Mountainside Real Estate

Mountainside Real Estate

Welcome to Mountainside, a picturesque subdivision nestled in the heart of Oakland, Maryland, within the scenic Garrett County. This charming community offers a perfect blend of natural beauty and modern convenience, making it an ideal place for families, retirees, and nature enthusiasts alike.

Mountainside is renowned for its breathtaking views of the surrounding mountains and lush landscapes, providing residents with a serene escape from the hustle and bustle of everyday life. The area is characterized by its spacious lots, allowing for ample outdoor space where families can create lasting memories. Imagine waking up to the sound of rustling leaves and the sight of sun-dappled mountains right outside your window!

The subdivision is conveniently located near a variety of recreational activities. Whether you enjoy hiking, biking, or fishing, the nearby Deep Creek Lake and the pristine trails of the Garrett State Forest offer endless opportunities for adventure. In the winter months, residents can take advantage of the nearby ski resorts, making Mountainside a year-round destination for outdoor enthusiasts.

Community spirit thrives in Mountainside, with friendly neighbors and regular events that foster a warm and welcoming atmosphere. With easy access to local amenities, including shops, restaurants, and schools, everything you need is just a short drive away.

If you’re searching for a tranquil yet vibrant community that embraces the beauty of nature while providing modern conveniences, look no further than Mountainside in Oakland, MD. Come and discover your dream home in this enchanting subdivision today!

Newest Listings in Mountainside

4 Beds ⋅ 4 Baths

Welcome to “Memory Lane,” a thoughtfully designed home located in the highly desirable Mountainside community. Quality craftsmanship and a well thought out floor plan creates inviting spaces that are both comfortable and functional, while the finished lower level provides additional room for entertaining family and friends. Situated on more than an acre, the home features a spacious wraparound porch and private hot tub, creating an ideal setting for relaxing, gathering, and enjoying every season. “Memory Lane” was previously a successful short term rental with excellent guest reviews and offers outstanding potential as an investment property, second home, or full time residence. Mountainside amenities include lake access, a clubhouse, tennis and basketball courts, and eligibility for the annual dock slip lottery. Conveniently located just minutes from Deep Creek Lake, Wisp Resort, restaurants, and shopping, this home offers privacy, mountain charm, and easy access to year round recreation.

941 Mountainview Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Lake Access Lots 132 & 132A in the Mountainside Community offer 3.04 acres of privacy at the end of a quiet cul-de-sac on Tarn Drive. Combined and recorded in the land records as one building site, this property is already serviced by public water and sewer—making it ready for your future build. The gently wooded setting provides a peaceful, natural backdrop with plenty of space to design your ideal mountain retreat. Enjoy lake access along with the convenience of easy year-round access, all while being just minutes from Deep Creek Lake amenities, dining, and recreation. Plat and utility information available.

132 &132A Tarn Dr, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 3 Baths

Experience mountain living at its finest in this breathtaking mountaintop home overlooking Deep Creek Lake. With sweeping views from almost every room, your hardest decision may be where to sit to enjoy them. Offering three levels of living space, hardwood floors ( which were recently refinished), and some new appliances. The multiple decks are ideal to enjoy family and friends while taking in the beauty around you. The location is another plus, just minutes to the community club house where you can enjoy the lake, and minutes to Wisp Ski & Golf Resort, restaurants, coffee shops, cinemas, and grocery stores. Class A lake access. Call today to preview!

164 Grandview Dr, Oakland

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

Ready to build lot in Deep Creek Lake's Mountainside Subdivision. This wooded lot is relatively level can be connected to public water and has an approved percolation test for an onsite septic system. Build you dream home in this mountaintop community with homes values ranging up to $2,000,000.

Lot 53 Mountainview Dr, Oakland

Listing courtesy of Samson Properties. Contact: 2406308689

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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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