Airbnb Properties for Sale in Oakland, MD

Looking for a vacation rental investment in Oakland, MD with high ROI ?

Explore a range of newly added short-term rental homes in Oakland, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb Single Family Residential For Sale in Oakland, MD

Search for Single Family Residential for Sale in Oakland, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 31 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
609 Southern Pines Drive Oakland, MD Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built residen...	4 beds \| 3 baths \| 2,250 sq.ft.	$440,000	Airbnb cash on cash: 6.14% Traditional cash on cash: 5.89% Airbnb Rental Income: $4304 Traditional Rental Income: $3296 Airbnb ROI: 6.14% Traditional ROI: 5.89%
321 DEER PARK HOTEL ROAD Oakland, MD New Price Now $360,000! Beautifully Updated Mountain Retreat Near Deep Creek Lake Heres yo...	3 beds \| 2 baths \| 2,516 sq.ft.	$360,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 6.18% Airbnb Rental Income: $3503 Traditional Rental Income: $2692 Airbnb ROI: 6.3% Traditional ROI: 6.18%
98 BEAR RUN ROAD Oakland, MD TIRED OF CITY LIVING? ENJOY PLENTY OF ROOM TO ROAM ON THIS 2 ACRE TRACT WHICH INCLUDES A F...	3 beds \| 2 baths \| 1,080 sq.ft.	$268,900	Airbnb cash on cash: 9.01% Traditional cash on cash: 8.14% Airbnb Rental Income: $3503 Traditional Rental Income: $2510 Airbnb ROI: 9.01% Traditional ROI: 8.14%
25 SILVER TREE LANE Oakland, MD Beautiful lake access retreat located in the Silver Tree Landings community. This recently...	5 beds \| 4 baths \| 2,364 sq.ft.	$767,500	Airbnb cash on cash: 4.02% Traditional cash on cash: 1.75% Airbnb Rental Income: $5609 Traditional Rental Income: $2858 Airbnb ROI: 4.02% Traditional ROI: 1.75%
180 PARADISE RIDGE ROAD Oakland, MD Discover your perfect Deep Creek Lake getaway in the desirable Ridge at Paradise Point com...	3 beds \| 2 baths \| 1,152 sq.ft.	$425,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 3.39% Airbnb Rental Income: $3503 Traditional Rental Income: $2154 Airbnb ROI: 4.84% Traditional ROI: 3.39%
126 LEO FRIEND ROAD Oakland, MD Perched above the treetops with panoramic lake views, this three-level retreat blends comf...	4 beds \| 3 baths \| 2,235 sq.ft.	$529,900	Airbnb cash on cash: 5.09% Traditional cash on cash: 4.69% Airbnb Rental Income: $4304 Traditional Rental Income: $3200 Airbnb ROI: 5.09% Traditional ROI: 4.69%
1473 PERGIN FARM RD Oakland, MD TIME TO UNWIND at this absolutely stunning Deep Creek Lake retreat boasting million-dollar...	4 beds \| 2 baths \| N/A	$999,500	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.48% Airbnb Rental Income: $4304 Traditional Rental Income: $2753 Airbnb ROI: 2.17% Traditional ROI: 1.48%
473 CUMBERLAND ROAD Oakland, MD Nestled on a tranquil wooded hillside overlooking Deep Creek Lake, this charming home offe...	3 beds \| 2 baths \| 1,389 sq.ft.	$315,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 6.23% Airbnb Rental Income: $3503 Traditional Rental Income: $2446 Airbnb ROI: 7.19% Traditional ROI: 6.23%
328 STOOL ROCK ROAD Oakland, MD Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of cr...	4 beds \| 3 baths \| 1,860 sq.ft.	$565,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 3.97% Airbnb Rental Income: $4304 Traditional Rental Income: $3055 Airbnb ROI: 4.62% Traditional ROI: 3.97%
41 FOX DEN ROAD Oakland, MD Nestled in the heart of Deep Creek Lake, this charming and fully furnished cottage offers ...	2 beds \| 1 baths \| 1,569 sq.ft.	$239,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 4.81% Airbnb Rental Income: $2615 Traditional Rental Income: $1638 Airbnb ROI: 6.37% Traditional ROI: 4.81%
163 CRESTVIEW DRIVE Oakland, MD Welcome to 163 Crestview Drive a beautifully maintained 3-bedroom, 2.5-bath home nestled i...	3 beds \| 3 baths \| 1,416 sq.ft.	$335,000	Airbnb cash on cash: 6.8% Traditional cash on cash: 5.67% Airbnb Rental Income: $3503 Traditional Rental Income: $2376 Airbnb ROI: 6.8% Traditional ROI: 5.67%
127 PARADISE HEIGHTS Oakland, MD Beautifully renovated lake access log home located in the centrally located Paradise Cove ...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,199,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 0.46% Airbnb Rental Income: $3503 Traditional Rental Income: $2308 Airbnb ROI: 0.84% Traditional ROI: 0.46%
139 OVERLOOK RIDGE DRIVE Oakland, MD Perched atop Holiday Hill on a 1.5-acre site, you will find this contemporary home with be...	5 beds \| 5 baths \| 2,846 sq.ft.	$875,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 2.35% Airbnb Rental Income: $5609 Traditional Rental Income: $3448 Airbnb ROI: 3.62% Traditional ROI: 2.35%
155 BASSWOOD WAY Oakland, MD Tucked just off Lakeshore Drive, this log home nails that luxury treehouse feel. Wrapped i...	5 beds \| 3 baths \| 2,792 sq.ft.	$699,900	Airbnb cash on cash: 4.91% Traditional cash on cash: 2.95% Airbnb Rental Income: $5609 Traditional Rental Income: $3207 Airbnb ROI: 4.91% Traditional ROI: 2.95%
723 KINGS Oakland, MD ""Charming two-story home situated on a beautiful .292-acre level lot in a prime location ...	4 beds \| 3 baths \| N/A	$380,000	Airbnb cash on cash: 7.54% Traditional cash on cash: 6.39% Airbnb Rental Income: $4304 Traditional Rental Income: $2986 Airbnb ROI: 7.54% Traditional ROI: 6.39%
163 MITCHELL DRIVE Oakland, MD 3/4BR, 2.5BA, 2250sf+/- renovated home in Mitchell Manor! Newer roof in last 2 years, owne...	4 beds \| 3 baths \| 2,242 sq.ft.	$324,900	Airbnb cash on cash: 9.22% Traditional cash on cash: 8.8% Airbnb Rental Income: $4304 Traditional Rental Income: $3270 Airbnb ROI: 9.22% Traditional ROI: 8.8%
206 MAYHEW INN ROAD Oakland, MD Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath h...	1 beds \| 1 baths \| N/A	$229,000	Airbnb cash on cash: 7.9% Traditional cash on cash: 5.67% Airbnb Rental Income: $2748 Traditional Rental Income: $1618 Airbnb ROI: 7.9% Traditional ROI: 5.67%
969 HOYES RUN ROAD Oakland, MD Tucked among towering pines and hardwoods, this fully TURN KEY 5-bedroom log chalet blends...	5 beds \| 3 baths \| 3,614 sq.ft.	$725,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 3.38% Airbnb Rental Income: $5609 Traditional Rental Income: $3501 Airbnb ROI: 4.83% Traditional ROI: 3.38%
315 COOLIDGE AVENUE Oakland, MD Well maintained brick rancher located in the heart of Oakland. This home offers a large ki...	3 beds \| 2 baths \| 1,600 sq.ft.	$269,500	Airbnb cash on cash: 8.63% Traditional cash on cash: 7.51% Airbnb Rental Income: $3503 Traditional Rental Income: $2447 Airbnb ROI: 8.63% Traditional ROI: 7.51%
501 CHRISTOPHERS WAY Oakland, MD Check out this opportunity to own your own mountain top chalet getaway complete with 3 bed...	3 beds \| 2 baths \| 1,617 sq.ft.	$249,000	Airbnb cash on cash: 9.39% Traditional cash on cash: 8.12% Airbnb Rental Income: $3503 Traditional Rental Income: $2433 Airbnb ROI: 9.39% Traditional ROI: 8.12%
333 SLOAN TRACT ROAD Oakland, MD Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home ha...	4 beds \| 4 baths \| 1,492 sq.ft.	$475,000	Airbnb cash on cash: 5.57% Traditional cash on cash: 4.08% Airbnb Rental Income: $4304 Traditional Rental Income: $2737 Airbnb ROI: 5.57% Traditional ROI: 4.08%
511 E GREEN STREET Oakland, MD A must see complete renovation in Oakland! Taken down to the studs and updated with new wi...	4 beds \| 2 baths \| 1,880 sq.ft.	$309,000	Airbnb cash on cash: 9.81% Traditional cash on cash: 7.78% Airbnb Rental Income: $4304 Traditional Rental Income: $2808 Airbnb ROI: 9.81% Traditional ROI: 7.78%
20676 GARRETT HIGHWAY Oakland, MD CENTRAL DEEP CREEK LAKEFRONT LOG HOME ***Fully Furnished 5BR w/ Dock, Hot Tub & Fireplaces...	5 beds \| 5 baths \| 2,280 sq.ft.	$1,499,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 0.97% Airbnb Rental Income: $5609 Traditional Rental Income: $3831 Airbnb ROI: 1.44% Traditional ROI: 0.97%
873 PARADISE HEIGHTS Oakland, MD Escape to Sage Mountain Retreat, a beautifully crafted 5-bedroom, 4-bath custom home nestl...	5 beds \| 4 baths \| 2,934 sq.ft.	$829,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.55% Airbnb Rental Income: $5609 Traditional Rental Income: $3492 Airbnb ROI: 3.84% Traditional ROI: 2.55%
1570 GARRETT ROAD Oakland, MD Located between Oakland and Deep Creek Lake, this log ranch is situated on 14.82 acres, in...	3 beds \| 1 baths \| 1,408 sq.ft.	$300,000	Airbnb cash on cash: 7.78% Traditional cash on cash: 5.96% Airbnb Rental Income: $3503 Traditional Rental Income: $2214 Airbnb ROI: 7.78% Traditional ROI: 5.96%
1260 GNEGY CHURCH ROAD Oakland, MD Discover space, privacy, and mountain charm on this stunning property nestled on over 76.0...	3 beds \| 3 baths \| 4,420 sq.ft.	$449,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.94% Airbnb Rental Income: $3503 Traditional Rental Income: $2493 Airbnb ROI: 4.51% Traditional ROI: 3.94%
5202 HUTTON ROAD Oakland, MD Charming ranch-style home offering 3 bedrooms, 1 full bath, and loads of potential! This o...	3 beds \| 1 baths \| 1,199 sq.ft.	$239,000	Airbnb cash on cash: 9.95% Traditional cash on cash: 7.15% Airbnb Rental Income: $3503 Traditional Rental Income: $2097 Airbnb ROI: 9.95% Traditional ROI: 7.15%
215 N 10th Street Oakland, MD Welcome home to this recently renovated ranch featuring 3 bedrooms, 1 bathroom, and approx...	3 beds \| 1 baths \| 1,518 sq.ft.	$289,000	Airbnb cash on cash: 7.93% Traditional cash on cash: 5.89% Airbnb Rental Income: $3503 Traditional Rental Income: $2174 Airbnb ROI: 7.93% Traditional ROI: 5.89%
66 PARADISE RIDGE ROAD Oakland, MD Welcome to 66 Paradise Ridge Rd, a charming single-family home in the picturesque town of ...	4 beds \| 4 baths \| 2,550 sq.ft.	$650,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 3.12% Airbnb Rental Income: $4304 Traditional Rental Income: $2979 Airbnb ROI: 3.81% Traditional ROI: 3.12%
272 MCCOMAS BEACH TERRACE Oakland, MD Wake up to a light mist rising over Deep Creek Lake and enjoy level lakefront living with ...	5 beds \| 4 baths \| 2,448 sq.ft.	$1,690,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 0.91% Airbnb Rental Income: $5609 Traditional Rental Income: $3919 Airbnb ROI: 1.27% Traditional ROI: 0.91%
78 MOUNTAINSIDE COURT Oakland, MD If it's privacy and convenience you want, you will love this beautiful log home on a 1.6-a...	5 beds \| 3 baths \| 3,492 sq.ft.	$950,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 2.02% Airbnb Rental Income: $5609 Traditional Rental Income: $3702 Airbnb ROI: 2.91% Traditional ROI: 2.02%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Oakland, MD

609 Southern Pines Drive

Oakland, MD

4 beds | 3 baths | 2,250 sq.ft.

$440,000

Airbnb cash on cash: 6.14%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $4304

Traditional Rental Income: $3296

Airbnb ROI: 6.14%

Traditional ROI: 5.89%

321 DEER PARK HOTEL ROAD

Oakland, MD

3 beds | 2 baths | 2,516 sq.ft.

$360,000

Airbnb cash on cash: 6.3%

Traditional cash on cash: 6.18%

Airbnb Rental Income: $3503

Traditional Rental Income: $2692

Airbnb ROI: 6.3%

Traditional ROI: 6.18%

98 BEAR RUN ROAD

Oakland, MD

3 beds | 2 baths | 1,080 sq.ft.

$268,900

Airbnb cash on cash: 9.01%

Traditional cash on cash: 8.14%

Airbnb Rental Income: $3503

Traditional Rental Income: $2510

Airbnb ROI: 9.01%

Traditional ROI: 8.14%

25 SILVER TREE LANE

Oakland, MD

5 beds | 4 baths | 2,364 sq.ft.

$767,500

Airbnb cash on cash: 4.02%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $5609

Traditional Rental Income: $2858

Airbnb ROI: 4.02%

Traditional ROI: 1.75%

180 PARADISE RIDGE ROAD

Oakland, MD

3 beds | 2 baths | 1,152 sq.ft.

$425,000

Airbnb cash on cash: 4.84%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $3503

Traditional Rental Income: $2154

Airbnb ROI: 4.84%

Traditional ROI: 3.39%

126 LEO FRIEND ROAD

Oakland, MD

4 beds | 3 baths | 2,235 sq.ft.

$529,900

Airbnb cash on cash: 5.09%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $4304

Traditional Rental Income: $3200

Airbnb ROI: 5.09%

Traditional ROI: 4.69%

1473 PERGIN FARM RD

Oakland, MD

4 beds | 2 baths | N/A

$999,500

Airbnb cash on cash: 2.17%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $4304

Traditional Rental Income: $2753

Airbnb ROI: 2.17%

Traditional ROI: 1.48%

473 CUMBERLAND ROAD

Oakland, MD

3 beds | 2 baths | 1,389 sq.ft.

$315,000

Airbnb cash on cash: 7.19%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $3503

Traditional Rental Income: $2446

Airbnb ROI: 7.19%