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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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112 Osprey Point Dr, Osprey, FL - $4,999,000

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 #A4174521

136 Osprey Point Dr, Osprey, FL - $3,199,900

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...

468 Walls Way, Osprey, FL - $1,995,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,698 SQFT
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This Elegant Home Is Nestled On More Than A Half-acre Of Property Overlooking Tranquil Lake Waters Of The Oaks, Featuring An Array Of Beautiful Finishes Throughout. Majestic D├ęcor Greets You At Every Turn, Including Cathedral Ceilings, A Grand Spi...

Photo of Listing #A4173121

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,578 SQFT
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Set Gracefully Amidst The Lush Landscaping In The Oaks Bayside, This Stunning Residence Embodies Style, Sophistication And Understated Elegance At Every Turn. Idyllically Positioned, This Walled And Gated Lakefront Estate Features A Beautifully De...

Photo of Listing #A4167288

324 Osprey Point Dr, Osprey, FL - $1,895,000

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...

Photo of Listing #A4170988

854 Macewen Dr, Osprey, FL - $1,849,999

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...

Photo of Listing #A4174238

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

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 3,924 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...

419 Walls Way, Osprey, FL - $1,795,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,523 SQFT
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Sited On One Of The Oaks Premier Cul-de-sac Lots, This Impressive Residence Boasts Unrivaled Sunrise And Sunset, Lake And Golf Course Views Of The Heron Golf Course From Almost Every Room. The Grand Entry Includes A Double Staircase And 2-story Fo...

Photo of Listing #A4173463

393 North Point Rd #1002, Osprey, FL - $1,690,000

Residential, Condo
  • 3 Beds
  • 3 Baths
  • 3,738 SQFT
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Discover This Unique, Sophisticated Penthouse Overlooking The Wildlife Of Pristine Little Sarasota Bay. Beautiful Gulf Of Mexico Sunsets Are Yours To Enjoy Year Round. Through A Private Elevator Foyer The Interiors Are A Welcoming Experience In Ch...

Photo of Listing #A4146053

340 Osprey Point Dr, Osprey, FL - $1,599,900

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 #A4172028

221 Osprey Point Dr, Osprey, FL - $1,549,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,811 SQFT
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Located In The Prestigious District For 'pine View School For The Gifted', The Famed And Consistently Top Rated High School Nationwide, This Extraordinary Home Presents A Caliber Of Quality Usually Only Reserved For Multi-million Dollar Estates. A...

Photo of Listing #A4152178

497 Webbs Cv, Osprey, FL - $1,549,000

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...

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 April 27th, 2017 at 6:48am EDT.