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: -2.02%
|
16103 Pendio DrOakland, FL16103 Pendio Dr, MONTVERDE, FL 34756 | Single Family Residential |
5 beds | 6 baths | 5,466 sq.ft. |
$3,528,000 |
Airbnb cash on cash: -2.1%
|
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: -2.55%
|
15926 Pendio DrOakland, FL15926 Pendio Dr, Oakland, FL 34756 | Single Family Residential |
6 beds | 7 baths | 8,479 sq.ft. |
$5,499,000 |
Airbnb cash on cash: -2.02%
|
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: -2.57%
|
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: -2.61%
|
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: -2.08%
|
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: -2.13%
|
15942 Pendio DrOakland, FL15942 Pendio Dr, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$875,000 |
Airbnb cash on cash: -2.87%
|
16744 Artimino LoopOakland, FL16744 Artimino Loop, Oakland, FL 34756 | Single Family Residential |
5 beds | 7 baths | 6,475 sq.ft. |
$5,087,750 |
Airbnb cash on cash: -2.04%
|
16129 Pendio DrOakland, FL16129 Pendio Dr, Oakland, FL 34756 | Single Family Residential |
4 beds | 4 baths | 4,051 sq.ft. |
$2,962,840 |
Airbnb cash on cash: -0.88%
|
16 Oakland Pointe CirOakland, FLMove-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, W... |
5 beds | 3 baths | 3,413 sq.ft. |
$799,999 |
Airbnb cash on cash: -1.16%
|
409 E Gulley AveOakland, FLTucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home cap... |
3 beds | 2 baths | 1,630 sq.ft. |
$499,999 |
Airbnb cash on cash: 1.23%
|
620 N Tubb StOakland, FL620 N Tubb St, Oakland, FL 34760 | Single Family Residential |
6 beds | 7 baths | 5,614 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -1.49%
|
312 Briley AveOakland, FL312 Briley Ave, Oakland, FL 34760 | Single Family Residential |
6 beds | 6 baths | 5,144 sq.ft. |
$3,295,000 |
Airbnb cash on cash: -1.8%
|
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: -1.4%
|
250 N Walker StOakland, FL250 N Walker St, Oakland, FL 34760 | Single Family Residential |
4 beds | 2 baths | 2,469 sq.ft. |
$1,125,000 |
Airbnb cash on cash: 1.88%
|
38 S Pollard StOakland, FL38 S Pollard St, Oakland, FL 34760 | Single Family Residential |
4 beds | 2 baths | 1,872 sq.ft. |
$619,999 |
Airbnb cash on cash: 4.92%
|
521 W Herriott AveOakland, FL521 W Herriott Ave, Oakland, FL 34760 | Single Family Residential |
3 beds | 2 baths | 1,170 sq.ft. |
$455,000 |
Airbnb cash on cash: 1.48%
|
1937 Standing Rock CirOakland, FLOakland Trails is located right on the scenic West Orange Trail and just a bike ride away ... |
3 beds | 2 baths | 2,069 sq.ft. |
$499,000 |
Airbnb cash on cash: 0.68%
|
2259 White Feather LoopOakland, FLABSOLUTELY STUNNING 4/2.5 PLUS LOFT HOME LOCATED ON A CORNER LOT IN OAKLAND TRAILS. UPON E... |
4 beds | 2 baths | 2,204 sq.ft. |
$515,000 |
Airbnb cash on cash: 6.14%
|
710 Regina CirOakland, FLExperience the ultimate gated community of John's Lake in this captivating home with a pri... |
5 beds | 4 baths | 3,285 sq.ft. |
$659,900 |
Airbnb cash on cash: -1.02%
|
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%
|
223 Largovista DrOakland, FLThis beautiful 4-bedroom, 2.5-bath home offers plenty of space, both inside and out, makin... |
4 beds | 2 baths | 2,486 sq.ft. |
$540,000 |
Airbnb cash on cash: 5.4%
|
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. |
$639,000 |
Airbnb cash on cash: 4.84%
|
1970 Standing Rock CirOakland, 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: -1.48%
|
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. |
$539,900 |
Airbnb cash on cash: 0.6%
|
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: 0.07%
|
13861 Easdale AlyOakland, FL13861 Easdale Aly, Oakland, FL 34787 | Townhouse |
4 beds | 3 baths | 2,031 sq.ft. |
$539,000 |
Airbnb cash on cash: 5.6%
|
13877 Easdale AlyOakland, FL13877 Easdale Aly, Oakland, FL 34787 | Townhouse |
4 beds | 4 baths | 2,593 sq.ft. |
$615,000 |
Airbnb cash on cash: 4.69%
|
12928 Westhaven Oak DrOakland, FL12928 Westhaven Oak Dr, Oakland, FL 34787 | Single Family Residential |
5 beds | 4 baths | 3,626 sq.ft. |
$929,000 |
Airbnb cash on cash: -1.46%
|
14780 Field Daisy DrOakland, FL14780 Field Daisy Dr, Oakland, FL 34787 | Single Family Residential |
4 beds | 4 baths | 2,441 sq.ft. |
$653,118 |
Airbnb cash on cash: 4.16%
|
1412 Johns Cove LnOakland, FL1412 Johns Cove Ln, Oakland, FL 34787 | Single Family Residential |
4 beds | 4 baths | 3,613 sq.ft. |
$1,509,900 |
Airbnb cash on cash: 0.79%
|
812 Johns Point DrOakland, FLExperience unparalleled lakefront living in this fully renovated Mediterranean-style estat... |
5 beds | 6 baths | 4,373 sq.ft. |
$2,550,000 |
Airbnb cash on cash: -1.8%
|
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. |
$350,000 |
Airbnb cash on cash: 0.13%
|
2017 Boss Hewett StOakland, FLVirtually Staged. Enjoy single-level living in lakefront Hull Island in this meticulously ... |
4 beds | 4 baths | 2,852 sq.ft. |
$699,900 |
Airbnb cash on cash: 3.47%
|
219 Largovista DrOakland, FL219 Largovista Dr, Oakland, FL 34787 | Single Family Residential |
5 beds | 4 baths | 3,951 sq.ft. |
$1,025,000 |
Airbnb cash on cash: -1.53%
|
12788 Sunset Walk DrOakland, FL161 Sunset Walk Dr, Winter Garden, FL 34787 | Townhouse |
4 beds | 3 baths | 2,031 sq.ft. |
$529,025 |
Airbnb cash on cash: 5.75%
|
14001 RUGBY STREETOakland, FLOne or more photo(s) has been virtually staged. Price improved and ready for its next owne... |
5 beds | 4 baths | 4,240 sq.ft. |
$825,000 |
Airbnb cash on cash: -1.29%
|
Real Estate investment in Oakland, FL
There are 73 properties for sale in the city of Oakland . The median list price in Oakland is $682,592 and the average price per square foot is $340. In August 2026, the average monthly cash on cash return in Oakland is 2.00%. The average monthly rental income in Oakland is $2,779.