Real Estate Investment Properties for Sale in Oakland, FL

Looking for investment property in Oakland, FL with high ROI ?

Explore a variety of short-term homes & houses in Oakland, FL. Invest wisely with VRBO & Oakland, FL 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, FL

Search for Single Family Residential for Sale in Oakland, Florida. 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 23 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
16834 Artimino Loop Oakland, FL 16834 Artimino Loop, Oakland, FL 34756 \| Single Family Residential	5 beds \| 5 baths \| 6,676 sq.ft.	$5,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.47% Airbnb Rental Income: $null Traditional Rental Income: $8482 Airbnb ROI: N/A Traditional ROI: -0.47%
16020 Pendio Dr Oakland, FL 16020 Pendio Dr, Oakland, FL 34756 \| Single Family Residential	5 beds \| 5 baths \| 4,978 sq.ft.	$2,375,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.32% Airbnb Rental Income: $null Traditional Rental Income: $8313 Airbnb ROI: N/A Traditional ROI: 1.32%
16103 Pendio Dr Oakland, FL 16103 Pendio Dr, MONTVERDE, FL 34756 \| Single Family Residential	5 beds \| 6 baths \| 5,466 sq.ft.	$3,448,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.36% Airbnb Rental Income: $null Traditional Rental Income: $11634 Airbnb ROI: N/A Traditional ROI: 1.36%
15926 Pendio Dr Oakland, FL 15926 Pendio Dr, Oakland, FL 34756 \| Single Family Residential	6 beds \| 7 baths \| 8,479 sq.ft.	$5,690,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $12620 Airbnb ROI: N/A Traditional ROI: 0.27%
16123 Pendio Dr Oakland, FL 16123 Pendio Dr, Oakland, FL 34756 \| Single Family Residential	5 beds \| 5 baths \| 6,584 sq.ft.	$3,997,500	Airbnb cash on cash: N/A Traditional cash on cash: -0.88% Airbnb Rental Income: $null Traditional Rental Income: $4969 Airbnb ROI: N/A Traditional ROI: -0.88%
16000 Pendio Dr Oakland, FL 16000 Pendio Dr, Oakland, FL 34756 \| Single Family Residential	6 beds \| 7 baths \| 6,973 sq.ft.	$3,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.1% Airbnb Rental Income: $null Traditional Rental Income: $7073 Airbnb ROI: N/A Traditional ROI: 0.1%
620 N Tubb St Oakland, FL 620 N Tubb St, Oakland, FL 34760 \| Single Family Residential	6 beds \| 7 baths \| 5,614 sq.ft.	$1,499,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.33% Airbnb Rental Income: $null Traditional Rental Income: $11532 Airbnb ROI: N/A Traditional ROI: 6.33%
250 N Walker St Oakland, FL 250 N Walker St, Oakland, FL 34760 \| Single Family Residential	4 beds \| 2 baths \| 2,469 sq.ft.	$1,145,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 0.38% Airbnb Rental Income: $5064 Traditional Rental Income: $2504 Airbnb ROI: 1.81% Traditional ROI: 0.38%
38 S Pollard St Oakland, FL 38 S Pollard St, Oakland, FL 34760 \| Single Family Residential	4 beds \| 2 baths \| 1,872 sq.ft.	$659,999	Airbnb cash on cash: 4.51% Traditional cash on cash: 1.99% Airbnb Rental Income: $5064 Traditional Rental Income: $2480 Airbnb ROI: 4.51% Traditional ROI: 1.99%
1258 RIDGE LAKE WAY Oakland, FL Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve...	4 beds \| 4 baths \| 4,557 sq.ft.	$2,098,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 0.82% Airbnb Rental Income: $5064 Traditional Rental Income: $4543 Airbnb ROI: 0.56% Traditional ROI: 0.82%
1970 STANDING ROCK CIRCLE Oakland, FL Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath hom...	5 beds \| 3 baths \| 3,528 sq.ft.	$796,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $3714 Airbnb ROI: N/A Traditional ROI: 2.79%
2065 White Feather Loop Oakland, FL Welcome to the highly desirable Oakland Trails community, where this exceptional 2019 Meri...	3 beds \| 2 baths \| 2,089 sq.ft.	$549,900	Airbnb cash on cash: 3.58% Traditional cash on cash: 3.21% Airbnb Rental Income: $3912 Traditional Rental Income: $2879 Airbnb ROI: 3.58% Traditional ROI: 3.21%
1270 Stationside Drive Dr Oakland, FL 1270 Stationside Drive Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 2,046 sq.ft.	$519,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $2126 Airbnb ROI: 6.17% Traditional ROI: 2.24%
1156 CIVITAS WAY Oakland, FL Motivated seller!! Experience luxury in this immaculate 2022 custom RCB home, featuring hi...	4 beds \| 3 baths \| 2,710 sq.ft.	$1,268,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 0.69% Airbnb Rental Income: $5064 Traditional Rental Income: $3349 Airbnb ROI: 1.27% Traditional ROI: 0.69%
1412 Johns Cove Ln Oakland, FL 1412 Johns Cove Ln, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 3,613 sq.ft.	$1,499,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 0.48% Airbnb Rental Income: $5064 Traditional Rental Income: $3584 Airbnb ROI: 0.81% Traditional ROI: 0.48%
812 JOHNS POINT DRIVE Oakland, FL Experience unparalleled lakefront living in this fully renovated Mediterranean-style estat...	5 beds \| 6 baths \| 4,373 sq.ft.	$2,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.94% Airbnb Rental Income: $null Traditional Rental Income: $12477 Airbnb ROI: N/A Traditional ROI: 2.94%
1231 Foltz Loop Oakland, FL 1231 Foltz Loop, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 3,134 sq.ft.	$874,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3036 Airbnb ROI: 2.72% Traditional ROI: 1.5%
505 E GULLEY AVENUE Oakland, FL One or more photo(s) has been virtually staged. Welcome to this truly exceptional home off...	4 beds \| 4 baths \| 3,399 sq.ft.	$899,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.69% Airbnb Rental Income: $5064 Traditional Rental Income: $4716 Airbnb ROI: 2.87% Traditional ROI: 3.69%
2017 BOSS HEWETT STREET Oakland, FL One or more photo(s) has been virtually staged. This meticulously maintained 2,852 sq ft, ...	4 beds \| 4 baths \| 2,852 sq.ft.	$749,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.54% Airbnb Rental Income: $5064 Traditional Rental Income: $3586 Airbnb ROI: 3.17% Traditional ROI: 2.54%
219 Largovista Dr Oakland, FL 219 Largovista Dr, Oakland, FL 34787 \| Single Family Residential	5 beds \| 4 baths \| 3,951 sq.ft.	$1,099,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $3532 Airbnb ROI: N/A Traditional ROI: 1.4%
1216 HULL ISLAND DRIVE Oakland, FL Experience the ultimate lakefront lifestyle in this stunning MI Homes Endeavor, perfectly ...	5 beds \| 5 baths \| 4,224 sq.ft.	$1,799,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.03% Airbnb Rental Income: $null Traditional Rental Income: $7189 Airbnb ROI: N/A Traditional ROI: 2.03%
1108 Riverway Dr Oakland, FL 1108 Riverway Dr, Oakland, FL 34787 \| Single Family Residential	5 beds \| 3 baths \| 2,999 sq.ft.	$1,025,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.74% Airbnb Rental Income: $null Traditional Rental Income: $2822 Airbnb ROI: N/A Traditional ROI: 0.74%
2618 BOBCAT CHASE BOULEVARD Oakland, FL Welcome to this beautiful 3 bedroom, 2 bath home featuring 1,565 square feet of inviting l...	3 beds \| 2 baths \| 1,565 sq.ft.	$519,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 1.44% Airbnb Rental Income: $3912 Traditional Rental Income: $2214 Airbnb ROI: 3.21% Traditional ROI: 1.44%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oakland, FL

16834 Artimino Loop

Oakland, FL

5 beds | 5 baths | 6,676 sq.ft.

$5,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.47%

Airbnb Rental Income: $null

Traditional Rental Income: $8482

Airbnb ROI: N/A

Traditional ROI: -0.47%

16020 Pendio Dr

Oakland, FL

5 beds | 5 baths | 4,978 sq.ft.

$2,375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.32%

Airbnb Rental Income: $null

Traditional Rental Income: $8313

Airbnb ROI: N/A

Traditional ROI: 1.32%

16103 Pendio Dr

Oakland, FL

5 beds | 6 baths | 5,466 sq.ft.

$3,448,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.36%

Airbnb Rental Income: $null

Traditional Rental Income: $11634

Airbnb ROI: N/A

Traditional ROI: 1.36%

15926 Pendio Dr

Oakland, FL

6 beds | 7 baths | 8,479 sq.ft.

$5,690,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.27%

Airbnb Rental Income: $null

Traditional Rental Income: $12620

Airbnb ROI: N/A

Traditional ROI: 0.27%

16123 Pendio Dr

Oakland, FL

5 beds | 5 baths | 6,584 sq.ft.

$3,997,500

Airbnb cash on cash: N/A

Traditional cash on cash: -0.88%

Airbnb Rental Income: $null

Traditional Rental Income: $4969

Airbnb ROI: N/A

Traditional ROI: -0.88%

16000 Pendio Dr

Oakland, FL

6 beds | 7 baths | 6,973 sq.ft.

$3,150,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.1%

Airbnb Rental Income: $null

Traditional Rental Income: $7073

Airbnb ROI: N/A

Traditional ROI: 0.1%

620 N Tubb St

Oakland, FL

6 beds | 7 baths | 5,614 sq.ft.

$1,499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.33%

Airbnb Rental Income: $null

Traditional Rental Income: $11532

Airbnb ROI: N/A

Traditional ROI: 6.33%

250 N Walker St

Oakland, FL

4 beds | 2 baths | 2,469 sq.ft.

$1,145,000

Airbnb cash on cash: 1.81%

Traditional cash on cash: 0.38%

Airbnb Rental Income: $5064

Traditional Rental Income: $2504

Airbnb ROI: 1.81%