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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 #A4569805

293 Turquoise Lane, OSPREY, FL
$895,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,271 SQFT
  • 3 DOM
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**rare Opportunity** This Stunning, Updated, Maintenance-free Home Is Located In Emerald Woods, Behind The Secure Gates Of The Distinguished Oaks Preserve Neighborhood. Offering 3-beds (or 2-beds Plus Den), 2-baths And 2-car Garage, Premium Finish...

Photo of Listing #A4572210

401 N Point Road 304, OSPREY, FL
$855,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 4 DOM
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Give Yourself The Gift Of Luxury Living! This 2,778 Square Foot Residence Is The Largest Non-penthouse Floor Plan Available In Meridian At The Oaks Preserve. With Three Bedroom, Plus A Dining Room And An Office/den, This Unit Offers All The Space ...

Photo of Listing #A4570865

465 Macewen Drive, OSPREY, FL
$1,950,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,357 SQFT
  • 5 DOM
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Elegance Abounds In This Spacious 2 Story Home With New Roof In The Oaks Clubside. With 5 Bedrooms, Plus An Office, 4 Full And 2 Half Baths, There Is Room For Everyday Living, And For Hosting Guests. Beautifully Landscaped, The Curb Appeal Is A Ha...

Photo of Listing #A4570656

51 Mac Ewen Drive 17, OSPREY, FL
$200,000

Residential, Condominium
  • 1 Bed
  • 1 Bath
  • 595 SQFT
  • 12 DOM
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Rarely Available. Now Offered At The Windsor Lodge, Located Within The Oaks Club – A Second-floor, Maintenance-free Lakeside Efficiency Condominium Overlooking The Pool. Enjoy The Benefits And Country Club Lifestyle Of The Oaks Club – A Private, ...

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

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,095 SQFT
  • 13 DOM
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With Just Under 3,100 Square Feet Of Living Area, This 3 Bedroom, 3 Bath Home In The Oaks Clubside Offers All You Need To Live, Work And Play In South Sarasota. A Large, Pavered Circular Drive Leads To The 897 Sq. Ft Attached Garage On One Side, ...

Photo of Listing #A4566630

600 Macewen Drive, OSPREY, FL
$2,100,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,111 SQFT
  • 14 DOM
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This Stunning Traditional Style Home, Meticulously Maintained And Updated, Is Your Opportunity To Live The Gulf Coast Country Club Lifestyle. From The Moment You See It, You Will Fall In Love With This 4 Bedroom (+ Office), 4.5 Bath Beauty. The E...

Photo of Listing #A4570326

67 Sugar Mill Drive, OSPREY, FL
$1,900,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,020 SQFT
  • 15 DOM
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**elegant, Traditional, Custom-built Estate In The Coveted Oaks Bayside Country Club Neighborhood On Sarasota Bay Waters Is Sure To Impress, Boasting Many Updates And Remarkable Architectural Detail Throughout And Consists Of 4 Beds + 3 Full Baths...

29 Bayhead Lane, OSPREY, FL
$820,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,192 SQFT
  • 17 DOM
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Welcome To "bishops Court" At The Oaks Preserve A Maintenance-free Gated Neighborhood Where The Streets Are Lined With Canopy Trees, Rich Lush Fauna Is All Abound And Wonderful Memories Begin! This Comfortable 3 Bedroom, 2 Bath Home Was Custom Des...

Photo of Listing #A4570226 OPEN HOUSE
Jun4th
Sunday1-3PM

558 Dove Pointe, OSPREY, FL
$1,795,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,521 SQFT
  • 24 DOM
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**impressive Country Club Estate With Water And Golf Course View On An Oversized Corner Lot** Located Behind The Secure Gates Of The Oaks-clubside Country Club Neighborhood, This Meticulously Maintained, Single Story Home With An Ideal Open Floorp...

401 N Point Road 603, OSPREY, FL
$994,900

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,203 SQFT
  • 25 DOM
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Beautiful Full Water View And 2nd Floor Private 2 Car Garage! This Incredible Offering Has Everything You Need To Live A Luxury Condominium Lifestyle In Comfort And Ease; 3 Bedrooms, 3 Full Baths And A Formal Dining Room. Add To This, Gorgeous Vie...

3603 North Point Road 703, OSPREY, FL
$1,595,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,680 SQFT
  • 31 DOM
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**ultimate View From This 7th Floor Penthouse Unit** Behind The Gates Of The Highly Sought After Oaks-preserve Neighborhood. As You Emerge From Your Private Elevator Foyer Entrance, You Will Be Enthralled By The Stunning, Unobstructed 90+ Degree ...

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 June 4th, 2023 at 10:34am EDT.