Skip to Content Skip to Navigation Skip to Dashboard Skip to Search

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

Search The Oaks Real Estate Listings

Map View New Construction Save this Search
Sort listings by:New Listings First
Photo of Listing #A4547984

433 East Macewen Drive, OSPREY, FL
$2,150,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,012 SQFT
  • 7 DOM
View Details & More Photos Save

Beautiful House On A Great Golf Lot.

603 Eagle Watch Lane, OSPREY, FL
$1,750,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,872 SQFT
  • 11 DOM
View Details & More Photos Save

Live A Life Of Comfort And Elegance In Sarasota’s Premier Golf And Country Club Community! 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. A...

452 Blue Garden Lane, OSPREY, FL
$1,950,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,910 SQFT
  • 11 DOM
View Details & More Photos Save

Drive Through The Gates Of Oaks Bayside And You Will Quickly Understand Why Residents Love This Well-established, Luxurious Community. Notice The Quiet Streets And Beautiful Mature Trees As You Make Your Way To This Bo Macewen Masterpiece Built O...

Photo of Listing #A4546629

861 Macewen Drive, OSPREY, FL
$1,549,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,336 SQFT
  • 25 DOM
View Details & More Photos Save

**gorgeous Mediterranean Estate** This 3-bed + Large Office, Beautifully Appointed, Single-story Home Features Premium Finishes Throughout. The Spacious, Open Floor Plan Boasts Crown Moldings In Every Room, Italian Porcelain Tile Throughout Nearl...

340 Osprey Point Dr, OSPREY, FL
$2,650,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,001 SQFT
  • 35 DOM
View Details & More Photos Save

This Grand Estate Is Just As One Might Expect Tucked Behind The Gates Of The Oaks Bayside. Set Back From The Street And Surrounded By Lush Landscaping Which Includes Mature Oak Trees, Tropical Plants, And Beautiful Shrubs. The Driveway Is Made U...

Photo of Listing #A4545790

385 North Point Road 503, OSPREY, FL
$750,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,203 SQFT
  • 38 DOM
View Details & More Photos Save

Enjoy The Luxury Condo Lifestyle In This 3 Bedroom, 3 Bath Residence In Meridian At The Oaks Preserve. Enter Through The Secure Lobby And Take Your Private Elevator To This Lovely Unit. Take Advantage Of The Nearby Meridian Residents-only Pool, Sp...

134 Marys Chapel Court, OSPREY, FL
$2,649,000

Residential, Single Family Residence
  • 6 Beds
  • 8 Baths
  • 5,521 SQFT
  • 45 DOM
View Details & More Photos Save

Completely Remodeled, 6 Br / 8 Ba Estate, With 3-car Side-entry Garage And Upgraded Luxurious Pool Area, Located In The Exclusive Bayside Neighborhood Of The Oaks Club And Backing To The Historic Spanish Point Preserve. Wide Open Floor Plan Featur...

Photo of Listing #A4543763

409 North Point Road 902, OSPREY, FL
$1,050,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,055 SQFT
  • 46 DOM
View Details & More Photos Save

This 3 Bedroom, 3 Bath 9th Floor Penthouse With Private 2 Car Garage In Meridian At The Oaks Preserve Offers The Perfect Living Space For Those Who Seek Luxury And Comfort In A Country Club Community. Updated And Meticulously Maintained, This Resi...

401 North Point Road 703, OSPREY, FL
$925,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,203 SQFT
  • 46 DOM
View Details & More Photos Save

From Dawn-to-dusk This 3 Bedroom, 3 Bath Residence With Formal Dining Room Provides The Ultimate Place To Live The Luxury Condo Lifestyle. Located In The Heart Of South Sarasota It Is Situated In Meridian Behind The Gates Of The Oaks Preserve. Ent...

Photo of Listing #A4542825

232 Saint James Park, OSPREY, FL
$850,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,128 SQFT
  • 65 DOM
View Details & More Photos Save

Beautiful Home Overlooking A Lake And The First Fairway Of The Heron Course

Photo of Listing #A4543207

465 East Macewen Drive, OSPREY, FL
$2,300,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,357 SQFT
  • 66 DOM
View Details & More Photos Save

The Well-designed Floor Plan Perfectly Enhances A Warm, Welcoming Interior That Is Bathed In Natural Light And Includes A Formal Dining Room, Large Entertainment Spaces, First-floor Guest Suite, First-floor Master, Generous Living Spaces, Bonus Ro...

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

Gulf Shores Realty: 627781033 Gulf Shores Realty: 1613877538 Gulf Shores Realty: 1264807147 Gulf Shores Realty: 473835121 Gulf Shores Realty: 1447348502 Gulf Shores Realty: 506248133 Gulf Shores Realty: 368704368 Gulf Shores Realty: 1771245611 Gulf Shores Realty: 268716939 Gulf Shores Realty: 1926597494 Gulf Shores Realty: 614281769 Gulf Shores Realty: 836552199 Gulf Shores Realty: 1409377882 Gulf Shores Realty: 1284606319 Gulf Shores Realty: 861737261 Gulf Shores Realty: 523379917 Gulf Shores Realty: 1890278202 Gulf Shores Realty: 164965010 Gulf Shores Realty: 315557599 Gulf Shores Realty: 1061200894 Gulf Shores Realty: 856064521 Gulf Shores Realty: 1290081770 Gulf Shores Realty: 1999328186 Gulf Shores Realty: 40831177 Gulf Shores Realty: 1332063478 Gulf Shores Realty: 646081603 Gulf Shores Realty: 67202262

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

^ Back to: The Oaks Homes

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 September 30th, 2022 at 9:18am EDT.