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 5:26 PM
| Class | Total | Price | Beds | Baths | Age |
|---|---|---|---|---|---|
| Residential | 23 | $1,066,774 | 2.7 | 2.3 | 36.1 |
| Vacant Land | 2 | $697,000 | - | - | - |
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
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...
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...
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...
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...
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
75 Osprey Point Drive
Osprey, FL 34229
Oaks
Residential
MLS# A4695145 / Active
Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling oppo...
422 Blue Garden Lane
Osprey, FL 34229
Oaks
Residential
MLS# A4664436 / Active
Discover incredible value and endless potential in this beautifully maintained 3 bedroom, 3.5 bath home, tucked into lush tropical landscaping, on ...
Reduced -$55,000
25 Sugar Mill Drive
Osprey, FL 34229
Oaks
Residential
MLS# A4678423 / Active
METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESER...
Reduced -$61,000
156 Bishops Court Road
Osprey, FL 34229
Oaks
Residential
MLS# A4691664 / Active
One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned ...
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MLS IDX data last updated on 06-11-2026 8:46 AM EST.