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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 Preserve is further divided into:

The Oaks

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Photo of Listing #A4492883

664 North Macewen Drive, OSPREY, FL
$1,050,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,607 SQFT
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This Beautifully Appointed Home Beckons You To Enjoy Peaceful And Elegant Living On A Quiet Cul-de-sac In One Of The Most Prestigious Private Country Clubs In Sarasota. Delight In The Attention To Detail Throughout, Combined With A Well Thought Ou...

Photo of Listing #A4492884

708 North Macewen Drive, OSPREY, FL
$1,450,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,266 SQFT
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Great House On One Of The Best Lake And Golf Course Lots In The Oaks

Photo of Listing #A4492940

144 Osprey Point Drive, OSPREY, FL
$3,450,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,575 SQFT
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Beautifully Positioned Within Sarasota’s Elite Country Club The Oaks, This Sophisticated, Multi-level Key West-style Home Reflects The Best In Bespoke Design. Driving Into The Oaks, You’ll Instantly Feel The Privacy And Attention To Detail That Se...

Photo of Listing #A4492789

933 Blue Heron Overlook, OSPREY, FL
$1,575,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,856 SQFT
  • 3 DOM
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Premier Courtyard Estate Home With Picturesque Southwest Views Located In A Cul-de-sac In The Oaks Clubside Behind Heron's 1st Green. A Single Floor Home With 4856 Sq Ft Under Air Plus A 2900 Sq Ft Lanai With Heated Ig Salt Water Pool. Very Desira...

Photo of Listing #A4492323

937 Blue Heron Overlook, OSPREY, FL
$769,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,823 SQFT
  • 5 DOM
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This Exquisitely Appointed Golf Course Home Lies On Half An Acre Of Pastoral Beauty In One Of Sarasota’s Finest Golf And Country Clubs, The Oaks Club. Surrounded By Oak Trees And Wildlife, This Lovely Corner Lot Location Offers A Classic Estate Wi...

Photo of Listing #A4492197

393 North Point Road 602, OSPREY, FL
$699,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,055 SQFT
  • 7 DOM
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Live Inspired Every Day In This Sixth-floor, Three-bedroom, Three-bathroom Residence Offering The Most Extraordinary Water Views And Sunsets With Direct Elevator Access To Your Sanctuary. As Soon As You Enter Your Private Foyer It Is Hard To Ignor...

Photo of Listing #A4491620

409 North Point Road 402, OSPREY, FL
$475,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,055 SQFT
  • 7 DOM
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The Meridian Condominiums Are A Collection Of Six Mediterranean Inspired Towers Overlooking A Preserve, Little Sarasota Bay, And The Intracoastal Waterway. Located In The Fourth Tower And Built With Hurricane Impact Windows, This 3 Bedroom, 3 Bat...

Photo of Listing #A4491045

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

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 5,510 SQFT
  • 10 DOM
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*must See 3d Virtual Tour And Aerial Video* Of This Exquisite Estate Home Just Steps Away From Sarasota Bay Waters And Situated On A Private Lot Behind The Gates Of The Secluded And Highly Sought-after “oaks-bayside” Neighborhood. Relish In The C...

168 Coastal Hammock Court, OSPREY, FL
$1,790,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,924 SQFT
  • 10 DOM
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Enjoy The Privacy And Bay Breezes From This Spectacular Bayfront Mizner Style Home In The Oaks Bayside. Views Of Little Sarasota Bay And The Gulf Of Mexico And Amazing Florida Sunsets Make This Home Special. Rarely Available Private Cul-de-sac Loc...

Photo of Listing #A4491047

404 Macewen Drive, OSPREY, FL
$925,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,454 SQFT
  • 13 DOM
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This Architect-designed, Custom-built 3 Bedroom, 3 Bath Home Will Captivate You From The Moment You See It. Situated In The Oaks Clubside, As You Enter Your Eyes Will Be Drawn To The Incredible Lake And Golf Course Views Beyond The Lanai, Expanded...

Photo of Listing #A4491351

867 Macewen Drive, OSPREY, FL
$1,100,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,606 SQFT
  • 15 DOM
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Situated Behind The Gates Of The Oaks, This 4 Bedroom, 4.5 Bath Exudes Warm And Charm. Set Among Mature Trees That Give The Home A Feeling Of Calm, Tropical Privacy. Home Has Been Beautifully Updated And Has A New Roof, And Features A Floor Plan T...

The Oaks Community Information

  • 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 1st, 2021 at 2:53pm EST.