Real Estate Investment Properties for Sale in Oakland, MD

Looking for investment property in Oakland, MD with high ROI ?

Explore a variety of short-term homes & houses in Oakland, MD. Invest wisely with VRBO & Oakland, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes 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 57 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.	$450,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 5.74% Airbnb Rental Income: $4304 Traditional Rental Income: $3296 Airbnb ROI: 5.98% Traditional ROI: 5.74%
198 GRANDVIEW DRIVE Oakland, MD Lake views for days and room to relax in every direction!Welcome to 198 Grandview Drive, a...	3 beds \| 3 baths \| 2,744 sq.ft.	$825,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.35% Airbnb Rental Income: $3503 Traditional Rental Income: $3488 Airbnb ROI: 1.36% Traditional ROI: 2.35%
783 MOUNTAINVIEW DRIVE Oakland, MD Beautiful, 3 bedroom, 3 bath home located in the sought after community of Mountainside at...	3 beds \| 3 baths \| 1,971 sq.ft.	$529,900	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.46% Airbnb Rental Income: $3503 Traditional Rental Income: $2914 Airbnb ROI: 3.09% Traditional ROI: 3.46%
1256 BOILING SPRING RD Oakland, MD About 1256 Boiling Spring Rd, Oakland, MD 1256 Boiling Spring Road is a raised-ranch, sin...	3 beds \| 2 baths \| N/A	$250,000	Airbnb cash on cash: 9.42% Traditional cash on cash: 8.18% Airbnb Rental Income: $3503 Traditional Rental Income: $2438 Airbnb ROI: 9.42% Traditional ROI: 8.18%
444 WOODLANDS HILL LANE Oakland, MD Experience the serenity of Deep Creek Lake from this updated luxury 4 bedroom home with ov...	4 beds \| 6 baths \| 4,744 sq.ft.	$1,295,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 3.55% Airbnb Rental Income: $4304 Traditional Rental Income: $6676 Airbnb ROI: 0.82% Traditional ROI: 3.55%
62 MIDDLETON ROAD Oakland, MD Tucked in the trees at The Blakeslee, this 3-bed, 2.5-bath home delivers space, style, and...	3 beds \| 3 baths \| 2,397 sq.ft.	$799,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 1.6% Airbnb Rental Income: $3503 Traditional Rental Income: $2989 Airbnb ROI: 1.25% Traditional ROI: 1.6%
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%
522 E GREEN STREET Oakland, MD If you are looking for a low maintenance stone home sitting on a level lot in the town of ...	3 beds \| 4 baths \| 1,503 sq.ft.	$329,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 6.64% Airbnb Rental Income: $3503 Traditional Rental Income: $2878 Airbnb ROI: 6.16% Traditional ROI: 6.64%
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%
366 GLENDALE ROAD Oakland, MD Discover the perfect blend of comfort and convenience at 366 Glendale Rd. Situated just s...	3 beds \| 2 baths \| 1,392 sq.ft.	$369,900	Airbnb cash on cash: 5.64% Traditional cash on cash: 4.61% Airbnb Rental Income: $3503 Traditional Rental Income: $2376 Airbnb ROI: 5.64% Traditional ROI: 4.61%
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.	$775,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 1.72% Airbnb Rental Income: $5609 Traditional Rental Income: $2858 Airbnb ROI: 3.98% Traditional ROI: 1.72%
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%
1674 PARADISE POINT ROAD Oakland, MD Beautifully remodeled lakefront home offering private dock and stunning views of Deep Cree...	4 beds \| 3 baths \| 2,340 sq.ft.	$1,599,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 0.75% Airbnb Rental Income: $4304 Traditional Rental Income: $3589 Airbnb ROI: 0.62% Traditional ROI: 0.75%
20698 GARRETT HIGHWAY Oakland, MD Beautiful lakefront home offering 89' of lakefront and a private dock. This home has been ...	4 beds \| 3 baths \| 1,844 sq.ft.	$1,299,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 1.26% Airbnb Rental Income: $4304 Traditional Rental Income: $3578 Airbnb ROI: 1.11% Traditional ROI: 1.26%
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%
1019 LAKE SHORE DRIVE Oakland, MD Tucked among the trees, Blue Spruce offers a perfect blend of modern comfort and serene na...	4 beds \| 5 baths \| 2,605 sq.ft.	$1,755,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.18% Airbnb Rental Income: $4304 Traditional Rental Income: $3069 Airbnb ROI: 0.39% Traditional ROI: 0.18%
1720 PYSELL CROSSCUT ROAD Oakland, MD 'Four Winds' is a Frank Lloyd Wright inspired masterpiece at Deep Creek Lake. Restored & r...	5 beds \| 6 baths \| 8,000 sq.ft.	$999,999	Airbnb cash on cash: 2.89% Traditional cash on cash: 3.56% Airbnb Rental Income: $5609 Traditional Rental Income: $5107 Airbnb ROI: 2.89% Traditional ROI: 3.56%
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%
39 LEO FRIEND ROAD Oakland, MD Beautiful split Lakefront Home with Breathtaking Views and Type A Dock. Discover unparalle...	3 beds \| 4 baths \| 3,897 sq.ft.	$985,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.18% Airbnb Rental Income: $3503 Traditional Rental Income: $3611 Airbnb ROI: 1.22% Traditional ROI: 2.18%
2719 BROADFORD ROAD Oakland, MD Stunning Brick Ranch Near Broadford Lake Park! This magnificent one-level brick ranch sits...	3 beds \| 3 baths \| 4,253 sq.ft.	$599,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.28% Airbnb Rental Income: $3503 Traditional Rental Income: $2803 Airbnb ROI: 3.15% Traditional ROI: 3.28%
1001 SUTTER LN Oakland, MD Set on a serene 2.4-acre wooded lot, this thoughtfully crafted Southern-inspired property ...	5 beds \| 6 baths \| N/A	$879,900	Airbnb cash on cash: 3.5% Traditional cash on cash: 5.61% Airbnb Rental Income: $5609 Traditional Rental Income: $6210 Airbnb ROI: 3.5% Traditional ROI: 5.61%
2725 STOCKSLAGER ROAD Oakland, MD Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This c...	5 beds \| 7 baths \| 5,376 sq.ft.	$2,750,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 1.26% Airbnb Rental Income: $5609 Traditional Rental Income: $6125 Airbnb ROI: 0.62% Traditional ROI: 1.26%
621 PARADISE HEIGHTS Oakland, MD Opportunity to own one of Deep Creek Lake's most unique homes! 621 Paradise Heights is a g...	4 beds \| 3 baths \| 3,242 sq.ft.	$695,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 3.53% Airbnb Rental Income: $4304 Traditional Rental Income: $3451 Airbnb ROI: 3.44% Traditional ROI: 3.53%
1118 LAKE SHORE DRIVE Oakland, MD Escape to Serenity: Your Dream Log Home Awaits! Nestled in the heart of a picturesque lake...	3 beds \| 2 baths \| 2,446 sq.ft.	$675,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 2.47% Airbnb Rental Income: $3503 Traditional Rental Income: $2755 Airbnb ROI: 2.43% Traditional ROI: 2.47%
45 VILLAGE DRIVE #4 Oakland, MD Nestled in the serene Yellowstone Village community, 45 Village Drive offers a fully furni...	2 beds \| 2 baths \| 1,096 sq.ft.	$450,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 3.24% Airbnb Rental Income: $2615 Traditional Rental Income: $2188 Airbnb ROI: 2.77% Traditional ROI: 3.24%
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.	$899,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 2.26% Airbnb Rental Income: $5609 Traditional Rental Income: $3448 Airbnb ROI: 3.5% Traditional ROI: 2.26%
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%
2849 SHINGLE CAMP ROAD Oakland, MD Vintage 3BR Lakefront Dome Home with Private Type "A" Dock! & no HOA . Own a piece of Deep...	3 beds \| 2 baths \| 2,034 sq.ft.	$1,100,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 1.17% Airbnb Rental Income: $3503 Traditional Rental Income: $2988 Airbnb ROI: 0.92% Traditional ROI: 1.17%
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	$387,700	Airbnb cash on cash: 7.38% Traditional cash on cash: 6.24% Airbnb Rental Income: $4304 Traditional Rental Income: $2986 Airbnb ROI: 7.38% Traditional ROI: 6.24%
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%
62 DUCK COVE ROAD Oakland, MD Panoramic lakefront living greets you on the point of this remarkable 4 bedroom, 4 bathroo...	4 beds \| 4 baths \| 4,150 sq.ft.	$2,095,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.7% Airbnb Rental Income: $4304 Traditional Rental Income: $4578 Airbnb ROI: 0.09% Traditional ROI: 0.7%
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%
1737 KING WILDESEN ROAD Oakland, MD Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-si...	3 beds \| 2 baths \| 1,736 sq.ft.	$299,900	Airbnb cash on cash: 7.69% Traditional cash on cash: 8.47% Airbnb Rental Income: $3503 Traditional Rental Income: $2950 Airbnb ROI: 7.69% Traditional ROI: 8.47%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oakland, MD

609 Southern Pines Drive

Oakland, MD

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

$450,000

Airbnb cash on cash: 5.98%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $4304

Traditional Rental Income: $3296

Airbnb ROI: 5.98%

Traditional ROI: 5.74%

198 GRANDVIEW DRIVE

Oakland, MD

3 beds | 3 baths | 2,744 sq.ft.

$825,000

Airbnb cash on cash: 1.36%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $3503

Traditional Rental Income: $3488

Airbnb ROI: 1.36%

Traditional ROI: 2.35%

783 MOUNTAINVIEW DRIVE

Oakland, MD

3 beds | 3 baths | 1,971 sq.ft.

$529,900

Airbnb cash on cash: 3.09%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $3503

Traditional Rental Income: $2914

Airbnb ROI: 3.09%

Traditional ROI: 3.46%

1256 BOILING SPRING RD

Oakland, MD

3 beds | 2 baths | N/A

$250,000

Airbnb cash on cash: 9.42%

Traditional cash on cash: 8.18%

Airbnb Rental Income: $3503

Traditional Rental Income: $2438

Airbnb ROI: 9.42%

Traditional ROI: 8.18%

444 WOODLANDS HILL LANE

Oakland, MD

4 beds | 6 baths | 4,744 sq.ft.

$1,295,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $4304

Traditional Rental Income: $6676

Airbnb ROI: 0.82%

Traditional ROI: 3.55%

62 MIDDLETON ROAD

Oakland, MD

3 beds | 3 baths | 2,397 sq.ft.

$799,900

Airbnb cash on cash: 1.25%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $3503

Traditional Rental Income: $2989

Airbnb ROI: 1.25%

Traditional ROI: 1.6%

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%

522 E GREEN STREET

Oakland, MD

3 beds | 4 baths | 1,503 sq.ft.

$329,000

Airbnb cash on cash: 6.16%

Traditional cash on cash: 6.64%

Airbnb Rental Income: $3503

Traditional Rental Income: $2878

Airbnb ROI: 6.16%