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 18 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
565 GLENDALE Road #306 Oakland, MD Experience the best of Deep Creek Lake living from this beautifully appointed studio loft ...	2 beds \| 1 baths \| 772 sq.ft.	$249,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 5.25% Airbnb Rental Income: $880 Traditional Rental Income: $1747 Airbnb ROI: 0.15% Traditional ROI: 5.25%
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	$539,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 5.33% Airbnb Rental Income: $1166 Traditional Rental Income: $3765 Airbnb ROI: -0.58% Traditional ROI: 5.33%
55 VILLAGE Drive #5 Oakland, MD Tucked in the Yellowstone Village community at Deep Creek Lake, "Dan's Mountain" is a char...	3 beds \| 3 baths \| 2,280 sq.ft.	$595,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 3.58% Airbnb Rental Income: $728 Traditional Rental Income: $3088 Airbnb ROI: -1.22% Traditional ROI: 3.58%
565 GLENDALE Road #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: -0.6% Traditional cash on cash: 6.1% Airbnb Rental Income: $653 Traditional Rental Income: $1813 Airbnb ROI: -0.6% Traditional ROI: 6.1%
13 LAUREL BROOK Drive #13 Oakland, MD Affordable well maintained 2 Bedroom 2 Bath townhouse style condominium less than 1 mile f...	2 beds \| 2 baths \| 1,320 sq.ft.	$245,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 7.14% Airbnb Rental Income: $880 Traditional Rental Income: $2179 Airbnb ROI: 0.08% Traditional ROI: 7.14%
157 JEFFREY Lane #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: -0.32% Traditional cash on cash: 2.8% Airbnb Rental Income: $880 Traditional Rental Income: $1422 Airbnb ROI: -0.32% Traditional ROI: 2.8%
232 JEFFREY Lane #33 Oakland, MD Turn-key and fully furnished, this beautifully maintained duplex offers the perfect blend ...	2 beds \| 3 baths \| 2,960 sq.ft.	$414,999	Airbnb cash on cash: -0.51% Traditional cash on cash: 4.47% Airbnb Rental Income: $880 Traditional Rental Income: $2480 Airbnb ROI: -0.51% Traditional ROI: 4.47%
565 GLENDALE Road #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: -0.35% Traditional cash on cash: 7.75% Airbnb Rental Income: $653 Traditional Rental Income: $1886 Airbnb ROI: -0.35% Traditional ROI: 7.75%
178 WINDING TRAIL Lane #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: -0.43% Traditional cash on cash: 6.54% Airbnb Rental Income: $1420 Traditional Rental Income: $4826 Airbnb ROI: -0.43% Traditional ROI: 6.54%
531 GLENDALE Road #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.	$339,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 4.07% Airbnb Rental Income: $880 Traditional Rental Income: $1981 Airbnb ROI: -0.43% Traditional ROI: 4.07%
20160 GARRETT Highway #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: -0.41% Traditional cash on cash: 3.06% Airbnb Rental Income: $880 Traditional Rental Income: $1811 Airbnb ROI: -0.41% Traditional ROI: 3.06%
20160 GARRETT Highway #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: -1.17% Traditional cash on cash: 3.24% Airbnb Rental Income: $728 Traditional Rental Income: $2790 Airbnb ROI: -1.17% Traditional ROI: 3.24%
181 JEFFREY Lane #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.	$259,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.95% Airbnb Rental Income: $880 Traditional Rental Income: $1567 Airbnb ROI: -0.22% Traditional ROI: 3.95%
565 GLENDALE Road #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: -0.75% Traditional cash on cash: 6.16% Airbnb Rental Income: $653 Traditional Rental Income: $2052 Airbnb ROI: -0.75% Traditional ROI: 6.16%
130 TIMBERLOFT Circle #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: -1.56% Traditional cash on cash: 2.11% Airbnb Rental Income: $728 Traditional Rental Income: $2985 Airbnb ROI: -1.56% Traditional ROI: 2.11%
565 GLENDALE Road #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: -0.6% Traditional cash on cash: 3.73% Airbnb Rental Income: $653 Traditional Rental Income: $1699 Airbnb ROI: -0.6% Traditional ROI: 3.73%
135 JEFFREY Lane #19A Oakland, MD Experience the best of lakeview living in this great condo at Deep Creek Lake. Offering tw...	2 beds \| 1 baths \| 2,344 sq.ft.	$294,999	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.48% Airbnb Rental Income: $880 Traditional Rental Income: $1575 Airbnb ROI: -0.23% Traditional ROI: 3.48%
565 GLENDALE Road #303B Oakland, MD Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This ...	2 beds \| 1 baths \| 887 sq.ft.	$399,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 3.22% Airbnb Rental Income: $880 Traditional Rental Income: $1977 Airbnb ROI: -0.6% Traditional ROI: 3.22%

Your search for investment property begins and ends here

Condos for Sale in Oakland, MD

565 GLENDALE Road #306

Oakland, MD

2 beds | 1 baths | 772 sq.ft.

$249,900

Airbnb cash on cash: 0.15%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $880

Traditional Rental Income: $1747

Airbnb ROI: 0.15%

Traditional ROI: 5.25%

24 TRAILSIDE WAY

Oakland, MD

4 beds | 4 baths | N/A

$539,900

Airbnb cash on cash: -0.58%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1166

Traditional Rental Income: $3765

Airbnb ROI: -0.58%

Traditional ROI: 5.33%

55 VILLAGE Drive #5

Oakland, MD

3 beds | 3 baths | 2,280 sq.ft.

$595,000

Airbnb cash on cash: -1.22%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $728

Traditional Rental Income: $3088

Airbnb ROI: -1.22%

Traditional ROI: 3.58%

565 GLENDALE Road #106 B

Oakland, MD

1 beds | 1 baths | N/A

$229,900

Airbnb cash on cash: -0.6%

Traditional cash on cash: 6.1%

Airbnb Rental Income: $653

Traditional Rental Income: $1813

Airbnb ROI: -0.6%

Traditional ROI: 6.1%

13 LAUREL BROOK Drive #13

Oakland, MD

2 beds | 2 baths | 1,320 sq.ft.

$245,000

Airbnb cash on cash: 0.08%

Traditional cash on cash: 7.14%

Airbnb Rental Income: $880

Traditional Rental Income: $2179

Airbnb ROI: 0.08%

Traditional ROI: 7.14%

157 JEFFREY Lane #21B

Oakland, MD

2 beds | 1 baths | 550 sq.ft.

$299,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $880

Traditional Rental Income: $1422

Airbnb ROI: -0.32%

Traditional ROI: 2.8%

232 JEFFREY Lane #33

Oakland, MD

2 beds | 3 baths | 2,960 sq.ft.

$414,999

Airbnb cash on cash: -0.51%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $880

Traditional Rental Income: $2480

Airbnb ROI: -0.51%

Traditional ROI: 4.47%

565 GLENDALE Road #212A

Oakland, MD

1 beds | 1 baths | 527 sq.ft.

$199,000

Airbnb cash on cash: -0.35%

Traditional cash on cash: 7.75%

Airbnb Rental Income: $653

Traditional Rental Income: $1886

Airbnb ROI: -0.35%