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.

Investment Property for Sale in Oakland, FL

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
1301 JOHNS COVE LANE Oakland, FL Under contract-accepting backup offers. Back on the market! Huge price improvement!! Moti...	4 beds \| 2 baths \| 2,495 sq.ft.	$729,999	Airbnb cash on cash: 4% Traditional cash on cash: 2.56% Airbnb Rental Income: $5064 Traditional Rental Income: $3046 Airbnb ROI: 4% Traditional ROI: 2.56%
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%
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%
2340 STANDING ROCK CIRCLE Oakland, FL Under contract-accepting backup offers. Welcome to an extraordinary residence nestled in t...	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 SELLERS MOTIVATED!!!! $10,000 Seller Concession offered at closing. Welcome to your beauti...	4 beds \| 2 baths \| 2,490 sq.ft.	$570,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 3.08% Airbnb Rental Income: $5064 Traditional Rental Income: $2640 Airbnb ROI: 5.69% Traditional ROI: 3.08%
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%
233 LARGOVISTA DRIVE Oakland, FL Under contract-accepting backup offers. Luxury, Convenience, and Comfort in Johnâs Landi...	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.	$489,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 3.09% Airbnb Rental Income: $5064 Traditional Rental Income: $2685 Airbnb ROI: 6.03% Traditional ROI: 3.09%
2163 WHITE FEATHER LOOP Oakland, FL Under contract-accepting backup offers. This recently built energy-efficient home, constru...	3 beds \| 3 baths \| 1,744 sq.ft.	$475,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 3.02% Airbnb Rental Income: $3912 Traditional Rental Income: $2441 Airbnb ROI: 4.44% Traditional ROI: 3.02%
2120 GOPHER TORTOISE TERRACE Oakland, FL Welcome Home to Longleaf at Oakland! Discover this beautifully upgraded townhouse, perfect...	3 beds \| 3 baths \| 1,620 sq.ft.	$390,000	Airbnb cash on cash: 4.9% Traditional cash on cash: 3.02% Airbnb Rental Income: $3912 Traditional Rental Income: $2385 Airbnb ROI: 4.9% Traditional ROI: 3.02%
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.	$470,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 3.27% Airbnb Rental Income: $3912 Traditional Rental Income: $2766 Airbnb ROI: 3.97% Traditional ROI: 3.27%
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.	$614,900	Airbnb cash on cash: 3.38% Traditional cash on cash: 2.87% Airbnb Rental Income: $3912 Traditional Rental Income: $2777 Airbnb ROI: 3.38% Traditional ROI: 2.87%
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.	$674,900	Airbnb cash on cash: 3.87% Traditional cash on cash: 3.07% Airbnb Rental Income: $5064 Traditional Rental Income: $3527 Airbnb ROI: 3.87% Traditional ROI: 3.07%
2217 GOPHER TORTOISE TERRACE Oakland, FL Priced aggressively! Welcome to 2217 Gopher Tortoise Terrace, an exquisite townhome nestle...	2 beds \| 3 baths \| 1,472 sq.ft.	$375,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 2.83% Airbnb Rental Income: $3176 Traditional Rental Income: $2415 Airbnb ROI: 2.95% Traditional ROI: 2.83%
529 JOHNS LANDING WAY Oakland, FL Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-ba...	4 beds \| 3 baths \| 2,650 sq.ft.	$675,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 3.84% Airbnb Rental Income: $5064 Traditional Rental Income: $3592 Airbnb ROI: 4.53% Traditional ROI: 3.84%

Real Estate investment in Oakland, FL

There are 17 properties for sale in the city of Oakland . The median list price in Oakland is $534,900 and the average price per square foot is $219. In October 2025, the average monthly cash on cash return in Oakland is 3.00%. The average monthly rental income in Oakland is $2,663.

Oakland, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 17 investment properties available for sale in Oakland.

In 2025, the best neighborhood to buy investment property is Oakland.

The ROI for Short-Term is higher than the Long-Term in Oakland with average rental income of $3,912.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, FL

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%

1301 JOHNS COVE LANE

Oakland, FL

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

$729,999

Airbnb cash on cash: 4%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $5064

Traditional Rental Income: $3046

Airbnb ROI: 4%

Traditional ROI: 2.56%

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%

Traditional ROI: 1.04%

409 E GULLEY AVENUE

Oakland, FL

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%

2340 STANDING ROCK CIRCLE

Oakland, FL

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

4 beds | 2 baths | 2,490 sq.ft.

$570,000

Airbnb cash on cash: 5.69%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $5064

Traditional Rental Income: $2640

Airbnb ROI: 5.69%

Traditional ROI: 3.08%

1207 RIDGE LAKE WAY

Oakland, FL

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%

233 LARGOVISTA DRIVE

Oakland, FL

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%