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 4 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.	$425,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 6.13% Airbnb Rental Income: $1631 Traditional Rental Income: $3296 Airbnb ROI: 0.79% Traditional ROI: 6.13%
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	$359,700	Airbnb cash on cash: 1.42% Traditional cash on cash: 6.8% Airbnb Rental Income: $1631 Traditional Rental Income: $2986 Airbnb ROI: 1.42% Traditional ROI: 6.8%
697 MONTE VISTA Road Oakland, MD Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with ...	5 beds \| 4 baths \| 3,682 sq.ft.	$339,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 11.48% Airbnb Rental Income: $1968 Traditional Rental Income: $4331 Airbnb ROI: 2.44% Traditional ROI: 11.48%
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.	$292,500	Airbnb cash on cash: 0.59% Traditional cash on cash: 5.61% Airbnb Rental Income: $1148 Traditional Rental Income: $2150 Airbnb ROI: 0.59% Traditional ROI: 5.61%
Other Investment Properties for Sale in Oakland
24 TRAILSIDE WAY Oakland , MD Tucked in the Silver Ridge community at Deep Creek Lake, this inviting home blends rustic ...	4 beds \| 4 baths \| N/A	$555,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 5.16% Airbnb Rental Income: $1631 Traditional Rental Income: $3765 Airbnb ROI: 0.16% Traditional ROI: 5.16%
98 BEAR RUN Road Oakland , MD Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 ...	3 beds \| 2 baths \| 1,080 sq.ft.	$550,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.29% Airbnb Rental Income: $1148 Traditional Rental Income: $2510 Airbnb ROI: -0.1% Traditional ROI: 3.29%
25 SILVER TREE Lane Oakland , MD Beautiful lake access retreat located in the Silver Tree Landings community with an availa...	5 beds \| 4 baths \| 2,364 sq.ft.	$749,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.81% Airbnb Rental Income: $1968 Traditional Rental Income: $2858 Airbnb ROI: -0.2% Traditional ROI: 1.81%
1544 STOCKSLAGER Road Oakland , MD Enjoy lakefront living at its finest in this beautifully remodeled home with a private doc...	5 beds \| 4 baths \| 3,456 sq.ft.	$1,750,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.2% Airbnb Rental Income: $1968 Traditional Rental Income: $4663 Airbnb ROI: -0.78% Traditional ROI: 1.2%
3749 MARYLAND Highway Oakland , MD Set on a beautiful lot in Deep Creek, Maryland, this stunning property offers the perfect ...	2 beds \| 2 baths \| 2,015 sq.ft.	$325,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 5.59% Airbnb Rental Income: $1132 Traditional Rental Income: $2334 Airbnb ROI: 0.42% Traditional ROI: 5.59%
267 SAN FRANCISCO Street Oakland , MD Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake ...	4 beds \| 3 baths \| 3,278 sq.ft.	$899,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.5% Airbnb Rental Income: $1631 Traditional Rental Income: $2874 Airbnb ROI: -0.53% Traditional ROI: 1.5%
467 PARADISE RIDGE Road Oakland , MD Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge,...	4 beds \| 4 baths \| 3,780 sq.ft.	$799,900	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.7% Airbnb Rental Income: $1631 Traditional Rental Income: $3685 Airbnb ROI: -0.68% Traditional ROI: 2.7%
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: 0.6% Traditional cash on cash: 4.69% Airbnb Rental Income: $1631 Traditional Rental Income: $3200 Airbnb ROI: 0.6% Traditional ROI: 4.69%
285 LAKE SHORE Drive Oakland , MD Nestled on 1.52 private acres with 500 feet of frontage on Deep Creek Lake, this 5-bedroom...	5 beds \| 5 baths \| 2,593 sq.ft.	$1,149,800	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.94% Airbnb Rental Income: $1968 Traditional Rental Income: $4868 Airbnb ROI: -0.26% Traditional ROI: 2.94%
449 S 3RD Street Oakland , MD Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where hist...	4 beds \| 2 baths \| 1,928 sq.ft.	$275,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 7.55% Airbnb Rental Income: $1631 Traditional Rental Income: $2676 Airbnb ROI: 1.76% Traditional ROI: 7.55%
565 GLENDALE Road unit: 106 B #106 B Oakland , MD Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs...	1 beds \| 1 baths \| N/A	$229,900	Airbnb cash on cash: 1.02% Traditional cash on cash: 6.1% Airbnb Rental Income: $1077 Traditional Rental Income: $1813 Airbnb ROI: 1.02% Traditional ROI: 6.1%

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.

$425,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 6.13%

Airbnb Rental Income: $1631

Traditional Rental Income: $3296

Airbnb ROI: 0.79%

Traditional ROI: 6.13%

723 KINGS

Oakland, MD

4 beds | 3 baths | N/A

$359,700

Airbnb cash on cash: 1.42%

Traditional cash on cash: 6.8%

Airbnb Rental Income: $1631

Traditional Rental Income: $2986

Airbnb ROI: 1.42%

Traditional ROI: 6.8%

697 MONTE VISTA Road

Oakland, MD

5 beds | 4 baths | 3,682 sq.ft.

$339,000

Airbnb cash on cash: 2.44%

Traditional cash on cash: 11.48%

Airbnb Rental Income: $1968

Traditional Rental Income: $4331

Airbnb ROI: 2.44%

Traditional ROI: 11.48%

505 SOUTHERN PINES Drive

Oakland, MD

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

$292,500

Airbnb cash on cash: 0.59%

Traditional cash on cash: 5.61%

Airbnb Rental Income: $1148

Traditional Rental Income: $2150

Airbnb ROI: 0.59%

Traditional ROI: 5.61%

Other Investment Properties for Sale in Oakland

Oakland , MD

4 beds | 4 baths | N/A

$555,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $1631

Traditional Rental Income: $3765

Airbnb ROI: 0.16%

Traditional ROI: 5.16%

Oakland , MD

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

$550,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1148

Traditional Rental Income: $2510

Airbnb ROI: -0.1%

Traditional ROI: 3.29%

Oakland , MD

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

$749,900

Airbnb cash on cash: -0.2%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $1968

Traditional Rental Income: $2858

Airbnb ROI: -0.2%

Traditional ROI: 1.81%

Oakland , MD

5 beds | 4 baths | 3,456 sq.ft.

$1,750,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $1968

Traditional Rental Income: $4663

Airbnb ROI: -0.78%

Traditional ROI: 1.2%

Oakland , MD

2 beds | 2 baths | 2,015 sq.ft.