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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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112 Osprey Point Dr, Osprey, FL
$4,450,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 8,973 SQFT
  • 113 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
  • 103 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 #A4413743

95 Osprey Point Dr, Osprey, FL
$2,100,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 7,531 SQFT
  • 164 DOM
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Concierge Auction: Bid 2/26-28 | Previously $2.1m, Selling Without Reserve | Open Daily 1-4pm By Appointment. This Home Is Free And Clear Of Any Mortgage. Nestled Inside The Oaks Bayside, Welcome Home To 95 Osprey Point Drive. As You Enter Throu...

Photo of Listing #A4208052

91 Osprey Point Dr, Osprey, FL
$1,995,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,100 SQFT
  • 417 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...

Photo of Listing #A4205202

N Point Rd, Osprey, FL
$1,795,000

Land, Residential Development
  • 348 DOM
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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 The Type Of Home Product Inclu...

Photo of Listing #A4419256

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

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,924 SQFT
  • 124 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 #A4208738

409 N Point Rd #1003, Osprey, FL
$1,500,000

Residential, Condo
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 413 DOM
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Don't Be Shy - Owner Wants It Sold - Bring All Offers! The Best Penthouse Views In All Of Meridian! Experience The Luxurious Florida Lifestyle With Gorgeous Open Views That Encompass Casey Key, Siesta Key, Downtown Sarasota, Little Sarasota Bay &...

Photo of Listing #A4203589

419 Walls Way, Osprey, FL
$1,400,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,523 SQFT
  • 441 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 #N5915808

854 Macewen Dr, Osprey, FL
$1,399,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
  • 771 DOM
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Offering Over 9,000 Square Feet Of Exquisite Living Space, This Richly-detailed Custom Home Is Nestled On A Guarded, Private Cul-de-sac. Entertain Guests Or Simply Relax As A Family In The Multitude Of Well-designed Rooms– From The Living Room Wit...

Photo of Listing #A4215527

676 Eagle Watch Ln, Osprey, FL
$1,399,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 5,399 SQFT
  • 347 DOM
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Just Reduced $100,000. Classic Elegance At The Oaks Club Side! This Custom Built 5400sf Single Story Has Been Extensively Renovated To Include Fresh Interior Paint Throughout, New High-end Hardwood Floors And New Bathrooms. Master Suite Has 2 Lar...

497 Webbs Cv, Osprey, FL
$1,390,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 6,863 SQFT
  • 71 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 #A4410275

586 N Macewen Dr, Osprey, FL
$1,375,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,163 SQFT
  • 224 DOM
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Exceptional And Meticulously Maintained Best Describes This Fabulous 4100+ Sf, 4 Bedroom, 5 1/2 Bath, 5-car Garage Residence With Golf Course Views In The Highly Acclaimed Gated Golf Community - The Oaks Club. A Serene And Private Setting, With ...

Photo of Listing #A4207974

340 Osprey Point Dr, Osprey, FL
$1,350,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,002 SQFT
  • 414 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 #A4420718

644 Fernwalk Ln, Osprey, FL
$1,200,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 3,793 SQFT
  • 48 DOM
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This Traditional 3/4 Bedroom, 4 Bath Home In The Oaks Bayside Offers Elegant Country Club Living, With Panoramic Vistas Of The Lake And Golf Course. From The Moment You Drive Down The Private Cul-de-sac Street, And Get Your First View Of This Home...

Photo of Listing #A4409213

388 Bunker Hl, Osprey, FL
$1,195,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,937 SQFT
  • 232 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...

384 Bunker Hill, Osprey, FL
$1,175,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,794 SQFT
  • 64 DOM
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Looking For True Country Club Living... This 4 Bedroom, 3 1/2 Bath Home Is A Must See. Located Behind The Gates Of The Oaks With Views Of The Lake And The Third Green Of The Eagle Golf Course. This Arthur Rutenberg Home Is Well Appointed And Metic...

738 N Macewen Dr, Osprey, FL
$1,175,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 4,614 SQFT
  • 499 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...

Photo of Listing #A4423006

454 Macewen Dr, Osprey, FL
$1,150,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,940 SQFT
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Quality & Craftsmanship Define This Luxurious John Canon-inspired Custom Home, Built For The Discriminating Buyer. Located On The 7th Green Of The Eagle Golf Course, This Spacious 4br, 3.5 Ba Home Is Packed With Top-end Amenities. This Home Is Mad...

585 N Macewen Dr, Osprey, FL
$1,100,000

Residential, Single Family Home
  • 5 Beds
  • 5 Baths
  • 4,083 SQFT
  • 10 DOM
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Elegant. Gracious. Peaceful And Private. These Are The Hallmarks Of This Stately 5 Bedroom Home, In The Oaks Clubside. This Residence Is Positioned Back On The Lot To Allow For An Expansive Lawn With Mature Landscaping, And A Paver Brick, Circul...

566 Eagle Watch Ln, Osprey, FL
$1,100,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,553 SQFT
  • 68 DOM
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This 4 Bedroom, 4.5 Custom-built Home Is A Study In Elegance. From The Impressive Marble Entryway To The Magnificent Large Lanai With Pool Spa And Gorgeous Golf Course Views, This Home Has All The Touches You Would Expect In A Luxurious County Clu...

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

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,826 SQFT
  • 75 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...

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

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 4,020 SQFT
  • 334 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 ...

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

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 3,912 SQFT
  • 482 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
  • 187 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...

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.

Listing information last updated on March 19th, 2019 at 11:15pm EDT.