Luxury Homes for Sale in Oakland, FL
The luxury market in Oakland starts at $1,240,000 — about 1.5× the city’s median asking price. This page is every active listing at that level, refreshed nightly from the MLS, with what has actually closed, where the inventory sits and how long it takes to sell. For the wider picture see luxury communities in Orange County.
10 luxury homes are for sale in Oakland, FL at $1,240,000 and up — median asking $2,437,580, the top listing at $3,295,000, $564 per square foot. 20 homes closed above $1,240,000 in the last 12 months at a median of $2,287,500. 20% of the luxury inventory is waterfront; 80% is new construction. Median days on market: 78.
Newest luxury listings in Oakland
The most expensive homes for sale in Oakland
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 312 Briley Avenue | $3,295,000 | 5,144 | $641 | briley farm |
| 1152 Prado Lane | $2,615,320 | 4,658 | $561 | Grove/Oakland |
| 1155 Prado Lane | $2,575,000 | 4,210 | $612 | Grove/Oakland |
| 812 Johns Point Drive | $2,550,000 | 4,373 | $583 | Johns Cove 43 104 Oakland |
| 1134 Prado Lane | $2,495,000 | 4,433 | $563 | Grove/Oakland |
| 1173 Prado Lane | $2,380,160 | 4,204 | $566 | Grove At The Harvest District |
| 1146 Prado Lane | $2,310,600 | 3,992 | $579 | Grove At The Harvest District |
| 1258 Ridge Lake Way | $2,098,000 | 4,557 | $460 | Oakland Park |
| 1106 Sarah Mathews Drive | $1,975,000 | 3,596 | $549 | Grove At The Harvest District |
| 1112 Hull Island Drive | $1,400,000 | 3,562 | $393 | Hull Island At Oakland |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Grove At The Harvest District | 3 | $2,310,600 |
| Grove/Oakland | 3 | $2,575,000 |
| Johns Cove 43 104 Oakland | 1 | $2,550,000 |
| Hull Island At Oakland | 1 | $1,400,000 |
| Oakland Park | 1 | $2,098,000 |
| briley farm | 1 | $3,295,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,240,000–$1,500,000 | 1 | 10% |
| $1,500,000–$2,000,000 | 1 | 10% |
| $2,000,000–$3,000,000 | 7 | 70% |
| $3,000,000–$5,000,000 | 1 | 10% |
How to read this
Luxury is defined here as asking prices at or above $1,240,000. Counts, medians and closings come from active and closed MLS listings as of September 15, 2026; closings are the trailing 12 months. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 33 homes for sale in Oakland and what $1M buys across Orange County.