The current prices for all Real Estate Listings in oaks - Osprey, FL are reflected in the the table below.
Market Snapshot
Averages based on current search criteria as of 06/11/2026 8:26 PM
| Class | Total | Price | Beds | Baths | Age |
|---|---|---|---|---|---|
| Residential | 23 | $1,066,774 | 2.7 | 2.3 | 36.1 |
| Vacant Land | 2 | $697,000 | - | - | - |
402 Macewen Drive
Osprey, FL 34229
Oaks
Residential
MLS# A4690018 / Active
Tucked behind the private gates of The Oaks Club side, in one of Sarasotas most prestigious and sought-after country club enclaves, this exquisite ...
Reduced -$51,000
97 Sugar Mill Drive
Osprey, FL 34229
Oaks
Residential
MLS# A4691789 / Active
Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota Countys most prestigious gated...
448 E Macewen Drive
Osprey, FL 34229
Oaks
Residential
MLS# A4687195 / Active
**IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulous...
362 Macewen Drive
Osprey, FL 34229
Oaks
Residential
MLS# A4676567 / Active
Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal liv...
433 E Macewen Drive
Osprey, FL 34229
Oaks
Residential
MLS# A4676505 / Active
An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acr...
49 Osprey Point Drive
Osprey, FL 34229
Oaks
Residential
MLS# A4671762 / Active
Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creat...
Reduced -$101,000
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MLS IDX data last updated on 06-11-2026 7:48 PM EST.