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 27 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
1319 JOHNS COVE LN Oakland, FL Welcome to a home that blends comfort, function, and fun for all behind the gates of a pea...	4 beds \| 6 baths \| 3,564 sq.ft.	$799,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 9.35% Airbnb Rental Income: $5064 Traditional Rental Income: $9053 Airbnb ROI: 2.6% Traditional ROI: 9.35%
2127 BAY LINE ROAD Oakland, FL WELCOME HOME TO HULL ISLAND! This home offers a serene retreat for those looking for a ble...	4 beds \| 4 baths \| 2,858 sq.ft.	$650,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.64% Airbnb Rental Income: $5064 Traditional Rental Income: $3607 Airbnb ROI: 4.34% Traditional ROI: 3.64%
1873 WHITE FEATHER LOOP Oakland, FL This well-designed 4-bedroom, 3-bathroom home with a private office is located in one of O...	4 beds \| 3 baths \| 2,418 sq.ft.	$579,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 2.86% Airbnb Rental Income: $5064 Traditional Rental Income: $2899 Airbnb ROI: 4.96% Traditional ROI: 2.86%
1787 WHITE FEATHER LOOP Oakland, FL **This home qualifies for loan options with NO DOWN PAYMENT required, 100% financing avail...	3 beds \| 3 baths \| 2,152 sq.ft.	$525,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 3.25% Airbnb Rental Income: $3912 Traditional Rental Income: $2839 Airbnb ROI: 3.72% Traditional ROI: 3.25%
1877 STANDING ROCK CIRCLE Oakland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 2 baths \| 2,008 sq.ft.	$520,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 2.56% Airbnb Rental Income: $3912 Traditional Rental Income: $2515 Airbnb ROI: 3.71% Traditional ROI: 2.56%
1301 JOHNS COVE LANE Oakland, FL Back on the market! Huge price improvement!! Motivated sellers! Donât miss out on this ...	4 beds \| 2 baths \| 2,495 sq.ft.	$749,999	Airbnb cash on cash: 3.87% Traditional cash on cash: 2.46% Airbnb Rental Income: $5064 Traditional Rental Income: $3046 Airbnb ROI: 3.87% Traditional ROI: 2.46%
500 W OAKLAND AVENUE Oakland, FL One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Hi...	3 beds \| 2 baths \| 1,336 sq.ft.	$375,000	Airbnb cash on cash: 6.41% Traditional cash on cash: 4.58% Airbnb Rental Income: $3912 Traditional Rental Income: $2425 Airbnb ROI: 6.41% Traditional ROI: 4.58%
1258 RIDGE LAKE WAY Oakland, FL Pre-Construction. To be built. Welcome 1258 Ridge Lake Way, nestled in the final phase of ...	4 beds \| 4 baths \| 4,557 sq.ft.	$1,996,500	Airbnb cash on cash: 0.92% Traditional cash on cash: 1.04% Airbnb Rental Income: $5064 Traditional Rental Income: $4252 Airbnb ROI: 0.92% Traditional ROI: 1.04%
619 LARGOVISTA DRIVE Oakland, FL Welcome to 619 Largovista Drâa custom-built, recently remodeled home in the highly desir...	5 beds \| 4 baths \| 3,728 sq.ft.	$964,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $4418 Airbnb ROI: N/A Traditional ROI: 2.69%
409 E GULLEY AVENUE Oakland, FL Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home cap...	3 beds \| 2 baths \| 1,630 sq.ft.	$500,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.38% Airbnb Rental Income: $3912 Traditional Rental Income: $2530 Airbnb ROI: 4.54% Traditional ROI: 3.38%
410 E GULLEY AVENUE Oakland, FL Charming 1959 Gem in the Town of Oakland with In-Law Suite. Find where timeless character...	5 beds \| 3 baths \| 2,458 sq.ft.	$645,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.95% Airbnb Rental Income: $null Traditional Rental Income: $3867 Airbnb ROI: N/A Traditional ROI: 4.95%
1382 FOLTZ LOOP Oakland, FL Under contract-accepting backup offers. **ASSUMABLE VA MORTGAGE AT A 5.375 INTEREST RATE...	4 beds \| 3 baths \| 2,268 sq.ft.	$648,900	Airbnb cash on cash: 4% Traditional cash on cash: 2.09% Airbnb Rental Income: $5064 Traditional Rental Income: $2876 Airbnb ROI: 4% Traditional ROI: 2.09%
310 E GULLEY AVENUE Oakland, FL Under contract-accepting backup offers. Welcome to 310 E Gulley Aveâthis inviting 3-bedr...	3 beds \| 2 baths \| 1,419 sq.ft.	$489,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 3.92% Airbnb Rental Income: $3912 Traditional Rental Income: $2482 Airbnb ROI: 5.21% Traditional ROI: 3.92%
2340 STANDING ROCK CIRCLE Oakland, FL Welcome to an extraordinary residence nestled in the highly sought-after Oakland Trails co...	5 beds \| 3 baths \| 3,493 sq.ft.	$749,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.58% Airbnb Rental Income: $null Traditional Rental Income: $3353 Airbnb ROI: N/A Traditional ROI: 2.58%
610 STRIHAL LOOP Oakland, FL * Seller is giving $10,000 in concessions for closing costs/prepaids or a rate buy down. W...	4 beds \| 2 baths \| 2,490 sq.ft.	$585,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 2.98% Airbnb Rental Income: $5064 Traditional Rental Income: $2640 Airbnb ROI: 5.52% Traditional ROI: 2.98%
312 W HULL AVENUE Oakland, FL Discover the wonderful blend of functionality, efficiency, and flexibility in this beautif...	4 beds \| 2 baths \| 1,681 sq.ft.	$495,000	Airbnb cash on cash: 6.58% Traditional cash on cash: 3.02% Airbnb Rental Income: $5064 Traditional Rental Income: $2384 Airbnb ROI: 6.58% Traditional ROI: 3.02%
1207 RIDGE LAKE WAY Oakland, FL Pre-Construction. To be built. This is a pre-construction, to be built, custom home locate...	5 beds \| 4 baths \| 3,909 sq.ft.	$1,700,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.42% Airbnb Rental Income: $null Traditional Rental Income: $4308 Airbnb ROI: N/A Traditional ROI: 1.42%
2035 WHITE FEATHER LOOP Oakland, FL Welcome to 2035 White Feather Loop, a stunning haven nestled in the serene community of Oa...	3 beds \| 3 baths \| 2,082 sq.ft.	$550,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.14% Airbnb Rental Income: $3912 Traditional Rental Income: $2766 Airbnb ROI: 3.74% Traditional ROI: 3.14%
233 LARGOVISTA DRIVE Oakland, FL Luxury, Convenience, and Comfort in Johnâs Landing! This thoughtfully updated and move-i...	4 beds \| 2 baths \| 2,176 sq.ft.	$534,900	Airbnb cash on cash: 5.94% Traditional cash on cash: 2.74% Airbnb Rental Income: $5064 Traditional Rental Income: $2431 Airbnb ROI: 5.94% Traditional ROI: 2.74%
2755 BOBCAT CHASE BOULEVARD Oakland, FL Live just minutes from the charm of Downtown Winter Garden in the desirable Oakland commun...	3 beds \| 3 baths \| 1,822 sq.ft.	$514,913	Airbnb cash on cash: 3.61% Traditional cash on cash: 2.59% Airbnb Rental Income: $3912 Traditional Rental Income: $2583 Airbnb ROI: 3.61% Traditional ROI: 2.59%
2435 STANDING ROCK CIRCLE Oakland, FL Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and...	4 beds \| 3 baths \| 2,017 sq.ft.	$528,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 2.79% Airbnb Rental Income: $5064 Traditional Rental Income: $2685 Airbnb ROI: 5.52% Traditional ROI: 2.79%
2163 WHITE FEATHER LOOP Oakland, FL *Seller is offering $10,000 closing cost contribution to any buyer!*This recently buil...	3 beds \| 3 baths \| 1,744 sq.ft.	$489,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 2.91% Airbnb Rental Income: $3912 Traditional Rental Income: $2441 Airbnb ROI: 4.28% Traditional ROI: 2.91%
309 W OAKLAND AVENUE Oakland, FL Seller is willing to give concessions towards closing costs! Charming Renovated Home in ...	4 beds \| 3 baths \| 2,386 sq.ft.	$779,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 2.38% Airbnb Rental Income: $5064 Traditional Rental Income: $3058 Airbnb ROI: 3.72% Traditional ROI: 2.38%
2023 WHITE FEATHER LOOP Oakland, FL One or more photo(s) has been virtually staged. Your dream home is waiting for you! This h...	3 beds \| 3 baths \| 2,089 sq.ft.	$475,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 3.23% Airbnb Rental Income: $3912 Traditional Rental Income: $2766 Airbnb ROI: 3.92% Traditional ROI: 3.23%
2090 STANDING ROCK CIRCLE Oakland, FL Stunning Home in Oakland Trails! This immaculate 3-bedroom, 2.5 bath home blends thoughtf...	3 beds \| 3 baths \| 2,000 sq.ft.	$649,900	Airbnb cash on cash: 3.14% Traditional cash on cash: 2.66% Airbnb Rental Income: $3912 Traditional Rental Income: $2777 Airbnb ROI: 3.14% Traditional ROI: 2.66%
1143 BOBCAT CHASE BOULEVARD Oakland, FL One or more photo(s) has been virtually staged. Take advantage of a 1% of the loan amount ...	3 beds \| 3 baths \| 1,811 sq.ft.	$510,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.27% Airbnb Rental Income: $3912 Traditional Rental Income: $2608 Airbnb ROI: 3.24% Traditional ROI: 2.27%
326 LARGOVISTA DRIVE Oakland, FL Welcome to your dream home in the highly sought-after Johns Landing community! This immacu...	4 beds \| 3 baths \| 3,182 sq.ft.	$699,900	Airbnb cash on cash: 3.69% Traditional cash on cash: 2.92% Airbnb Rental Income: $5064 Traditional Rental Income: $3527 Airbnb ROI: 3.69% Traditional ROI: 2.92%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oakland, FL

1319 JOHNS COVE LN

Oakland, FL

4 beds | 6 baths | 3,564 sq.ft.

$799,000

Airbnb cash on cash: 2.6%

Traditional cash on cash: 9.35%

Airbnb Rental Income: $5064

Traditional Rental Income: $9053

Airbnb ROI: 2.6%

Traditional ROI: 9.35%

2127 BAY LINE ROAD

Oakland, FL

4 beds | 4 baths | 2,858 sq.ft.

$650,000

Airbnb cash on cash: 4.34%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $5064

Traditional Rental Income: $3607

Airbnb ROI: 4.34%

Traditional ROI: 3.64%

1873 WHITE FEATHER LOOP

Oakland, FL

4 beds | 3 baths | 2,418 sq.ft.

$579,000

Airbnb cash on cash: 4.96%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $5064

Traditional Rental Income: $2899

Airbnb ROI: 4.96%

Traditional ROI: 2.86%

1787 WHITE FEATHER LOOP

Oakland, FL

3 beds | 3 baths | 2,152 sq.ft.

$525,000

Airbnb cash on cash: 3.72%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $3912

Traditional Rental Income: $2839

Airbnb ROI: 3.72%

Traditional ROI: 3.25%

1877 STANDING ROCK CIRCLE

Oakland, FL

3 beds | 2 baths | 2,008 sq.ft.

$520,000

Airbnb cash on cash: 3.71%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $3912

Traditional Rental Income: $2515

Airbnb ROI: 3.71%

Traditional ROI: 2.56%

1301 JOHNS COVE LANE

Oakland, FL

4 beds | 2 baths | 2,495 sq.ft.

$749,999

Airbnb cash on cash: 3.87%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $5064

Traditional Rental Income: $3046

Airbnb ROI: 3.87%

Traditional ROI: 2.46%

500 W OAKLAND AVENUE

Oakland, FL

3 beds | 2 baths | 1,336 sq.ft.

$375,000

Airbnb cash on cash: 6.41%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $3912

Traditional Rental Income: $2425

Airbnb ROI: 6.41%

Traditional ROI: 4.58%

1258 RIDGE LAKE WAY

Oakland, FL

4 beds | 4 baths | 4,557 sq.ft.

$1,996,500

Airbnb cash on cash: 0.92%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $5064

Traditional Rental Income: $4252

Airbnb ROI: 0.92%