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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 #A4559902

385 North Point Road 601, OSPREY, FL
$1,250,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
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Situated At The End Of Building I In The Meridian, This Beautiful 3 Bedroom, 3 Bath Residence Offers Spectacular Views From Almost Every Room. As You Pass Through The Secure Entrance, And Step Off Your Private Elevator, You Will Immediately Know ...

Photo of Listing #A4558072

134 Marys Chapel Court, OSPREY, FL
$2,625,000

Residential, Single Family Residence
  • 5 Beds
  • 8 Baths
  • 5,521 SQFT
  • 11 DOM
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**striking, Move-in Ready, Contemporary, Fully-renovated Estate** Found Behind The Gates Of The Coveted Oaks-bayside Country Club Neighborhood On Sarasota Bay Waters… Entails 5 Beds + 6 Full & 2 Half Baths + Elevator + 3-car Oversized Garage. Cou...

Photo of Listing #A4558410

65 Osprey Point Drive, OSPREY, FL
$2,500,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 5,508 SQFT
  • 11 DOM
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On The Market For The First Time, The Sellers Had This 4 Bedroom (plus Study), 3.5 Bath House Custom Built By Baron As Their Dream Home. And Now, You Can Make This Spectacular Home Yours! It Will Be Love At First Sight When You Drive Up To This S...

Photo of Listing #U8188846

63 Sugar Mill Drive, OSPREY, FL
$1,395,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 3,125 SQFT
  • 11 DOM
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**newly Renovated** Home In The Prestigious “oaks Bayside” Is The One You’ve Been Waiting For! Premium Updates In The Past 2 Years Include, A Saltwater Heated Pool And Spa Combo With Travertine Pavers And Pool Cage, Soft-close All Wood Kitchen, La...

Photo of Listing #A4557956

221 Osprey Point Drive, OSPREY, FL
$2,595,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,811 SQFT
  • 13 DOM
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**exquisite And Sophisticated Country Club Estate** Custom Built In 2007 By Renowned Tandem Construction As Found Behind The Gates Of The Coveted Oaks-bayside Neighborhood On Sarasota Bay Waters Offers Nearly 5000 Sf Of Elegant Accommodation Inclu...

3621 North Point Road 301, OSPREY, FL
$850,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,680 SQFT
  • 14 DOM
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Welcome To Your Slice Of Paradise. Ready To Live A Stress-free Luxury Condo Lifestyle? There Is No Place Better To Do It Than This 3 Bedroom, 3 Bath Residence In Meridian At The Oaks Preserve. Nestled Among The Treetops, This End Unit Has A Split ...

Photo of Listing #A4556689

393 North Point Road 602, OSPREY, FL
$949,900

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,055 SQFT
  • 20 DOM
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**dazzling Water And Sunset Views From This Gorgeous, Custom-renovated, Upper Floor Condo Unit** May Be Found Behind The Gates Of The Oaks Preserve. This Re-imagined, Beautifully Updated, Contemporary 3-bed / 3-bath Condo Is Found On The 6th Floo...

Photo of Listing #A4556514

127 Turquoise Lane, OSPREY, FL
$1,195,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,258 SQFT
  • 23 DOM
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Double Your Pleasure, Double Your Fun! This 3 Bedroom, 2 Bath Home In Emerald Woods Offers Double Living Space…a Lovely Interior, And An Amazing Outdoor Area! From Your First Glimpse, You Will Know You Have Found A Unique Treasure. Surrounded By L...

Photo of Listing #A4555198

36 Bishops Court Road 111, OSPREY, FL
$595,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,678 SQFT
  • 24 DOM
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Enjoy The Perfect Maintenance Free Country Club Lifestyle With Private Tranquil Views In This Single Level End Unit In Charming Bishopscourt Townhomes. Architecturally Designed By Bo Macewen, These Homes Feature A Formal Entry Hall, Two Bedrooms A...

402 Macewen Drive, OSPREY, FL
$1,525,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,565 SQFT
  • 24 DOM
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Located Behind The Gates Of The Oaks Clubside, Within Close Proximity To The Clubhouse, This 3 Bedroom Plus Office, 3.5 Bath Home Has Over 3,500 Square Feet Of Quiet Elegance, And Comfortable Living Space. Situated On The 4th Hole Of The Eagle Cou...

Photo of Listing #A4555624

3621 North Point Road 601, OSPREY, FL
$1,240,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,680 SQFT
  • 41 DOM
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Offered Turnkey Furnished (with Few Exceptions)! Located On The South End Of Building 5 In Meridian At The Oaks Preserve, This 3 Bedroom, 3 Bath Residence Is An Incredible Find. Enter Through The Secure Lobby, Go Up The Private Elevator And Step T...

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 February 7th, 2023 at 11:18pm EST.