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 3 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: 0.73% Traditional cash on cash: 5.89% Airbnb Rental Income: $1631 Traditional Rental Income: $3296 Airbnb ROI: 0.73% Traditional ROI: 5.89%
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: 1.29% Traditional cash on cash: 6.39% Airbnb Rental Income: $1631 Traditional Rental Income: $2986 Airbnb ROI: 1.29% Traditional ROI: 6.39%
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.	$245,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 7.49% Airbnb Rental Income: $1148 Traditional Rental Income: $2214 Airbnb ROI: 1.24% Traditional ROI: 7.49%
Other Investment Properties for Sale in Oakland
65 VILLAGE Drive unit: 6 #6 Oakland , MD One of Deep Creek Lake's best performing vacation rental properties! Over 65 Village Drive...	3 beds \| 3 baths \| 1,740 sq.ft.	$625,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 2.18% Airbnb Rental Income: $1148 Traditional Rental Income: $2798 Airbnb ROI: -1.3% Traditional ROI: 2.18%
444 WOODLANDS HILL Lane Oakland , MD Welcome to 444 Woodlands Hill Ln, in Oakland, MD. Nestled in the private community of The ...	4 beds \| 6 baths \| 4,744 sq.ft.	$1,199,990	Airbnb cash on cash: -1.03% Traditional cash on cash: 3.91% Airbnb Rental Income: $1631 Traditional Rental Income: $6676 Airbnb ROI: -1.03% Traditional ROI: 3.91%
565 GLENDALE Road unit: 116 #116 Oakland , MD Don't miss this rare opportunity to own a beautifully updated 1-bedroom unit at Silver Tre...	1 beds \| 1 baths \| 484 sq.ft.	$169,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 7.08% Airbnb Rental Income: $1077 Traditional Rental Income: $1539 Airbnb ROI: 1.92% Traditional ROI: 7.08%
175 ROMAN RIDGE Road unit: 15 #15 Oakland , MD Welcome to one of the most spacious and inviting homes in Trader's Landing. This rare stan...	4 beds \| 5 baths \| 3,192 sq.ft.	$537,500	Airbnb cash on cash: 0.19% Traditional cash on cash: 8.55% Airbnb Rental Income: $1631 Traditional Rental Income: $5368 Airbnb ROI: 0.19% Traditional ROI: 8.55%
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%
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: -0.09% Traditional cash on cash: 3.39% Airbnb Rental Income: $1148 Traditional Rental Income: $2154 Airbnb ROI: -0.09% 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: 0.6% Traditional cash on cash: 4.69% Airbnb Rental Income: $1631 Traditional Rental Income: $3200 Airbnb ROI: 0.6% Traditional ROI: 4.69%
20160 GARRETT Highway unit: H708 #H708 Oakland , MD Welcome to Will O' the Wisp Condominiums, where premium upgrades meet penthouse-level lake...	1 beds \| 1 baths \| 550 sq.ft.	$289,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.48% Airbnb Rental Income: $1077 Traditional Rental Income: $1530 Airbnb ROI: 0.47% Traditional ROI: 3.48%
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	$239,900	Airbnb cash on cash: 0.94% Traditional cash on cash: 5.81% Airbnb Rental Income: $1077 Traditional Rental Income: $1813 Airbnb ROI: 0.94% Traditional ROI: 5.81%
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.	$545,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 4.15% Airbnb Rental Income: $1631 Traditional Rental Income: $3055 Airbnb ROI: 0.45% Traditional ROI: 4.15%
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: 0.9% Traditional cash on cash: 4.81% Airbnb Rental Income: $1132 Traditional Rental Income: $1638 Airbnb ROI: 0.9% Traditional ROI: 4.81%
163 CRESTVIEW Drive Oakland , MD Welcome to 163 Crestview Drive - a beautifully maintained 3-bedroom, 2.5-bath home nestled...	3 beds \| 3 baths \| 1,416 sq.ft.	$325,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 5.87% Airbnb Rental Income: $1148 Traditional Rental Income: $2376 Airbnb ROI: 0.61% Traditional ROI: 5.87%
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.	$1,749,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.19% Airbnb Rental Income: $1631 Traditional Rental Income: $3069 Airbnb ROI: -0.98% Traditional ROI: 0.19%

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.

$440,000

Airbnb cash on cash: 0.73%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $1631

Traditional Rental Income: $3296

Airbnb ROI: 0.73%

Traditional ROI: 5.89%

723 KINGS

Oakland, MD

4 beds | 3 baths | N/A

$380,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 6.39%

Airbnb Rental Income: $1631

Traditional Rental Income: $2986

Airbnb ROI: 1.29%

Traditional ROI: 6.39%

1570 GARRETT Road

Oakland, MD

3 beds | 1 baths | 1,408 sq.ft.

$245,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 7.49%

Airbnb Rental Income: $1148

Traditional Rental Income: $2214

Airbnb ROI: 1.24%

Traditional ROI: 7.49%

Other Investment Properties for Sale in Oakland

Oakland , MD

3 beds | 3 baths | 1,740 sq.ft.

$625,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $1148

Traditional Rental Income: $2798

Airbnb ROI: -1.3%

Traditional ROI: 2.18%

Oakland , MD

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

$1,199,990

Airbnb cash on cash: -1.03%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $1631

Traditional Rental Income: $6676

Airbnb ROI: -1.03%

Traditional ROI: 3.91%

Oakland , MD

1 beds | 1 baths | 484 sq.ft.

$169,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 7.08%

Airbnb Rental Income: $1077

Traditional Rental Income: $1539

Airbnb ROI: 1.92%

Traditional ROI: 7.08%

Oakland , MD

4 beds | 5 baths | 3,192 sq.ft.

$537,500

Airbnb cash on cash: 0.19%

Traditional cash on cash: 8.55%

Airbnb Rental Income: $1631

Traditional Rental Income: $5368

Airbnb ROI: 0.19%

Traditional ROI: 8.55%

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