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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
  • 359 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 #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
  • 6,461 SQFT
  • 349 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...

285 Sugar Mill Dr, Osprey, FL
$1,695,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,578 SQFT
  • 103 DOM
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Escape To Paradise. Located In The Waterfront Community Of Oaks Bayside, This One-of-a-kind Walled And Gated Estate Is A Private Oasis Perfect For Entertaining Guests Or For Multi-generational Living. The Expansive Open Pool And Patio Area Is Posi...

643 Fernwalk Ln, Osprey, FL
$1,695,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,246 SQFT
  • 125 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...

Photo of Listing #A4208052

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,100 SQFT
  • 663 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
  • 246 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
  • 84 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
  • 134 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...

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
  • 96 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...

Photo of Listing #A4423128

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

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 6,863 SQFT
  • 317 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
  • 660 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 #A4442718

402 Walls Way, Osprey, FL
$1,263,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,464 SQFT
  • 111 DOM
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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 One Acre Lot, Outdoor Lighting Showcases T...

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,743 SQFT
  • 169 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...

Photo of Listing #A4203589

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

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,523 SQFT
  • 687 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 #A4451482

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,163 SQFT
  • 7 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 ...

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

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,152 SQFT
  • 73 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 Equi...

Photo of Listing #A4449900

409 N Point Rd #1003, Osprey, FL
$1,100,000

Residential, Condo
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 6 DOM
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Priced To Sell! A Tropical Florida Lifestyle Awaits In The Desirable Meridian At Oaks Preserve. Private Elevator Will Transport You To The Superbly Crafted 2778 Sq.ft. Corner Ducal Penthouse. Picturesque Views Of Casey Key, Siesta Key, & Little S...

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

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 3,095 SQFT
  • 41 DOM
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Welcome To The Oaks With Over 1,000 Acres Of Luxury, Shady Oaks, Rich Flower Beds, And Impeccably Maintained Homes, None More Than 894 Macewen Drive. Enter Through The Hand Carved Mahogany Doors To Discover A Completely Transformed, Contemporary H...

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

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 3,912 SQFT
  • 41 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 ...

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

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,826 SQFT
  • 321 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...

384 Bunker Hl, Osprey, FL
$1,085,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,794 SQFT
  • 286 DOM
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An Amazing Combination Of Cozy Cottage And Contemporary Chic, This Custom 4 Bedroom, Plus Office, 3.5 Bath Home Is Situated On Beautiful Private Lot In The Oaks Clubside. Nestled Under Oaks And Beautifully Landscaped, You Will Be Enchanted By The...

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

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,543 SQFT
  • 198 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...

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

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,774 SQFT
  • 259 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...

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 November 21st, 2019 at 9:01am EST.