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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:

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$300,000 - $400,000 $400,000 - $600,000 $600,000 - $1,000,000
Over $1,000,000
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112 Osprey Point Dr, Osprey, FL
$4,450,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 8,973 SQFT
  • 231 DOM
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Most Desirable Location In The Oaks Bayside Country Club; Truly A Boater's Dream! Featuring Your Own Private Dock With 3 Power Lifts..12,000/16,000. Driving Thru This Private Gated Community You Are Surrounded By A Canopy Of Mature Oak Trees. The ...

136 Osprey Point Dr, Osprey, FL
$2,790,000

Residential, Single Family Home
  • 5 Beds
  • 8 Baths
  • 6,461 SQFT
  • 221 DOM
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Opportunity Of A Life Time! This Magnificent Three-level Mansion Is Located In The Exclusive Private Gated Community Oaks Bayside. This Home Is Priced To Sell And Is Below Market And Replacement Value. Exquisite Brazillan Cherry Wood Flooring Thro...

Photo of Listing #A4208052

91 Osprey Point Dr, Osprey, FL
$1,695,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,100 SQFT
  • 535 DOM
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Iconic Architecture In Sarasota’s Premiere Golf And Country Club. This Magnificent 4-bedroom Estate Was Designed And Built By Bo Macewen And Brims With The Essence Of Warm, Southern Hospitality. Bo Was The Original Architect For The Oaks And He Cr...

425 Macewen Dr, Osprey, FL
$1,500,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,153 SQFT
  • 118 DOM
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This Spacious 5 Bedroom, 5.5 Bath Home Offers Over 5,100 Square Feet Of Living Space And Overlooks The Par 3 Fourth Hole Of The Oaks Heron Course. The Huge Gourmet Kitchen Features Top Of The Line Stainless Steel Appliances Including A Gas Range. ...

Photo of Listing #A4419256

168 Coastal Hammock Ct, Osprey, FL
$1,500,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,924 SQFT
  • 242 DOM
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Bayfront In The Oaks. Custom Designed Walled Mizner-style Estate In Private Cul-de-sac Location With A 5 Stop Elevator. Views From Several Areas Showcasing The Gulf And Bay. Very Livable Floor Plan With Expansive Master Suite Offering A Separate S...

Photo of Listing #A4439437

860 Macewen Dr, Osprey, FL
$1,450,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 5,084 SQFT
  • 6 DOM
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The Exclusive Oaks Golf & Tennis Country Club! Only Platinum And Elite Club In The Sarasota Area (top 10 Nationwide). This Well Designed Home With Gourmet Kitchen Has Top Of The Line Appliances With Adjoining Breakfast Area, And Is Open Convenie...

776 Macewen Dr, Osprey, FL
$1,350,000

Residential, Single Family Home
  • 5 Beds
  • 5 Baths
  • 4,596 SQFT
  • 80 DOM
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This Toll Brothers Built 5 Bedroom, 4.5 Bath Home Is Beautiful Inside & Out. Situated On The 14th Hole Of The Eagle Course, And Professionally Landscaped, The Lot Appeal Is Beyond Compare. Enchanted From The Outside, You Will Not Be Disappointed W...

Photo of Listing #A4423128

497 Webbs Cv, Osprey, FL
$1,340,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 6,863 SQFT
  • 189 DOM
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Seller Will Pay $25k Toward Club Membership With Approved Contract. Located In The Exclusive Gated Community Of The Oaks Bayside. Totally Remodeled Home With Too Many Improvements To List, Everything Is New Including; New Roof, Air Conditioners, N...

Photo of Listing #A4207974

340 Osprey Point Dr, Osprey, FL
$1,295,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,002 SQFT
  • 532 DOM
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If You Want To Live An Enviable Lifestyle With The Comfort Of Being Surrounded By Nature, Combined With The Elegance Of Country Club Living, This 5 Bedroom French Country Styled Home, With 5 Full And 2 Half Baths Is Perfect For You! Play An Early ...

Photo of Listing #A4431484

398 Macewen Dr, Osprey, FL
$1,250,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,743 SQFT
  • 101 DOM
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Incredible 4 Bedroom, 5.5 Bath Home With Separate Guest House Located Behind The Gates Of The Oaks Clubside. Situated On The 4th Fairway Of The Eagle Course, There Is A Great Deal To Love About This Large 4,743 Square Foot House. Custom-built In 1...

Photo of Listing #A4203589

419 Walls Way, Osprey, FL
$1,200,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,523 SQFT
  • 559 DOM
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A Recent Price Reduction Makes This Spectacular 4 Bedroom, 4.5 Bath Colonial An Opportunity Too Good To Pass By! If You Are A Discriminating Buyer, Seeking The Utmost In Fine, Country Club Living, You Need To Look No Further. There Is A Reason Thi...

Photo of Listing #A4431527

518 E Macewen Dr, Osprey, FL
$1,195,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 3,914 SQFT
  • 111 DOM
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Privately Located On The 9th Fairway Of The Oaks Club’s Eagle Course, The Tall Pines And Lake Views Offer A Serene Retreat From Everyday Life. This Casually Elegant Home Is Replete With Unsurpassed Quality And Detailing Throughout. A Smart Floor ...

Photo of Listing #A4410275

586 N Macewen Dr, Osprey, FL
$1,195,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,163 SQFT
  • 342 DOM
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It Is Difficult To Find A Home In The Oaks Which Has Been As Exceptionally And Meticulously Maintained As This Fabulous 4100+ Sf, 4 Bedroom, 5 ½ Bath, 5 Car Garage Golf Course Residence. The Countless Upgrades And Extras - Such As 5 Garages, 3,00...

Photo of Listing #A4205202

N Point Rd, Osprey, FL
$1,150,000

Land, Residential Development
  • 466 DOM
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Unbelievable Price Reduction - The Oaks Preserve Phase Iv - Located Behind The Gates Of The Oaks, This 3.12 Acre Development Site Is Entitled For 30 Single Family Residential Units. The Zoning Allows For Up To Four Stories And Great Flexibility In...

464 Walls Way, Osprey, FL
$1,100,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,826 SQFT
  • 193 DOM
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This Uniquely Designed, Custom Built 3 Bedroom, 3.5 Bath Home Is A Country Club Enthusiast's Dream Come True! Situated On A Cul-de-sac On The Heron Course In The Oaks Clubside, This Magnificent Home Was Built By Baron Construction. The Impressive...

165 Sugar Mill Dr, Osprey, FL
$1,100,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 3,912 SQFT
  • 600 DOM
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Picture This. Gracious Country Club Living On The Bayside Of The Oaks Club In This 4 Bedroom, 4.5 Bath Home. As You Enter The New Paver Circular Driveway, With Three Car Side Entry Garage, It Is Evident How Special This House Is. Ideally Situat...

Photo of Listing #A4429433

97 Sugar Mill Dr, Osprey, FL
$1,080,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,902 SQFT
  • 305 DOM
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Just Reintroduced To The Market With A Beautiful New Remodel! A Storybook Modern Day Estate Awaits Behind The Gates Of The Oaks Bayside, An Opulent Country Club Community In Osprey. Discover This Beautifully Proportioned Architectural Gem Perfectl...

794 Lytham Cir, Osprey, FL
$1,050,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,543 SQFT
  • 70 DOM
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Well Appointed, And Completely Updated, This 4 Bedroom, 4 Bath Beauty Will Please The Most Discriminating Buyer. You Will Be Intrigued When You Pull Into The New Pavered Circular Driveway With Fountain. Once You Enter Though The Double Front Door...

Photo of Listing #A4199246

738 Macewen Dr, Osprey, FL
$1,050,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 4,614 SQFT
  • 617 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. Set Back On A Cul-de-sac Lot, With Gorgeous Lake And Golf Views, The Floor Plan Offers...

466 E Macewen Dr, Osprey, FL
$1,050,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,754 SQFT
  • 256 DOM
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Welcome To The Oaks, Sarasota's Only 2019-2020 Platinum Clubs Of America Recipient. This Custom Built Garry Group Home Boasts 4 Bedroom 4 Bathroom And Is Truly A Southern Charmer. Traditional Combined With Perfectly Symmetrical Style With 3700+ Sq...

53 Fairway Oaks Ln, Osprey, FL
$1,019,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,774 SQFT
  • 131 DOM
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Welcome To The Oaks Sarasota's Only 2019-2020 Platinum Clubs Of America Recipient. This Custom Built Home Set On A Private Cul-de-sac Is Lushly Landscaped And Boasts Over 3700 Sq. Ft. The Elegant Entrance Is Lined With Columns Leading To The Cover...

Photo of Listing #A4409213

388 Bunker Hill, Osprey, FL
$1,000,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,937 SQFT
  • 350 DOM
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Lush, Luxurious, And Private. This Beautiful Residence Located In The Much Sought-after Oaks Club Community Offers A Large, Warm Home Situated At The End Of A Cul-de-sac On Lushly Landscaped Grounds. High Ceilings, Marble Flooring, Crown Molding A...

Photo of Listing #A4403751

601 Fernwalk Ln, Osprey, FL
$1,000,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,547 SQFT
  • 406 DOM
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This Extraordinary Bo Macewen Designed Home, With Beautiful Southern Charm, Is Situated On A Double Lot With A Private Park-like Setting In Oaks Bayside. All The Light-filled, Spacious Rooms Are On The Same Level. The Traditional Interior Is Respl...

Photo of Listing #A4400278

67 Sugar Mill Dr, Osprey, FL
$999,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 4,020 SQFT
  • 452 DOM
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This Traditional 4 Bedroom, 3.5 Bath (plus Pool Bath) Home Exudes Sophistication. From The Moment You Approach, The Style & Grace Of This Masterpiece Is Apparent. Pass Through The Columned Entrance Way, Open The Front Door & Imagine What It Would ...

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

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.

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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 15th, 2019 at 4:30pm EDT.