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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
  • 672 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 ...

552 Eagle Watch Lane, OSPREY, FL
$3,790,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 6,340 SQFT
  • 289 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...

Photo of Listing #A4475272

136 Osprey Point Drive, OSPREY, FL
$2,790,000

Residential, Single Family Residence
  • 5 Beds
  • 9 Baths
  • 6,881 SQFT
  • 45 DOM
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Behold Color-soaked Sunsets, Sparkling Little Sarasota Bay Views And Endless Privacy Overlooking The Preserve. This Rare And Exquisite Residence Of Architectural Excellency Located In The Premier Gated Community Of The Oaks Bayside Is One To Marve...

68 Osprey Point, OSPREY, FL
$1,950,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,571 SQFT
  • 265 DOM
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Set Gracefully Amidst Lush Tropical Landscaping In The Gated Waterfront Community Of The Oaks Bayside, This Stunning Residence Has Been Masterfully Designed To Blend Classic Architectural Elements And Exceptional Finishes With Grand Scale And Ligh...

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,578 SQFT
  • 240 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...

318 Osprey Point Drive, OSPREY, FL
$1,840,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 6,981 SQFT
  • 268 DOM
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Built In 2008, The Newest Resale Home Available In The Oaks Club. Located On A Super Private Street With A 24-7 Manned Gate Entrance In One Of Sarasota’s Most Highly Regarded Golf & Country Club Neighborhoods. If You Haven't Heard It Yet, West Of ...

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,698 SQFT
  • 142 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 #A4475278

643 Fernwalk Lane, OSPREY, FL
$1,590,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 5,246 SQFT
  • 45 DOM
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Elegantly Defined, European And Traditional, Custom Build Home In The Cul-de Sac Private Street Of The Gated Community Of The Oaks. The Moment You Pull Into The Circular Paver Driveway And Porte Cochere, Set On The Lush Tropical Landscaping, You ...

Photo of Listing #A4456557

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

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,416 SQFT
  • 261 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 #A4428519

425 Macewen Drive, OSPREY, FL
$1,450,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,153 SQFT
  • 545 DOM
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Recently Reduced! 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 Inclu...

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,610 SQFT
  • 183 DOM
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Enjoy The 3d Virtual Tour Of This Elegant, Custom-built, 5-6 Bed / 5.5 Bath, Pool/spa, Luxury Estate Situated On The 16th Fairway Of The Heron Golf Course. Relish In The Coveted Lifestyle Of The Oaks Club, Featuring "luxury Coastal Living In The H...

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

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 6,863 SQFT
  • 235 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 ...

676 Eagle Watch Lane, OSPREY, FL
$1,295,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 5,399 SQFT
  • 313 DOM
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Recent Price Adjustment. Classic Elegance At The Oaks Club Side! Owner Will Entertain Owner Financing, Or A Trade For Smaller Residential Or Commercial Property. This Custom Built 5400sf Single Story Has Been Extensively Renovated To Include Fresh...

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,856 SQFT
  • 53 DOM
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What Would The Lot Premium Be For This Location If You Were Building New?...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 Single F...

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

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,975 SQFT
  • 19 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
  • 24 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...

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

Land, Unimproved Land
  • 280 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...

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,813 SQFT
  • 31 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 #A4475057

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

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,152 SQFT
  • 48 DOM
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You Will Love The Incredible Light That Fills This 3 Bedroom Plus Office, 3.5 Bath Home In The Oaks Clubside. Situated On A Beautiful Lot, It Offers Stunning Views Of The Lake/pond And Golf Course. With A Young Roof, Refinished Pool With New Equip...

Photo of Listing #A4464783

42 Osprey Point Drive, OSPREY, FL
$1,100,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,706 SQFT
  • 134 DOM
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Have You Been Imagining What Your Home In Florida Should Look Like? Well, Think Big! This 3 Bedroom, Plus Office And Bonus Room, 3 Bath Custom Built-home With Whole House Impact Glass In The Oaks Bayside Will Not Only Meet, But Exceed, Every Expe...

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

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,743 SQFT
  • 369 DOM
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One Or More Photo(s) Has Been Virtually Staged. Seller Will Credit Will Buyer $40,000 Towards Oaks Club Dues! Incredible 4 Bedroom, 5.5 Bath Home With Separate Guest Quarters Located Behind The Gates Of The Oaks Clubside. Situated On The 4th Fair...

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

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,826 SQFT
  • 597 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 #A4439437

860 Macewen Drive, OSPREY, FL
$1,079,000

Residential, Single Family Residence
  • 4 Beds
  • 7 Baths
  • 5,084 SQFT
  • 447 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...

34 Osprey Point Dr, OSPREY, FL
$1,050,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,696 SQFT
  • 31 DOM
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This Incredible 3 Bedroom, 3.5 Bath True Brick Home Is In A Class By Itself. Distinctly Different From Other Homes In The Community, You Can Enjoy All The Unique Features Of Living Here, Plus All The Amenities Of Living In The Oaks Bayside. Majest...

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 September 29th, 2020 at 10:10am EDT.