Carefree Country Club is an active 55+ resident-owned gated community located on the shores of Lake Bess in Winter Haven, Florida. Carefree has its own private 9-hole golf course along with numerous other amenities which include a large, geo-thermally heated pool; bocce, tennis, Pickleball, and shuffleboard courts; horseshoe pits and bean bag toss area; billiards; library; fitness center; boat launch area with dock; and a 5-acre wilderness area. Our large colonial style clubhouse hosts a multitude of community functions throughout the year (dinners, dances, holiday events, cards, fitness classes, Sunday church service and other special events).

Carefree is set on 68.70 acres. As a cooperative, each membership includes 1/500 ownership of common grounds and amenities. Members own their own homes and hold proprietary leases on their lots which can be sold, transferred or willed to heirs.

Reasonably-priced association fees include access to all amenities including golf privileges, lawn maintenance, garbage disposal, sewer and water. The office is open year-round and has full-time management and maintenance staff.

Make a new circle of warm, supportive friends, filling your retirement years with an active, healthy lifestyle and many new interests. We invite you to join us and become our new friends and neighbors