Private · 18 Holes

Carefree Country Club

9705 Lake Bess Road, Winter Haven, Florida

PrivateMembership

18Holes

4.8★29 Reviews

Winter Haven, FLLocation

The Club

About Carefree Country Club

Carefree Country Club is an exclusive 55+ resident-owned gated community situated on the picturesque shores of Lake Bess in Winter Haven, Florida. The club features a private 9-hole golf course and a wide array of amenities including a geo-thermal heated pool, bocce, tennis, pickleball, and shuffleboard courts. Members can also enjoy a billiards room, library,...

Facilities

Club Amenities

Motor Cart

Pull Cart

Club Rental

Club Fitting

Pro Shop

Golf Lessons

Driving Range

Putting Green

Practice Bunker

Restaurant

Fitness Center

Swimming Pool

Tennis Courts

Pickleball

Reception Hall

Real Estate

Nearby Listings

No listings at this club yet — here are nearby properties:

9705 Lake Bess Rd Lot 715

Winter Haven, FL

$119,000

221 Golf Aire Blvd

Winter Haven, FL

$315,000

239 Golf Aire Blvd

Winter Haven, FL

$394,000

Membership

Joining Carefree Country Club

Carefree Country Club offers a unique cooperative membership where each member holds a 1/500 ownership of the common grounds and amenities. Members enjoy access to the private golf course, a variety of sports courts, a fitness center, and a large clubhouse that hosts social events. The community is designed for active adults seeking a supportive and engaging environment.

Reviews

What People Say

4.8/5

★★★★★

Google · 29 reviews

In summary

Carefree Country Club is highly praised for its welcoming community and enjoyable golf course, with many visitors appreciating the friendly and helpful staff. The club provides a pleasant living environment with opportunities for social engagement and activities. However, some mention that the on-site administration office can be busy and may have limited staffing.

★★★★★a year ago

Very nice place. Enjoyed the golf ⛳️. Lovely community.

— Scott Whitworth

★★★★★3 years ago

Beautiful ❤️😘. I had lunch with my friend at her house 🏠 their. It is A very nice place. , Lynette Philbrick

— Cricket Philbrick

★★★★★Edited a year ago

Busy on-site administration office with limited staffing. Doing the "best" that they can.

— Scott Rathje

★★★★★3 years ago

Family stays here awesome place

— Bob Kurtz

★★★★★4 years ago

Great place to live!

— Jeff Eklund

★★★★★2 years ago

Karen was extremely helpful

— Allen Gilbert

★★★★★5 years ago

Played golf and all was enjoyable

— Michael Lapinski

★★★★★Edited 6 months ago

Informative, helpful, professional.

— Mike Piekarski

★★★★★5 years ago

Nice

— Susan Shepard

★★★★★Edited 2 months ago

Will be here a year on June 2nd when I bought my home . Have not been disappointed with my decision !! It is the best park , the community within is the best , friendly, everyone is so helpful! You can be as busy as you want, participating , volunteering or not doing a thing. You won't be disappointed living in this community that's for sure !! Love it here !!!

— Debbi Dashnier

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