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898 Macewen Drive, OSPREY, FL $1,950,000
- 4 Beds
- 4 Baths
- 4,132 SQFT
- 9 DOM
Large 4 Bedroom, 4 Bath Home On Over Half An Acre Bordering The 7th Fairway Of The Heron Golf Course In The Oaks Clubside. Located In The Heart Of South Sarasota, The Oaks Offers 2 Championship Golf Courses, A World-class Tennis Facility, A State-...
550 Dove Pointe, OSPREY, FL $3,300,000
- 4 Beds
- 6 Baths
- 7,842 SQFT
- 25 DOM
Sited At The End Of A Quiet Cul-de-sac Behind The Gates Of The Prestigious Oaks Clubside In Osprey, Florida, This Stately Traditional Custom Estate Offers Refined Living In One Of Sarasota County’s Most Exclusive Communities. Perfectly Positioned ...
140 Sugar Mill Drive, OSPREY, FL $1,970,000
- 4 Beds
- 4 Baths
- 3,286 SQFT
- 31 DOM
**brillianty Designed, Fully Renovated, Stunning And Serene Estate With Lush Garden Landscape** Is Located Behind The Secure Gates Of The Oaks Bayside, Country Club Neighborhood. Featuring 4 Bedrooms (2 En Suite) And 4 Full Baths, This Open Floorp...
33 Bishops Court Road 118, OSPREY, FL $695,000
Come And Enjoy The Perfect Maintenance Free Lifestyle In This Exquisite Townhouse Located In One Of The Finest Country Clubs On The Gulf Coast, The Oaks Golf And Country Club. Previously Redesigned, This Tuscan Style Home In The Quaint And Charmin...
401 North Point Road 504, OSPREY, FL $1,150,000
Fully Updated ~ Water Views ~ Private 2 Car Garage ~ Office/4th Bedroom Option ~ The Eye Of An Artist And Perfected Skill Of A Craftsman Created This Spacious, Expertly Designed Residence. From The Moment The Elevator Doors Open To The Private Foy...
112 Osprey Point Drive, OSPREY, FL $3,705,000
- 4 Beds
- 6 Baths
- 8,635 SQFT
- 71 DOM
Premier Waterfront Opportunity In The Oaks Bayside This Grand Estate Home, Perfectly Positioned On A Rarely Available Direct Waterfront Lot In The Exclusive, Gated Oaks Bayside Community, Offers Sweeping Views Of Little Sarasota Bay And Exception...
385 North Point Road 903, OSPREY, FL $1,295,000
From The Moment The Private Elevator Doors Open, The Panorama Of The View Has You At ‘hello,” With A Northwest-facing Expanse Over The Preserve, The Lagoon Below, Sarasota Bay And The Gulf Beyond. This Orientation Brings Cooler Interiors, Dramatic...
600 Eagle Watch Lane, OSPREY, FL $2,382,500
- 3 Beds
- 3 Baths
- 3,681 SQFT
- 97 DOM
Located On One Of The Most Desirable Streets In The Oaks Clubside, This Completely Renovated Pool Home Sits On A Generous 0.71-acre Lot With Wide Views Of The Third Hole Of The Heron Golf Course. Nearly Every Aspect Of The Property Has Been Update...
3621 North Point Road 603, OSPREY, FL $1,350,000
Prepare To Be Captivated By This Completely Updated, Meticulously Maintained, And Thoughtfully Appointed 3 Bedroom, 3 Bath Condo Located In Meridian At The Oaks Preserve. This Spacious Residence Has Everything You Need To Embrace A Carefree, Luxur...
340 Osprey Point Dr, OSPREY, FL $2,500,000
- 5 Beds
- 7 Baths
- 6,001 SQFT
- 100 DOM
Introducing The Grand Estate At The Oaks Bayside—a True Masterpiece Of Refined Living Within One Of Sarasota’s Most Prestigious Gated Communities. Surrounded By Majestic Oak Trees And Lush Tropical Landscaping, This Extraordinary Residence Offers ...
13 Bayhead Lane, OSPREY, FL $965,000
- 2 Beds
- 2 Baths
- 2,310 SQFT
- 102 DOM
**impressive, Move-in Ready, Pool Home In The Secure And Coveted Oaks Preserve, Maintenance-free Community** This Residence Boasts An Open Floor Plan That Is Ideal For Entertaining, Along With A Screened And Spacious Outdoor Pool Area That Provide...
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.
BROWSE OSPREY COMMUNITIES
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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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on July 14th, 2025 at 2:21am EDT.