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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 - $5,200,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 8,973 SQFT
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Most Desirable Location In The Oaks Bayside Country Club; Truly A Boater's Dream! Featuring Your Own Private Dock With 3 Power Lifts..12,000/16,000. Driving Thru This Private Gated Community You Are Surrounded By A Canopy Of Mature Oak Trees. The ...

552 Eagle Watch Ln, Osprey, FL - $3,685,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 6,300 SQFT
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New Construction With Separate Guest House. Unparalleled Construction Quality And Features. Located In One Of Sw Florida’s Finest Golf/tennis Communities - The Oaks. This Energy Efficient Masterpiece, Nestled On A Premium Golf Course And Lake Vie...

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 ...

Photo of Listing #A4196744

136 Osprey Point Dr, Osprey, FL - $2,750,000

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 #A4190304

95 Osprey Point Dr, Osprey, FL - $2,100,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 7,500 SQFT
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It Doesn’t Get Any Better Than This…serene, Secure, Secluded, And Significantly Reduced From The Original Asking Price, You Must See This Spectacular Home Now. Stepping Onto The Beautifully Manicured Grounds Is Like Stepping Onto Your Own Private ...

Photo of Listing #A4208052

91 Osprey Point Dr, Osprey, FL - $1,995,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,100 SQFT
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Iconic Architecture In Sarasota’s Premiere Golf And Country Club. This Magnificent 4-bedroom Estate Was Designed And Built By Bo Macewen And Brims With The Essence Of Warm, Southern Hospitality. Bo Was The Original Architect For The Oaks And He Cr...

Photo of Listing #A4173121

285 Sugar Mill Dr, Osprey, FL - $1,871,000

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 - $1,795,000

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...

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...

409 N Point Rd #1003b4, Osprey, FL - $1,750,000

Residential, Condo
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
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The Best Views In All Of Meridian! Experience The Luxurious Florida Lifestyle With Gorgeous Open Views That Encompass Casey Key, Siesta Key, Downtown Sarasota, Little Sarasota Bay & The Gulf. This Private, Rarely Available Corner Residence Is Loca...

854 Macewen Dr, Osprey, FL - $1,600,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
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Offering Over 9,000 Square Feet Of Exquisite Living Space, This Richly-detailed Custom Home Is Nestled On A Guarded, Private Cul-de-sac. Entertain Guests Or Simply Relax As A Family In The Multitude Of Well-designed Rooms– From The Living Room Wit...

Photo of Listing #A4203589

419 Walls Way, Osprey, FL - $1,550,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,523 SQFT
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Best Lot In The Oaks; On A Cul-de-sac Street, Known As “the Street Of Dreams”, Is The Location For One Of The Most Incredible Homes In The Oaks. With Over $1,000,000 In Renovations, This Spectacular Colonial Home Gives New Meaning To Move In Ready...

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 23rd, 2018 at 7:00am EDT.