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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 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
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112 Osprey Point Dr, Osprey, FL - $4,449,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 8,973 SQFT
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No Water Tease Here! Truly A Boater's Dream! This Grand Custom 3 Floor Home Sits On One Of The Premier Lots In Oaks Bayside. Enjoy Magical Full Waterview With Amazing Sunsets Either At Home Or In Your Boat Crewing On The Open Bay To The Gulf Of...

Photo of Listing #A4132353

136 Osprey Point Dr, Osprey, FL - $3,449,900

Residential, Single Family Home
  • 7 Beds
  • 9 Baths
  • 8,843 SQFT
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Fantastic Opportunity To Own This Prestigious Home In The Oaks Bayside. You Will Be Immediately Impressed With The Georgian Style Of Architecture As You First Approach The Circular Driveway And The Lush Tropical Foliage. The Front Facade Of This H...

Photo of Listing #A4136097

931 Blue Heron Overlook, Osprey, FL - $2,599,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 6,977 SQFT
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Located Clubside At 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 And Strategically Located On The New Fry/straka (course Architects Of Erin Hill...

285 Sugar Mill Dr, Osprey, FL - $2,100,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,578 SQFT
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Grand And Impressive-yet Warm And Comfortable At The Same Time, This Private Walled Estate Exudes A Feeling Of Both Tranquility And Joy. Set In The Wooded Enclave Of The Oaks Bayside, You Arrive After Driving Down Canopied Sugar Mill Dr. The Pro...

419 Walls Way, Osprey, FL - $1,845,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,523 SQFT
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Prepare To Be Inspired At The Sight Of This Grand Colonial Revival Estate Home Sited Gracefully On Arguably One Of The Oaks' Premier Cul-de-sac Lots. Enjoy Unrivaled Sunrise, Sunset, Lake And Golf Course Views Of The New Fry- And Straka-designed (...

497 Webbs Cv, Osprey, FL - $1,749,000

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 Conditions, New Flooring, New Kitchens And Baths, New Pool, Lanai Screens, New Trav...

340 Osprey Point Dr, Osprey, FL - $1,695,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,001 SQFT
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Timeless Grandeur! This Exquisite Traditional Estate Was Designed To Perfection For Luxury Living With 5 Bedrooms And 5.2 Baths In The Highly Desirable Oaks Bayside. Volume Ceilings, Crown Molding And Architectural Details Are Evident Throughout...

Photo of Listing #A4112665

478 Oriskany Ct, Osprey, FL - $1,679,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 5,856 SQFT
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Closest Home To Brand New Construction You Will Find In The Oaks. New Roof, New Windows, All New Kitchen With Viking Professional Appliances, New Stone And Wood Flooring Throughout, All New Interior Doors, New Plumbing, New Second Story, New Pool...

695 Trenton Way, Osprey, FL - $1,629,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,294 SQFT
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Absolutely The Best View In All The Oaks, 270+ Degrees Of Lake And Golf Views! This Large 4 Bedroom, 4.5 Bath (plus Pool Bath) 5,294 Square Foot Home In The Oaks Clubside Offers A Location And View Rivaled By None. As You Enter, The Formal Livin...

296 Osprey Point Dr, Osprey, FL - $1,599,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 7,092 SQFT
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Featuring His And Hers Master Bedrooms And Bathrooms, This 4 Bedroom + Office, 5.5 Bath, 7,092 Sq Ft Home Has It All! You Need To Look No Further For The Home That Offers Space, Beauty, Comfort & Privacy! Travertine Marble Floors Gleam Throughout ...

373 Sugar Mill Dr, Osprey, FL - $1,595,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,717 SQFT
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A Rare Opportunity That Brings Together Lush Landscaping And A Prime Lakefront Location In Oaks Bayside With The Attributes Of A Reconstructed And Redesigned Model-like Home. This Estate Home Has Just Recently Been Transformed To Suit Today's Mode...

530 N Mac Ewen Dr, Osprey, FL - $1,365,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,346 SQFT
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A Tastefully Understated Fa├žade Gives Entry To Dramatic Style And Sophistication In This Recently Remodeled Estate Home Located In The Private Gated Community Of The Oaks. Expertly Renovated And Meticulously Maintained, This Home Showcases Stunnin...

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 5th, 2016 at 1:56pm EDT.