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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
507 W OAKLAND AVENUEOakland, FLOne or more photo(s) has been virtually staged. One or more photo(s) has been virtually st... |
3 beds | 2 baths | 1,338 sq.ft. |
$364,900 |
Airbnb cash on cash: 6.69%
|
1787 WHITE FEATHER LOOPOakland, FLUnder contract-accepting backup offers. **This home qualifies for loan options with NO DOW... |
3 beds | 3 baths | 2,152 sq.ft. |
$525,000 |
Airbnb cash on cash: 3.72%
|
1304 FOLTZ LOOPOakland, FLImpeccably maintained 5 bed 3 bath,3563 sq/ft home that combines luxury with natural beaut... |
5 beds | 3 baths | 3,563 sq.ft. |
$999,000 |
Airbnb cash on cash: N/A
|
1258 RIDGE LAKE WAYOakland, FLPre-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%
|
610 STRIHAL LOOPOakland, FLWelcome to 610 Strihal Loop, a beautifully updated home in a desirable Oakland location. S... |
4 beds | 2 baths | 2,490 sq.ft. |
$535,000 |
Airbnb cash on cash: 6.13%
|
1207 RIDGE LAKE WAYOakland, FLPre-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
|
2755 BOBCAT CHASE BOULEVARDOakland, FLLive just minutes from the charm of Downtown Winter Garden in the desirable Oakland commun... |
3 beds | 3 baths | 1,822 sq.ft. |
$500,000 |
Airbnb cash on cash: 3.74%
|
2435 STANDING ROCK CIRCLEOakland, FLPerfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and... |
4 beds | 3 baths | 2,017 sq.ft. |
$477,500 |
Airbnb cash on cash: 6.2%
|
2023 WHITE FEATHER LOOPOakland, FLOne 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. |
$455,000 |
Airbnb cash on cash: 4.13%
|
2090 STANDING ROCK CIRCLEOakland, FLPrice reduced to $585,000 on this Stunning Home in Oakland Trails! This immaculate 3-bedr... |
3 beds | 3 baths | 2,010 sq.ft. |
$585,000 |
Airbnb cash on cash: 3.6%
|
326 LARGOVISTA DRIVEOakland, FLWelcome to your dream home in the highly sought-after Johns Landing community! This immacu... |
4 beds | 3 baths | 3,182 sq.ft. |
$649,900 |
Airbnb cash on cash: 4.05%
|
529 JOHNS LANDING WAYOakland, FLWelcome 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%
|
2690 BOBCAT CHASE BOULEVARDOakland, FLLove Where You Live â in Longleaf at Oakland! ? Welcome to Longleaf at Oakland, one o... |
3 beds | 2 baths | 1,554 sq.ft. |
$465,000 |
Airbnb cash on cash: 4.48%
|
2218 GOPHER TORTOISE TERRACEOakland, FLUnder contract-accepting backup offers. Enjoy low-maintenance living in this beautifully k... |
2 beds | 3 baths | 1,472 sq.ft. |
$389,000 |
Airbnb cash on cash: 3.29%
|
501 E OAKLAND AVENUEOakland, FLOne or more photo(s) has been virtually staged. Welcome to your private retreat in the hea... |
4 beds | 4 baths | 3,448 sq.ft. |
$899,000 |
Airbnb cash on cash: 2.91%
|
1751 STANDING ROCK CIRCLEOakland, FLUnder contract-accepting backup offers. Nestled in the highly desirable Oakland Trails com... |
5 beds | 3 baths | 3,493 sq.ft. |
$749,000 |
Airbnb cash on cash: N/A
|
1970 STANDING ROCK CIRCLEOakland, FLDiscover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath hom... |
5 beds | 3 baths | 3,528 sq.ft. |
$800,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Oakland, FL
There are 17 properties for sale in the city of Oakland . The median list price in Oakland is $585,000 and the average price per square foot is $220. In December 2025, the average monthly cash on cash return in Oakland is 3.00%. The average monthly rental income in Oakland is $2,766.