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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 #A4631057

401 Walls Way, OSPREY, FL
$1,850,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,388 SQFT
  • 1 DOM
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Exquisite Executive Home In The Oaks Clubside, Step Into Elegance And Luxury With This Stunning Two-story Masterpiece. Perfectly Situated To Capture Breathtaking Views Of The 9th Fairway On The Heron Course And A Serene Lake Preserve, This Home Of...

Photo of Listing #A4629938

378 Macewen Drive, OSPREY, FL
$1,500,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,094 SQFT
  • 7 DOM
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Beautiful Lakefront 3 Bedroom, 3 Bath Home In The Oaks Clubside With View Of The Eagle 3. The Oaks, Sarasota’s Premier Golf And Country Club, Has Two Championship Golf Courses, An Outstanding Tennis Program, Pickle Ball And Croquet Courts, A Junio...

703 Macewen Drive, OSPREY, FL
$2,500,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,641 SQFT
  • 8 DOM
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Bathed In Natural Light, With Highly Sought After Southern Lanai Exposure, Is This Stunning And Meticulously Maintained Custom Built John Cannon Home In The Oaks Clubside. With 4 Bedrooms, And 3 Full And One Half Bathrooms, There Is Room For Love...

Photo of Listing #A4627082 OPEN HOUSE
Dec8th
Sunday1-3PM

21 Bayhead Lane, OSPREY, FL
$959,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,216 SQFT
  • 14 DOM
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This Incredible Newly Updated House With Many Upgrades And Amenities Is The Home You Have Been Waiting For! Ideally Located In The Beautiful Oaks Preserve Between Siesta Key And Casey Key, The Private Enclave Is In A Shaded Neighborhood Where Res...

385 N Point Road 404, OSPREY, FL
$1,150,000

Residential, Condominium
  • 4 Beds
  • 3 Baths
  • 2,778 SQFT
  • 20 DOM
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*beautifully Updated Condo With Wide Water Views* This Spacious Residence Of 3150 Sf Total Living Space (largest Non Penthouse) Features 4 Bedrooms, 3 Bathrooms, Sweeping Balcony With Wide Water Views Is Located Behind The Secure Gates Of The Cov...

186 Turquoise Lane, OSPREY, FL
$950,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,294 SQFT
  • 22 DOM
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This Lee Wetherington Built Maintenance Free Home Is Nestled In The Emerald Woods Section Of The Oaks Preserve. Enter Through The Double Doors With Leaded Glass, And You Will Find A Wonderful Open Floor Plan. This Home Is Move-in Ready. From Count...

393 N Point Road 603, OSPREY, FL
$850,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,203 SQFT
  • 29 DOM
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Enjoy Breathtaking Views Of The Gulf Of Mexico, Little Sarasota Bay And The Intercoastal Waterway From Your Living Room, Bedroom, Or Lanai. The Sunsets Are Absolutely Gorgeous From This 3 Bedroom, 3 Bath Condo, Which Offers All The Views And The S...

854 Macewen Drive, OSPREY, FL
$4,495,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
  • 30 DOM
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One Or More Photo(s) Has Been Virtually Staged. **newly Renovated, Spacious, Golf Course Estate** Boasts Over 9,000sf And Is Situated On A Prominent, Private Cul De Sac Lot Of Over 3/4 Acres. Expansive Room Abounds In This Light And Bright Open Fl...

Photo of Listing #A4626406

219 Saint James Park, OSPREY, FL
$1,295,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,844 SQFT
  • 31 DOM
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Under Contract-accepting Backup Offers. **beautifully Renovated, Golf Course Estate, Ideally Located** In The Coveted “saint James Park” Cul De Sac Neighborhood, Offers Close Proximity To The Oaks Country Club And Amenities. Overlooking The Eagle...

393 N Point Road 801, OSPREY, FL
$1,650,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 3,029 SQFT
  • 36 DOM
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Rare In Every Way, This 3 Bedroom, 3 Bath Penthouse, With Private Two Car Garage, Is Only One Of Six Units In Meridian That Enjoys This Incredible Floor Plan. The Elegant Interior Is Punctuated By Spectacular Views. This Residence Provides Everyth...

325 Osprey Point Drive, OSPREY, FL
$1,690,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 3,905 SQFT
  • 40 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 Mai...

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 3rd, 2024 at 10:19pm EST.