The Oaks Golf & Country Club is 1000 acre development featuring two private 18-hole championship golf courses. The development is situated on both the east and west sides of US 41 in Osprey, Florida just 12 miles south of downtown Sarasota. Amenities include the private equity country club, guest lodge, 14 Har-Tru tennis courts, croquet court, 34,000 square foot Georgian-style clubhouse, fitness center, junior Olympic pool and an active social calendar.
Below are all of the homes for sale in the Oaks Club neighborhood in Osprey Florida. All real estate listings are updated daily from the Multiple Listing Service (MLS). To learn more about any of these properties or receive email updates when new listings hit the market, simply give us a call at 941-923-7777 or send us an email. We are here to help!
… Read More| Total Listings: | 16 |
| Average Price: | $1,604,063 |
| Highest Price: | $4,790,000 |
| Lowest Price: | $235,000 |
| Average Size: | 3,424 ft² |
| Average Price Per Square Foot: | $452 per ft² |
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Lakefront Living And Elevated Architecture Come Together At 101 Osprey Point Drive, A Bo Macewen-designed Estate Privately Positioned On Nearly An Acre Within The Gates Of Sarasota’s Prestigious Oaks Bayside Community. Spanning More Than 5,000 Squ...
Multigenerational Living Behind The Gates Of The Oaks Golf & Country Club. Set On A Rare Double Lot At The End Of A Quiet Cul-de-sac, This Exceptional Home Is Perfectly Positioned On The 1st Hole Of The Heron Course, Capturing Sweeping Golf Course...
Nestled In The Prestigious Gated Enclave Of The Oaks Bayside In Sarasota, This Sedona-inspired Retreat Was Recently Updated From Wall To Wall Creating A Like Brand New Home. The Estate Seamlessly Blends Modern Luxury, Comfort, And Serenity. With A...
**charming And Private, Golf Course Estate** Is Located Behind The Secure Gates Of The Highly Sought After Oaks Country Club Community And Offers A Lovely, Golf Course View Of The 17th Fairway Of The Interior, Heron Golf Course. This Spacious, Li...
**elegant Updated Residence In The Oaks | Modern Comfort On A .83-acre Corner Lot** Welcome To 538 Dove Pointe, An Exceptional Residence In The Secure And Gated Oaks Country Club Community In Osprey, Florida. Set On A Generous .83-acre Elevated L...
Welcome To An Exceptional Estate In The Oaks Bayside, Where Timeless Elegance Meets Modern Luxury In One Of Sarasota County’s Most Prestigious Gated Communities. Perfectly Positioned On A Private, Lush Homesite Beneath A Canopy Of Majestic Oaks, T...
Virtually Staged. A Rare Canvas Of Luxury, Positioned On A Lush Double Lot Within The Sought-after, Gated Community Of The Oaks, In Osprey, Adjacent To Stunning Sarasota, Known For The Arts. Bordering The Heron Course On The Eighth Fairway, This ...
**stunning Golf Course Estate In The Highly Sought-after Oaks Country Club Community** Situated On An Over Half Acre Lot Overlooking The 12th Fairway Of The Interior, Heron Golf Course. With Its Delightful Curb Appeal And Manicured Landscape, Thi...
Offered At A Price Approaching The Value Of The Two Buildable Lots Alone, This Architect-designed Estate Represents One Of The Most Compelling Opportunities Currently Available In The Oaks. Nestled Beneath Majestic Oak Trees And Surrounded By E...
One Or More Photo(s) Has Been Virtually Staged. Designed By Renowned Architect Frank Folsom Smith, This Timeless Residence Is Privately Positioned On An Expansive Double Lot At The End Of A Quiet Cul-de-sac Within The Oaks Preserve. The Property I...
Looking For A Home You Can Truly Fall In Love With? Your Search Ends Here. This Thoughtfully Updated, Impeccably Maintained 3 Bedroom, 2 Bath Residence In The Oaks Preserve Offers The Perfect Blend Of Comfort, Style, And Privacy. And You Can Buy W...
**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...
**located In A Desirable, Maintenance-free, Country Club Community** This Charming And Cozy 3-bedroom, 2-full Bath Home Sits On A Premium Corner Lot Directly Across From The Community Pool. Featuring A New Roof, 2-car Garage, And A Spacious And Pr...
This Completely Updated 595 Sq Ft Second-floor Condominium Is Located In The Windsor Lodge Behind The Gates Of The Oaks. It Features Top-of-the-line Finishes And Is Accessible By Both Elevator And Stairs. Offered Turn-key Furnished, The Unit Inclu...
Situated In Windsor Lodge In The Oaks Clubside, This Updated Second Floor Condo Has A Kitchenette With Quartz Countertops, A Modern Bath, A Bonus Space Set Up As A Small Office Area And In-unit Laundry. An End Unit, It Has More Windows Than The Ty...
Discover A Rare Opportunity To Own A Serene Retreat In The Oaks, One Of Sarasota’s Most Sought-after Private Golf And Country Club Communities. This Bright, Beautifully Updated Ground-floor Studio Is Offered Fully Turnkey Furnished, Making It Idea...
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 August 18th, 2026 at 8:08am EDT.
Features & Amenities
Homeowners Association Information
Nearby Schools
Membership is mandatory with any real estate purchase in Oaks I, Oaks II Oaks Preserve and Meridian. Equity and social memberships are available.
Location
The Oaks Club
301 MacEwen Dr.
Osprey, FL 34229
Website: http://www.theoaksclub.com
Directions: The Oaks is located just south of Sarasota in Osprey, FL. Take US 41 two miles south of Sarasota Square Mall.
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