Carefree Country Club has lots with double wide or single units with and without Florida rooms or screen porches.

Marketing Re-Sales are handled by the Carefree Marketing Group

For more information phone or mail.

Our address is:

Carefree Country Club – Marketing,

9705 Lake Bess Road,

Winter Haven, Florida, 33884.

Our Carefree Marketing Group telephone number is


Marketing Inquiries during the summer should be made to the Carefree office

Telephone # 863-326-1774

Marketing Email:


Carefree Country Club Logo
Sunset on Lake Bess Picture

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.

Enjoy good health —

Keep up the pace at indoor exercise classes and aqua-fit classes, take advantage of the fitness center or just walk around our gated community. Medical issues can be addressed at nearby urgent care and other clinics and hospitals. Feed your spirit, too, at chapel services and Bible studies.

Carefree Clubhouse Picture

Enjoy creativity – –

Classes and interest groups focus on various arts and crafts, including painting, jewelry making, quilting, and more.

Bean Bag Toss Game Picture

Enjoy the Sun – –

Membership does have its privileges – like free golf; large geo-thermally heated pool with lounging area and spa, bocce, tennis, Pickleball and shuffleboard courts; bean bag toss; or a stroll around the 5-acres wilderness area.

Golfers on course picture

Enjoy Friends – –

A stranger today is a friend tomorrow at Carefree. Join in on any, or all, of Carefree’s activities lots of different card games, dances, dinners, movie and music nights, coffee club, special and holiday-themed events, weekly golf events and annual tournaments, fishing, organized groups such as biking, bowling and lots of committees that are always looking for new volunteers.

Fisherman in boat Picture

Active Retirement Community
in the Heart of Florida

Conveniently located near
popular attractions and facilities

Disney’s Magic Kingdom
Animal Kingdom
Hollywood Studios
Universal Studios
Sea World
Busch Gardens
Kennedy Space Center
Bok Tower
Daytona Int’l Speedway
Orlando Airport
Florida beaches
Great shopping

Blue Heron Picture
Map of Carefree Location from Main Highways
Picture of Palmetto Plant

9705 Lake Bess Road; Winter Haven, FL 33884  (863) 324 3892