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. |
$2,525,000 |
Airbnb cash on cash: N/A
|
16039 Pendio DrOakland, FL16039 Pendio Dr, Oakland, FL 34756 | Single Family Residential |
5 beds | 6 baths | 6,475 sq.ft. |
$3,850,000 |
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%
|
16015 Pendio DrOakland, FL16015 Pendio Dr, Oakland, FL 34756 | Other |
N/A beds | N/A baths | N/A |
$595,000 |
Airbnb cash on cash: -2%
|
15926 Pendio DrOakland, FL15926 Pendio Dr, Oakland, FL 34756 | Single Family Residential |
6 beds | 7 baths | 8,479 sq.ft. |
$5,990,000 |
Airbnb cash on cash: N/A
|
1118 Sarah Mathews DrOakland, FL1118 Sarah Mathews Dr, Oakland, FL 34760 | Single Family Residential |
4 beds | 4 baths | 3,902 sq.ft. |
$2,300,000 |
Airbnb cash on cash: -0.12%
|
620 N Tubb StOakland, FL620 N Tubb St, Oakland, FL 34760 | Single Family Residential |
6 beds | 7 baths | 5,614 sq.ft. |
$1,650,000 |
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. |
$2,995,000 |
Airbnb cash on cash: N/A
|
101 N Starr StOakland, FL101 N Starr St, Oakland, FL 34760 | Single Family Residential |
3 beds | 3 baths | 2,502 sq.ft. |
$1,450,000 |
Airbnb cash on cash: 0.33%
|
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%
|
507 W OAKLAND AVENUEOakland, FLOne or more photo(s) has been virtually staged. One or more photo(s) has been virtually st... |
3 beds | 2 baths | 1,338 sq.ft. |
$364,900 |
Airbnb cash on cash: 6.69%
|
847 Cura CtOakland, FLWelcome Home to this highly desirable gated, waterfront community of John's Landing. This ... |
4 beds | 3 baths | 3,000 sq.ft. |
$645,000 |
Airbnb cash on cash: 4.99%
|
2029 White Feather LoopOakland, FLLooking for a "like new" home with the pros of new construction, but without the con of ha... |
3 beds | 2 baths | 1,909 sq.ft. |
$489,900 |
Airbnb cash on cash: 4.41%
|
2139 Bay Line RdOakland, FLThis new home is a single-story, 3-way split plan with 4 bedrooms and 3 baths. Off the foy... |
4 beds | 3 baths | 2,281 sq.ft. |
$649,000 |
Airbnb cash on cash: 5.01%
|
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. |
$1,998,000 |
Airbnb cash on cash: 0.64%
|
729 Strihal LoopOakland, FLOne or more photo(s) has been virtually staged. *Once-in-a-Lifetime Opportunity! **EXTERIO... |
5 beds | 3 baths | 3,381 sq.ft. |
$700,000 |
Airbnb cash on cash: N/A
|
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
|
2755 BOBCAT CHASE BOULEVARDOakland, FLWelcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, bu... |
3 beds | 3 baths | 1,822 sq.ft. |
$495,000 |
Airbnb cash on cash: 3.79%
|
2435 STANDING ROCK CIRCLEOakland, FLPerfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and... |
4 beds | 3 baths | 2,017 sq.ft. |
$471,900 |
Airbnb cash on cash: 6.28%
|
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. |
$655,000 |
Airbnb cash on cash: 4.7%
|
501 E OAKLAND AVENUEOakland, FLOne or more photo(s) has been virtually staged. Welcome to your private retreat in the hea... |
4 beds | 4 baths | 3,448 sq.ft. |
$875,000 |
Airbnb cash on cash: 3.01%
|
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. |
$800,000 |
Airbnb cash on cash: N/A
|
717 STRIHAL LOOPOakland, FLWelcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath resi... |
4 beds | 2 baths | 2,065 sq.ft. |
$480,000 |
Airbnb cash on cash: 7.01%
|
2065 WHITE FEATHER LOOPOakland, FLWelcome to the highly desirable Oakland Trails community, where this exceptional 2019 Meri... |
3 beds | 3 baths | 2,089 sq.ft. |
$560,000 |
Airbnb cash on cash: 3.5%
|
2135 STANDING ROCK CIRCLEOakland, FLASSUMABLE 2.4% Interest Rate. Welcome to this beautifully appointed single-family home ... |
3 beds | 3 baths | 2,078 sq.ft. |
$494,000 |
Airbnb cash on cash: 4.24%
|
2451 SKY STONE COURTOakland, FLWelcome to Oakland Trails, a beautiful and well-established community located in the charm... |
5 beds | 4 baths | 3,007 sq.ft. |
$735,000 |
Airbnb cash on cash: N/A
|
1490 Stone Arrow CtOakland, FL1490 Stone Arrow Ct, Oakland, FL 34787 | Single Family Residential |
5 beds | 3 baths | 3,248 sq.ft. |
$620,000 |
Airbnb cash on cash: N/A
|
2450 Standing Rock CirOakland, FL2450 Standing Rock Cir, Oakland, FL 34787 | Single Family Residential |
5 beds | 4 baths | 3,163 sq.ft. |
$704,500 |
Airbnb cash on cash: N/A
|
624 Hull Island DrOakland, FL624 Hull Island Dr, Oakland, FL 34787 | Single Family Residential |
4 beds | 2 baths | 2,708 sq.ft. |
$1,000,000 |
Airbnb cash on cash: 2.35%
|
610 Simeon RdOakland, FL610 Simeon Rd, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$385,000 |
Airbnb cash on cash: 1.17%
|
552 Walker StOakland, FL552 Walker St, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$1,250,000 |
Airbnb cash on cash: -1.08%
|
1161 Prado LnOakland, FL1161 Prado Ln, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$420,000 |
Airbnb cash on cash: 0.49%
|
529 N Pollard StOakland, FL529 N Pollard St, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$895,000 |
Airbnb cash on cash: -0.76%
|
1215 Ridge Lake WayOakland, FL1215 Ridge Lake Way, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$374,900 |
Airbnb cash on cash: 0.62%
|
1203 Ridge Lake WayOakland, FL1203 Ridge Lake Way, Oakland, FL 34787 | Other |
N/A beds | N/A baths | N/A |
$449,900 |
Airbnb cash on cash: 0.21%
|
610 STRIHAL LOOPOakland, FLUnder contract-accepting backup offers. Welcome to 610 Strihal Loop, a beautifully updated... |
4 beds | 2 baths | 2,490 sq.ft. |
$535,000 |
Airbnb cash on cash: 6.13%
|
2090 STANDING ROCK CIRCLEOakland, FLUnder contract-accepting backup offers. Price reduced to $585,000 on this Stunning Home in... |
3 beds | 3 baths | 2,010 sq.ft. |
$585,000 |
Airbnb cash on cash: 3.6%
|
326 LARGOVISTA DRIVEOakland, FLUnder contract-accepting backup offers. Welcome to your dream home in the highly sought-af... |
4 beds | 3 baths | 3,182 sq.ft. |
$649,600 |
Airbnb cash on cash: 4.05%
|
2690 BOBCAT CHASE BOULEVARDOakland, FLUnder contract-accepting backup offers. Love Where You Live â in Longleaf at Oakland! ? ... |
3 beds | 2 baths | 1,554 sq.ft. |
$465,000 |
Airbnb cash on cash: 4.48%
|
Real Estate investment in Oakland, FL
There are 41 properties for sale in the city of Oakland . The median list price in Oakland is $675,000 and the average price per square foot is $357. In January 2026, the average monthly cash on cash return in Oakland is 2.00%. The average monthly rental income in Oakland is $2,732.