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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

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Photo of Listing #A4515936

51 Mac Ewen Drive 14, OSPREY, FL
$129,000

Residential, Condominium
  • 1 Bed
  • 1 Bath
  • 595 SQFT
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A Rare Opportunity To Acquire Membership In The Enviable Lifestyle Of The Oaks Club Is Now Available With The Purchase Of This Charming Guest House Condominium In Windsor Lodge. Cherished For Its Architectural Heritage And The Superb Traditional ...

Photo of Listing #A4513309

259 Osprey Point Drive, OSPREY, FL
$1,325,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,867 SQFT
  • 10 DOM
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Set Gracefully Among Lush Landscaping On A Large Lakefront Lot In The Gated Waterfront Community Of The Oaks Bayside, This Stunning Bo Macewen-designed, Single-story Home Is Welcoming From The Moment One Approaches The Long Paver Driveway And Cour...

720 North Macewen Drive, OSPREY, FL
$1,250,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,308 SQFT
  • 11 DOM
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**don’t Miss This Opportunity** Situated On An Extraordinary Lot With Stunning Water View While Looking Out Toward The 13th Green Of The Oaks’ Eagle Course, This Gorgeous, Impeccably Maintained Home Offers An Ideal, Single-story, Open Floorplan W...

Photo of Listing #A4514610

409 North Point Road 301, OSPREY, FL
$525,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 17 DOM
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Welcome Home To Meridian Iv At The Oaks Preserve. Invite Family And Friends Through The Secure Lobby Into A Private Elevator Access To Only Your Front Door. This End Unit Boasts Over 2,500 Square Feet, Three Bedrooms And Bathrooms, Plus A Flex Roo...

Photo of Listing #A4514402

249 Shell Midden Court, OSPREY, FL
$2,800,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,620 SQFT
  • 18 DOM
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Beautiful Country French Home On Two Lots In A Private Cul-de-sac Location. Designed By Bo Mcewen And Featuring Outstanding Millwork With Double And Triple Crown Moldings, Solid Wood Doors, Soaring Ceilings And Large Open Rooms With Ample Closets ...

Photo of Listing #A4513606

55 Osprey Point Drive, OSPREY, FL
$1,889,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,339 SQFT
  • 20 DOM
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Newly Remodeled Lakefront Home In The Oaks Bayside. Pristine 0.4-acre Setting Overlooking Lakeside Peninsula Bordered By Mature Oaks Trees. Designed By 20th Century Architect Bo Macewen, The Home’s Clean Lines, Symmetry And Classical Style Accentu...

Photo of Listing #A4514191

490 East Macewen Drive, OSPREY, FL
$1,190,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,192 SQFT
  • 22 DOM
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Gorgeous Golf Course Home Featuring An Open Floor Plan With An Abundance Of Natural Light And 12 Foot Ceilings. Ideal For Entertaining Both Indoors And Outdoors With An Expansive Lanai Featuing A Heated Salt Water Pool And Spa Overlooking The 9th ...

Photo of Listing #A4512910

416 Macewen Drive, OSPREY, FL
$1,595,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,262 SQFT
  • 27 DOM
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Pristine Oaks Clubside Residence. A Spectacular Light-filled Home With Fabulous Serene Views Of A Tranquil Pond, Scenic Golf And Lush Landscaping All Set In Coveted Southern Exposure. The Quintessential In Florida Distinguished Country Club Living...

Blue Garden Lane, OSPREY, FL
$275,000

Incredible Opportunity! This Lot Is Situated On A Cul-de-sac Behind The Gates Of The Oaks Bayside. The Only Lot Currently Available In This Upscale, Private Golf And Country Club Community, It Is Ideal For Building The Home Of Your Dreams. With Ma...

Photo of Listing #N6117709

677 Trenton Way, OSPREY, FL
$2,150,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 5,045 SQFT
  • 30 DOM
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Welcome To This Elegant, Spacious, Open Concept Custom-built Home. It Is Located On An Oversized Lot At The End Of A Cul-de-sac, Providing You With The Privacy And Convenience. Upon Entering This Spectacular Home You Will Be Impressed By The Hig...

Photo of Listing #A4505428

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

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 33 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...

The Oaks Community Information

The Oaks Preserve is further divided into:

  • 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 October 26th, 2021 at 8:53pm EDT.