Oakland, MD Real Estate Search

Oakland, MD 5 Bedroom Homes for Sale

Oakland, MD, nestled in the picturesque mountains of western Maryland, offers a charming selection of five-bedroom homes for sale that appeal to families and outdoor enthusiasts alike. These spacious residences are often situated on generous lots, providing ample space for outdoor activities and entertaining. Many homes showcase stunning views of the surrounding landscape, with access to nearby lakes and hiking trails, perfect for those who appreciate nature. The local real estate market reflects a blend of traditional and modern styles, ensuring buyer preferences are met. Oakland's close-knit community, excellent schools, and vibrant local culture further enhance the allure of finding a five-bedroom home in this serene mountain town.

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Newest Oakland, MD 5 Bedroom Homes for Sale

$365,000
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:

$775,000
5 Beds ⋅ 5 Baths
One-of-a-kind Youghiogheny riverfront estate offering 224 feet of water frontage . Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent walls and exposed beams. Features include multiple fireplaces (wood & gas), Andersen doors & windows, trex decking, hardwood floors, metal roof, custom cabinets in kitchen & bedroom suites, eat-in kitchen, and sold furnished! Enjoy a picturesque setting in a riverfront setting with NO HOA restraints for this home. Seller also offering an adjacent unbuilt riverfront lot (#9) for $175,000 MLS #MDGA2012380

251 Robinwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$350,000
5 Beds ⋅ 3 Baths
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
$765,000
5 Beds ⋅ 3 Baths
Welcome to this stunning 5-bedroom, 3-bath home, completed in 2023 and designed for modern mountain living. Featuring two private ensuite bedrooms, spacious living areas, and a fresh, contemporary design, this home is ready for you to enjoy from day one. This home features a stylish modern kitchen with an open layout that is perfect for entertainment. In the winter months, cozy up by the wood burning fireplace in the living room. Step outside and enjoy plenty of deck space for entertaining, grilling, or simply relaxing with your morning coffee. Gather around the fire pit under the stars after a day on the lake. Located just minutes from Deep Creek Lake's top attractions including boating, dining, shopping, Deep Creek Lake State Park and Wisp Resort—this home is perfectly positioned for every season of adventure. No HOA! This property is a current Airbnb rental "Paradise Getaway" with proven rental income. Contact me today for a private showing!

943 Paradise Hts, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$615,000
5 Beds ⋅ 5 Baths
5BR, 4.5BA duplex with LAKE VIEWS! Enjoy 3300sf of living space in the heart of Deep Creek Lake. Features include 3 spacious suites, multiple stacked stone fireplaces and two living room areas, plus an impressive outdoor fire pit. You will love the open kitchen/dining area and the covered back deck. Other features include wood floors, granite, instant hot water, pool table and hot tub. Attached garage is a plus and over-sized yard area offers extra room to roam. Conveys furnished! One-time capital contribution of $1500 due at closing.

308 Winding Trail Ln Unit #11B, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$599,000
5 Beds ⋅ 4 Baths
Welcome to this beautifully appointed 5-bedroom, 3.5-bath home located in one of Oakland’s most desirable neighborhoods—Country Club Acres, bordering The Golf Club at Oakland. Offering the perfect blend of modern style, comfort, and convenience, this spacious home is designed to accommodate both everyday living and entertaining. Step inside to discover an inviting open-concept floor plan featuring upscale finishes throughout. The heart of the home is the stunning kitchen, complete with sleek cabinetry, solid surface countertops, stainless steel appliances, a large center island, and contemporary lighting that creates a bright and welcoming atmosphere. The adjoining dining and living spaces flow seamlessly together, making gatherings effortless. The home offers five generously sized bedrooms, including a spacious primary suite, along with 3.5 well-appointed bathrooms. The finished basement provides valuable additional living space perfect for a family room, recreation area, home gym, office, or guest accommodations. Outside, enjoy the charm of the covered front porch and the peaceful setting of this established community. The oversized attached one-car garage offers ample room for parking, storage, and outdoor equipment. Located just minutes from downtown Oakland, schools, shopping, dining, and Deep Creek Lake attractions, this exceptional property combines modern living with a highly desirable location.

428 Sam Snead Cir, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$899,900
5 Beds ⋅ 5 Baths
One-of-a-kind Youghiogheny riverfront estate offering 400 feet of water frontage on 5+ acres and 2 separate lots. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent walls and exposed beams. Features include multiple fireplaces (wood & gas), Andersen doors & windows, trex decking, hardwood floors, metal roof, custom cabinets in kitchen & bedroom suites, eat-in kitchen, and sold furnished! Enjoy a picturesque setting in a riverfront setting with NO HOA restraints for this home. The house on lot 8 is also offered on its own WITHOUT the adjacent riverfront building lot for $775,000, MLS listing #MDGA2012378. Lot #9 offered by itself for $175,000 MLS #MDGA2012380

251 Robinwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$1,649,000
5 Beds ⋅ 5 Baths
Experience what may be the most spectacular view in all of Deep Creek Lake! Perched in an extraordinary setting, this exceptional Yellowstone Log Home showcases breathtaking panoramic water views that create a true “top of the world” feel. Designed to capture the scenery from every angle, the main level features an open-concept layout with soaring natural light, a stunning stone fireplace, luxury kitchen, spacious primary suite, and a beautiful three-season room with its own stone fireplace. Step outside to the expansive deck—perfect for entertaining, relaxing, and taking in unforgettable sunsets. The loft offers flexible living space ideal for an office, rec room, or additional lounge area. Downstairs, the finished lower level includes a second family room with stone fireplace, an additional primary suite, two more bedrooms, full bath, and walk-out access to a covered patio. The impressive 40’ x 28’ detached garage provides three bays of storage plus finished living space above with a bedroom suite, living area, bunks, and private deck overlooking the lake. A rare opportunity to own one of Deep Creek Lake’s most unforgettable vantage points—where luxury, space, and unmatched scenery come together.

670 Woodlands Hill Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$365,000
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
$745,000
5 Beds ⋅ 3 Baths
Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth from the moment you enter. This established rental property “Terp’s Hideaway” features an open and inviting floorplan, five bedrooms, two family rooms, and three levels of living space, making it an ideal layout for hosting family and friends. Step outside onto the large deck to take in beautiful views or unwind in the private hot tub after a day of adventure. Conveniently located just minutes from Deep Creek Lake State Park, Wisp Ski & Golf Resort, Thousand Acres Golf Club, several dining options, convenience stores, ice cream, coffee shops, and cinema. Easy access to year-round recreation, dining, and entertainment. A fantastic opportunity, call today to preview!

638 Glendale Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$749,000
5 Beds ⋅ 4 Baths
Tucked away on a picturesque 1.83-acre parcel, this charming log home offers the perfect blend of rustic character and modern comfort. Amongst the 4,200+ SF, you will find five spacious bedrooms, two family rooms, a playroom, an office/den, a large loft, spacious pantry, granite counter tops, hardwood flooring and two fireplaces. The warm wood interior and classic log construction create a cozy, inviting atmosphere throughout. A two-car attached garage provides everyday convenience, while the expansive detached garage offers endless possibilities—ideal for hobbies, a workshop, and plenty of space for equipment and boat storage, plus an unfinished room above. The Moss Creek community is centrally located off Sand Flat Road between Oakland and DCL, and this home happens to be at the end of the cul-de-sac on a no-thru street. Enjoy the peace and privacy of country-style living with ample outdoor space, which includes a great yard, large deck, and front covered porch, perfect for entertaining family and friends. Well-suited as a primary or secondary residence!

312 Moss Creek Cir, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$1,400,000
5 Beds ⋅ 4 Baths
Custom built by the original owners and thoughtfully expanded with a recent addition, this exceptional five-bedroom, 3.5-bath home is set on 100 feet of split lakefront in desirable Penn Cove. Featuring a coveted Type A dock permit, lakeside fire pit and pavilion, and easy shoreline access, the property is designed to embrace lake living in every season. Set on a generously sized lot with abundant parking, oversized multi-car garage with interior access, usable backyard, wooded walking paths, and nearby UTV and snowmobile trails, the setting offers a rare balance of privacy and recreation. Inside, natural light fills the home, where hardwood floors, cathedral ceilings, wood-burning fireplaces, and open-concept living spaces create warmth and character. A flexible layout with multiple living areas offers room for gathering, multi-generational living, or separate guest quarters, with potential for vacation rental use. Minutes from Pawn Run, downtown Oakland, and a short drive or boat ride to Wisp Resort, restaurants, and shopping, this is a rare opportunity to own a legacy property designed for making memories for generations.

827 Penn Point Rd, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$699,000
5 Beds ⋅ 3 Baths
Private Mountain Retreat on 8+ Acres Near Oakland Discover the peace and beauty of Garrett County living on over 8 private wooded acres filled with mountain views, abundant wildlife, and endless opportunities to enjoy the outdoors. Deer, turkey, songbirds, and other native wildlife are frequent visitors, creating a true nature lover's paradise. Conveniently located just minutes from Oakland's shops, restaurants, schools, and everyday amenities, this property offers the perfect balance of privacy and accessibility. Outdoor enthusiasts will appreciate the home's proximity to Wolf Den Run State Park, Deep Creek Lake, Potomac State Forest, Jennings Randolph Lake, and thousands of acres of public land. Enjoy hiking, fishing, boating, hunting, swimming, and over 50 miles of ORV trails, with street-legal UTV access directly from the neighborhood. This custom-built 4-5 bedroom, 3-bath home offers over 3,900 square feet of thoughtfully designed living space. Designed with flexibility in mind, the main level features two dedicated office spaces ideal for remote work, homeschooling, hobbies, guest accommodations, or future bedroom needs. The spacious eat-in kitchen showcases granite countertops, custom cabinetry, high-end appliances, a trash compactor, and generous gathering space for family and friends. Throughout the home, you'll find whole-house luxury vinyl plank flooring, oak stairs, a cozy wood-burning fireplace, a finished garage, and a walk-out basement with rough-in plumbing for a future full bathroom and exceptional expansion potential. Owners have invested extensively in quality upgrades and peace of mind, including a Generac backup generator, tankless hot water system, whole-house water filtration system, owned 1,000-gallon propane tank, upgraded fire sprinkler system, exterior security cameras, attic storage, and an additional storage building. Step outside to enjoy a covered front porch, expansive rear deck with automatic SunSetter awning, mature trees, and beautiful mountain views. Located within a laid-back HOA that allows chickens, this property offers a rare combination of acreage, privacy, modern amenities, and epic outdoor adventure. Whether you're seeking a full-time residence, a mountain getaway, or a future retirement retreat, this exceptional property delivers the best of Garrett County living. You may never want to leave after seeing this gem!

170 Cherrywood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact: 3013874700
$1,100,000
5 Beds ⋅ 3 Baths
Welcome to 660 Glendale Road — a luxury, mountain-chalet log home in the heart of Deep Creek Lake. This well appointed 5-bedroom, 3-bath home offers nearly 2,600 square feet of thoughtfully upgraded living space designed for lake life at its best. Enjoy lake views with western exposure on the expansive wraparound decks on main and lower levels. Many recent upgrades including roof, decks, covered porch, hot tub, retaining walls, furnace, countertops, appliances, flooring, paint, bathrooms, and much more. The open-concept main level features a spacious great room with abundant natural light, cozy fireplace, and seamless flow to the kitchen. Enjoy multiple living areas inside and out, providing plenty of room to expand and embrace time at the lake. Highlights include upgraded interior finishes throughout, private primary suite with balcony and creek views, covered deck with wood burning fireplace and a lower-level game room, four total fireplaces and only a short drive to local dining and the lake's most desirable attractions. Enjoy access to the lake at the Deep Creek State Park only a mile away or at one of the nearby marinas. No HOA! If you would like to discuss this home further or schedule a private showing, call today!

660 Glendale Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$729,000
5 Beds ⋅ 2 Baths
Lake cottage (5 Bedrooms) on large level lot with path to your own private class A dock & 25' of Lakefront, directly across the street. This comfy (one level living) cottage sits on 1.8 level acres with 2 storage garages and mature landscaping. 5BRs, open living, dinning & kitchen area, with lots of sunlight. 1 full & 1-1/2 bath, with 5 Bedrooms! Laundry room located off back of the home. Cute and cozy, well maintained and move in ready, with sleeping for 12 heads on beds (several bunks)! 2 garages with plenty of storge for your lake & yard toys. The lot has mature landscaping & circular paved driveway, for easy in and out during all seasons. Private path to your lakefront dock is an easy walk across the street. Nice level lake front, no steps to go onto your dock! Buydown Included on Lakefront. Great opportunity to get onto the lake at an affordable price, call agent to set up an appointment or with any questions.

222 Skippers Point Rd, Oakland

Listing courtesy of The KW Collective. Contact:

$559,000
5 Beds ⋅ 5 Baths
Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene atmosphere with the ease of low-maintenance living and a welcoming community feel through the HOA. Already an established and successful vacation rental, this property is truly ready to enjoy or generate income from day one. Just minutes from Wisp Resort, Deep Creek Lake State Park, restaurants, shopping, and endless outdoor adventure—this is the lifestyle and investment opportunity you’ve been waiting for!

178 Winding Trail Ln Unit #5B, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$679,900
5 Beds ⋅ 5 Baths
Discover refined mountain-lake living in this new construction townhome at Mystic Creek on Deep Creek Lake. Designed with today’s lifestyle in mind, the home features a modern open-concept main level ideal for entertaining, with clean lines, abundant natural light, and seamless flow between living, dining, and kitchen spaces. This spacious residence offers three primary suites, each with upscale attached bathrooms, providing comfort and privacy for owners and guests alike. Step outside to expansive rear decks that overlook a peaceful, wooded setting—perfect for relaxing after a day on the lake or slopes. The finished lower level includes Jack-and-Jill bedrooms, a full bath, and a second living area, creating an ideal space for guests, family, or recreation. Whether hosting large gatherings or enjoying quiet weekends, the layout offers flexibility and room for everyone. Mystic Creek is nestled along the banks of Deep Creek Lake, offering a serene setting while remaining close to area attractions. Enjoy being just 10 minutes from Wisp Ski Resort and Swallow Falls State Park, making this an exceptional four-season retreat. Ideal as a primary residence, vacation getaway, or investment property—this townhome delivers style, comfort, and location in one of Deep Creek Lake’s most desirable communities. *Home is still being finished, providing buyers the opportunity to choose bedroom flooring as well as kitchen countertops, appliances and cabinetry hardware.*

4A Mystic Creek Trl, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

$749,900
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
$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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