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 $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 75 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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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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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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5 Bed • 6 Bath • 5,153 Sf • 1 Acres


425 E Macewen Dr, Osprey

This Spacious 5 Bedroom, 5.5 Bath Home Offers Over 5,100 Square Feet Of Living Space And Overlooks The Par 3 Fourth Hole Of The Oaks Heron Course. ...

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Reduced 6%

3 Bed • 4 Bath • 4,924 Sf


168 Coastal Hammock Ct, Osprey

Bayfront In The Oaks. Custom Designed Walled Mizner-style Estate In Private Cul-de-sac Location With A 5 Stop Elevator. Views From Several Areas Sh...

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Reduced 9%

3 Bed • 3 Bath • 2,778 Sf


409 N Point Rd #1003, Osprey

Don't Be Shy - Owner Wants It Sold - Bring All Offers! The Best Penthouse Views In All Of Meridian! Experience The Luxurious Florida Lifestyle Wit...

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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.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on June 17th, 2019 at 9:00pm CDT.

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