Oakland Condos for Sale

Oakland Condos for Sale

**Discover the Charm of Oakland, Maryland: Your Ideal Condo Awaits!**

Nestled in the heart of Garrett County, Oakland, Maryland, is a picturesque town that beautifully blends small-town charm with vibrant community spirit. Surrounded by the stunning natural landscapes of Deep Creek Lake and the majestic mountains, Oakland offers residents a unique lifestyle that embraces both tranquility and adventure. Known for its rich history and friendly atmosphere, this lovely town is perfect for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

As you explore Oakland, you'll find a delightful array of local shops, restaurants, and cultural attractions that reflect the town's warm, welcoming nature. Outdoor enthusiasts will revel in the plethora of recreational opportunities, including hiking, fishing, and skiing, all just a stone's throw away. The annual events, such as the Autumn Glory Festival, showcase the town's vibrant community spirit and offer fun for all ages.

If you're considering making Oakland your home, you'll be pleased to know that a variety of condos for sale are currently available. These modern residences provide a perfect blend of comfort and style, often featuring spacious layouts, contemporary amenities, and breathtaking views of the surrounding landscape. Whether you're looking for a cozy weekend getaway or a permanent residence, Oakland's condos offer an ideal solution for those seeking a low-maintenance lifestyle without sacrificing quality or charm.

Embrace the beauty and community of Oakland, Maryland, and find your dream condo today! Your new adventure awaits in this enchanting town.

Newest Oakland Condos for Sale

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:

1 Beds ⋅ 1 Baths

Turnkey lakeview studio at The Suites at Silver Tree! This condo has an average annual gross rental of $25,342. Enjoy beautiful views of Deep Creek Lake from your private covered balcony while owning one of the area's most desirable vacation destinations. This fully furnished studio offers an open floor plan with a king bed, sleeper sofa, cozy gas fireplace, kitchenette, dining area, and full bath, making it the perfect weekend getaway or investment opportunity. The Suites at Silver Tree features an impressive timber-frame lobby with soaring ceilings and massive stone fireplaces, an expansive lakeside deck, sandy beach, lake access, on-site marina, fitness center, sauna, game room, and Dutch's at Silver Tree restaurant. Ideally located in the heart of Deep Creek Lake, you're just minutes from Wisp Resort, golf, hiking, shopping, and year-round recreation. Whether you're looking for a low-maintenance vacation home, rental property, or your own place at the lake, this one checks all the boxes. Call today for your private showing!

565 Glendale Rd Unit #213, Oakland

Listing courtesy of The KW Collective. Contact: 4435741600

2 Beds ⋅ 2 Baths

Ultimate lakefront living awaits at Red Run! This stunning 2-3BR, 2BA condo features a second-floor loft and a versatile den easily used as a 3rd bedroom. Enjoy breathtaking lake views from your gorgeous primary suite and private lakeside balcony. Extensively upgraded with a extensively upgraded kitchen boasting granite countertops and soft-close cabinetry, a newly remodeled laundry room with a new water heater and sink, an upgraded electrical panel, and premium cement-backed luxury vinyl plank flooring for ultimate durability. Stunning new shiplap ceilings with recessed lighting illuminate the freshly painted main living spaces, complete with a cozy wood-burning fireplace. Includes an assigned deep-water boat slip, outdoor storage, and access to 11 acres of incredible amenities: a heated pool, tennis courts, playground, kayak racks, and a stone fire pit. Major community updates include a new metal roof and resurfaced courts. Just minutes from downtown Oakland, Garret Cinemas, and shopping! Seller will sell his 2011 Sea Ray 195 with 4.2 L EFI engine for $4500.00 OBO "As=Is " see photos and dock slip

193 Red Run Rd Unit #1-B-3, Oakland

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005

1 Beds ⋅ 1 Baths

Experience the best of Deep Creek Lake from this beautifully situated 2-story, 1-bedroom, 1-bath condominium at Will O' The Wisp. Offering 636 square feet of comfortable living space and spectacular lake views, this waterfront retreat is the perfect personal getaway, year-round residence, or vacation rental investment. Enjoy your morning coffee while taking in panoramic views of the water, then spend the day enjoying the incredible amenities that make Will O' The Wisp one of Deep Creek Lake's most sought-after destinations. Residents and guests have access to an indoor swimming pool and hot tub, racquetball court, fitness center, and arcade, providing year-round entertainment for all ages. 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. Boating enthusiasts will appreciate the community's 22 dock slips available for reservation and 4 dedicated jet ski docks, making it easy to get out and enjoy the lake. When it's time to relax, take advantage of two exceptional waterfront restaurant and bar venues located on-site, both featuring stunning lake views and convenient commercial docking. With professional on-site management, resort-style amenities, and a premier lakefront location just minutes from Wisp Resort, state parks, golf courses, and countless outdoor activities, this property offers an incredible opportunity to own a piece of Deep Creek Lake's waterfront lifestyle. Whether you're looking for a weekend escape or a property with strong rental appeal, this lakeview condo checks all the boxes.

20160 Garrett Hwy Unit #C307, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

1 Beds ⋅ 1 Baths

Welcome to Will O' the Wisp Unit H706, a beautiful top-floor lakefront condo offering some of the most breathtaking views of Deep Creek Lake. Perched on the 7th floor and overlooking one of the lake's widest sections, this fully furnished two-level condo features 1 bedroom, 1 bath, and 550 square feet of comfortable, low-maintenance living - ideal as a vacation retreat, year-round getaway, or income-producing rental. Start your mornings with exceptional sunrises from your private lakefront balcony, then enjoy the many resort-style amenities Will O' the Wisp has to offer, including an indoor heated pool, hot tubs, fitness room, sauna, arcade/game room, sandy beach, covered garage parking, restaurant access, community boat slip access through the POA, and a fully serviced front desk for guest support and added convenience. Currently operating as a successful short-term rental through Railey Vacations, this rarely available lakefront condo is located just minutes from Wisp Resort, state parks, dining, shopping, and four-season Deep Creek Lake recreation.

20160 Garrett Hwy Unit #H706, Oakland

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

2 Beds ⋅ 1 Baths

Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added functionality of the upper-level loft living space with desk area and additional bedroom. A custom wine rack with built-in liquor cabinet adds the perfect finishing touch to this inviting mountain-lake retreat. Community amenities include; a game room, fitness center, meeting room and convenient on-site laundry facilities. Located just steps from one of the lake's most popular waterfront dining destinations, Dutch's at Silver Tree. Also, conveniently located to a host of other attractions; State parks, Wisp Golf and Ski Resort, Thousand Acres Lakeside Golf Club and more! Call today to schedule your private tour.

565 Glendale Rd Unit #303B, Oakland

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

2 Beds ⋅ 1 Baths

Experience the best of Deep Creek Lake living from this beautifully appointed studio loft at Silver Tree Suites—one of the lake’s most sought-after locations! Offering two separate sleeping areas, a kitchenette, gas fireplace, and private balcony, this unit is designed for comfort and easy getaway living. Tastefully updated with new carpet and flooring, as well as kitchen and bathroom countertops. Enjoy lake access along with on-site amenities including a fitness room, sauna, marina, and expansive lakefront deck. Directly adjoining Dutch’s at Silver Tree and minutes to Wisp Resort, state parks, and year-round recreation, this prime location puts everything you love about Deep Creek right at your fingertips. Active vacation rental, giving you turn-key investment potential. Call today for more details!

565 Glendale Rd Unit #306, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

1 Beds ⋅ 1 Baths

Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefront living with unbeatable access to everything Deep Creek Lake has to offer. Enjoy effortless days on the water, then relax with on-site amenities including a fitness room, sauna, game room, and expansive lakeside decking. Walk to Dutch’s at Silver Tree, The Harbor Bar, and the marina for dining, drinks, and boating convenience—all just steps away. This property is not only the perfect getaway, but also a proven Vacation Rental Income Producing Condo —Recognized as one of the top-performing rental units in the SilverTree building, averaging $30,000 per year in Vacation Rental Income. Whether you're looking for a low-maintenance lake retreat or a high-performing income-producing property, this unit delivers the best of both worlds in one of Deep Creek’s most desirable lakefront communities. Call today to schedule a private showing.

565 Glendale Rd Unit #125, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

2 Beds ⋅ 1 Baths

Charming true 1-bedroom + loft (can be used as 2nd bedroom) condo at Silver Tree Suites, LAKEFRONT living at its finest! This spacious second-floor unit features a private balcony, fully equipped kitchenette, cozy gas fireplace and abundant natural light. Enjoy resort-style amenities including a fitness center, sauna, on-site laundry and game room, plus steps-away fine dining at Dutch’s at Silver Tree and cocktails on Harbor Bar’s waterfront deck with breathtaking views of Deep Creek Lake. Here, every day is a promise of relaxation, adventure, and luxury living. Located just minutes from Wisp Ski Resort, Swallow Falls, hiking trails, whitewater rafting, golf courses, Deep Creek Lake State Park beach and boat ramp, and local shopping, this property is ideally situated. Take this rare opportunity to own your own slice of Lakefront paradise at Deep Creek Lake! Schedule your private showing today!

565 Glendale Rd Unit #B206, Oakland

Listing courtesy of Jason Mitchell Group. Contact: 4105335486

2 Beds ⋅ 1 Baths

Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located in the desirable Roman Ridge at Traders Landing community. Enjoy peaceful lake views from your covered front deck—the perfect spot to relax with your morning coffee or unwind in the evening. Inside, you’ll find a warm and inviting living space featuring a wood-burning fireplace to take the chill off during cool lake evenings. This home offers an easy-flow layout ideal for full-time living or a weekend getaway. Located just moments from all the lake amenities, including Brenda’s Pizza and Traders Coffee, you’ll have dining and recreation right at your fingertips. Come experience lake life at its coziest—schedule your showing today!

181 Jeffrey Ln Unit #23A, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

2 Beds ⋅ 1 Baths

Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath unit in Silver Tree Suites—one of the largest units in the complex! This beautifully designed unit features an open floorplan centered around a cozy fireplace, perfect for relaxing after a day on the lake. A generous loft area creates a distinct separation between living and sleeping spaces, offering flexibility and privacy. Take in views of Deep Creek Lake and just a stones throw from your door, enjoy unbeatable proximity to Dutch’s at Silver Tree and The Harbor Bar. Whether you're looking for a weekend retreat or a hassle-free getaway, this turnkey condo is truly maintenance-free—just drop your bags and start enjoying lake life!

531 Glendale Rd Unit #B302, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

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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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