The Oaks in Osprey FL…A life of grandeur for those who seek tradition and timelessness. Established originally as the dream home amongst stately oaks and exotic palms for Chicago “grande dame” Bertha Honoré Palmer nearly a hundred years ago. The Oaks offers everything from waterfront mansions on the Bay to maintenance free villas. The community contains three gated neighborhoods; Oaks Bayside, Oaks Clubside and Oaks Preserve.
One Or More Photo(s) Has Been Virtually Staged. This Incredible Offering Has Everything You Need To Live A Luxury Condominium Lifestyle In Comfort And Ease; 3 Bedrooms, 3 Full Baths, A Formal Dining Room And A 2nd Floor Private 2 Car Garage! Add T...
Nestled In The Prestigious Gated Enclave Of The Oaks Bayside In Sarasota, This Sedona-inspired Retreat Was Recently Updated From Wall To Wall Creating A Like Brand New Home. The Estate Seamlessly Blends Modern Luxury, Comfort, And Serenity. With A...
Experience Breathtaking Views Of The Bay And Gulf From This Spacious 3 Bedroom, 3 Bath End Unit, Featuring A Separate Dining Room And Den. Completely Updated And Meticulously Maintained, This Unit Is Beautifully Appointed And Custom Features Aboun...
**elegant Updated Residence In The Oaks | Modern Comfort On A .83-acre Corner Lot** Welcome To 538 Dove Pointe, An Exceptional Residence In The Secure And Gated Oaks Country Club Community In Osprey, Florida. Set On A Generous .83-acre Elevated L...
Nestled Within The Exclusive Gated Community Of The Oaks Club In Osprey, Florida. This Singular Estate Represents A Masterful Confluence Of Architectural Refinement And Modern Luxury, Encompassing Nearly 7000 Ft.² Of Conditioned Living Space, The ...
Under Contract-accepting Backup Offers. **beautifully Updated Country Club Estate With Ideal Southern Exposure And Water View** Is Located In The Coveted, Oaks Bayside Country Club Neighborhood On Little Sarasota Bay. Enjoy The Private And Tranqui...
**incredible Transformation Of This Move-in Ready, Golf Course Estate** From The Reimagined Entryway And Through The Stunning Iron Double Front Door, You Will Be Captivated By The Attention To Detail Throughout This Elegantly Appointed Residence ...
Under Contract-accepting Backup Offers. Set An Appointment To Experience This Thoughtfully Designed Arthur Rutenberg Home, Where Craftsmanship And Details Are Truly On Display. Upon Entering Through The Double Door Entrance, The Quality And Attent...
Come And Enjoy The Perfect Maintenance Free Lifestyle In This Exquisite Townhouse Located In One Of The Finest Country Clubs On The Gulf Coast, The Oaks Golf And Country Club. Previously Redesigned, This Tuscan Style Home In The Quaint And Charm...
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One Or More Photo(s) Has Been Virtually Staged. **brilliantly Updated, Move-in Ready, Golf Course Estate In The Highly Sought-after Oaks Country Club Community** Offers An Ideal Southern-exposure And View Across The 3rd Fairway Of The Interior, He...
Step Into A Residence That Redefines Elegance And Sophistication. This Stunning 2,778 Sq Ft Condo Has Been Completely Reimagined. Every Inch Has Been Thoughtfully Redesigned To Create A Truly Exceptional Living Experience. Boasting 3 Spacious Bedr...
The Oaks Preserve is further divided into:
A dynamic community where the eagles soar…Protective of the natural Florida habitat, The Oaks Club employs environmentally sound practices and have created a ten-acre bald eagle preserve in Oaks Bayside, to allow this regal, endangered species to flourish. With the club’s sensational location on Little Sarasota Bay, access to a variety of marinas is convenient and deep water sailing and fishing are just a short drive from the Club entrance. The community is accented by the lush vegetation of the natural shoreline with sea myrtle, beach elder, and mangroves housing native birds and wildlife.
The Oaks community is home to their private country club, The Oaks Club, offering the finest in championship-style golf on two 18-hole courses, a professional tennis facility with 12 Har-Tru tennis courts, and exquisite restaurants including The Glen Room, an elegant option for fine dining with a fireplace and Old English ambiance. The clubhouse is an extensive 42,000 square feet of comfort and luxury. The Oaks Club also has a junior olympic pool, professional croquet court, and a playground.
The Oaks Club is located at 301 MacEwen Drive, Osprey, Florida 34239. The community is located directly off of Tamiami Trail S. (U.S. 41) and has an entrance on both the east and west side of Tamiami Trial S.
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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on November 16th, 2025 at 4:54pm EST.
