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The Oaks in Sarasota, Florida

The Oaks in Sarasota, FloridaSituated along the bayfront, The Oaks offers a tropical paradise of stately elegance. It captures and maximizes the natural beauty of Florida with mature oaks that sway across winding, canopied streets. Exclusive and opulent, this 1000-acre area features homes in a variety of styles, including contemporary, Mediterranean, and Georgian.  Read more.

 

The Oaks Homes for Sale

All Listings $100,000 - $200,000 $200,000 - $300,000
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$900,000 - $1,000,000 Over $1,000,000
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Photo of Listing #A4104460

136 Osprey Point Dr, Osprey, FL - $3,545,000

Residential, Single Family Home
  • 7 Beds
  • 9 Baths
  • 8,843 SQFT
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This Three-level Mansion With Elevator Located In The Exclusive, Gated Oaks Community Is Priced To Sell Fast!!! No Stone Has Been Left Unturned Following A One-year, One Million-dollar Renovation. It Sits On High In All Its Glory, With Never End...

Photo of Listing #A4100470

931 Blue Heron Overlook, Osprey, FL - $2,995,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 6,977 SQFT
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Priced $1,000,000 Below Replacement Costs This Artistically Crafted And Beautifully Designed Residence Sits Gracefully On A Private Cul-de-sac Within The Oaks Club, One Of The Area’s Most Sought-after Private Country Club Communities Located Minut...

324 Osprey Point Dr, Osprey, FL - $2,200,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,758 SQFT
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Nestled On Nearly An Acre Of Lush Tropical Foliage Along The Banks Of North Creek Is This Extraordinary Custom Designed Estate Home And Guest House. Truly A World Apart, The Neighborhood Boasts More Than 200 Acres Of Pristine Florida Foliage With ...

95 Osprey Point Dr, Osprey, FL - $1,999,999

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 8,531 SQFT
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French Chateaux With Guest House And 4 Car Garage In The Oaks Bayside. This Incredible Bo Macewen Designed Masterpiece Was Finished In 1997 And Major Renovations Were Done In 2001. As You Enter The Main House You Are Met With A Spectacular Wooden ...

Photo of Listing #A4112665

478 Oriskany Ct, Osprey, FL - $1,849,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 5,856 SQFT
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Completely Re-built In 2014, This Stunning Oaks Club Home Is Positioned Overlooking The 14th Hole Of The Newly Designed Heron Course. With Long Fairway And Expansive Lake Views That Stretch For As Far As The Eye Can See, You Will Be Dazzled From T...

385 N Point Rd # 1002b1, Osprey, FL - $1,800,000

Residential, Condo
  • 3 Beds
  • 4 Baths
  • 3,738 SQFT
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For Those Who Demand Only The Best... Top Floor, Never On The Market, A Penthouse Masterpiece With European Flavor Befitting The Elegance Of The Oaks. This Is The Largest Penthouse In Building One Where You Will Live And Entertain Without Compromi...

222 Sugar Mill Dr, Osprey, FL - $1,799,999

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,736 SQFT
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As You Drive Through The Gates Of This Prestigious Community, Oaks Bayside (located On 235 Acre Peninsula W/a Portion Of Little Sarasota Bay), The Beautiful Canopied Roads Will Lead You To This Exquisite Estate Sized Home Set On Almost 1 Acre Lot ...

Photo of Listing #U7612371

296 Osprey Point Dr, Osprey, FL - $1,575,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 7,092 SQFT
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Ultra Spacious Residence Located In The Oaks Country Club With Gated Security,2 Championship Golf Courses, Fine Dining,and Professional Tennis. This Home Is Built For Entertaining That Can Accommodate A Formal Affair In The Living Or Dining Room O...

530 N Mac Ewen Dr, Osprey, FL - $1,395,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,346 SQFT
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4300 Sq. Ft. Home With Over 7000 Sq. Ft. Of Granite And Marble!...transitional Styled Splendor Is The Only Way To Describe This Beautiful Former Regent Versailles Model Home. Built In 2002 The Current Owner Completely Remodeled This Home From The ...

3603 North Point # 801, Osprey, FL - $1,395,000

Residential, Condo
  • 4 Beds
  • 4 Baths
  • 3,991 SQFT
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... Exquisite Sunsets, Towering Oak Trees And A Lush Landscape Welcome You! Endless Water Views Of The Gulf And Bay From Your Penthouse Balcony... Almost 4000 Sq/ft Of Living Area And A Private 2-car Garage. Fourth Bedroom Could Be A Den Or Offic...

425 E Macewen Dr, Osprey, FL - $1,390,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,153 SQFT
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New, New, New Is What You Will Find In This 5100 Sqft. This Incredibly Remodeled Home Overlooks The Par 3 4th Hole Of The Oaks Heron Course. New Kitchen, New Bathrooms, New Flooring, New Summer Kitchen, New Paver Pool Area, New Hvac, New Sheetrock...

Photo of Listing #A4107179

376 Sugar Mill Dr, Osprey, FL - $1,349,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,472 SQFT
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Sold Furnished With A Few Exceptions, Exceptional Oaks Bayside Home With Over 5400 Sq. Ft. Enter Through Courtyard With A Tranquil Fountain And Carved Wood Double Doors That Open To Elegant Entry Foyer. This Grand Manor House With Classic Mediterr...

The Oaks Golf & Country Club

The Oaks is comprised of three gated communities with 24-hour security. On Sarasota Bay, you will find almost 200 homes in The Oaks Bayside and The Preserve. Situated along the lush fairways of our 36-hole championship golf course is The Oaks Clubside, with more than 350 homes.

The Oaks offers homes for every lifestyle, including maintenance-free villas, townhomes, high-rise condominiums, golf course homes, and waterfront executive homes—all designed with high-end amenities and distinctive luxury appointments. 

The Oaks Club is also the perfect community for those who love to enjoy all that the beautiful climate of Florida offers.  Take advantage of two championship golf courses; enjoy one of the 12 Har-Tru tennis courts; or take a swim in the junior Olympic pool.  If that’s not enough, you could enjoy the regulation croquet court, or simply indulge in an afternoon or evening with friends at the clubhouse.  Also a perfect location for avid boaters, residents have easy access from canal or bay front properties to a day of fun on the water.

With a long history that dates back to the 1900s, The Oaks was the original estate of Bertha Palmer, a Chicago socialite and businesswoman who purchased 80,000 acres in Sarasota. Her name and influence are still felt in the community today.  She chose 1,000 acres for her personal estate and dubbed it “The Oaks,” a name that became synonymous for the elegant lifestyle of Mrs. Palmer and of the distinguished guests she entertained in her home.

Today, The Oaks is a thriving community that offers a luxurious setting for Florida living, along with easy access to the thriving community life of Sarasota. Only 20 minutes from downtown Sarasota, The Oaks is also only 5 minutes from Sarasota Square Mall, along with a plethora of dining and shopping establishments, the Legacy Trail for cycling or walking, Oscar Sherer State Park, and much more.


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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 May 25th, 2015 at 2:45am EDT.