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: 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: -1.76%
|
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: N/A
|
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: -1.76%
|
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. |
$3,100,000 |
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: -1.7%
|
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: N/A
|
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: N/A
|
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: N/A
|
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: N/A
|
16221 Pendio DrOakland, FL16221 Pendio Dr, Oakland, FL 34756 | Single Family Residential |
5 beds | 5 baths | 4,626 sq.ft. |
$3,238,200 |
Airbnb cash on cash: N/A
|
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: N/A
|
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: N/A
|
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: 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: -0.12%
|
250 N Walker StOakland, FL250 N Walker St, Oakland, FL 34760 | Single Family Residential |
4 beds | 2 baths | 2,469 sq.ft. |
$999,000 |
Airbnb cash on cash: 2.35%
|
38 S Pollard StOakland, FL38 S Pollard St, Oakland, FL 34760 | Single Family Residential |
4 beds | 2 baths | 1,872 sq.ft. |
$619,000 |
Airbnb cash on cash: 4.93%
|
100 Mather Smith DrOakland, FL100 Mather Smith Dr, Oakland, FL 34760 | Single Family Residential |
3 beds | 2 baths | 1,571 sq.ft. |
$600,000 |
Airbnb cash on cash: 3.94%
|
137 Petris AveOakland, FL137 Petris Ave, Oakland, FL 34760 | Single Family Residential |
4 beds | 3 baths | 3,620 sq.ft. |
$1,495,000 |
Airbnb cash on cash: 0.95%
|
81 Millholland StOakland, FL81 Millholland St, Oakland, FL 34760 | Single Family Residential |
3 beds | 3 baths | 3,887 sq.ft. |
$1,275,000 |
Airbnb cash on cash: 0.8%
|
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. |
$355,000 |
Airbnb cash on cash: 6.42%
|
150 Hammock Preserve LoopOakland, FLUnder Construction. Welcome to the charming, storybook community of Oakland Park! This col... |
4 beds | 3 baths | 2,246 sq.ft. |
$890,000 |
Airbnb cash on cash: 3.32%
|
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: 3.57%
|
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: N/A
|
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: N/A
|
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: N/A
|
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: N/A
|
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: -0.87%
|
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: N/A
|
13861 Easdale AlyOakland, FL13861 Easdale Aly, Oakland, FL 34787 | Townhouse |
4 beds | 3 baths | 2,031 sq.ft. |
$499,000 |
Airbnb cash on cash: 6.2%
|
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%
|
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: N/A
|
Real Estate investment in Oakland, FL
There are 82 properties for sale in the city of Oakland . The median list price in Oakland is $735,713 and the average price per square foot is $353. In October 2026, the average monthly cash on cash return in Oakland is 2.00%. The average monthly rental income in Oakland is $2,626.