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The Oaks Homes for Sale

The Oaks in Osprey FL…A life of grandeur for those who seek tradition and timelessness. Established originally as the dream home amongst stately oaks and exotic palms for Chicago “grande dame” Bertha Honoré Palmer nearly a hundred years ago. The Oaks offers everything from waterfront mansions on the Bay to maintenance free villas. The community contains three gated neighborhoods; Oaks Bayside, Oaks Clubside and Oaks Preserve. The Oaks Preserve is further divided into:

The Oaks

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Photo of Listing #A4507345

925 Blue Heron Overlook, OSPREY, FL
$990,700

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,975 SQFT
  • 4 DOM
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Located Behind The Gates Of The Oaks, On A Quiet Cul-sac, This 3 Bedroom, 3.5 Bath Home Is Situated On A Lovely, Private Lot. From The Moment You See The Unique Facade, You Will Anticipate What Is Behind The Double Front Doors. As You Enter You W...

156 Bishops Court Road, OSPREY, FL
$825,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,112 SQFT
  • 14 DOM
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Enjoy The Privacy Of The Oaks Preserve In This Mini Estate, As Your Backyard Is A Pristine Nature Sanctuary And A Deeded Nature Preserve. This Cape Cod Style Home Has So Much Charm, Is A Hidden Jewel, And Is Part The Legendary Oaks Country Club. ...

91 Osprey Point Drive, OSPREY, FL
$1,995,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,100 SQFT
  • 20 DOM
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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 #A4505428

393 North Point Road 701, OSPREY, FL
$850,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 27 DOM
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Live The Carefree Country Club Lifestyle In This 3 Bedroom, 3 Bath (plus Den/office And 2 Car Garage) Residence In Meridian At The Oaks Preserve. The Gorgeous Views Of The Bay And Beyond To The Gulf Will Delight You Throughout The Day. Greet Th...

Photo of Listing #A4503626

282 Osprey Point Drive, OSPREY, FL
$1,589,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 4,599 SQFT
  • 31 DOM
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One Of Florida’s Finest Estate Homes, This Residence Is The Definition Of Luxury And Design; Situated In A Coveted Gated Neighborhood Of Sarasota That Is Known For Its Beautiful Tree-lined Streets And Gorgeous Landscaping. The Home Boasts Custom U...

Photo of Listing #A4503345

409 North Point Road 404, OSPREY, FL
$525,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 31 DOM
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At Meridian At The Oaks Preserve, A Legendary Country Club And Pristine Nature Sanctuary Provide The Perfect Backdrop For A Life Of Recreation And Relaxation. Enjoy The Serenity Of Surrounding Nature Preserves With Abundant Bird Life. This Condomi...

Photo of Listing #A4502875

409 North Point Road 304, OSPREY, FL
$575,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 31 DOM
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Live A Country Club Luxury Lifestyle In The Premier Gated Golf Club In Sarasota. You Will Have Access To 2 Championship Golf Courses, An Active Tennis Community With 12 Har-tru Courts, And A Variety Of Social Activities Including Dining In 3 Resta...

Photo of Listing #A4504800

796 Lytham Circle, OSPREY, FL
$1,850,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,639 SQFT
  • 32 DOM
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Welcome To One Of The Single Largest And Most Private Homesites In All Of The Oaks Clubside. Poised On An Impressive .73 Acres With Complete Privacy, Unobstructed Golf And Lake Views, And Your Seemingly Private Enclave Of Only 7 Total Homes, Make...

Photo of Listing #A4503604

627 Macewen Drive, OSPREY, FL
$1,600,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,857 SQFT
  • 33 DOM
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From The Moment You See This 4 Bedroom, 4.5 Bath Home, Set Back From The Road And Surrounded By Tropical Landscape, You Will Know This Is A Special Offering. Step Through The Double Leaded Glass Doors And You Will Immediately Be Taken With Its Qui...

Photo of Listing #A4503834

744 North Mac Ewen Drive, OSPREY, FL
$1,849,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,513 SQFT
  • 34 DOM
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Pre-construction. To Be Built. Pre-construction To Be Built. This Home And Homesite Package Features The Kylie Model's Floor Plan By John Cannon Homes. The Home Represents An Exciting Transitional Mixture Of Coastal And Modern Architecture. The Pr...

Photo of Listing #A4503087

429 Walls Way, OSPREY, FL
$1,700,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 4,669 SQFT
  • 43 DOM
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Enjoy The Ultimate In Sarasota Country Club Living At The Oaks! This Is The Most Desirable Location Currently Offered In The Oaks Clubside, With Views Across Water And The Heron Course To The Majestic Clubhouse And Spectacular Sunsets. This Except...

The Oaks Community Information

  • Bishop’s Court-Mostly single family homes and a few townhomes
  • Emerald Woods-Maintenance free villas
  • The Meridian-six luxury mid-rise condominiums, each with a private elevator foyer. The Meridian has breathtaking views of Sarasota Bay.

A dynamic community where the eagles soar…Protective of the natural Florida habitat, The Oaks Club employs environmentally sound practices and have created a ten-acre bald eagle preserve in Oaks Bayside, to allow this regal, endangered species to flourish. With the club’s sensational location on Little Sarasota Bay, access to a variety of marinas is convenient and deep water sailing and fishing are just a short drive from the Club entrance. The community is accented by the lush vegetation of the natural shoreline with sea myrtle, beach elder, and mangroves housing native birds and wildlife.

The Oaks Image Gallery

Gulf Shores Realty: 627781033 Gulf Shores Realty: 1613877538 Gulf Shores Realty: 1264807147 Gulf Shores Realty: 473835121 Gulf Shores Realty: 1447348502 Gulf Shores Realty: 506248133 Gulf Shores Realty: 368704368 Gulf Shores Realty: 1771245611 Gulf Shores Realty: 268716939 Gulf Shores Realty: 1926597494 Gulf Shores Realty: 614281769 Gulf Shores Realty: 836552199 Gulf Shores Realty: 1409377882 Gulf Shores Realty: 1284606319 Gulf Shores Realty: 861737261 Gulf Shores Realty: 523379917 Gulf Shores Realty: 1890278202 Gulf Shores Realty: 164965010 Gulf Shores Realty: 315557599 Gulf Shores Realty: 1061200894 Gulf Shores Realty: 856064521 Gulf Shores Realty: 1290081770 Gulf Shores Realty: 1999328186 Gulf Shores Realty: 40831177 Gulf Shores Realty: 1332063478 Gulf Shores Realty: 646081603 Gulf Shores Realty: 67202262

The Oaks Community Amenities

The Oaks community is home to their private country club, The Oaks Club, offering the finest in championship-style golf on two 18-hole courses, a professional tennis facility with 12 Har-Tru tennis courts, and exquisite restaurants including The Glen Room, an elegant option for fine dining with a fireplace and Old English ambiance. The clubhouse is an extensive 42,000 square feet of comfort and luxury. The Oaks Club also has a junior olympic pool, professional croquet court, and a playground.

Location and Directions

The Oaks Club is located at 301 MacEwen Drive, Osprey, Florida 34239. The community is located directly off of Tamiami Trail S. (U.S. 41) and has an entrance on both the east and west side of Tamiami Trial S.

Call us today at 941-488-6644

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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 DBA Stellar MLS.

Listing information last updated on July 27th, 2021 at 2:51pm EDT.