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 |
|---|---|---|---|
16834 Artimino LoopOakland, FL16834 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
|
16020 Pendio DrOakland, FL16020 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
|
16103 Pendio DrOakland, FL16103 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
|
16842 Artimino LoopOakland, FL16842 Artimino Loop, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$1,295,000 |
Airbnb cash on cash: -1.94%
|
15926 Pendio DrOakland, FL15926 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
|
16901 Crete WayOakland, FL16901 Crete Way, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$685,000 |
Airbnb cash on cash: -1.68%
|
16802 Artimino LoopOakland, FL16802 Artimino Loop, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$1,275,000 |
Airbnb cash on cash: -1.94%
|
16822 Artimino LoopOakland, FL16822 Artimino Loop, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$1,200,000 |
Airbnb cash on cash: -1.94%
|
16123 Pendio DrOakland, FL16123 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
|
16000 Pendio DrOakland, FL16000 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
|
15942 Pendio DrOakland, FL15942 Pendio Dr, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$875,000 |
Airbnb cash on cash: -1.97%
|
17117 Crete WayOakland, FL17117 Crete Way, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$1,350,000 |
Airbnb cash on cash: -1.94%
|
620 N Tubb StOakland, FL620 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
|
410 W Gulley AveOakland, FL410 W Gulley Ave, Oakland, FL 34760 | Other |
N/A beds | N/A baths | N/A |
$800,000 |
Airbnb cash on cash: -0.4%
|
250 N Walker StOakland, FL250 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%
|
38 S Pollard StOakland, FL38 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%
|
1318 PAINTED BUNTING AVENUEOakland, FLOne or more photo(s) has been virtually staged. Youâre going to love this beautifully ma... |
2 beds | 3 baths | 1,472 sq.ft. |
$360,000 |
Airbnb cash on cash: 3.3%
|
1258 RIDGE LAKE WAYOakland, FLPre-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%
|
2120 GOPHER TORTOISE TERRACEOakland, FLWelcome to 2120 Gopher Tortoise Terrace in charming Oakland, Florida, a beautifully mainta... |
3 beds | 3 baths | 1,620 sq.ft. |
$379,900 |
Airbnb cash on cash: 4.98%
|
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. |
$796,000 |
Airbnb cash on cash: N/A
|
2065 White Feather LoopOakland, FLWelcome 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%
|
2100 Gopher Tortoise TerOakland, FL2100 Gopher Tortoise Ter, Oakland, FL 34787 | Townhouse |
2 beds | 2 baths | 1,620 sq.ft. |
$375,000 |
Airbnb cash on cash: 3.57%
|
537 N PollardOakland, FL537 N Pollard, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$895,000 |
Airbnb cash on cash: -0.76%
|
1270 Stationside Drive DrOakland, FL1270 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%
|
1156 CIVITAS WAYOakland, FLMotivated 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%
|
2228 Gopher Tortoise TerOakland, FL2228 Gopher Tortoise Ter, Oakland, FL 34787 | Townhouse |
3 beds | 2 baths | 1,620 sq.ft. |
$395,000 |
Airbnb cash on cash: 4.88%
|
556 Walker StOakland, FL556 Walker St, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$1,295,000 |
Airbnb cash on cash: -1.09%
|
2222 GOPHER TORTOISE TERRACEOakland, FLYOU Must see this absolutely Gorgeous 3BEDS,3 FULL BATH Townhouse in Oakland. located Betw... |
3 beds | 3 baths | 1,809 sq.ft. |
$416,900 |
Airbnb cash on cash: 4.13%
|
1412 Johns Cove LnOakland, FL1412 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%
|
812 JOHNS POINT DRIVEOakland, FLExperience 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
|
1231 Foltz LoopOakland, FL1231 Foltz Loop, Oakland, FL 34787 | Single Family Residential |
4 beds | 4 baths | 3,134 sq.ft. |
$874,900 |
Airbnb cash on cash: 2.72%
|
2117 Gopher Tortoise TerOakland, FL2117 Gopher Tortoise Ter, Oakland, FL 34787 | Townhouse |
2 beds | 2 baths | 1,497 sq.ft. |
$364,900 |
Airbnb cash on cash: 3.64%
|
505 E GULLEY AVENUEOakland, FLOne 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%
|
2017 BOSS HEWETT STREETOakland, FLOne 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%
|
219 Largovista DrOakland, FL219 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
|
1216 HULL ISLAND DRIVEOakland, FLExperience 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
|
1108 Riverway DrOakland, FL1108 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
|
2618 BOBCAT CHASE BOULEVARDOakland, FLWelcome 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%
|
Real Estate investment in Oakland, FL
There are 38 properties for sale in the city of Oakland . The median list price in Oakland is $689,000 and the average price per square foot is $368. In May 2026, the average monthly cash on cash return in Oakland is 1.00%. The average monthly rental income in Oakland is $2,680.