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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 #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 Exclusive Private Country Club Communities Located Minutes ...

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 ...

Photo of Listing #A4116615

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

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 ...

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 #A4112665

478 Oriskany Ct, Osprey, FL - $1,799,000

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...

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 7,092 SQFT
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Spacious Home Located In The Exclusive Oaks Country Club! As Soon As You Enter This Beautiful Neighborhood Lined With Oak Trees You Immediately Feel Welcomed. Oaks Bayside Features A Community Day Dock To Launch Your Kayak And Enjoy Living The F...

370 Sugar Mill Dr, Osprey, FL - $1,430,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 4,783 SQFT
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Detail, Privacy And Quality Capture The Spirit Of This Magnificent, Five-bedroom Residence, With An Elegance Befitting Of Its Peaceful Preserve Location In The Oaks Bayside. Custom-built By Baron, The Over 4,700 Sq. Ft. Of Living Area Exhibits Mas...

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...

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...

Photo of Listing #N5903506

446 E. Mac Ewen Dr, Osprey, FL - $1,324,735

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,003 SQFT
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Limited Opportunity To Own Brand New Emerald Homes Distinctive Mirabella Home In Oaks Club On Fairway 7 W/magnificent Views From Every Angle Of This Masterfully Crafted Home. This Exceptionally Designed 3-bdrm 3.5 Ba 1-story W/den, Over-sized Bonu...

580 N Macewen Dr, Osprey, FL - $1,290,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,495 SQFT
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As You Enter Your Extended Brick Paver Driveway Graced By A Picturesque Fountain, You Feel Like You're Driving Up To Your Mediterranean Home. A Beautiful Custom Creation, Built By John Cannon In 2008, Features The Latest Hurricane Protection Inclu...

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 August 3rd, 2015 at 7:04pm EDT.