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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 #A4499758

296 Osprey Point Drive, OSPREY, FL
$2,300,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 7,092 SQFT
  • 4 DOM
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Featuring His And Hers Master Bedrooms And Bathrooms, This 4 Bedroom + Office, 5.5 Bath, 7,092 Sq Ft Home Has It All! You Need To Look No Further For The Home That Offers Space, Beauty, Comfort & Privacy! Separate Guest House With Interior Lock-of...

Photo of Listing #N6115093

642 Trenton Way, OSPREY, FL
$1,100,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,939 SQFT
  • 5 DOM
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Beautiful And Spacious. This 3939 Sq.ft., Rutenberg Designed Home Offers Four Bedrooms, Five Bathrooms, An Office, A Bonus Room And A Four Car Garage. The Home Also Offers A Heated Freeform Pool And Spa, All Overlooking A Pond And The Fourteenth...

Photo of Listing #A4500409

51 Mac Ewen Drive 16, OSPREY, FL
$96,000

Residential, Condominium
  • 1 Bed
  • 1 Bath
  • 595 SQFT
  • 5 DOM
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Enjoy True Country Club Living At Its Finest... Two Championship Golf Courses, Tennis, Swimming, Pickle Ball, Gourmet Or Casual Dining And So Much More. This Windsor Lodge At The Oaks Second Floor Unit Offers Views Of The Pool, The 18th Hole Of Th...

Photo of Listing #A4498666

77 Bayhead Lane, OSPREY, FL
$675,000

Residential, Single Family Residence
  • 4 Beds
  • 2 Baths
  • 2,917 SQFT
  • 6 DOM
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Best Priced Home In The Prestigious Oaks Golf And Country Club. This Gorgeous Custom Built Home Offers Many High End Features Including Double French Doors, Tray Ceilings And Arches Throughout. The Spacious Open Floor Plan Is Perfect For Entert...

Photo of Listing #A4500458

3621 North Point Road 501, OSPREY, FL
$725,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,680 SQFT
  • 6 DOM
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***to Much To Say In This Small Description Box - You Have To Come See For Yourself**seller Is Contributing $40,000 Towards Their Choice Of Mandatory Equity Or Social Membership At Closing.*welcome Home To Your Luxurious 5th Floor Dream Condo. Fro...

Photo of Listing #N6114795

401 North Point Road 401, OSPREY, FL
$474,900

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 9 DOM
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*** The Oaks Club***award Winning***one Of America's Healthiest Clubs ***luxury Coastal Living In Sarasota County *** Pristine Golf Courses ** Top Tier Tennis*** Endless Luxury Amenities*** Wellfit Center***award Winning Culinary Team 3 Onsite Res...

Photo of Listing #A4499019

409 North Point Road 502, OSPREY, FL
$425,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,055 SQFT
  • 9 DOM
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Gorgeous View From This Move-in Ready, 5th Floor, 3-bed Luxury Condo!! The Coveted Lifestyle Of The Oaks Club With The Convenience And Amenities Of Maintenance-free Condominium Living Come Together At This Gorgeous Meridian 5th Floor Residence. Up...

Photo of Listing #A4500137 OPEN HOUSE
May16th
Sunday1-4PM

40 Bayhead Lane, OSPREY, FL
$410,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,129 SQFT
  • 9 DOM
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Best Priced Home In The Prestigious Oaks Golf And Country Club. Arguably The Best Lot In The Bishopscourt Community, Located With A Ope View Of The Lake And Fountain, This Gorgeous Home Offers Many High End Features Including High Ceilings, Cut ...

56 Bayhead Lane, OSPREY, FL
$645,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,010 SQFT
  • 13 DOM
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Back On Market! Nestled Amid Lush Greenery In The Oaks Preserve This 3-bedroom And 3 Full Bath Home Will Not Disappoint. On Entering From The Brick Paved Porch, It Is Evident The Home Has Been Meticulously Maintained With Real Oak Hardwood Floorin...

33 Bishops Court Road 118, OSPREY, FL
$299,000

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 1,890 SQFT
  • 13 DOM
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This Exquisite Townhome Is Located In One Of The Most Well-regarded Country Clubs On The Gulf Coast, The Oaks. Tuscan Style Features Adorn This Spacious 2 Bedroom 2.5 Bathroom Home. Enter Into Your Open Foyer And You Are Greeted With Venetian Plas...

Photo of Listing #A4494298

871 Macewen Drive, OSPREY, FL
$1,480,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,168 SQFT
  • 22 DOM
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Sited On Arguably One Of The Best Lots In The Oaks Club Side Along The Heron Course’s 13th Green And Adjacent Wooded Preserve, This Majestic Georgian Style Home With Guest House Blends Perfectly With The Surrounding Landscape To Deliver Both Priva...

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 May 16th, 2021 at 5:31am EDT.