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 12 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
552 BLACK OAK DR Oakland, MD Looking for a vacation spot or main living, Check out this nicely remolded home in a gated...	3 beds \| 2 baths \| N/A	$349,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 5.12% Airbnb Rental Income: $1309 Traditional Rental Income: $2330 Airbnb ROI: 0.77% Traditional ROI: 5.12%
8956 OAKLAND SANG RUN Road Oakland, MD Welcome to The Wise Quack - our cozy cabin in the center of Deep Creek Lake activities...a...	3 beds \| 2 baths \| 1,064 sq.ft.	$219,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 9.26% Airbnb Rental Income: $1309 Traditional Rental Income: $2302 Airbnb ROI: 2.54% Traditional ROI: 9.26%
321 N 3RD Street Oakland, MD Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spaci...	5 beds \| 2 baths \| 3,660 sq.ft.	$375,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 6.22% Airbnb Rental Income: $2422 Traditional Rental Income: $2944 Airbnb ROI: 3.06% Traditional ROI: 6.22%
511 HILLTOP Road Oakland, MD Tucked away on a quiet cul-de-sac in the desirable Royal Charlotte community, this stunnin...	4 beds \| 3 baths \| 2,406 sq.ft.	$424,900	Airbnb cash on cash: 2.12% Traditional cash on cash: 6.46% Airbnb Rental Income: $2035 Traditional Rental Income: $3234 Airbnb ROI: 2.12% Traditional ROI: 6.46%
321 DEER PARK HOTEL Road Oakland, MD Double lots! Lot 4 & 5 of Hunting Ridge Estates will be sold together to bring up a total ...	3 beds \| 2 baths \| 2,476 sq.ft.	$399,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 5.41% Airbnb Rental Income: $1309 Traditional Rental Income: $2692 Airbnb ROI: 0.64% Traditional ROI: 5.41%
113 G St Oakland, MD 113 G St, Oakland, MD 21550 \| Single Family Residential	9 beds \| 3 baths \| 3,840 sq.ft.	$499,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.39% Airbnb Rental Income: $2422 Traditional Rental Income: $3111 Airbnb ROI: 1.64% Traditional ROI: 4.39%
127 S Oakhall Dr Oakland, MD Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakla...	4 beds \| 2 baths \| 1,913 sq.ft.	$265,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 8.91% Airbnb Rental Income: $2035 Traditional Rental Income: $2854 Airbnb ROI: 3.72% Traditional ROI: 8.91%
809 N St Oakland, MD 809 N St, Oakland, MD 21550 \| Single Family Residential	N/A beds \| N/A baths \| 792 sq.ft.	$63,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 9.13% Airbnb Rental Income: $708 Traditional Rental Income: $797 Airbnb ROI: 2.84% Traditional ROI: 9.13%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oakland, MD

552 BLACK OAK DR

Oakland, MD

3 beds | 2 baths | N/A

$349,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1309

Traditional Rental Income: $2330

Airbnb ROI: 0.77%

Traditional ROI: 5.12%

8956 OAKLAND SANG RUN Road

Oakland, MD

3 beds | 2 baths | 1,064 sq.ft.

$219,900

Airbnb cash on cash: 2.54%

Traditional cash on cash: 9.26%

Airbnb Rental Income: $1309

Traditional Rental Income: $2302

Airbnb ROI: 2.54%

Traditional ROI: 9.26%

321 N 3RD Street

Oakland, MD

5 beds | 2 baths | 3,660 sq.ft.

$375,000

Airbnb cash on cash: 3.06%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $2422

Traditional Rental Income: $2944

Airbnb ROI: 3.06%

Traditional ROI: 6.22%

511 HILLTOP Road

Oakland, MD

4 beds | 3 baths | 2,406 sq.ft.

$424,900

Airbnb cash on cash: 2.12%

Traditional cash on cash: 6.46%

Airbnb Rental Income: $2035

Traditional Rental Income: $3234

Airbnb ROI: 2.12%

Traditional ROI: 6.46%

321 DEER PARK HOTEL Road

Oakland, MD

3 beds | 2 baths | 2,476 sq.ft.

$399,900

Airbnb cash on cash: 0.64%

Traditional cash on cash: 5.41%

Airbnb Rental Income: $1309

Traditional Rental Income: $2692

Airbnb ROI: 0.64%

Traditional ROI: 5.41%

113 G St

Oakland, MD

9 beds | 3 baths | 3,840 sq.ft.

$499,000

Airbnb cash on cash: 1.64%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $2422

Traditional Rental Income: $3111

Airbnb ROI: 1.64%

Traditional ROI: 4.39%

127 S Oakhall Dr

Oakland, MD

4 beds | 2 baths | 1,913 sq.ft.

$265,000

Airbnb cash on cash: 3.72%

Traditional cash on cash: 8.91%

Airbnb Rental Income: $2035

Traditional Rental Income: $2854

Airbnb ROI: 3.72%

Traditional ROI: 8.91%

809 N St

Oakland, MD

N/A beds | N/A baths | 792 sq.ft.

$63,000

Airbnb cash on cash: 2.84%

Traditional cash on cash: 9.13%

Airbnb Rental Income: $708

Traditional Rental Income: $797

Airbnb ROI: 2.84%