The Oaks, The Preserve and The Oaks Bayside

The Oaks is one of the area’s premier golf and country clubs.  It features three distinct and different neighborhoods, the Oaks Bayside, The Preserve, and the Oaks Clubside all situated on over 1000 acres just south of Sarasota in Osprey. The homes all sit on larger parcels taking advantage of the space and views.   Membership in the Oaks Country Club is mandatory.  The club offers tennis, golf, and a Junior Olympic size swimming pool.  The Oaks have just completed an $11 million investment expanding the 34,000 square feet Georgian inspired clubhouse.  There are two separate 18 hole golf courses designed by golf architect legends Arthur Hills and Willard Byrd along with 12 Har-Tru tennis courts and a croquet court.  Although, the members of the Oaks always boast their tremendous social calendar, those who move there never want to leave their activities and their new friends. 

The Oaks

All Listings Under $100,000 $200,000 - $300,000
$300,000 - $400,000 $400,000 - $500,000 $500,000 - $600,000
$600,000 - $700,000 $700,000 - $800,000 $800,000 - $900,000
$900,000 - $1,000,000 Over $1,000,000
1 – 6 of 71 Listings
Price, High to Low

6 Bed • 7 Bath • 8,973 Sf • 1 Acres


112 Osprey Point Dr, Osprey

Most Desirable Location In The Oaks Bayside Country Club; Truly A Boater's Dream! Featuring Your Own Private Dock With 3 Power Lifts..12,000/16,000...

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4 Bed • 7 Bath • 6,977 Sf • 1 Acres


931 Blue Heron Overlook, Osprey

The Oaks, This Distinguished Residence Is Sited At The End Of A Cul-de-sac Boasting Breathtaking Views Stretching All The Way To The Oaks Clubhouse...

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5 Bed • 8 Bath • 6,461 Sf • 1 Acres


136 Osprey Point Dr, Osprey

Opportunity Of A Life Time! This Magnificent Three-level Mansion Is Located In The Exclusive Private Gated Community Oaks Bayside. This Home Is Pri...

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4 Bed • 6 Bath • 5,578 Sf • 1 Acres


285 Sugar Mill Dr, Osprey

Escape To Paradise. Located In The Waterfront Community Of Oaks Bayside, This One-of-a-kind Walled And Gated Estate Is A Private Oasis Perfect For ...

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4 Bed • 5 Bath • 5,246 Sf • 1 Acres


643 Fernwalk Ln, Osprey

Elegantly Defined, European And Traditional, Custom Build Home In The Cul-de Sac Private Street Of The Gated Community Of The Oaks. The Moment You ...

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Reduced 6%

4 Bed • 6 Bath • 5,100 Sf


91 Osprey Point Dr, Osprey

Iconic Architecture In Sarasota’s Premiere Golf And Country Club. This Magnificent 4-bedroom Estate Was Designed And Built By Bo Macewen And Brims ...

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on August 19th, 2019 at 10:15am CDT.

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