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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.
Learn more about The Oaks Golf & Country Club.

 

The Oaks Homes for Sale

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931 Blue Heron Overlook, Osprey, FL - $3,100,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,977 SQFT
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Experience Life In One Of Florida’s Finest Country Clubs, The Oaks, From This Exquisitely Crafted Estate Home. Strategically Positioned To Overlook The Signature Heron Golf Course, This Extraordinary Residence Presents Over 6,900 Sq. Ft. Of Space ...

136 Osprey Point Dr, Osprey, FL - $2,999,000

Residential, Single Family Home
  • 5 Beds
  • 8 Baths
  • 6,461 SQFT
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One Of The Most Beautiful Homes In Sarasota, This Immaculate Residence In The Oaks Bayside Is A Flourish Of Custom Finishes And Designer Upgrades Inside And Out. Located On An Oversized Parcel (more Than Half An Acre) Overlooking The Preserve And ...

Photo of Listing #A4183696

162 Osprey Point Dr, Osprey, FL - $2,800,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 6,807 SQFT
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Secluded Sanctuary For Nature Lovers. "luxury Home" Can Often Be An Oxymoron. The Luxury May Exist, But What Makes A House A “home”? This Property Answers That Question, As It Embodies The True Meaning Of The Phrase. The Classic Elegance Of This R...

95 Osprey Point Dr, Osprey, FL - $2,250,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 7,500 SQFT
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French Chateaux With Guest House And 4+ (tandem) 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 Spectacul...

Photo of Listing #A4173121

285 Sugar Mill Dr, Osprey, FL - $1,971,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,578 SQFT
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An Award-winning Golf Club, #1 Beach, Nationally Ranked School And Peace Of Mind. What More Could You Ask For? Updated To The Hurricane Standards, This Home Features Impact Resistant Garage Doors And High Velocity Hurricane Zone Approved Screen Pr...

Photo of Listing #A4167288

324 Osprey Point Dr, Osprey, FL - $1,825,000

Residential, Single Family Home
  • 5 Beds
  • 5 Baths
  • 5,758 SQFT
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Perfectly Positioned Along North Creek In The Oaks Bayside, This Architecturally Significant And Beautifully Designed Residence Is Uniquely Representative Of What Modern Buyers Are Looking For In A Home. Understated Elegance, Clean Lines, Dramatic...

168 Coastal Hammock Ct, Osprey, FL - $1,800,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,924 SQFT
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Bayfront In The Oaks. Custom Designed Walled Mediterranean Estate In Private Cul-de-sac Location With A 5 Stop Elevator. Views From Several Locations Showcasing The Gulf And The Bay. Very Livable Floor Plan With Expansive Master Suite Offering A S...

669 Trenton Way, Osprey, FL - $1,750,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,806 SQFT
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This Truly Unique One Story Home Is Located On A Quiet Cul-de-sac Street Overlooking The Oaks Club (clubside) Heron Golf Course And A Sparkling Lake View. A Great Combination. New Pavered Circular Driveway. Enter The 10ft Solid Wood Front Doors To...

Photo of Listing #A4170988

854 Macewen Dr, Osprey, FL - $1,649,999

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
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Immerse Yourself In Luxury! One Of The Most Exquisite Estate Offerings Is Nestled Within The Oaks Most Distinguished Clubside Enclaves. This Incomparable Dream Unfolds Over 9,000 Square Feet Of Quality Craftsmanship Including Automated Smart Ho...

393 North Point Rd #1002, Osprey, FL - $1,600,000

Residential, Condo
  • 3 Beds
  • 3 Baths
  • 3,738 SQFT
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This 3 Bedroom, 2.5 Bath Penthouse With Private 2 Car Garage In Meridian At The Oaks Preserve Is The Definition Of Luxury. Discriminating Buyers Know That True Luxury In A Home Comes From A Combination Of Quality Appliances And Finishes, Quiet Ele...

Photo of Listing #A4152178

497 Webbs Cv, Osprey, FL - $1,500,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 6,341 SQFT
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Located In The Exclusive Gated Community Of The Oaks Bayside. Totally Remodeled Home With Too Many Improvements To List, Everything Is New Including; New Roof, Air Conditioners, New Flooring, New Kitchens And Baths, New Pool, Lanai Screens, New Tr...

402 Walls Way, Osprey, FL - $1,450,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,464 SQFT
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Spectacular Waterfront Home Exhibits Unsurpassed Excellence In Design And Detail. Situated On A Premier One Acre Lot In The Beautiful The Oaks Club. Grande Entry Doors And Breathtaking Foyer Open To Reveal A Pool And Patio. Graceful Top Name Appl...

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 December 15th, 2017 at 2:19pm EST.