5 Bedroom homes for sale & real estate in Oakland, MD

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3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Discover this spacious 5-bedroom, 3-bath chalet in The View community at Deep Creek Lake, offering three finished levels of comfortable living and a strong history as the well-known rental 'Divided Sky'. The foyer greets you with a beautiful built-in for hanging jackets, leave your ski boots on the convenient tile floor and proceed in to the main level, where two-story ceilings paneled in solid oak create an impressive chalet feel. This open-concept layout includes a stone fireplace wall in the spacious family room, and clear sightlines from both the dining area and the kitchen. The kitchen features stainless steel appliances, high-end granite countertops, and a slider door opening to a lar

$775,000

5 beds3 baths2,660 sq ft

220 Woodlands Hill Ln, Oakland, MD 21550

2.58 acre lot • 6 parking spots • Built 2003

(301) 921-4500

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Lovely level lot with path to your own private class A dock, directly across the street. This comfy 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, large closet for storge, laundry room off back of the home. 2 garages with plenty of storge for your lake and yard toys. The lot has mature landscaping and circular paved driveway, for easy in and out during all seasons. Private path to your lakefront dock is across the street. Great opportunity to get onto the lake at an affordable price, call agent to set up an appointment or with any questions. This sale includes 2

$779,000

5 beds1.5 baths1,278 sq ft

222 Skippers Point Rd, Oakland, MD 21550

Private class a dock • Mature landscaping • 1.84 acre lot

(301) 259-1119

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Architecturally unique, private and spacious lakefront home with a perfect central location! Step into a home that blends striking architectural design with the best of lake living. The living room showcases a dramatic wall of glass and a floor-to-ceiling stone fireplace, while a large glass-walled rec room on the lower level offers another light-filled space to relax or entertain. This 5-bedroom, 3-bath residence includes a spacious private primary suite with its own balcony, plus a main level bedroom, and three lower-level bedrooms, two overlooking the lake! Multiple decks, and a hot tub with a peaceful water view backdrop. Enjoy the rare combination of being centrally located yet tucked

$1,499,000

5 beds3 baths2,826 sq ft

336 Paradise Hts, Oakland, MD 21550

Private balcony • Architectural design • Wall of glass

(301) 387-2000

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with over 3,500 sq. ft. of living space on 1.88 acres with breathtaking farm and mountain views. Step inside the main level, where the master suite awaits along with two additional large bedrooms and a full bath, plus a mudroom area with a convenient half bath—perfect for entertaining. Cozy evenings are made even better with one of two fireplaces, while the lower level offers 2 bedrooms, a full bath, a living area, and a huge rec room with a pool table that conveys with the home. Outside, enjoy gatherings around the firepit on the back patio, take in the views from the front deck, or explore the attac

$359,000

5 beds3.5 baths3,682 sq ft

697 Monte Vista Rd, Oakland, MD 21550

1.88 acre lot • 2 garage spots • Built 1962

(301) 387-4700

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Instant opportunity for $50k equity! Appraised on 08/11/2025 for $868,000 with a new price you don't want to miss this chance. Beautifully maintained 5 bedroom 5 bathroom lake area chalet. Beautifully landscaped and situated on 4 +/- acres with partial views of the south side of Deep Creek Lake. This home offers it's new owners a tremendous amount of room for storage and entertaining. As well as 3 levels of finished living space. Featuring a large heated garage with multiple car storage and additional partially finished accessory room, a beautifully built pavilion with bar area for outdoor entertaining, an almost brand new salt water hot tub, wraparound porch with expansive views, finished

$799,000

5 beds5 baths3,664 sq ft

1875 Pysell Crosscut Rd, Oakland, MD 21550

3.92 acre lot • Built 2004 • Listed 133 days

(301) 387-4700

Property at 155 Basswood Way, Oakland, MD 21550, 5 beds, 3 baths

$699,900

5 beds3 baths2,792 sq ft

155 Basswood Way, Oakland, MD 21550

(301) 387-2000

Property at 139 Overlook Ridge Dr, Oakland, MD 21550, 5 beds, 4.5 baths

$875,000

5 beds4.5 baths2,846 sq ft

139 Overlook Ridge Dr, Oakland, MD 21550

(301) 387-4700

Property at 25 Silver Tree Ln, Oakland, MD 21550, 5 beds, 4 baths

$759,900

5 beds4 baths2,364 sq ft

25 Silver Tree Ln, Oakland, MD 21550

(301) 387-4700

Property at 611 E Oak St, Oakland, MD 21550, 5 beds, 3 baths

$295,000

5 beds3 baths1,800 sq ft

611 E Oak St, Oakland, MD 21550

(301) 387-2000

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3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Discover the ultimate mountain–lake getaway in this stunning 5BR Southern-style home on a private 2.4-acre wooded lot bordering Broadford Lake recreational area! Located just minutes from Deep Creek Lake and Wisp Resort, this magnificent property offers over 6,500 sq ft. and delivers unforgettable space, luxury, and privacy. Step inside to soaring cathedral ceilings, skylights, oak floors, and a gourmet kitchen featuring solid cherry cabinets cut from trees on the property, granite counters, and a center island built for gathering. The main-level primary suite feels like a retreat, complete with a cozy fireplace, walk-in closets, and a spa-worthy bath with custom tilework and an overs

$829,000

5 beds5 baths6,550 sq ft

1001 Sutter Ln, Oakland, MD 21550

Gourmet kitchen • Private wooded lot • Center island

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
This striking 5 bed/7 bath log home sits in one of Wisp Mountain’s most sought-after locations, offering a warm four-season retreat just minutes from Deep Creek Lake, Lodestone Golf Course, Wisp Resort, and the area’s top dining and recreation. Seasonal lake views from the living room and deck enhance the setting and connect the home to its surroundings. The main level features a bright, open layout with a wall of windows, a floor-to-ceiling stone fireplace, and a well-equipped kitchen with granite, stainless appliances, gas range, farm sink, and a large island. Sliding doors extend the space onto an expansive deck with a covered outdoor fireplace, making indoor-outdoor entertai

$1,395,000

5 beds6 baths4,416 sq ft

19 Greenside Ct, Mc Henry, MD 21541

0.65 acre lot • 2 garage spots • Built 2021

(301) 387-2000

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Hazelhurst community is on the Southern end of the lake. Here you will find less commercial activity and more peace and quiet to enjoy. This three-level chalet offers 5 bedrooms, with bedrooms on each floor, 3 baths, large living room, dining room, and 2 fireplaces to enjoy. One gas and one wood. An over-sized family/rec room. Large walk-out deck on the main level with views of the lake or the lower level covered patio with a hot tub. Home has been well maintained and is ready to move-in and enjoy. The yard area offers a fire ring, horse shoes and plenty of space for other recreational activities. This is a must-see lakefront opportunity with a great location. Enjoy all four seasons.

$699,000

5 beds3 baths3,100 sq ft

32 Hazelhurst Ln, Swanton, MD 21561

Hot tub • Fire ring • Horse shoes

(301) 387-2000

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Conveys ALL FURNISHED, AS IS CONDITION. See the bill of sale in docs. Currently, rental is mostly through Airbnb. Please call the Agent to request an appointment! Do not miss this fantastic log cabin home in the heart of Deep Creek Lake! This beautiful home has 5 bedrooms and three full bathrooms. It has an open kitchen, dining room, and a stone fireplace. The large wraparound deck includes a covered hot tub with plenty of entertainment space. Outside, there is a hardscaped patio area that leads to a stone fire pit.

$799,999

5 beds3 baths2,128 sq ft

229 Rock Lodge Rd, Mc Henry, MD 21541

Log cabin home • Hardscaped patio • Stone fireplace

(703) 462-8081

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Stunning Lakefront Home in Exclusive Thousand Acres Neighborhood - Welcome to your dream waterfront retreat! This meticulously maintained lakefront home has been cherished by its original owners for 19 years, hosting unforgettable family gatherings. Now, it’s time for you to create your own memories in this exclusive Thousand Acres neighborhood, where tranquility and luxury meet. Key Features: Prime Location: Nestled in the peaceful North Glade Cove, this property offers serene waterfront access while remaining just minutes away from the vibrant main lake and Thousand Acres premier golf course. Enjoy peace and quiet with no short-term rentals allowed. Sold Turnkey: Step into a fully

$2,089,000

5 beds4.5 baths3,980 sq ft

294 N Shoreline Dr, Swanton, MD 21561

Fully furnished home • Lakefront home • 0.98 acre lot

(301) 387-4700

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Oakland, MD
Rare Lake Mountain Chalet – The Perfect Vacation Rental & Retreat with $90K+ annual revenue. Tucked into the hillside just one road back from Deep Creek Lake, and one of the largest in the area. This 4-level, 5-bedroom, 5-bath home combines privacy, convenience, and exceptional rental potential. Currently one of the area’s most sought-after and successful Airbnb destinations, it offers investors proven income and buyers a spacious getaway to enjoy with family and friends. All furniture conveys, making this a true turn-key investment—ready to go with systems in place to simplify hosting and maximize revenue. The design offers multiple gathering areas, a game room, and

$974,900

5 beds5 baths3,716 sq ft

723 Pinnacle Dr, Swanton, MD 21561

1 acre lot • Built 2003 • Listed 101 days

(703) 378-8810

Property at 21 Lakefront Links Dr, Swanton, MD 21561, 5 beds, 4 baths

$2,200,000

5 beds4 baths5,190 sq ft

21 Lakefront Links Dr, Swanton, MD 21561

(410) 533-5486

Property at 116 Chimney Rock Ln, Mc Henry, MD 21541, 5 beds, 4.5 baths

$879,900

5 beds4.5 baths2,964 sq ft

116 Chimney Rock Ln, Mc Henry, MD 21541

(301) 387-2000

Property at 425 Hines Dr, Swanton, MD 21561, 5 beds, 4.5 baths

$1,699,000

5 beds4.5 baths4,640 sq ft

425 Hines Dr, Swanton, MD 21561

(301) 387-2000

Property at 90 Biltmore Ridge Trl, Mc Henry, MD 21541, 5 beds, 4.5 baths

$1,299,000

5 beds4.5 baths4,016 sq ft

90 Biltmore Ridge Trl, Mc Henry, MD 21541

(301) 387-2000

Property at 342 Lakefront Links Dr, Swanton, MD 21561, 5 beds, 5.5 baths

$1,650,000

5 beds5.5 baths3,606 sq ft

342 Lakefront Links Dr, Swanton, MD 21561

(301) 387-4700

Property at 165 Westward Way, Mc Henry, MD 21541, 5 beds, 4 baths

$859,000

5 beds4 baths3,152 sq ft

165 Westward Way, Mc Henry, MD 21541

(301) 387-4700

Property at 18 Catbird, Terra Alta, WV 26764, 5 beds, 3 baths

$410,000

5 beds3 baths2,516 sq ft

18 Catbird, Terra Alta, WV 26764

Property at 56 Vista Ct, Swanton, MD 21561, 5 beds, 3.5 baths

$1,200,000

5 beds3.5 baths4,230 sq ft

56 Vista Ct, Swanton, MD 21561

(301) 387-4700

Property at 78 Cedar Shores Dr, Mc Henry, MD 21541, 5 beds, 4.5 baths

$750,000

5 beds4.5 baths2,746 sq ft

78 Cedar Shores Dr, Mc Henry, MD 21541

(301) 387-2000

Property at 1909 Marsh Hill Rd, Mc Henry, MD 21541, 5 beds, 4.5 baths

$2,499,000

5 beds4.5 baths5,030 sq ft

1909 Marsh Hill Rd, Mc Henry, MD 21541

(301) 387-2000

Property at 1723 Marsh Hill Rd, Mc Henry, MD 21541, 5 beds, 3 baths

$1,375,000

5 beds3 baths2,224 sq ft

1723 Marsh Hill Rd, Mc Henry, MD 21541

(301) 387-4700

Property at 1026 North Camp Rd, Mc Henry, MD 21541, 5 beds, 5.5 baths

$1,225,000

5 beds5.5 baths3,742 sq ft

1026 North Camp Rd, Mc Henry, MD 21541

(301) 387-2000

Property at 511 Main St, Oakland, MD 21550, 5 beds, 1.5 baths

$180,000

5 beds1.5 baths1,536 sq ft

511 Main St, Oakland, MD 21550

(301) 387-8300

Property at 219 Mountaintop Rd, Mc Henry, MD 21541, 5 beds, 4 baths

$999,900

5 beds4 baths5,850 sq ft

219 Mountaintop Rd, Mc Henry, MD 21541

(301) 387-2000

5 Bedroom Homes for Sale in Oakland

There are currently 9 5 bedroom homes in Oakland. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oakland stay on the market for 149 days. This map is refreshed with the newest listings in Oakland every 15 minutes.

In the past month, 5 homes have been sold in Oakland. In addition to houses in Oakland, there was also 1 condo, 3 townhouses, and 1 multi-family unit for sale in Oakland last month. Find your dream home in Oakland using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Oakland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oakland. Our Oakland real estate stats and trends will give you more information about home buying and selling trends in Oakland. If you're looking to sell your home in the Oakland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oakland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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