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.

Condos for Sale in Oakland, MD

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

Showing 19 Condo 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
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%
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%
565 GLENDALE Road unit: 212A #212A Oakland, MD Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western expos...	1 beds \| 1 baths \| 527 sq.ft.	$199,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 7.75% Airbnb Rental Income: $1077 Traditional Rental Income: $1886 Airbnb ROI: 1.52% Traditional ROI: 7.75%
531 GLENDALE Road unit: B302 #B302 Oakland, MD Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath uni...	2 beds \| 1 baths \| 887 sq.ft.	$369,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.68% Airbnb Rental Income: $1132 Traditional Rental Income: $1981 Airbnb ROI: 0.13% Traditional ROI: 3.68%
20160 GARRETT Highway unit: G507 Oakland, MD Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep ...	2 beds \| 1 baths \| 912 sq.ft.	$389,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.06% Airbnb Rental Income: $1132 Traditional Rental Income: $1811 Airbnb ROI: 0.16% Traditional ROI: 3.06%
565 GLENDALE Road unit: 210A #210A Oakland, MD Studio unit at Silver Tree Suites, one of Deep Creek Lake's most premier condo/hotel commu...	1 beds \| 1 baths \| 382 sq.ft.	$160,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 10.01% Airbnb Rental Income: $1077 Traditional Rental Income: $1895 Airbnb ROI: 2.25% Traditional ROI: 10.01%
20160 GARRETT Highway unit: F501-701 #F501-701 Oakland, MD Lakefront living at it's best can be found in this completely renovated spacious condo. Th...	3 beds \| 2 baths \| 1,700 sq.ft.	$575,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.24% Airbnb Rental Income: $1148 Traditional Rental Income: $2790 Airbnb ROI: -0.52% Traditional ROI: 3.24%
181 JEFFREY Lane unit: 23A #23A Oakland, MD Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located i...	2 beds \| 1 baths \| 670 sq.ft.	$269,900	Airbnb cash on cash: 0.58% Traditional cash on cash: 3.77% Airbnb Rental Income: $1132 Traditional Rental Income: $1567 Airbnb ROI: 0.58% Traditional ROI: 3.77%
565 GLENDALE Road unit: 103B #103B Oakland, MD Ground-floor end unit with lake views at Silver Tree Suites! This inviting one-bedroom lay...	1 beds \| 1 baths \| N/A	$260,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 6.16% Airbnb Rental Income: $1077 Traditional Rental Income: $2052 Airbnb ROI: 0.69% Traditional ROI: 6.16%
178 WINDING TRAIL Lane unit: 5B Oakland, MD Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lak...	5 beds \| 5 baths \| 3,300 sq.ft.	$589,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 7.81% Airbnb Rental Income: $1968 Traditional Rental Income: $5526 Airbnb ROI: 0.4% Traditional ROI: 7.81%
175 ROMAN RIDGE Road unit: 15 Oakland, MD Welcome to this 4-bedroom, 4.5-bath stand-alone, multi-level unit in Traders Landing! Offe...	4 beds \| 5 baths \| 3,192 sq.ft.	$509,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 8.88% Airbnb Rental Income: $1631 Traditional Rental Income: $5286 Airbnb ROI: 0.23% Traditional ROI: 8.88%
130 TIMBERLOFT Circle unit: 14 Oakland, MD Centrally located in the heart of Deep Creek Lake, this beautifully maintained 3 bedroom, ...	3 beds \| 3 baths \| 1,900 sq.ft.	$749,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 2.11% Airbnb Rental Income: $1148 Traditional Rental Income: $2985 Airbnb ROI: -1.06% Traditional ROI: 2.11%
8 LAUREL BROOK Drive unit: 8 Oakland, MD Re-positioned price to sell. Beautiful Renovated 2-bedroom, 2-bath condo is Turnkey Ready ...	2 beds \| 2 baths \| 1,340 sq.ft.	$284,900	Airbnb cash on cash: 0.72% Traditional cash on cash: 6.45% Airbnb Rental Income: $1132 Traditional Rental Income: $2294 Airbnb ROI: 0.72% Traditional ROI: 6.45%
157 JEFFREY Lane unit: 21B Oakland, MD Nestled in the charming Traders Landing community, this delightful end-of-row townhouse of...	2 beds \| 1 baths \| 550 sq.ft.	$299,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.14% Airbnb Rental Income: $1132 Traditional Rental Income: $1518 Airbnb ROI: 0.43% Traditional ROI: 3.14%
232 JEFFREY Lane unit: 33 #33 Oakland, MD Turn-key and fully furnished, this beautifully maintained duplex offers the perfect blend ...	2 beds \| 3 baths \| 2,960 sq.ft.	$425,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 5.22% Airbnb Rental Income: $1132 Traditional Rental Income: $2830 Airbnb ROI: 0.01% Traditional ROI: 5.22%
565 GLENDALE Road unit: 125 Oakland, MD Wake up to the lake at your doorstep. This ground-level, end-unit condo offers true lakefr...	1 beds \| 1 baths \| 496 sq.ft.	$329,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 3.73% Airbnb Rental Income: $1077 Traditional Rental Income: $1699 Airbnb ROI: 0.54% Traditional ROI: 3.73%

Your search for investment property begins and ends here

Condos for Sale in Oakland, MD

24 TRAILSIDE WAY

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%

565 GLENDALE Road unit: 106 B #106 B

Oakland, MD

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%

565 GLENDALE Road unit: 212A #212A

Oakland, MD

1 beds | 1 baths | 527 sq.ft.

$199,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 7.75%

Airbnb Rental Income: $1077

Traditional Rental Income: $1886

Airbnb ROI: 1.52%

Traditional ROI: 7.75%

531 GLENDALE Road unit: B302 #B302

Oakland, MD

2 beds | 1 baths | 887 sq.ft.

$369,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $1132

Traditional Rental Income: $1981

Airbnb ROI: 0.13%

Traditional ROI: 3.68%

20160 GARRETT Highway unit: G507

Oakland, MD

2 beds | 1 baths | 912 sq.ft.

$389,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $1132

Traditional Rental Income: $1811

Airbnb ROI: 0.16%

Traditional ROI: 3.06%

565 GLENDALE Road unit: 210A #210A

Oakland, MD

1 beds | 1 baths | 382 sq.ft.

$160,000

Airbnb cash on cash: 2.25%

Traditional cash on cash: 10.01%

Airbnb Rental Income: $1077

Traditional Rental Income: $1895

Airbnb ROI: 2.25%

Traditional ROI: 10.01%

20160 GARRETT Highway unit: F501-701 #F501-701

Oakland, MD

3 beds | 2 baths | 1,700 sq.ft.

$575,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $1148

Traditional Rental Income: $2790

Airbnb ROI: -0.52%

Traditional ROI: 3.24%

181 JEFFREY Lane unit: 23A #23A

Oakland, MD

2 beds | 1 baths | 670 sq.ft.

$269,900

Airbnb cash on cash: 0.58%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $1132

Traditional Rental Income: $1567

Airbnb ROI: 0.58%