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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 #A4604118

3621 North Point Road 601, OSPREY, FL
$1,340,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,680 SQFT
  • 2 DOM
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Welcome To Luxury Living At Its Finest In The Highly Regarded Meridian At The Oaks Preserve! This Condominium Offers An Unparalleled Blend Of Elegance, Comfort, And Breathtaking Views That Will Leave You Speechless. Enter This Expansive Sanctuary ...

Photo of Listing #A4606371

406 Walls Way, OSPREY, FL
$2,400,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,284 SQFT
  • 3 DOM
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Big Views Across The Lake To 12th Fairway Of The Heron Golf Course Adorn This Rutenberg Built Home. This Home Features 4 Bedroom Plus Office With Large Rooms Volume Ceilings And Crown Molding Throughout. Executive Office Is Complimented With Buil...

165 Sugar Mill Drive, OSPREY, FL
$1,995,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,912 SQFT
  • 18 DOM
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This 4 Bedroom, 4.5 Bath Home In The Oaks Bayside Has Been Continuously Updated And Redecorated Over The Past Several Years, Making It A Pristine, Elegant Showcase. This Is The Perfect Home For The Refined Country Club Lifestyle You Seek To Live. ...

497 Webbs Cove, OSPREY, FL
$3,600,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,863 SQFT
  • 20 DOM
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Magnificent Updated Estate! Located In The Highly Sought After Oaks Country Club! As You Enter The Double Doors You Will Be Amazed At This Master-piece That Words Alone Can Not Describe This 5-bedroom 6.5 Bath With 6-car Garage Residence. Also Inc...

601 Fernwalk Lane, OSPREY, FL
$3,995,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,453 SQFT
  • 21 DOM
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**exquisitely Designed Estate Boasts Modern & Contemporary Elegance** This Fully Updated Residence Features A Main House With 3beds/4.5baths Plus Guest House (1bed/1bath, Kitchen/laundry, Living Area) And Is Situated On An Oversized, Private And S...

12 Bishops Court Rd Road, OSPREY, FL
$995,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,182 SQFT
  • 21 DOM
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Welcome To The Oaks Preserve, A Wonderful Neighborhood Of Natural Beauty And Lush Canopied Surroundings, Yet Close To Sarasota's #1 Beaches And The Ideal Location For Easy Living! This Gracious And Charming Courtyard Home With A Separate Guest/cas...

Photo of Listing #A4601951

922 Macewen Drive, OSPREY, FL
$2,875,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,443 SQFT
  • 26 DOM
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Under Contract-accepting Backup Offers. **stunningly Updated, Custom Golf Course Estate On A Spectacular, Stand Alone, Beautifully Landscaped Lot With Golf And Lake View ** Is Located Behind The Secure Gates Of The Oaks Country Club Neighborhood A...

401 N Point Road 301, OSPREY, FL
$675,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 27 DOM
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One Or More Photo(s) Has Been Virtually Staged. Enter Through The Secure Foyer And Take The Private Elevator To The Third Floor Where You Will Find This Charming 3 Bedroom, 3 Bath Residence. Situated At Treetop Level, Overlooking The Preserve And ...

Photo of Listing #A4600903

37 Bayhead Lane, OSPREY, FL
$789,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,168 SQFT
  • 28 DOM
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Under Contract-accepting Backup Offers. Brand New Roof 2024! This Beautiful 3 Bed/2ba Home Is Located In Bishops Court In The Oaks Preserve. Once Through The 24 Hour Guarded Security Gate You Will Be Treated To Rich Fauna, Streets Lined With Canop...

325 Osprey Point Drive, OSPREY, FL
$1,689,900

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 3,905 SQFT
  • 31 DOM
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**beautifully Updated Estate With Water View And Stunning Architectural Details** Is Located In The Coveted, Oaks Bayside Country Club Neighborhood On Little Sarasota Bay. Enjoy The Private And Tranquil, Lake-front Setting Of This Meticulously Ma...

409 N Point Road 603, OSPREY, FL
$785,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,203 SQFT
  • 35 DOM
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Beautiful Full Water Views Of North Creek, Sarasota Bay, And The Gulf From The Lowest Priced Condo With A Water View In The Meridian. Watch The Eagles And Osprey Fish And Enjoy Truly Stunning Sunsets From The Balcony Of This Condo With 3 Bedrooms...

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 April 12th, 2024 at 5:50pm EDT.