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 06/12/2026 3:39 AM
| Class | Total | Price | Beds | Baths | Age |
|---|---|---|---|---|---|
| Residential | 23 | $1,066,774 | 2.7 | 2.3 | 36.1 |
| Vacant Land | 2 | $697,000 | - | - | - |
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 ...
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...
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...
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
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...
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...
57 Bishops Court Road UNIT #121
Osprey, FL 34229
Oaks
Residential
MLS# A4680582 / Active
Enjoy the perfect maintenance free country club lifestyle in the charming and quaint Bishopscourt Townhomes located in The Oaks Preserve. Architect...
Reduced -$30,000
410 Blue Garden Lane
Osprey, FL 34229
Oaks
Vacant Land
MLS# A4679677 / Active
Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasotas most prestigious gated golf and country club communities. Si...
33 Bishops Court Road UNIT #118
Osprey, FL 34229
Oaks
Residential
MLS# A4678425 / Active
**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve...
Reduced -$18,500
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
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MLS IDX data last updated on 06-12-2026 2:00 AM EST.