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 $100,000 - $200,000
$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 68 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 • 5 Bath • 6,340 Sf • 1 Acres


552 Eagle Watch Ln, Osprey

The Ultimate In Luxury, Location And Design. As You Open The 13’ Cast Iron Front Doors, You Will Immediately Feel The Grandeur Of This Expansive Re...

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4 Bed • 4 Bath • 4,571 Sf • 1 Acres


68 Osprey Point, Osprey

Set Gracefully Amidst Lush Tropical Landscaping In The Gated Waterfront Community Of The Oaks Bayside, This Stunning Residence Has Been Masterfully...

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Reduced 5%

5 Bed • 6 Bath • 6,981 Sf • 1 Acres


318 Osprey Point Dr, Osprey

New Price $100,000 Reduction. Welcome To An Exquisite Lifestyle At A Price You Won’t Believe; All In The World-class, Incredibly Private Oaks Baysi...

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5 Bed • 7 Bath • 6,416 Sf • 1 Acres


562 N Macewen Dr, Osprey

** Virtual Showings Available. Check Out The Video And Slide Shows, Floor Plan Available** The Oaks…exceptional Home, Custom Built On One Of The Mo...

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5 Bed • 6 Bath • 5,578 Sf • 1 Acres


285 Sugar Mill Dr, Osprey

2 Br 2 Bath Guest House, 4 Car Garage, And Walled Motor Court! You Will Feel Like Nobility When You Enter This Gated Lakeside Estate In The Oaks Ba...

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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 July 2nd, 2020 at 4:45am CDT.

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