Luxury Homes for Sale in Osprey, FL
The luxury market in Osprey starts at $1,050,000 — 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 Sarasota County.
23 luxury homes are for sale in Osprey, FL at $1,050,000 and up — median asking $1,690,000, the top listing at $9,750,000, $545 per square foot. 23 homes closed above $1,050,000 in the last 12 months at a median of $1,700,000. 26% of the luxury inventory is waterfront. Median days on market: 35.
Newest luxury listings in Osprey
The most expensive homes for sale in Osprey
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 1216 N Casey Key Road | $9,750,000 | 8,050 | $1,211 | Casey Key |
| 121 N Casey Key Road | $6,100,000 | 4,096 | $1,489 | Casey Key |
| 313 Lookout Point Drive | $5,999,999 | 5,337 | $1,124 | Southbay Yacht & Racquet Club |
| 275 Lookout Point Drive | $4,590,000 | 5,279 | $869 | Southbay Yacht & Racquet Club |
| 650 Oaks Creek Court | $3,700,000 | 4,314 | $858 | Oaks 2 Ph 2 |
| 236 Saint James Park | $2,700,000 | 6,246 | $432 | Oaks 2 Ph 2 |
| 852 Macewen Drive | $2,395,000 | 4,519 | $530 | Oaks 2 Ph 2 |
| 154 Lookout Point Drive | $2,095,000 | 4,578 | $458 | Southbay Yacht & Racquet Club |
| 401 N Point Road #1001 | $1,995,000 | 3,029 | $659 | Meridian At The Oaks Preserve |
| 18 N Casey Key Road | $1,750,000 | 1,977 | $885 | Casey Key |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Southbay Yacht & Racquet Club | 6 | $1,892,500 |
| Meridian At The Oaks Preserve | 5 | $1,395,000 |
| Oaks 2 Ph 2 | 5 | $2,395,000 |
| Casey Key | 3 | $6,100,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,050,000–$1,500,000 | 10 | 43% |
| $1,500,000–$2,000,000 | 5 | 22% |
| $2,000,000–$3,000,000 | 3 | 13% |
| $3,000,000–$5,000,000 | 2 | 9% |
| $5,000,000+ | 3 | 13% |
How to read this
Luxury is defined here as asking prices at or above $1,050,000. Counts, medians and closings come from active and closed MLS listings as of October 6, 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 83 homes for sale in Osprey and what $1M buys across Sarasota County.