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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
  • 422 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 Ln, Osprey, FL
$3,790,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 6,340 SQFT
  • 33 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 #A4443284

931 Blue Heron Overlook, Osprey, FL
$3,000,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 6,977 SQFT
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The Oaks, This Distinguished Residence Is Sited At The End Of A Cul-de-sac Boasting Breathtaking Views Stretching All The Way To The Oaks Clubhouse And Strategically Located On The New Fry/straka (course Architects Of Erin Hill, Site Of The 2017 U...

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

Residential, Single Family Home
  • 5 Beds
  • 8 Baths
  • 6,733 SQFT
  • 409 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...

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

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 4,571 SQFT
  • 9 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...

318 Osprey Point Dr, Osprey, FL
$1,940,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 6,981 SQFT
  • 12 DOM
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One Or More Photo(s) Has Been Virtually Staged. Welcome To An Exquisite Lifestyle At A Price You Won’t Believe; All In The World-class, Incredibly Private Oaks Bayside Community. At 318 Osprey Point, You Will Live Without Limits Across Almost 7,00...

Photo of Listing #A4456557

562 N Macewen Dr, Osprey, FL
$1,700,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,416 SQFT
  • 5 DOM
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The Oaks…exceptional Home, Custom Built On One Of The Most Beautiful Lots In The Oaks Clubside With A Private Setting W/lake & Golf Beyond. Over 6200 Sf, 5/6 Bdrs, 6 ½ Ba, 2 Offices, 4 Car-garages. This Remarkable Floor Plan Accommodates Your Eve...

Photo of Listing #A4208052

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,100 SQFT
  • 726 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 #A4441248

643 Fernwalk Ln, Osprey, FL
$1,550,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,246 SQFT
  • 188 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 W...

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

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,153 SQFT
  • 309 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. ...

350 Sugar Mill Dr, Osprey, FL
$1,498,246

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 4,100 SQFT
  • 147 DOM
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Pre-construction. To Be Built. The Oaks Bayside. One Of The Few Remaining Homesites Available To Build Your Dream Home With Henson Contractors. There Is No Time Requirement For Building And There Is Freedom To Select Another Builder Of Your Choi...

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

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 5,084 SQFT
  • 197 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...

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

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 5,399 SQFT
  • 61 DOM
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Recent Price Adjustment. 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 La...

Photo of Listing #N6106697

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
  • 110 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 With...

497 Webbs Cv, Osprey, FL
$1,300,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 6,863 SQFT
  • 340 DOM
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Are 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 Oaks Bayside. Completely Renovated...

Photo of Listing #A4207974

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

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 6,002 SQFT
  • 723 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 #A4451482

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,163 SQFT
  • 46 DOM
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Visualize Yourself Living On A Beautiful Golf Course, Surrounded By Lush Tropical Landscape With Sounds Of A Waterfall And Nature Beyond. That Is Exactly What This Fabulous Home Offers. Set On Cul-de-sac, This Half-acre Lot Has Flourishing Plants ...

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

Land, Unimproved Land
  • 24 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 #A4447540

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,743 SQFT
  • 232 DOM
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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 This Large 4,743 Square Foot House. Custom-built I...

574 N Macewen Dr, Osprey, FL
$1,125,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,591 SQFT
  • 19 DOM
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Tucked Away Behind The Gates Of The Oaks, This Sophisticated Yet Comfortable Former Model Home Offers Sweeping Views Of The 11th Green Of The Eagle Golf Course. An Impressive Entry Experience Begins With The Pavered Driveway And Waterfall To The D...

894 Macewen Dr, Osprey, FL
$1,100,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 3,095 SQFT
  • 104 DOM
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3 Reasons To Fall In Love…1. Location: The Only Private, Member-owned Golf Community Located Minutes From Siesta Key Beach And Downtown Sarasota With Easy Access To I-75. 2. The Oaks Club: A Truly Unique Lifestyle Offering Two Championship Golf Co...

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

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 3,912 SQFT
  • 104 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 Situated ...

Photo of Listing #A4445561

413 Macewen Dr, Osprey, FL
$1,100,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,152 SQFT
  • 136 DOM
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Recently Reduced! 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...

Photo of Listing #A4442718

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

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,464 SQFT
  • 174 DOM
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New Price Makes This Home A Must See! Built In 2014 By Todd Johnston Homes, This Spectacular Courtyard Style Waterfront Property Has A Separate Casita That May Be Used As A Guest Quarters, Artists Studio Or In Law Suite. Situated On A Premier Corn...

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 January 23rd, 2020 at 12:31pm EST.