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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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112 Osprey Point Drive, OSPREY, FL
$4,450,000

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 8,973 SQFT
  • 730 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 ...

Photo of Listing #A4454431

552 Eagle Watch Lane, OSPREY, FL
$3,490,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 6,340 SQFT
  • 316 DOM
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The Ultimate In Luxury, Location And Design. As You Open The 13’ Cast Iron Front Doors, You Will Immediately Feel The Grandeur Of This Expansive Residence - Custom Crafted To Perfection. Each Of The 12 Rooms, Plus 4.5 Baths, Are Thoughtfully Desig...

95 Osprey Point Drive, OSPREY, FL
$2,450,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 7,231 SQFT
  • 23 DOM
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Presenting A Rare Opportunity For The Discerning Buyer To Own Two Waterfront Homes On One Private Estate In The Luxurious Oaks Bayside Spanning Well Over 7,000 Sqft On A Double Lot. Architectural Masterpieces, Both Tucked Away In A Storybook Setti...

Photo of Listing #A4456744

285 Sugar Mill Drive, OSPREY, FL
$1,895,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,578 SQFT
  • 291 DOM
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This Custom Designed Home Is The Must-see Property In The Oaks. With Space For Family, Working From Home And For Guests Or Multigenerational Living, This Private Sanctuary Has Everything—style, Luxury, And A Great Location, Minutes From Downtown A...

Photo of Listing #A4456074

318 Osprey Point Drive, OSPREY, FL
$1,798,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 6,981 SQFT
  • 321 DOM
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Located On A Private Street With A 24-7 Guard Gate Entrance In Sarasota’s Iconic Community, Custom Built In 2008 By John Cannon, It Is The Newest Home Available For Sale In The Oaks Club. This Five Bedroom Property Features A Spacious Pool Area Wi...

Photo of Listing #A4466028

468 Walls Way, OSPREY, FL
$1,600,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,698 SQFT
  • 195 DOM
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This 4 Bedroom Home With 4 Baths, And 2 Half Bath Enjoys One Of The Best Locations In The Oaks Clubside. Idyllically Situated At The End Of A Cul-de-sac, On A Beautifully Landscaped Half Acre Lot, This Home Offers Privacy, Tranquility And Beautif...

Photo of Listing #A4456557

562 North Macewen Drive, OSPREY, FL
$1,550,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,416 SQFT
  • 313 DOM
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The Perfect Home For Quarantine And Working From Home With 2 Separate Offices, Studio/exercise Room, Bonus Room For Home Schooling, 5 Bedrooms!! Exceptional Home In The Oaks, Custom Built On One Of The Most Beautiful Lots In The Oaks Clubside W/a...

Photo of Listing #A4483584

376 Sugar Mill Drive, OSPREY, FL
$1,500,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,472 SQFT
  • 12 DOM
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This 5,472 Sq. Ft. Grand Manor House, With Classic Mediterranean Architecture, Is Designed For Gracious Living. Enter Through The Courtyard With A Tranquil Fountain And Carved Wood Double Doors That Open To An Elegant Entry Foyer. Here You Will Fi...

548 Eagle Watch Lane, OSPREY, FL
$1,400,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,681 SQFT
  • 16 DOM
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From The Moment You See This 4 Bedroom, 3.5 Bath Home You Will Be Enchanted. Custom-built By Baron Construction, It Is Situated On A Large Lot That Is Just Over Three Quarters Of An Acre. On A Corner Of A Cul-de-sac, It Is Ideally Positioned To Pr...

Photo of Listing #D6114951

597 North Macewen Drive, OSPREY, FL
$1,395,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,610 SQFT
  • 7 DOM
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Executive Home Located In The Premier Oaks Club In Osprey Awaits A Buyer That Needs Room For Everyone. Home Has 6 Bedrooms With 5 ½ Baths, Custom Kitchen, Separate Dining Room, Kitchen Family Room Combination, Living Room With Architectural Elemen...

Photo of Listing #A4484221

409 North Point Road 1001, OSPREY, FL
$1,395,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 3,029 SQFT
  • 5 DOM
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Welcome To The Pinnacle Of Elegance And Sumptuous Living In This Rarely Available Penthouse Set Atop The Esteemed Meridian 4 Of The Oaks Preserve Featuring Mesmerizing Sunsets Over The Gulf Of Mexico. Arrive In Style By Your Private Elevator Entr...

Photo of Listing #A4481136

385 North Point Road 802, OSPREY, FL
$1,390,000

Residential, Condominium
  • 3 Beds
  • 4 Baths
  • 3,738 SQFT
  • 38 DOM
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The Prestige Of The Oaks, The Amenities Of Maintenance-free Living And Spectacular Views That Inspire, All Of This And More Can Be Found At This Extraordinary Meridian Tower I Residence. Simply Stated, Elegance Resonates Throughout This Southweste...

Photo of Listing #A4483742

658 Fernwalk Lane, OSPREY, FL
$1,349,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,612 SQFT
  • 7 DOM
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This Distinguished Residence Is Sited At The End Of A Cul-de-sac In The Oaks. From The Moment You Step Through The Double Doors You Will Be Taken In By The Warm Of This Home. The Open Floor Plan, High Ceilings Make The Interior Light And Bright, ...

Photo of Listing #A4452379

676 Eagle Watch Lane, OSPREY, FL
$1,329,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 5,399 SQFT
  • 364 DOM
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Recent Price Adjustment. Classic Elegance At The Oaks Club Side! Owner Will Entertain Short Term Owner Financing. This Custom Built 5400sf Single Story Has Been Extensively Renovated To Include Fresh Interior Paint Throughout, New High-end Hardwoo...

Photo of Listing #A4457045

497 Webbs Cove, OSPREY, FL
$1,300,000

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 6,863 SQFT
  • 284 DOM
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6 Car Garage, 2br 2 Bath Guest House ! You Seeking A One-of-a-kind Home Located In The Tropics Equipped To Entertain, And Accommodate, All The Guests You Want To Share Your Luxury Lifestyle With? Then You Will Love This Large, Unique Home In The ...

933 Blue Heron Overlook, OSPREY, FL
$1,275,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,856 SQFT
  • 107 DOM
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Can't Beat This Location. No Construction Noise...mature And Manicured Grounds...premier Cul De Sac Location In The Oaks Clubside - Picturesque Sunset Views From 2900 Sqft Lanai That Also Overlooks Heron's#1 Green - Entertaining Is A Breeze In Sin...

689 Eagle Watch Lane, OSPREY, FL
$1,185,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,975 SQFT
  • 72 DOM
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This Spectacular "cape Dutch-style" Residence Is In The Sought-after Oaks Club Community In Osprey, Fl. The Spacious And Immaculate Home Is Situated At The End Of A Cul-de-sac Overlooking The 7th Fairway Of One Of The Two 18-hole Championship Golf...

Photo of Listing #A4476281

388 Bunker Hill, OSPREY, FL
$1,150,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,937 SQFT
  • 62 DOM
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Situated At The End Of A Cul-de-sac Behind The Gates Of The Oaks, This 5 Bedroom Home With Four Full And Two Half Baths, Exudes Warm And Charm. Beautifully Set On A Verdant Lot, The Rich Vegetation Gives The Home A Feeling Of Calm, Tropical Privac...

Photo of Listing #A4454887

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

Land, Unimproved Land
  • 331 DOM
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Dramatic Price Reduction, Seller Says Bring All Offers. - The Oaks Preserve Phase Iv - Located Behind The Gates Of The Oaks, This 3.12 Acre Development Site Is The Last Remaining Developer Site In The Oaks And Is Entitled For 30 Single Family Resi...

Photo of Listing #A4479462

393 North Point Road 1001, OSPREY, FL
$1,129,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 3,029 SQFT
  • 52 DOM
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Rarely Available Penthouse Located At The Coveted Oaks Country Club. Building 2 At The Meridian Features This Tenth Floor Unit With No One Above Your Residence. A 3 Bedroom, 3 Full Bath Condo With True Den Offering Over 3,000 Sq. Ft. Of Living Spa...

721 North Macewen Drive, OSPREY, FL
$1,125,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,813 SQFT
  • 84 DOM
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*enjoy The 3d Virtual Tour* Of This Updated And Spacious, 5-bed / 6-bath, Pool/spa Home With Ideal South-facing Lanai, Situated On The 17th Fairway Of The Heron Golf Course - With Breathtaking Golf Course Views! Relish In The Coveted Lifestyle Of ...

Photo of Listing #A4483843

745 North Macewen Drive, OSPREY, FL
$1,100,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,649 SQFT
  • 7 DOM
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Custom Built Arthur Rutenberg Home. With A Spacious Master Bedroom Suite On One Side Of The House And Three Bedrooms And Two Baths On The Other, There Is Room And Privacy For The Residents Of The Home, And Their Guests. Formal Dining Room And Form...

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

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,826 SQFT
  • 650 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...

Photo of Listing #A4447540

398 Macewen Drive, OSPREY, FL
$1,060,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,743 SQFT
  • 422 DOM
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One Or More Photo(s) Has Been Virtually Staged. Incredible 4 Bedroom, 5.5 Bath Home With Separate Guest Quarters 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 Th...

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

Gulf Shores Realty: 627781033 Gulf Shores Realty: 1613877538 Gulf Shores Realty: 1264807147 Gulf Shores Realty: 473835121 Gulf Shores Realty: 1447348502 Gulf Shores Realty: 506248133 Gulf Shores Realty: 368704368 Gulf Shores Realty: 1771245611 Gulf Shores Realty: 268716939 Gulf Shores Realty: 1926597494 Gulf Shores Realty: 614281769 Gulf Shores Realty: 836552199 Gulf Shores Realty: 1409377882 Gulf Shores Realty: 1284606319 Gulf Shores Realty: 861737261 Gulf Shores Realty: 523379917 Gulf Shores Realty: 1890278202 Gulf Shores Realty: 164965010 Gulf Shores Realty: 315557599 Gulf Shores Realty: 1061200894 Gulf Shores Realty: 856064521 Gulf Shores Realty: 1290081770 Gulf Shores Realty: 1999328186 Gulf Shores Realty: 40831177 Gulf Shores Realty: 1332063478 Gulf Shores Realty: 646081603 Gulf Shores Realty: 67202262

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 November 26th, 2020 at 1:31pm EST.