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.

Townhouses for Sale in Oakland, MD

Search for Townhouse for Sale in Oakland, Maryland. Browse all of Mashvisor’s Townhouse listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 1 Townhouse 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
170 WINDING TRAIL LANE #4B Oakland, MD Spacious home located in the Timberlake Village community. This duplex home offers three l...	5 beds \| 5 baths \| 3,300 sq.ft.	$589,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 6.72% Airbnb Rental Income: $5609 Traditional Rental Income: $4869 Airbnb ROI: 6.03% Traditional ROI: 6.72%
Other Investment Properties for Sale in Oakland
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%
565 GLENDALE ROAD #124 Oakland , MD Public: If you are looking for an affordable way to own at Deep Creek Lake, this is it! Th...	1 beds \| 1 baths \| 382 sq.ft.	$175,000	Airbnb cash on cash: 6.9% Traditional cash on cash: 5.99% Airbnb Rental Income: $2748 Traditional Rental Income: $1949 Airbnb ROI: 6.9% Traditional ROI: 5.99%
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%
65 VILLAGE DRIVE #6 Oakland , MD Looking for that cozy cabin getaway at the lake? 65 Village Drive offers cabin living at i...	3 beds \| 3 baths \| 1,740 sq.ft.	$695,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.86% Airbnb Rental Income: $3503 Traditional Rental Income: $2798 Airbnb ROI: 1.76% Traditional ROI: 1.86%
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%
565 GLENDALE ROAD #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.	$179,000	Airbnb cash on cash: 9.94% Traditional cash on cash: 6.64% Airbnb Rental Income: $2748 Traditional Rental Income: $1539 Airbnb ROI: 9.94% Traditional ROI: 6.64%
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%
565 GLENDALE ROAD #303B Oakland , MD Fully Renovated Penthouse at Silver Tree Suites Been holding out for the nicest unit at Si...	2 beds \| 1 baths \| 887 sq.ft.	$399,900	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.32% Airbnb Rental Income: $2615 Traditional Rental Income: $1981 Airbnb ROI: 3.35% Traditional ROI: 3.32%
131 ROCK RIDGE LANE #12 Oakland , MD Craftsman-style home in the much sought after Silver Ridge community. Once you enter, you'...	4 beds \| 4 baths \| 2,422 sq.ft.	$509,900	Airbnb cash on cash: 5.02% Traditional cash on cash: 5.16% Airbnb Rental Income: $4304 Traditional Rental Income: $3466 Airbnb ROI: 5.02% Traditional ROI: 5.16%
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%
175 ROMAN RIDGE ROAD #15 Oakland , MD Amazing and rare opportunity in Trader's Landing! These wonderful stand alone homes in thi...	4 beds \| 5 baths \| 3,192 sq.ft.	$555,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 8.25% Airbnb Rental Income: $4304 Traditional Rental Income: $5368 Airbnb ROI: 4.45% Traditional ROI: 8.25%
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%

Your search for investment property begins and ends here

Townhouses for Sale in Oakland, MD

170 WINDING TRAIL LANE #4B

Oakland, MD

5 beds | 5 baths | 3,300 sq.ft.

$589,000

Airbnb cash on cash: 6.03%

Traditional cash on cash: 6.72%

Airbnb Rental Income: $5609

Traditional Rental Income: $4869

Airbnb ROI: 6.03%

Traditional ROI: 6.72%

Other Investment Properties for Sale in Oakland

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%

Oakland , MD

1 beds | 1 baths | 382 sq.ft.

$175,000

Airbnb cash on cash: 6.9%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $2748

Traditional Rental Income: $1949

Airbnb ROI: 6.9%

Traditional ROI: 5.99%

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%

Oakland , MD

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

$695,000

Airbnb cash on cash: 1.76%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $3503

Traditional Rental Income: $2798

Airbnb ROI: 1.76%

Traditional ROI: 1.86%

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%

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%

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%

Oakland , MD

1 beds | 1 baths | 484 sq.ft.

$179,000

Airbnb cash on cash: 9.94%

Traditional cash on cash: 6.64%