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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

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Photo of Listing #A4534361

409 North Point Road 602, OSPREY, FL
$795,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,055 SQFT
  • 4 DOM
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Meridian At The Oaks Preserve Provides Luxurious High-rise Living In Sarasota's Premier Country Club Community Which Overlooks Little Sarasota Bay And The Gulf Of Mexico. As You Enter Through The Guarded Gate You Will Drive Through A Pristine Nat...

Photo of Listing #A4528433

640 Tarleton Lane, OSPREY, FL
$1,250,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,818 SQFT
  • 5 DOM
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Accepting Offers Until 12pm 04/08/2022 And Seller Will Make A Decision By End Of The Day Saturday. Seller Reserves The Right To Cut Off Showings At Any Time. What Does Your Dream Home Look Like? Whatever Your Vision, Create It Here, In This 4 Bedr...

Photo of Listing #O6025166

134 Marys Chapel Court, OSPREY, FL
$2,999,000

Residential, Single Family Residence
  • 6 Beds
  • 8 Baths
  • 5,521 SQFT
  • 6 DOM
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Luxury Coastal Living In The Heart Of Sarasota! This Completely Remodeled 6 Br / 8 Ba Estate, With 3-car Side-entry Garage And Upgraded Luxurious Pool Area, Is Located In The Exclusive Bayside Neighborhood Of The Oaks Club. Wide Open Floor Plan Fe...

Photo of Listing #A4534692

565 Eagle Watch Lane, OSPREY, FL
$2,750,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 5,814 SQFT
  • 6 DOM
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**fantastic Golf Course Estate – Will Not Last!** This Elegant And Spacious, 5 Bedroom / 4.5 Bath + Large Office + Bonus Room Residence Is Light And Bright And Will Surely Delight Your Senses! Premium Finishes Abound Including High Ceilings, Marb...

603 Eagle Watch Lane, OSPREY, FL
$1,800,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,872 SQFT
  • 15 DOM
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This 3 Bedroom, 3.5 Bath Home, Located On A Private Cul-de-sac In The Oaks Clubside Is Surrounded By Beautiful Tropical Landscaping And Exterior Lighting. As You Approach The Custom Wood Entryway, You Will Immediately Be Drawn In. Featuring Impecc...

Photo of Listing #A4526326

905 Macewen Drive, OSPREY, FL
$3,700,000

Residential, Single Family Residence
  • 6 Beds
  • 5 Baths
  • 7,022 SQFT
  • 19 DOM
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The Oaks Clubside With 6 Bedrooms Plus Office And 4 Car Garage. Rare Opportunity To Own A One-of-a-kind Custom Built Home Overlooking The 12th Green, And Down The Length Of The 13th Hole, Of The Oaks Heron Course. Built By A Custom Cabinet Maker F...

Photo of Listing #A4530820

668 Trenton Way, OSPREY, FL
$1,395,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,547 SQFT
  • 23 DOM
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A Residence Sitting On A Half-acre Surrounded By Huge Oaks Trees And Beautiful Florida Landscaping. 2,547sqft With A Large Open Living Room And Dining Room, The Tray Ceilings Making This Space A Dream For Entertaining. Freshly Painted, High Ceilin...

Photo of Listing #A4531302

44 Bishops Court Road 112, OSPREY, FL
$649,500

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 1,890 SQFT
  • 25 DOM
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World Renowned Architect Guy Peterson Recently Created This Luxurious Townhouse Remodel In The Oaks Club Of Osprey Fl, A Member Owned Club Of 680 Golfers Sharing Two 18-hole Recently Revamped Championship Courses, 12 Immaculate Har-tru Tennis Cour...

Photo of Listing #A4532410

680 North Macewen Drive, OSPREY, FL
$2,500,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,998 SQFT
  • 27 DOM
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**extraordinary Golf Course Estate** This Beautifully Updated And Spacious, 5-bed / 6-bath, Pool/spa Home Overlooks The 13th Fairway Of The Eagle Golf Course And Is Ideally Positioned On An Oversized, Cul-de-sac Lot. This Move-in Ready Home Featu...

Photo of Listing #A4529798

401 North Point Road 703, OSPREY, FL
$949,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,203 SQFT
  • 31 DOM
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Have It All! Mesmerizing Sunsets Over The Gulf Of Mexico And Unobstructed Water Views Spanning Intracoastal Waterways, Island Preserves & The Long, Picturesque Coastline From This Meticulous 3-bedroom/3 Full Bath Residence Behind The Gates Of The ...

Photo of Listing #A4528938

32 Bayhead Lane, OSPREY, FL
$695,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,570 SQFT
  • 31 DOM
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If You Love A Spacious Lanai Overlooking A Lake, This Home Is For You! Situated Among Lovely, Large Oak Trees In The Oaks Preserve, This 3 Bedroom, 3 1/2 Bath Home Is Steps From The Bishops Court Pool And Pool House Where You Can Enjoy A Peaceful ...

The Oaks Community Information

The Oaks Preserve is further divided into:

  • 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

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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 May 18th, 2022 at 9:19am EDT.