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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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$300,000 - $400,000 $400,000 - $600,000 $600,000 - $1,000,000
Over $1,000,000
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112 Osprey Point Dr, Osprey, FL
$4,450,000

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 8,973 SQFT
  • 589 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 Residence
  • 4 Beds
  • 5 Baths
  • 6,340 SQFT
  • 200 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...

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

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,571 SQFT
  • 176 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...

Photo of Listing #A4456074

318 Osprey Point Dr, Osprey, FL
$1,840,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 6,981 SQFT
  • 179 DOM
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New Price $100,000 Reduction. 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 7,000 Square Feet Of S...

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

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,416 SQFT
  • 172 DOM
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** Virtual Showings Available. Check Out The Video And Slide Shows, Floor Plan Available** The Oaks…exceptional Home, Custom Built On One Of The Most Beautiful Lots In The Oaks Clubside W/a Private Setting W/lake & Golf Beyond. Over 6200 Sf, 5/6 B...

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,578 SQFT
  • 310 DOM
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2 Br 2 Bath Guest House, 4 Car Garage, And Walled Motor Court! You Will Feel Like Nobility When You Enter This Gated Lakeside Estate In The Oaks Bayside. This Spacious 4 Bedroom, 5.5 Bath Gives You All The Amenities Of An Exclusive Resort, And Th...

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,698 SQFT
  • 54 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 #A4428519

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

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,153 SQFT
  • 476 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 N Macewen Dr, Osprey, FL
$1,395,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,610 SQFT
  • 95 DOM
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**virtual, Interactive, Video Chat Tour Available.** 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 Th...

Photo of Listing #N6106697

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

Residential, Single Family Residence
  • 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...

676 Eagle Watch Ln, Osprey, FL
$1,345,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 5,399 SQFT
  • 224 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...

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

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 6,863 SQFT
  • 507 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 ...

Photo of Listing #A4207974

340 Osprey Point Dr, Osprey, FL
$1,250,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,002 SQFT
  • 890 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 ...

42 Osprey Point Dr, Osprey, FL
$1,200,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,706 SQFT
  • 50 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...

628 N Macewen Dr, Osprey, FL
$1,150,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 4,486 SQFT
  • 148 DOM
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The Oaks Is The Most Luxurious Golf And Tennis Community In Sarasota County Located On Two Outstanding Golf Courses. The Oaks Club Was Awarded The Distinguished Emerald Club Of The World Designation Award. Is The Only West Central Florida Country ...

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

Land, Unimproved Land
  • 191 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
$1,100,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,743 SQFT
  • 399 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...

Photo of Listing #A4422405

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

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,826 SQFT
  • 533 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...

388 Bunker Hill, Osprey, FL
$1,090,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,937 SQFT
  • 661 DOM
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Virtual Showing Available! Newly Updated Kitchen And New Roof! 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,...

Photo of Listing #A4439437

860 Macewen Dr, Osprey, FL
$1,079,000

Residential, Single Family Residence
  • 4 Beds
  • 7 Baths
  • 5,084 SQFT
  • 358 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...

402 Walls Way, Osprey, FL
$1,050,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,464 SQFT
  • 298 DOM
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One Or More Photo(s) Has Been Virtually Staged. This Stunning 4 Bedroom, 3.5 Bath Home In The Oaks Clubside Is Waiting For You To Come Make It Your Own! Built In 2014 By Todd Johnson Homes, The Courtyard Style, And Country Modern Flair, Gives It A...

Photo of Listing #A4465672

680 N Macewen Dr, Osprey, FL
$1,049,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,998 SQFT
  • 52 DOM
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**virtual, Interactive, Video Chat Tour Available.** Enjoy The 3d Virtual Tour Of This Updated And Spacious, 5-bed / 6-bath, Pool/spa Home Situated On The 13th Fairway Of The Eagle Golf Course. $40,000 Social Membership Paid By Seller With Suitabl...

Photo of Listing #A4470686

642 Trenton Way, Osprey, FL
$980,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 3,939 SQFT
  • 1 DOM
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Situated On A Corner Lot, This Gorgeous 3,939 Square Rutenberg-built 4 Bedroom Home, With 4 Full Baths And Two Half Baths, Has Long Views Of The Lake And The 18th Fairway Of The Heron Course. If You Are Dreaming Of Living The Country Club Lifestyl...

Photo of Listing #A4444689

97 Sugar Mill Dr, Osprey, FL
$980,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,902 SQFT
  • 488 DOM
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*new Price* Oaks Bayside 4 Bedroom Plus Office 5 Full And 1 Half Bath Home. If You Are Looking For Something That Is Not Your Standard “cookie Cutter” Florida Home That Offers A Traditional Feel With A Open Spaces, You Have Found Your Home! This S...

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.

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 July 8th, 2020 at 12:45am EDT.