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

5979 Cranesville Rd, Oakland
$339,000
5 Beds ⋅ 4 Baths
Stunning 1900 farmhouse situated on 7.82 acres, offering incredible mountain views, a spacious yard, and a beautiful setting adjacent to Nature Conservancy land.. The home features vinyl siding, a shingle roof, and a wraparound deck perfect for enjoying the surrounding scenery. Inside, you'll find five bedrooms, a welcoming entryway and mudroom, main-level laundry, and a spacious layout with three bedrooms on the main level, including a larger primary bedroom and one bedroom with an attached bathroom. The main bathroom features a double-sink vanity, while the upper level offers two additional bedrooms, including one with an attached bathroom featuring both a shower and bathtub. An electric heat pump with central air conditioning provides year-round comfort. The property also includes an impressive 30x50 detached garage with electricity and overhead doors at both the front and rear, offering plenty of space for vehicles, equipment, hobbies, or a workshop. With its acreage, breathtaking mountain views, and generous outdoor space this property offers a unique opportunity to enjoy the charm and possibilities of country living. A separate trailer on the property offers potential for a guest house or additional living space, with work needed to bring it to its full potential. The property is conveniently located just minutes from Deep Creek Lake and the town of Oakland, offering easy access to local shopping, dining, recreation, and year-round outdoor activities. Call today!

5979 Cranesville Rd, Oakland

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

1038 S Blakeslee Rd, Oakland
$2,100,000
5 Beds ⋅ 6 Baths
Get ready to relax & enjoy Deep Creek Lake at your 5 BR 5 Bath home offering a wooded level setting with the lake and dock slip right out in front of you. Located in the area's premiere community, Blakeslee, you'll appreciate the inviting open floor plan featuring two living areas, 5 suites with direct bath access, direct access to a large deck, covered porch or relax in the comfy screened porch. The outdoor area also offers a fire pit and room for outdoor games. Beautifully and tastefully decorated, the atmosphere within and without is perfect regardless of season. The home has had over 30 meaningful updates including bathroom remodels and major mechanical improvements allowing you the opportunity to spend more time relaxing and less time making updates and repairs. The Blakeslee offers the best amenity package on the lake including an indoor pool and community center along with multiple tennis, pickleball courts, a multi use play field, tot lot and more, community trash center, storage area and over 100 common area acres with trails to enjoy. The 5 mile private road system is safe and perfect for walking and biking. The property also currently provides revenue potential and is known as Unsalted Memories.

1038 S Blakeslee Rd, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

607 Pin Oak Cir, Oakland
$499,000
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:

395 Woodlands Hill Ln, Oakland
$899,900
5 Beds ⋅ 6 Baths
Welcome to Happy Hoursss... Hideaway, a stunning Deep Creek Lake retreat where breathtaking views, upscale amenities, and spacious indoor-outdoor living create the perfect getaway. With 5 bedrooms and 6 full bathrooms, this beautifully appointed home comfortably accommodates family and friends while offering plenty of room to relax and entertain. The main level features an inviting open-concept kitchen, dining, and living area with stainless steel appliances, a large center island, fireplace, abundant natural light, and beautiful lake views. A main-level primary suite and additional full bath add convenience. Upstairs, a second luxurious primary suite offers a walk-in closet and spa-like bath with a jetted tub and separate shower. The lower level is designed for fun and relaxation, with three bedrooms and three full baths, a second living area, fireplace, wet bar, and access to the deck and hot tub. The entertainment continues with a plenty of space to gather. Outside, enjoy two decks, a hot tub, fire pit, grill, room for games and entertainment, expansive yard space, ample parking, and a storage building for your outdoor gear. Whether you’re soaking in the hot tub under the stars, gathering around the fire, or enjoying a quiet morning, Happy Hoursss...Hideaway delivers an unforgettable Deep Creek Lake experience in every season.

395 Woodlands Hill Ln, Oakland

Listing courtesy of Railey Realty, Inc.. Contact:

704 Old Crellin Rd, Oakland
$430,000
5 Beds ⋅ 3 Baths
Back on the market through no fault of the house. Beautiful 5 bedroom/2.5 bath home situated on four acres in a peaceful country setting, yet conveniently located just two miles from town limits. The main level features three bedrooms, a spacious sunroom, living room, kitchen, separate dining area, full bathroom, and half bath. The lower level offers both interior and exterior access and includes a large family room, two additional bedrooms, full bathroom, utility room, and bonus room. The bonus room provides flexible space for a playroom, home office, or additional family room. Four mini-split systems were recently installed, providing efficient heating and cooling throughout the home for year-round comfort. Outside, enjoy four acres of property along with an impressive 38' x 24' garage, offering plenty of space for vehicles, equipment, hobbies, or storage. A great opportunity for those looking for space, privacy, and convenience. Call today with questions or to schedule a private showing!

704 Old Crellin Rd, Oakland

Listing courtesy of The KW Collective. Contact:

5154 Maryland Hwy, Oakland
$460,000
5 Beds ⋅ 2 Baths
Escape to the tranquility of country living in this spacious 5-bedroom, 2-bath home nestled on over 2 acres and conveniently located just minutes from the recreational opportunities of Deep Creek Lake and the charming town of Oakland, The property offers the perfect combination of peaceful country living and easy access to shopping, dining, and year-round activities. The kitchen has been thoughtfully updated with new stainless-steel appliances, including a microwave, refrigerator, gas range with oven, and gas wall oven. You'll also appreciate the new stainless-steel farmhouse sink with an updated faucet, and a new InSinkErator garbage disposal. The main floor also offers the convenience of a bedroom, full bathroom, and laundry area complete with a new washer and dryer, making one-level living a possibility. Upstairs, you'll find four generously sized bedrooms and an additional full bathroom, offering plenty of space for family and guests. Additional interior improvements include a new 50-gallon hot water heater, a new attic fan with humidifier, a new well water filtration system, and a newly installed ADT security system for added peace of mind. Recent exterior updates include new outdoor lighting and a new roof including all new sheathing, underlayment (roof wrap), and shingles, providing years of worry-free ownership. If you've been searching for privacy, space, and the beauty of rural living, this property is a must-see!

5154 Maryland Hwy, Oakland

Listing courtesy of Coldwell Banker Home Town Realty. Contact:

615 E Oak St, Oakland
$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:

251 Robinwood Dr, Oakland
$750,000
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:

943 Paradise Hts, Oakland
$699,000
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:

308 Winding Trail Ln Unit 11B, Oakland
$599,999
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:

428 Sam Snead Cir, Oakland
$549,000
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:

251 Robinwood Dr, Oakland
$850,000
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:

321 N 3rd St, Oakland
$350,000
5 Beds ⋅ 2 Baths
Aww shucks - the sellers have reduced the price!! 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:

638 Glendale Rd, Oakland
$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:

312 Moss Creek Cir, Oakland
$699,000
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:

827 Penn Point Rd, Oakland
$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:

660 Glendale Rd, Oakland
$949,000
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:

25 Silver Tree Ln, Oakland
$735,000
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:

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