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 |
|---|---|---|---|
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: -2.01%
|
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: -2.66%
|
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: -1.96%
|
16822 Artimino LoopOakland, FL16822 Artimino Loop, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$1,300,000 |
Airbnb cash on cash: -2.66%
|
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%
|
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: -2.03%
|
15942 Pendio DrOakland, FL15942 Pendio Dr, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$875,000 |
Airbnb cash on cash: -3.03%
|
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: -1.97%
|
16748 Artimino LoopOakland, FL16748 Artimino Loop, Oakland, FL 34756 | Single Family Residential |
6 beds | 7 baths | 6,118 sq.ft. |
$4,788,500 |
Airbnb cash on cash: -1.98%
|
16217 Pendio DrOakland, FL16217 Pendio Dr, Oakland, FL 34756 | Single Family Residential |
5 beds | 4 baths | 5,060 sq.ft. |
$3,995,000 |
Airbnb cash on cash: -2%
|
15934 Pendio DrOakland, FL15934 Pendio Dr, Oakland, FL 34756 | Single Family Residential |
5 beds | 5 baths | 5,879 sq.ft. |
$4,250,000 |
Airbnb cash on cash: -1.99%
|
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: -0.77%
|
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: -1.24%
|
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: -1.7%
|
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: -1.57%
|
250 N Walker StOakland, FL250 N Walker St, Oakland, FL 34760 | Single Family Residential |
4 beds | 2 baths | 2,469 sq.ft. |
$1,049,000 |
Airbnb cash on cash: 2.15%
|
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, FLVirtually Staged. Welcome to this brand-new construction home in the heart of Oakland! Thi... |
3 beds | 2 baths | 1,170 sq.ft. |
$415,000 |
Airbnb cash on cash: 6.17%
|
239 Largovista DrOakland, FLMASSIVE PRICE PRICE ADJUSTMENT. SELLER VERY MOTIVATED. They are ready to negotiate Today!.... |
4 beds | 2 baths | 3,652 sq.ft. |
$675,900 |
Airbnb cash on cash: 4.55%
|
1750 Standing Rock CirOakland, FLWelcome to this energy efficient two story home built in 2020, ideally located in the high... |
4 beds | 2 baths | 2,614 sq.ft. |
$640,000 |
Airbnb cash on cash: 4.1%
|
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%
|
1511 Sweet Apple StOakland, FLBuyer backed out to allow you an opportunity - Welcome home to this beautiful 3 bed, 2.5 b... |
3 beds | 2 baths | 1,620 sq.ft. |
$364,500 |
Airbnb cash on cash: 5.07%
|
166 Hammock Preserve LoopOakland, FLPre-Construction. To be built. To be built. AR Homes (Arthur Rutenberg Homes) , a renowned... |
4 beds | 4 baths | 3,186 sq.ft. |
$850,000 |
Airbnb cash on cash: 3.58%
|
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%
|
1112 Hull Island DrOakland, FLWelcome to this extraordinary custom lakefront estate offering breathtaking views of Lake ... |
4 beds | 3 baths | 3,562 sq.ft. |
$1,400,000 |
Airbnb cash on cash: 0.63%
|
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%
|
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: -1.08%
|
1173 Prado LnOakland, FL1173 Prado Ln, Winter Garden, FL 34787 | Single Family Residential |
5 beds | 5 baths | 4,204 sq.ft. |
$2,380,160 |
Airbnb cash on cash: -1.62%
|
1146 Prado LnOakland, FL1146 Prado Ln, Winter Garden, FL 34787 | Single Family Residential |
5 beds | 5 baths | 3,992 sq.ft. |
$2,310,600 |
Airbnb cash on cash: -1.61%
|
1101 Eagles Pass WayOakland, FL1101 Eagles Pass Way, Winter Garden, FL 34787 | Single Family Residential |
6 beds | 5 baths | 4,104 sq.ft. |
$1,644,999 |
Airbnb cash on cash: -1.54%
|
552 Walker StOakland, FL552 Walker St, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$1,195,000 |
Airbnb cash on cash: -1.85%
|
906 Allendale LnOakland, FL906 Allendale Ln, Winter Garden, FL 34787 | Single Family Residential |
5 beds | 4 baths | 3,784 sq.ft. |
$1,725,000 |
Airbnb cash on cash: -1.56%
|
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: -1.67%
|
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. |
$689,900 |
Airbnb cash on cash: 3.53%
|
219 Largovista DrOakland, FL219 Largovista Dr, Oakland, FL 34787 | Single Family Residential |
5 beds | 4 baths | 3,951 sq.ft. |
$995,900 |
Airbnb cash on cash: -1.21%
|
2241 White Feather LoopOakland, FL2241 White Feather Loop, Oakland, FL 34787 | Single Family Residential |
3 beds | 2 baths | 2,152 sq.ft. |
$525,000 |
Airbnb cash on cash: 3.73%
|
1155 Prado LnOakland, FL1155 Prado Ln, Winter Garden, FL 34787 | Single Family Residential |
5 beds | 5 baths | 4,210 sq.ft. |
$2,575,000 |
Airbnb cash on cash: -1.64%
|
1603 Johns Cove LnOakland, FL1603 Johns Cove Ln, Oakland, FL 34787 | Single Family Residential |
6 beds | 4 baths | 4,001 sq.ft. |
$809,000 |
Airbnb cash on cash: -1.15%
|
2010 Boss Hewett StOakland, FL2010 Boss Hewett St, Oakland, FL 34787 | Single Family Residential |
5 beds | 4 baths | 3,781 sq.ft. |
$1,500,000 |
Airbnb cash on cash: -1.48%
|
1134 Prado LnOakland, FL1134 Prado Ln, Winter Garden, FL 34787 | Single Family Residential |
5 beds | 5 baths | 4,433 sq.ft. |
$2,545,000 |
Airbnb cash on cash: -1.64%
|
Real Estate investment in Oakland, FL
There are 48 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 $334. In September 2026, the average monthly cash on cash return in Oakland is 1.00%. The average monthly rental income in Oakland is $3,499.