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 11:38 PM
| Class | Total | Price | Beds | Baths | Age |
|---|---|---|---|---|---|
| Residential | 23 | $1,066,774 | 2.7 | 2.3 | 36.1 |
| Vacant Land | 2 | $697,000 | - | - | - |
61 Bayhead Lane
Osprey, FL 34229
Oaks
Residential
MLS# A4685559 / Active
Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Fea...
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...
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
51 Mac Ewen Drive UNIT #14
Osprey, FL 34229
Oaks
Residential
MLS# A4690371 / Active
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-lin...
51 Macewen Drive UNIT #12
Osprey, FL 34229
Oaks
Residential
MLS# A4690540 / Active
Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus s...
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 ...
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...
103 Bishops Court Road
Osprey, FL 34229
Oaks
Residential
MLS# A4694468 / Active
**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lo...
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...
216 Osprey Point Drive
Osprey, FL 34229
Oaks
Vacant Land
MLS# A4696023 / Active
One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasotas distinguished private country club co...
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MLS IDX data last updated on 06-11-2026 7:48 PM EST.