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.
Enjoy The Perfect Maintenance Free Country Club Lifestyle In The Charming And Quaint Bishopscourt Townhomes Located In The Oaks Preserve. Architecturally Designed, This Classic Georgian Style Townhouse Features Two Bedrooms, Two Full Ensuite Baths...
Ready To Live A Stress-free Luxury Condo Lifestyle? There Is No Place Better To Do It Than This 3 Bedroom, 3 Bath Residence In Meridian At The Oaks Preserve. Nestled Among The Treetops, This End Unit Has A Split Floor Plan And Absolutely Breathtak...
**fantastic Gulf And Bay Views From This Updated 6th-floor Corner Residence** This Spacious, Light-filled Corner Unit Offers Nearly 2,600 Sq. Ft. Of Living Space And Features 3 Bedrooms Plus A Study/den, 3 Full Baths, Two Elevator Banks, Two Assig...
**rarely Available 10th-floor Penthouse Corner Residence Offering 3,029 Square Feet With Sweeping Gulf And Bay Views.** Ideally Situated Behind The Secure Gates Of The Highly Sought-after Preserve Neighborhood Within The Oaks Country Club, This Ex...
Perfectly Positioned On The 9th Hole Tee Box Within The Oaks Community, This Meticulously Appointed Estate Offers A Rare Opportunity For A Premier Sarasota Golf Course Lifestyle. Designed For The Discerning Enthusiast, The Property Features Panora...
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**exceptional, Fully Renovated, Country Club Estate Home Offering Tranquil Lake And Garden Views** Ideally Positioned On A Serene Interior Cul-de-sac Lot In Flood Zone X (no Flood Insurance Required). Located Behind The Secure Gates Of The Highly ...
Experience The Charm And Wonderful Location Of This Golf Course Home On Saint James Park, The Leafy And Quiet Cul-de-sac Where You Can Walk To Tennis, Golf, Pickleball, Croquet, Heated Pool And State Of The Art Fitness Center All Within The Oaks C...
Rarely Available Windsor Lodge Efficiency Condominium Located Within The Oaks Club. This Second-floor, Maintenance-free, Lakeside Unit Features A Covered Balcony With Views Of The Lake, Pool, And Golf Course. Elevator Access To The Second Floor. S...
Meticulously Maintained And Thoughtfully Updated, This Exceptional Residence Is Privately Situated On A Serene Lot With Beautiful Garden And Preserve Views. Located In Flood Zone “x” (no Flood Insurance Required), The Home Is Tucked Behind The Sec...
Exceptional Opportunity To Build Your Dream Estate In The Oaks, One Of South Sarasota’s Most Prestigious Gated Golf And Country Club Communities. Situated On A Rare Cul-de-sac Lot, This Generous Parcel Offers Privacy, Mature Landscaping, And An Id...
OPEN HOUSEThis Beautiful Custom Designed Home Will Captivate You From The Moment You Enter The Front Door. Located In The Extremely Sought After Oaks Country Club, This Recently Renovated Home Is Sure To Impress With Picturesque Views Of The Golf Course. P...
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 February 12th, 2026 at 11:24am EST.
