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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 #A4601951

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,443 SQFT
  • 2 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...

Photo of Listing #A4603773

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

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 3 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 #A4601618

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

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 3,905 SQFT
  • 6 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...

Photo of Listing #A4600134

284 Sugar Mill Drive, OSPREY, FL
$1,950,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,135 SQFT
  • 11 DOM
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Under Contract-accepting Backup Offers. Please View The 3d Matterport Tour By Clicking The Virtual Tour Link. Welcome To The Epitome Of Luxury Living Behind The Secure Gates Of The Oaks Bayside, Where Elegance Meets Tranquility In This Meticulo...

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

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,203 SQFT
  • 11 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...

17 Bayhead Lane, OSPREY, FL
$775,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,335 SQFT
  • 11 DOM
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Who Says You Can’t Have It All? This Home And Location Can’t Be Beat, And Will Surely Check All Of Your Must Have Items On That New House Wish List. Mature Landscaping Greets You As You Enter This Open And Spacious Home With Sliders That Allow Th...

84 Bishops Court Road, OSPREY, FL
$1,295,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,573 SQFT
  • 14 DOM
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Splendid Is In The Details Of This Lovely Three Bedroom, Three Bath, Move In Ready Home In The Oaks Preserve. No Need To Be Concerned With Remodeling, As This Wonderful Home Underwent A Total And Complete Interior And Exterior Renovation In 2023. ...

101 Sugar Mill Drive, OSPREY, FL
$3,200,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,875 SQFT
  • 19 DOM
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New. Notable. No Waiting For Your Dream Home! Rare Opportunity For A Luxury Florida Lifestyle With This Just Completed John Cannon Custom Build. A Coveted West Of Trail Location In The Oaks Bayside Positions You In One Of The Area’s Only Country...

201 Saint James Park, OSPREY, FL
$1,095,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,855 SQFT
  • 19 DOM
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Welcome Home To Your Sanctuary Located Behind The Gates Of The Exclusive Oaks Country Club. This Corner Lot In Saint James Park Is Situated Close To The Club, Tennis, And All The Amenities The Community Has To Offer. As You Approach The Home The L...

Photo of Listing #A4599336

621 North Macewen Drive, OSPREY, FL
$1,885,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,836 SQFT
  • 25 DOM
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**impressively Updated, Golf Estate With Water View In The Popular Oaks Country Club Community** Situated On The 15th Fairway Of The Interior, Heron Golf Course And With South-facing Pool/lanai. Featuring 4beds Plus Office/den, 4 Full And 1 Half ...

Photo of Listing #A4600762

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

Residential, Condominium
  • 4 Beds
  • 3 Baths
  • 2,778 SQFT
  • 26 DOM
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4th Floor Residence Offers An Uncommon Feature, Water Views Of Three Waterways, North Creek, The Intracoastal And The Gulf! And, Unlike Some Units At This Level, You Won’t Have To Play Peek-a-boo To Take In The Spectacular Views Of Water, Surroun...

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 March 19th, 2024 at 2:04am EDT.