake real estate market. I'm not here to sell you a house. I'm here to help you find the life that goes with it. I'd love the opportunity to learn your story.

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