Oakland Real Estate

Oakland Real Estate

Welcome to Oakland, Maryland—a charming gem nestled in the heart of Garrett County. Known for its stunning natural beauty and vibrant community spirit, Oakland is the perfect blend of small-town charm and outdoor adventure. This picturesque town, surrounded by the breathtaking landscape of the Appalachian Mountains, offers residents and visitors alike a unique opportunity to immerse themselves in nature while enjoying a close-knit community atmosphere.

With a rich history dating back to the 1800s, Oakland boasts a quaint downtown area filled with local shops, eateries, and galleries that reflect the town's heritage and artistic flair. Stroll along the tree-lined streets, where you can discover unique boutiques and savor delicious meals at family-owned restaurants. The annual events, such as the Autumn Glory Festival, bring the community together to celebrate the changing seasons with music, food, and fun for all ages.

For outdoor enthusiasts, Oakland is a gateway to adventure. The nearby Deep Creek Lake offers a variety of recreational activities, from boating and fishing in the summer to skiing and snowboarding in the winter. Hiking trails abound, providing stunning views and opportunities to explore the region's diverse wildlife.

Whether you’re looking to settle down in a welcoming community or simply seeking a weekend getaway, Oakland, MD, is a delightful destination that captures the essence of Maryland’s beauty. With its friendly residents, vibrant culture, and endless outdoor activities, Oakland is not just a place to live—it's a place to thrive. Come and discover the charm of Oakland, where every day feels like a getaway!

Newest Listings in Oakland

Whispering Pines Ln, Oakland

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

Nestled within the prestigious Paradise Ridge community, this exceptional 0.76-acre lot offers a rare opportunity to create your dream retreat, harmoniously blending luxury living with the serene beauty of nature. The property allows for a seamless integration of your vision while preserving the enchanting wooded areas that provide both privacy and a picturesque backdrop. The lot's unique features extend beyond its scenic vistas. The gentle rustle of trees and the soft sounds of nature create an inviting atmosphere, perfect for relaxation and rejuvenation. Picture evenings spent on your future patio, surrounded by the beauty of the landscape, as you entertain friends or unwind with a good book. This property is not just a piece of land; it's a canvas for your aspirations. The potential for luxurious outdoor living spaces is limitless, from expansive decks that overlook the lake to beautifully landscaped gardens that enhance the natural beauty of the surroundings. The combination of cleared areas and wooded charm provides the perfect balance for those seeking both openness and seclusion. Paradise Ridge is more than a location; it's a lifestyle. Here, you can enjoy the tranquility of nature while being part of a vibrant community that values exclusivity and sophistication. Whether you envision a grand estate or a cozy lakeside cottage, this lot offers the perfect foundation for your high-end living experience. Seize the opportunity to create a sanctuary that reflects your personal style and embraces the luxurious lifestyle you deserve. With its prime location, stunning views, and access to Deep Creek Lake, this property is a rare gem waiting for your vision to come to life. Embrace the essence of refined living in a setting that feels like a permanent vacation.

13 Laurel Court Ct, Oakland

Listing courtesy of The KW Collective. Contact:

2 Beds ⋅ 2 Baths

Comfy, cozy, and full of mountain charm! This inviting 2-bedroom, 1.5-bath cabin is nestled on 1.26 private acres within Yough Mountain Resort, offering the perfect setting for a weekend getaway, recreational retreat, or peaceful escape. The open floor plan creates a comfortable gathering space, highlighted by a beautiful stone fireplace with a wood-burning insert that adds warmth and character, while stainless steel appliances and recent updates make the home easy to enjoy. Recent improvements include laminate flooring, added washer and dryer hookups, a water filtration system, a vapor barrier installed in the crawlspace, a new gravel circular driveway, and a new shed for additional storage. Outside, enjoy the covered front porch, rear deck, and balcony off the bedroom, all surrounded by the privacy and beauty of the mountains. Yough Mountain Resort offers 50+ miles of ATV, snowmobile, and hiking trails, as well as fishing, hunting areas, and numerous community amenities. If you're looking for a cabin with privacy, updates, and plenty of outdoor recreation right at your doorstep, this one is ready to enjoy! Call today!

1959 Birchwood Dr, Oakland

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

5 Beds ⋅ 4 Baths

Immaculate from top to bottom, this exceptional five-bedroom home offers three levels of beautifully maintained living space, making it an ideal choice for a primary residence. Thoughtfully designed for comfortable everyday living, the home provides plenty of room to gather, relax, and spread out. A stunning fireplace creates a warm and inviting focal point, while the attached two-car garage adds convenience and storage. Above the garage, an unfinished room offers exciting potential for additional storage, an office, guest quarters, or additional living space. The downstairs family room offers expansive square footage for cozy gatherings. Numerous recent upgrades, including a new roof, high-efficiency mini-split units, and an upgraded energy-efficient boiler and hot water system, provide added peace of mind. The beautiful screened-in back porch is perfect for enjoying morning coffee, relaxing in the evening, or entertaining guests. Tucked away in a wonderful, private Oakland neighborhood, this home offers peaceful residential living while remaining conveniently close to Deep Creek Lake, Wisp Resort, and area amenities. A truly special property that checks all the boxes!

607 Pin Oak Cir, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 3 Baths

This exquisite Northern White Cedar Construction (naturally rot resistant) log home offers a harmonious blend of rustic charm and modern luxury. The spacious, open floor plan invites you to experience a warm and inviting atmosphere, accentuated by stunning wood floors and walls, cathedral beam ceiling, and a cozy stone fireplace with glass doors, perfect for intimate gatherings. The heart of the home features a well-appointed kitchen equipped with nice appliances, and an eat-in bar. Retreat to the spacious primary suite, complemented by two additional bedrooms, providing ample space for relaxation. The fully finished basement, with a convenient walkout entrance just steps from the driveway, offers endless possibilities while offering plenty of space to host friends and family. Step outside to discover a beautifully landscaped 0.63-acre fenced yard that backs to lush trees, and includes a playhouse/shed. Enjoy the expansive wrap-around deck with a covered roomy front and rear porch, perfect for morning coffee or entertaining family and friends while watching the valley full of wildlife. The location is just minutes to Deep Creek Lake, Wisp Ski Resort, restaurants, entertainment and food markets.

1529 Paradise Point Rd, Oakland

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

2 Beds ⋅ 2 Baths

Rare opportunity to own a thoughtfully designed container home in the Deep Creek Lake area! This distinctive 2BR/2BA retreat combines modern comfort with a private wooded setting. The open-concept interior features abundant natural light, a full kitchen, comfortable living space, and large sliders connecting the indoors to the outdoors. Enjoy a private backyard with hot tub, fire pit, and grill, plus additional storage for outdoor gear. Conveniently located near Deep Creek Lake, Wisp Resort, hiking, biking, golf, boating, fishing, state park trails, and local dining. Built with quality, this home features Superior foundation walls, high end finishes and a mountaintop setting that is sure to impress. A truly one-of-a-kind property with excellent appeal as a personal getaway, investment property, or short-term rental.

100 San Francisco St, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

3 Beds ⋅ 2 Baths

Location, location, location! Enjoy easy living in this one-level raised rancher featuring 3 bedrooms and 1.5 baths, with all bedrooms conveniently located on the main level. Beautiful hardwood floors add warmth, while the covered front porch and side covered deck offer inviting spaces to relax and enjoy the peaceful surroundings. The fenced-in backyard provides plenty of outdoor space for pets, play, or entertaining. The full basement is ready for your finishing touches and offers additional potential, while the attached one-car lower-level garage provides convenient parking or extra storage. Recent updates include a new roof and a full WaterGuard system installed along the interior basement foundation. Located in a peaceful neighborhood close to schools, the hospital, and shopping, this home offers comfort, convenience, and plenty of opportunity to make it your own. Call today to schedule your showing!

139 S Oakhall Dr, Oakland

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

4 Beds ⋅ 2 Baths

Spacious one level home, 4 BR with den, living room, extra office off Main BR, large back yard with huge deck. Very large main bedroom with bath and extra room (could be nursery, extra BR or office) . 2 Full baths, 2 fireplaces, Laundry and perfect location for privacy, yet close to all things fun in the Deep Creek Lake area. One mile from Deep Creek Lake, 2 miles from Swallow Falls State Park. Begin sold "AS IS" recent updates, - new Patio door to deck, new flooring in in Kitchen/dinning.

586 Bray School Rd, Oakland

Listing courtesy of The KW Collective. Contact:

1 Beds ⋅ 1 Baths

Will O the Wisp unit 105A is a charming one-bedroom, one-bath lakefront condominium. Unit 105A offers convenient first-floor living with ground-level access from a private patio directly to the waters edge, beach area and docks. . The unit features a fully equipped kitchen, comfortable living and dining areas, a cozy fireplace, one queen bed, and a sleeper sofa—accommodating up to three adults. Relax at the private patio, spending the day on the sandy beach, or taking advantage of the community’s indoor pool, game room, fitness center, and additional on-site amenities. An ideal lakefront getaway with comfort, convenience, and beautiful waterfront access!

20160 Garett Hwy Unit #105A, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Lot 28 Wild Turkey Lane is an affordable 1-acre corner lot in the private Deerfield Subdivision, conveniently located off Mayhew Inn Road. This homesite is perc approved and ready for you to build your dream home or mountain getaway. Enjoy a peaceful community setting just minutes from Deep Creek Lake, area state parks, shopping, dining, and other local attractions. Recorded survey available.

Wild Turkey Ln Unit #LOT 28, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

Discover this quiet .94 acre lot in the sought-after Yough Mountain Resort community, ideal for a mountain getaway, full-time home, or adventure basecamp. Enjoy access to over 2,000 acres of private wilderness, private hunting and fishing areas, ATV and snowmobile trails, community pavilions, playgrounds, sports courts, and green space, just minutes from Deep Creek Lake and Wisp Resort. A rare chance to own your own piece of one of the area's most desirable communities.

Cedar Ln Unit #LOT 66, Oakland

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

3 Beds ⋅ 1 Baths

INVESTOR SPECIAL!! GREAT FOR FIX AND FLIP OR HOLD! Property is sold completely as-is with all contents. Buyer to pay all closing,100% TT&Rs. CASH or Hard money only.

102 Roanoke Ave, Oakland

Listing courtesy of Samson Properties. Contact: 7033788810

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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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