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 20 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
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%
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%
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	$249,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 5.54% Airbnb Rental Income: $1077 Traditional Rental Income: $1813 Airbnb ROI: 0.86% Traditional ROI: 5.54%
4 LAUREL BROOK Drive unit: 4 #4 Oakland, MD Welcome to your peaceful mountain escape in Laurel Brook, where convenience meets cozy com...	2 beds \| 2 baths \| N/A	$225,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 6.16% Airbnb Rental Income: $1132 Traditional Rental Income: $1792 Airbnb ROI: 1.29% Traditional ROI: 6.16%
189 RED RUN Road unit: 1-C-2 #1-C-2 Oakland, MD 2+BR, 2BA waterfront condo at Red Run offering lake views and assigned deep water boat sli...	2 beds \| 2 baths \| 1,200 sq.ft.	$589,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 1.85% Airbnb Rental Income: $1132 Traditional Rental Income: $2053 Airbnb ROI: -0.51% Traditional ROI: 1.85%
565 GLENDALE Road unit: 212 #212 Oakland, MD Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western expos...	1 beds \| 1 baths \| 527 sq.ft.	$210,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 7.3% Airbnb Rental Income: $1077 Traditional Rental Income: $1886 Airbnb ROI: 1.39% Traditional ROI: 7.3%
15 VILLAGE Drive unit: 1 #1 Oakland, MD Escape to a simpler time with all the modern conveniences you desire at this 2-bedroom log...	2 beds \| 1 baths \| N/A	$425,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.75% Airbnb Rental Income: $1132 Traditional Rental Income: $1895 Airbnb ROI: -0.12% Traditional ROI: 2.75%
130 TIMBERLOFT Circle unit: 14 #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: -0.92% Traditional cash on cash: 2.32% Airbnb Rental Income: $1148 Traditional Rental Income: $3029 Airbnb ROI: -0.92% Traditional ROI: 2.32%
45 VILLAGE Drive unit: 4 #4 Oakland, MD Price Improved! Nestled in the serene Yellowstone Village community, 45 Village Drive offe...	2 beds \| 2 baths \| 1,096 sq.ft.	$415,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.59% Airbnb Rental Income: $1132 Traditional Rental Income: $2188 Airbnb ROI: -0.1% Traditional ROI: 3.59%
155 BASSWOOD Way Oakland, MD Tucked just off Lakeshore Drive, this log home nails that luxury treehouse feel. Wrapped i...	5 beds \| 3 baths \| 2,792 sq.ft.	$699,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.95% Airbnb Rental Income: $1968 Traditional Rental Income: $3207 Airbnb ROI: 0.26% Traditional ROI: 2.95%
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 #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.	$399,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 2.96% Airbnb Rental Income: $1132 Traditional Rental Income: $1811 Airbnb ROI: 0.13% Traditional ROI: 2.96%
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.	$175,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 9.1% Airbnb Rental Income: $1077 Traditional Rental Income: $1895 Airbnb ROI: 1.98% Traditional ROI: 9.1%
30 VILLAGE Drive unit: 3 #3 Oakland, MD Love Shack in Yellowstone Village at Deep Creek Lake! Welcome to your mountain retreat! Th...	2 beds \| 1 baths \| 916 sq.ft.	$409,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.01% Airbnb Rental Income: $1132 Traditional Rental Income: $1942 Airbnb ROI: -0.08% Traditional ROI: 3.01%
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: 204 #204 Oakland, MD Don't miss this opportunity to own a beautifully updated 1-bedroom unit at Silver Tree Sui...	1 beds \| 1 baths \| 460 sq.ft.	$195,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 7.27% Airbnb Rental Income: $1077 Traditional Rental Income: $1769 Airbnb ROI: 1.55% Traditional ROI: 7.27%
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%

Your search for investment property begins and ends here

Condos for Sale in Oakland, MD

65 VILLAGE Drive unit: 6 #6

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%

565 GLENDALE Road unit: 116 #116

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%

175 ROMAN RIDGE Road unit: 15 #15

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%

20160 GARRETT Highway unit: H708 #H708

Oakland, MD

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

1 beds | 1 baths | N/A

$249,900

Airbnb cash on cash: 0.86%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1077

Traditional Rental Income: $1813

Airbnb ROI: 0.86%

Traditional ROI: 5.54%

4 LAUREL BROOK Drive unit: 4 #4

Oakland, MD

2 beds | 2 baths | N/A

$225,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $1132

Traditional Rental Income: $1792

Airbnb ROI: 1.29%

Traditional ROI: 6.16%

189 RED RUN Road unit: 1-C-2 #1-C-2

Oakland, MD

2 beds | 2 baths | 1,200 sq.ft.

$589,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $1132

Traditional Rental Income: $2053

Airbnb ROI: -0.51%

Traditional ROI: 1.85%

565 GLENDALE Road unit: 212 #212

Oakland, MD

1 beds | 1 baths | 527 sq.ft.

$210,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 7.3%

Airbnb Rental Income: $1077

Traditional Rental Income: $1886

Airbnb ROI: 1.39%