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

425 East Macewen Drive, OSPREY, FL
$2,599,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 5,153 SQFT
  • 10 DOM
View Details & More Photos Save

Welcome Home - The Oaks Country Club - Sarasota, Fl. This Home @ #425, Boasts Beautiful Golf Course And Select Water Views Throughout. A 27,000 Sf +/- Private Lot. One Can Look Directly At The Par 3 - 4th Hole (the Oaks Heron Course). Mature Stunn...

393 N Point Road 503, OSPREY, FL
$785,000

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

**enjoy Spectacular Sunset Views From This 5th Floor, 3-bed / 3-bath Condo With Balcony Overlooking A Serene Lagoon, Intracoastal Waterway And Even The Gulf Of Mexico While Situated In The Luxury, High-rise, Meridian Condo Complex Behind The Secur...

627 Eagle Watch Lane, OSPREY, FL
$2,295,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,896 SQFT
  • 28 DOM
View Details & More Photos Save

**exquisitely Designed And Brilliantly Renovated, Custom Golf Course Estate With Spectacular Water View** Is Situated On The Interior Heron Golf Course And Is Located On A Tranquil, Cul-de-sac Street Behind The Secure Gates Of The Oaks Country Clu...

3621 N Point Road 601, OSPREY, FL
$1,300,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,680 SQFT
  • 35 DOM
View Details & More Photos Save

Located On The South End Of Building V In Meridian At The Oaks Preserve, This 3 Bedroom, 3 Bath Residence Is An Incredible Find. Enter Through The Secure Lobby, Go Up The Private Elevator And Step Through The Double Doors And You Will See How Spec...

360 North Point Road, OSPREY, FL
$1,595,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,913 SQFT
  • 48 DOM
View Details & More Photos Save

**don’t Wait To Build!** Exquisite, Newly-constructed And Never Lived-in, Spanish Mission Style Home Behind The Secure Gates Of The Coveted, Oaks Preserve Country Club Neighborhood On Sarasota Bay Waters Offers Superb Attention To Detail. This Cu...

57 Bishopscourt Road 121, OSPREY, FL
$750,000

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 1,890 SQFT
  • 52 DOM
View Details & More Photos Save

**updated, Maintenance-free Townhouse** Located Behind The Secure Gates Of The Coveted, Oaks Preserve Country Club Neighborhood On Sarasota Bay Waters Where Golf (or Social) Membership Is Immediately Available. This Traditional Residence Boasts A...

1108 Bayhead Lane, OSPREY, FL
$1,500,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,541 SQFT
  • 55 DOM
View Details & More Photos Save

**luxurious Turnkey Home In The Oaks, Sarasota** Amazing Sunsets ** Fine Accessories & Furniture W/leather & Textured Fabrics **dream Bathroom And Dressing Rooms With Fantastic Built-in's ** Large 2 Car Garage W/storage ** Solar Heated Salt Water...

409 North Point Road 702, OSPREY, FL
$1,150,000

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

One Or More Photo(s) Has Been Virtually Staged. Experience Stunning Views Of The Intracoastal And Gulf From This Well-maintained Seventh-floor Meridian Unit, Featuring A Private Entrance. With Beautiful Hardwood Floors, Marble And Granite Accents,...

738 Macewen Drive, OSPREY, FL
$1,800,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,614 SQFT
  • 75 DOM
View Details & More Photos Save

Imagine How You’d Like To Live The Ultimate Florida Lifestyle. Your Vision Can Become A Reality In This 5 Bedroom, 5.5 Bath Two Story Home In The Oaks Clubside. Currently Unfurnished, You Just Need To Pack Your Bags, Bring Your Own Style And Make ...

Photo of Listing #A4613147

402 Walls Way, OSPREY, FL
$1,875,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,464 SQFT
  • 87 DOM
View Details & More Photos Save

**newer Construction (2014) -- Impressive, Custom “courtyard Style” Golf Course Estate W/ Water View Built By Todd Johnson Homes** Is Situated On An Oversized, 0.64 Acre, Lakeside Corner Lot Behind The Secure Gates Of The Oaks Country Club Communi...

216 Osprey Point Drive, OSPREY, FL
$795,000

One Of The Last Lots Available To Build In The Prestigious Community Of The Oaks Bayside. Take Advantage Of This Rare Opportunity To Build Your Dream Home, Using The Builder You Choose, Within The Oaks Club – One Of The Most Exclusive Private Club...

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 10th, 2024 at 11:49pm EDT.