Carefree Country Club is an active 55+ resident-owned 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; 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). You’ll find it a pleasure to live in this gated and beautifully landscaped senior community.

Carefree is set on 107 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, recycling, sewer and water. The office is open year-round and has full-time management and maintenance staff.