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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 #A4591361

325 Osprey Point Drive, OSPREY, FL
$1,750,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 3,905 SQFT
  • 2 DOM
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This Beautiful Bo Macewen Home, Idyllically Set On A Lovely Lakeside Lot In The Oaks Bayside, Is Offered At A New Price. With 3 Bedrooms, 4.5 Baths And Over 3,900 Square Feet, It Offers Wonderful Living Space With Classic Elegant Touches. Majestic...

Photo of Listing #A4589700

651 Oriskany Court, OSPREY, FL
$1,295,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,826 SQFT
  • 7 DOM
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**beautifully Renovated, 1-story Home On Oversized Corner Lot With Golf Course View** Located On A Quiet Street Behind The Gates Of The Highly Sought After Oaks-clubside Neighborhood, This 3 Bed Plus Office (with Separate Entrance), 2.5 Bath Home ...

393 North Point Road 503, OSPREY, FL
$850,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,203 SQFT
  • 21 DOM
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This Condo In Meridian At The Oaks Preserve Is An Excellent Choice! Enter Through The Secure Foyer And Take The Private Elevator To The Fifth Floor Where You Will Find This Charming 3 Bedroom, 3 Bath Residence With Dining Room And Two Under The Bu...

147 Osprey Point Drive, OSPREY, FL
$850,000

Your Dream Homesite Awaits! This Lot Is Located Within The Oaks Bayside, One Of Southwest Florida‘s Most Exclusive Private, Gated Communities. This Amazing Property Is Near The Community Dock And Fountain And Is Surrounded By Some Of The Most Gran...

453 Webbs Cove, OSPREY, FL
$1,896,300

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,953 SQFT
  • 27 DOM
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Welcome Home To Not Only A Beautiful House But A Exclusive Lifestyle Of Security, Entertainment, Sense Of Community And Exercise Surrounded By Nature And Steps Away From The Gulf Of Mexico. This Home Is Located West Of 41 Putting You Steps Away F...

3603 North Point Road 701, OSPREY, FL
$1,475,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,680 SQFT
  • 35 DOM
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**spectacular View From This 7th Floor, Corner Penthouse Condo** Offering 3 En Suite Bedrooms, 3 Full Baths And Private 2-car Garage! Located Behind The Gates Of The Highly Sought After Oaks-preserve Neighborhood In The Newest Meridian Condo Towe...

401 N Point Road 901, OSPREY, FL
$1,750,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 38 DOM
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This Opulent 3 Bedroom Plus Den, 3 Bath Residence With A Private 2 Car Garage Located In Meridian At The Oaks Preserve, Is A Dream Come True! A Penthouse-level End Unit Situated On The North Side Of The Building, It Has Been Carefully Updated And ...

Photo of Listing #N6129134

385 North Point Road 902, OSPREY, FL
$2,145,000

Residential, Condominium
  • 3 Beds
  • 4 Baths
  • 3,738 SQFT
  • 45 DOM
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New To The Market This Stunning Residence Has Been Meticulously Renovated With Incredible Attention To Detail, Making It An Absolute Gem. Boasting A Spacious Floor Plan Spanning Over 3,700 Square Feet, This Oversized Unit Features Two Master Suit...

452 Blue Garden Lane, OSPREY, FL
$1,750,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,910 SQFT
  • 59 DOM
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Privacy Abounds In This Completely Updated Home W/newer Roof Located Behind The Gates Of The Oaks Bayside. This Custom-built 3 Bedroom, 3.5 Bath Home With Enormous Office/den Is The Personification Of A Sarasota Dream Come True! And It Is Move In...

252 Osprey Point Drive, OSPREY, FL
$2,095,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,780 SQFT
  • 63 DOM
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**renovated, Custom, Light-filled Courtyard-style Home That Embraces A True Indoor/outdoor Lifestyle And Offers Unparalleled Privacy In The Secure And Coveted, Oaks-bayside Neighborhood, While Overlooking A Scenic Nature Preserve With Water Views ...

853 Macewen Drive, OSPREY, FL
$1,700,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,185 SQFT
  • 66 DOM
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If You Are Seeking A Home That Offers You An Abundance Of Living Space, And An Incredible Lot With A Ton Of Privacy, Look No More. You Have Found It In This John Cannon Custom-built Home In The Oaks Clubside. With 4 Bedrooms And 4 Bathrooms, An ...

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

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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 December 7th, 2023 at 6:50pm EST.