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 10 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
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: 1.61% Traditional cash on cash: 9.26% Airbnb Rental Income: $1078 Traditional Rental Income: $2302 Airbnb ROI: 1.61% Traditional ROI: 9.26%
2918 OAKLAND SANG RUN Road Oakland, MD This charming 3-bedroom, 1-bathroom ranch-style home in the desirable Oakland Sang Run Rd ...	3 beds \| 1 baths \| 1,382 sq.ft.	$195,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 5.78% Airbnb Rental Income: $1078 Traditional Rental Income: $1562 Airbnb ROI: 1.17% Traditional ROI: 5.78%
5024 CRANESVILLE Road Oakland, MD Surrounded by 100+ Acres of Nature Conservancy conservation lands, on a 1.68-acre scenic h...	3 beds \| 3 baths \| 2,128 sq.ft.	$399,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 6.14% Airbnb Rental Income: $1078 Traditional Rental Income: $3081 Airbnb ROI: -0.2% Traditional ROI: 6.14%
505 SOUTHERN PINES Drive Oakland, MD Charming ranch-style home located in the desirable Southern Pines neighborhood. From the m...	3 beds \| 2 baths \| 1,248 sq.ft.	$287,500	Airbnb cash on cash: 0.4% Traditional cash on cash: 5.72% Airbnb Rental Income: $1078 Traditional Rental Income: $2150 Airbnb ROI: 0.4% Traditional ROI: 5.72%
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: 0.18% Traditional cash on cash: 5.12% Airbnb Rental Income: $1078 Traditional Rental Income: $2330 Airbnb ROI: 0.18% Traditional ROI: 5.12%
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: 1.84% Traditional cash on cash: 6.22% Airbnb Rental Income: $1908 Traditional Rental Income: $2944 Airbnb ROI: 1.84% 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.	$434,900	Airbnb cash on cash: 0.94% Traditional cash on cash: 6.29% Airbnb Rental Income: $1496 Traditional Rental Income: $3234 Airbnb ROI: 0.94% Traditional ROI: 6.29%
1499 FOSTER Road Oakland, MD Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 priva...	4 beds \| 2 baths \| 2,234 sq.ft.	$415,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 5.93% Airbnb Rental Income: $1496 Traditional Rental Income: $2965 Airbnb ROI: 1.03% Traditional ROI: 5.93%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oakland, MD

8956 OAKLAND SANG RUN Road

Oakland, MD

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

$219,900

Airbnb cash on cash: 1.61%

Traditional cash on cash: 9.26%

Airbnb Rental Income: $1078

Traditional Rental Income: $2302

Airbnb ROI: 1.61%

Traditional ROI: 9.26%

2918 OAKLAND SANG RUN Road

Oakland, MD

3 beds | 1 baths | 1,382 sq.ft.

$195,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 5.78%

Airbnb Rental Income: $1078

Traditional Rental Income: $1562

Airbnb ROI: 1.17%

Traditional ROI: 5.78%

5024 CRANESVILLE Road

Oakland, MD

3 beds | 3 baths | 2,128 sq.ft.

$399,000

Airbnb cash on cash: -0.2%

Traditional cash on cash: 6.14%

Airbnb Rental Income: $1078

Traditional Rental Income: $3081

Airbnb ROI: -0.2%

Traditional ROI: 6.14%

505 SOUTHERN PINES Drive

Oakland, MD

3 beds | 2 baths | 1,248 sq.ft.

$287,500

Airbnb cash on cash: 0.4%

Traditional cash on cash: 5.72%

Airbnb Rental Income: $1078

Traditional Rental Income: $2150

Airbnb ROI: 0.4%

Traditional ROI: 5.72%

552 BLACK OAK DR

Oakland, MD

3 beds | 2 baths | N/A

$349,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1078

Traditional Rental Income: $2330

Airbnb ROI: 0.18%

Traditional ROI: 5.12%

321 N 3RD Street

Oakland, MD

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

$375,000

Airbnb cash on cash: 1.84%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $1908

Traditional Rental Income: $2944

Airbnb ROI: 1.84%

Traditional ROI: 6.22%

511 HILLTOP Road

Oakland, MD

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

$434,900

Airbnb cash on cash: 0.94%

Traditional cash on cash: 6.29%

Airbnb Rental Income: $1496

Traditional Rental Income: $3234

Airbnb ROI: 0.94%

Traditional ROI: 6.29%

1499 FOSTER Road

Oakland, MD

4 beds | 2 baths | 2,234 sq.ft.

$415,000

Airbnb cash on cash: 1.03%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $1496

Traditional Rental Income: $2965

Airbnb ROI: 1.03%