Oakland, MD Real Estate Search

Oakland, MD Homes for Sale

The Real Estate Market in Oakland, MD

Oakland, MD is a quaint town located in Garrett County, known for its picturesque surroundings and outdoor recreational opportunities. The real estate market in Oakland is diverse, offering a range of options for homebuyers looking to settle down in this charming town. From historic Victorian homes to modern new construction, there is something for everyone in Oakland.

Home Prices and Trends

The median home price in Oakland, MD is currently around $200,000, making it an affordable option for homebuyers on a budget. The real estate market in Oakland has been steadily growing in recent years, with an increase in property values and new developments popping up throughout the town. As more people discover the beauty and charm of Oakland, demand for housing continues to rise.

Popular Neighborhoods in Oakland

One of the most popular neighborhoods in Oakland is the historic downtown area, with its tree-lined streets and Victorian homes. This area is perfect for those who appreciate a small-town atmosphere and enjoy being within walking distance to shops and restaurants. Another sought-after neighborhood is the Deep Creek Lake area, offering waterfront properties and stunning views of the lake.

Investment Opportunities in Oakland

Real estate investment opportunities abound in Oakland, from fixer-upper properties in need of renovation to commercial developments in up-and-coming areas. With the town's growing popularity as a vacation destination and outdoor recreational hub, there is plenty of potential for long-term returns on investment in the Oakland real estate market.

Conclusion

Overall, Oakland, MD offers a diverse and thriving real estate market for homebuyers and investors alike. Whether you're looking for a charming historic home or a modern waterfront property, Oakland has something for everyone. With its affordable home prices, beautiful surroundings, and endless recreational opportunities, Oakland is a great place to call home.

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Oakland, MD Homes for Sale

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Newest Oakland, MD Homes for Sale

$164,000
3 Beds ⋅ 1 Baths
Remodeled Rancher Near the North Branch Potomac River This charming 3-bedroom, 1-bath rancher has been completely remodeled, with all new appliances. Located within walking distance of the scenic North Branch of the Potomac River, the home offers both convenience and natural beauty at your doorstep. A recently enclosed front porch with a wood stove provides extra warmth and a welcoming spot to relax year-round. The property also includes a spacious 33’ x 18’ detached garage—perfect for vehicles, storage, or a workshop—as well as a wood shed for added utility. Call now for your private tour!

63 Wallman Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$699,000
4 Beds ⋅ 5 Baths
Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just minutes from Deep Creek Lake and Oakland. This 4-bedroom, 4.5-bath home has been carefully updated to balance comfort, practicality, and modern style. The main level features hardwood floors, radiant heat for added comfort, and open gathering spaces with quiet nooks for reading or hobbies. Upstairs, two primary bedrooms with private baths provide flexibility for family or guests. The full apartment-style basement includes its own kitchen, laundry, and heated floors, offering an inviting space for extended stays or independent living. Outdoors, a stamped concrete driveway leads to an oversized two-car garage, with additional garages and sheds for storage or projects. A fenced in-ground pool, hot tub, and wood decking create a welcoming space for entertaining and relaxation. With thoughtful upgrades throughout, extensive amenities, and close proximity to both town and lake, this property offers the best of convenience and privacy in one setting.

1909 Pysell Crosscut Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$299,000
4 Beds ⋅ 3 Baths
Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement is an entertainer’s dream, featuring a pool table, wood stove, mudroom, half bath, and a bedroom with its own attached full bath—ideal for guests. Additional features include an attached 1-car garage, carport beneath the covered deck, and a layout designed for both everyday living and mountain getaways. Lovingly maintained and in excellent condition, this home combines rustic charm with modern comfort in an incredible setting. Located within the gated recreation community of Yough Mountain Resort, you'll have access to over 50 miles of ATV, snowmobile, and hiking trails, as well as river access, fishing, and hunting. For those seeking even more adventure, Deep Creek Lake, the town of Oakland, Swallow Falls, and Herrington Manor State Park are just minutes away, offering endless possibilities. Call today!

961 Cedar Ln, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$499,900
4 Beds ⋅ 3 Baths
Perched above the treetops with panoramic lake views, this three-level retreat blends comfort with clean, considered upgrades. Vaulted ceilings and a spacious loft crown 2,235 square feet of living space, wrapped in new flooring with fresh paint inside and out. The kitchen, smartly updated with new countertops, connects to open dining and living anchored by a wood stove. A detached garage sits off the drive; while the private deck draws the eye to the water. An established rental, “Views and Brews” is being sold fully furnished and ready to go. Just minutes to marinas, Wisp Resort, and the lake’s best bites. Call today for details!

126 Leo Friend Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$339,900
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:

$264,500
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
$285,500
3 Beds ⋅ 2 Baths
Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-sided home offers the perfect blend of rustic charm and modern comfort—all just 10 minutes from downtown Oakland. This well-maintained home features 3 spacious bedrooms and 2 full bathrooms, including a main floor master suite for added convenience. Inside, you’ll find brand-new luxury vinyl plank (LVP) flooring that adds style and durability throughout the living spaces. The large, inviting kitchen provides plenty of room for cooking, entertaining, and gathering with loved ones. Recent upgrades include a brand-new metal roof, offering peace of mind and long-lasting durability. Outside, the property showcases a beautiful mix of mature woods and open fields—ideal for nature lovers, outdoor enthusiasts, or those simply seeking privacy and space to roam. Whether you're looking for a peaceful weekend retreat or a full-time residence with easy access to town, this unique property delivers the best of both worlds.

1737 King Wildesen Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$545,000
4 Beds ⋅ 3 Baths
Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of craftsmanship featuring handmade woodwork crafted from trees sourced directly from the property. Many specialty items will remain, including bathroom vanities, multiple dressers, a primary suite custom TV console, a built-in bunk bed, and more. The spacious primary suite was added in 2016 and offers a separate living area, cozy gas fireplace, and beautiful hardwood floors. The open floor plan on the main living level with kitchen and dining areas is perfect for family gatherings and entertaining guests. The entry-level laundry with dog wash, a screened porch, and separate office space check all the boxes for your "wish list". Enjoy your outside space with a little over 3 acres, complete with a firepit area and walking trails throughout the property. Two detached garages, one oversized and both finished, are insulated for cars, additional storage, or hobby workshop. The A-frame cottage for kids is perfect for the ultimate in playtime Make an appointment today to tour this one-of-a-kind home in this beautiful "park-like" setting! Special Financing Options Available.

328 Stool Rock Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$739,000
5 Beds ⋅ 4 Baths
Beautiful lake access retreat located in the Silver Tree Landings community with an available home warranty. This recently updated contemporary home feels warm and inviting from the moment you walk in (upgrade list available). Offering hardwood flooring, granite countertops, two stone propane fireplaces and cathedral ceilings. The abundance of windows allows the natural light to brighten any season, while offering views from almost every room. The covered and uncovered decks offer plenty of outdoor space to enjoy with family and friends during any season, and the hot tub is always a big hit. If all this isn't enough, take a short walk down to the community docks/lake access area, where you can enjoy the lake and everything it offers. The location checks off one more box, centrally located and just minutes to Unos/Honi Honi, grocery stores, Deep Creek State Park/beach area, Dutch's Restaurant & Harbor Bar, Cinema, Ice Cream, Thousand Acres Golf Club, and Wisp Ski Resort. “Crosswinds” is an established rental. Call today to preview this gorgeous home!

25 Silver Tree Ln, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$175,000
1 Beds ⋅ 1 Baths
Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western exposure centrally located to all area amenities. Unit 212A offers a one level floorpan with private bedroom on the second floor of building A which offers easy access to the lobby, elevator, gym, sauna, game room and patio area overlooking the lake. Condominium ownership at Silver Tree Suites offers ease of maintenance as the association takes care of all of the grounds and building maintenance. This unit is an established vacation rental ready for you to take ownership this summer! Call today to schedule a private showing!

565 Glendale Rd Unit #212A, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$1,329,000
6 Beds ⋅ 5 Baths
Stunning 6-Bedroom Kathadin Log Home with Breathtaking 180° views of Deep Creek Lake with Lake Access and a Boat Slip! This exceptional vacation home offers the perfect blend of rustic charm and modern luxury. Boasting 180-degree panoramic views of the sparkling lake, this property is a true mountain retreat. Every room is designed to capture the beauty of the surrounding landscape, with expansive windows allowing natural light to flood the interior and provide endless vistas of the tranquil water. With over 4,000 sq ft of living space, this spacious home features soaring ceilings, rich wood finishes, and an open-concept floor plan that’s perfect for entertaining. The main level living room, with its impressive stone fireplace, is the heart of the home, leading seamlessly into the kitchen and dining area. Whether you’re hosting gatherings or relaxing by the fire, this space offers comfort and style in equal measure. The home includes six generously-sized bedrooms, each offering a serene escape and 5 of them with picturesque lake views. Step outside to the expansive deck that spans the length of the home, perfect for enjoying morning sunrises . A boat slip provides direct access to Deep Creek Lake, offering the ultimate convenience for boating, fishing, and water sports enthusiasts. Additional highlights include a fully finished lower level with a family room, second fireplace, and walk-out access to the outdoor living spaces. The property is complemented by a detached garage and additional parking areas off the drive that can accommodate up to 4 additional cars. Whether you’re looking for a year-round residence, a vacation home, or rental home, this stunning log home offers unparalleled views, a prime location, and a serene lake lifestyle. High rental potential and projection. Don’t miss the opportunity to make this magnificent property your own!

439 Paradise Hts, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$2,350,000
5 Beds ⋅ 7 Baths
Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built log home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. This home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled comfort. Nestled on 1.03 acres, it ensures abundant privacy and is just a short, level walk to lake access with a deeded dock slip. With soaring cathedral ceilings that bathe the interior in natural light, the home features four finished levels, providing generous space for everyone. The property itself boasts a luxurious soaking hot tub, sauna, multiple bars, a family room, game room, den, dual washers and dryers, bar areas, an exquisite outdoor fireplace, a new Blackstone grill, radiant floor heating, and a custom wine barrel deck firepit along with an attached two-car garage and a detached 2-car garage with unfinished loft space. Recently upgraded with several enhancements, this meticulously maintained home features fresh exterior staining, a Savant home control system, a house generator, a new alarm system, and two new hot water heaters and boiler for radiant floor heating. New outdoor furniture and LED lighting enhance the exterior ambiance. Inside, you'll find a warm and elegant atmosphere, featuring a native stone gas fireplace and custom touches that add rustic charm. Retreat to one of five en-suite bedrooms, each designed for maximum comfort with a private bath and a cozy fireplace. The loft area offers stunning views, perfect for entertaining or quiet relaxation. Don’t miss this rare opportunity to own a remarkable property that seamlessly combines luxury, comfort, and natural beauty in the prestigious Sandy Beach community of Deep Creek Lake. This residence epitomizes resort living. Schedule your private tour today to discover the pinnacle of Deep Creek Lake real estate. Adjoining lot is also included in the sale giving you an additional 1.03 acres of privacy.

2725 Stockslager Rd, Oakland

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