Picture of Carefree Entrance

Where To Find Us…

Carefree Country Club is located south east of Winter Haven, Florida just off Highway 540 (Cypress Gardens Blvd), 3 miles east of Legoland Florida and 1.3 miles west of Highway 27 on Lake Bess Road just across Highway 540 from “State Farm Insurance” and next to “Cypress Campground & RV Park” and “Wal-Mart Super Store”

Our Civic and Mailing Address is:

Carefree Country Club

9705 Lake Bess Road

Winter Haven, Florida


For membership information, please contact the Carefree Country Club office at 863-324-3892 or by writing to the address below.

To send an e-mail to the club office or accounting please click on the icon below.

Carefree Office Email: office@carefreecountryclub.org

Carefree Accounting Email: accounting@carefreecountryclub.org