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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 #A4617671 OPEN HOUSE
Jul28th
Sunday1-3PM

360 North Point Road, OSPREY, FL
$1,595,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,913 SQFT
  • 3 DOM
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**don’t Wait To Build!** Exquisite, Newly-constructed And Never Lived-in, Spanish Mission Style Home Behind The Secure Gates Of The Coveted, Oaks Preserve Country Club Neighborhood On Sarasota Bay Waters Offers Superb Attention To Detail. This Cu...

Photo of Listing #A4614440

57 Bishopscourt Road 121, OSPREY, FL
$750,000

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 1,890 SQFT
  • 7 DOM
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**updated, Maintenance-free Townhouse** Located Behind The Secure Gates Of The Coveted, Oaks Preserve Country Club Neighborhood On Sarasota Bay Waters Where Golf (or Social) Membership Is Immediately Available. This Traditional Residence Boasts A...

1108 Bayhead Lane, OSPREY, FL
$1,399,999

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,541 SQFT
  • 10 DOM
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Seller May Consider Buyer Concessions If Made In An Offer. **luxurious Turnkey Home In The Oaks, Sarasota** Luxuriously Furnished, Turnkey, And Meticulously Maintained, This Immaculate Home Offers Stunning Sunsets And A Private Pool. Located In...

409 North Point Road 702, OSPREY, FL
$1,150,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,055 SQFT
  • 18 DOM
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One Or More Photo(s) Has Been Virtually Staged. Experience Stunning Views Of The Intracoastal And Gulf From This Well-maintained Seventh-floor Meridian Unit, Featuring A Private Entrance. With Beautiful Hardwood Floors, Marble And Granite Accents,...

738 Macewen Drive, OSPREY, FL
$1,800,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,614 SQFT
  • 30 DOM
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Imagine How You’d Like To Live The Ultimate Florida Lifestyle. Your Vision Can Become A Reality In This 5 Bedroom, 5.5 Bath Two Story Home In The Oaks Clubside. Currently Unfurnished, You Just Need To Pack Your Bags, Bring Your Own Style And Make ...

402 Walls Way, OSPREY, FL
$1,895,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,464 SQFT
  • 42 DOM
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**newer Construction (2014) -- Impressive, Custom “courtyard Style” Golf Course Estate W/ Water View Built By Todd Johnson Homes** Is Situated On An Oversized, 0.64 Acre, Lakeside Corner Lot Behind The Secure Gates Of The Oaks Country Club Communi...

216 Osprey Point Drive, OSPREY, FL
$795,000

One Of The Last Lots Available To Build In The Prestigious Community Of The Oaks Bayside. Take Advantage Of This Rare Opportunity To Build Your Dream Home, Using The Builder You Choose, Within The Oaks Club – One Of The Most Exclusive Private Club...

409 N Point Road 501, OSPREY, FL
$1,050,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 54 DOM
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One Or More Photo(s) Has Been Virtually Staged. Welcome To Luxury Condo Living In The Oaks Preserve. This 3 Bedroom, 3 Bath Corner Unit With Office, Offers Everything You Need To Live The Country Club Lifestyle With Comfort And Ease. Take Your Pr...

Photo of Listing #A4611812

385 N Point Road 802, OSPREY, FL
$2,500,000

Residential, Condominium
  • 3 Beds
  • 4 Baths
  • 3,738 SQFT
  • 63 DOM
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This 3 Bedroom, Study, 3 1/2 Bath Penthouse Residence In Meridian At The Oaks Preserve Is Beautifully Renovated With High End Finishes, A 2 Car Garage, Has Splendid Sunsets And Is Offered Furnished. Membership In The Oaks Country Club Is Required.

Photo of Listing #A4611882

497 Webbs Cove, OSPREY, FL
$3,350,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,863 SQFT
  • 63 DOM
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Welcome To A Sanctuary Of Elegance And Comfort At 497 Webb's Cove, Nestled In The Highly Regarded Community Of The Oaks Country Club. This Exceptional Property Offers An Unparalleled Blend Of Sophistication And Warmth, Making It A True Gem In The ...

Photo of Listing #A4611113 OPEN HOUSE
Jul27th
Saturday10AM-12PM

75 Osprey Point Drive, OSPREY, FL
$1,695,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,001 SQFT
  • 65 DOM
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Opulent Exclusivity Awaits You At The Oaks, Osprey Florida. Nestled In The Prestigious Waterfront Community Of The Oaks - Bayside, 75 Osprey Point Dr. Stands As A Testament To Luxurious Living And Architectural Magnificence. This Expansive Estate ...

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 July 27th, 2024 at 10:34am EDT.