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 |
|---|---|---|---|
1319 JOHNS COVE LNOakland, FLWelcome 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%
|
2127 BAY LINE ROADOakland, FLWELCOME 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%
|
1873 WHITE FEATHER LOOPOakland, FLThis 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%
|
1787 WHITE FEATHER LOOPOakland, 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%
|
1877 STANDING ROCK CIRCLEOakland, FLUnder 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%
|
1301 JOHNS COVE LANEOakland, FLBack 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%
|
500 W OAKLAND AVENUEOakland, FLOne 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%
|
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%
|
619 LARGOVISTA DRIVEOakland, FLWelcome 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
|
409 E GULLEY AVENUEOakland, FLTucked 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%
|
410 E GULLEY AVENUEOakland, FLCharming 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
|
1382 FOLTZ LOOPOakland, FLUnder 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%
|
310 E GULLEY AVENUEOakland, FLUnder 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%
|
2340 STANDING ROCK CIRCLEOakland, FLWelcome 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
|
610 STRIHAL LOOPOakland, 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%
|
312 W HULL AVENUEOakland, FLDiscover 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%
|
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
|
2035 WHITE FEATHER LOOPOakland, FLWelcome 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%
|
233 LARGOVISTA DRIVEOakland, FLLuxury, 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%
|
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. |
$514,913 |
Airbnb cash on cash: 3.61%
|
2435 STANDING ROCK CIRCLEOakland, FLPerfectly 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%
|
2163 WHITE FEATHER LOOPOakland, 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%
|
2120 GOPHER TORTOISE TERRACEOakland, FL***Rare Financial Advantage- Low interest rate of 2.75% ASSUMABLE LOAN is available with a... |
3 beds | 3 baths | 1,620 sq.ft. |
$393,000 |
Airbnb cash on cash: 4.85%
|
309 W OAKLAND AVENUEOakland, 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%
|
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. |
$475,000 |
Airbnb cash on cash: 3.92%
|
2090 STANDING ROCK CIRCLEOakland, FLStunning 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%
|
1143 BOBCAT CHASE BOULEVARDOakland, FLOne 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%
|
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. |
$699,900 |
Airbnb cash on cash: 3.69%
|
Real Estate investment in Oakland, FL
There are 28 properties for sale in the city of Oakland . The median list price in Oakland is $564,500 and the average price per square foot is $235. In September 2025, the average monthly cash on cash return in Oakland is 3.00%. The average monthly rental income in Oakland is $2,766.