The Cypresswood Community is an exclusive, established master planned community, featuring spectacular estate homes, patio homes, villas and condominiums. Conveniently located in Central Florida. This 600 acre development currently has about 1062 developed homes and home sites.
Cypresswood Golf & Country Club has a 18 hole championship golf course with pro shop, junior olympic sized swimming pool, six lighted tennis courts, Wellness Center, and a clubhouse with a restaurant and lounge.
Cypresswood offers the tranquility of a country club lifestyle for either year round or seasonal residents. The most exciting collection of home style choices anywhere awaits you in this prestigious community.
Information on the Golf Course or Clubhouse businesses can be found in the link below:
The Cypresswood Community is a No Soliciting neighborhood. The last CCA meeting featured a discussion and prevention method to keep solicitors out of Cypresswood.
Residents who witness solicitors or soliciting in the Cypresswood Community should report such rule infractions to the Polk County Sheriff's Non-Emergency Line: 863-298-6200
Effective June 1st, 2021, vendors who are not a “regular”(those who have been granted an extended pass such as lawn maintenance, private duty nurses, housekeepers...) MUST be called into the gate house staff prior to their arrival at the gate. Hence, if a periodic or (house guests, relatives, appliance repair person, handyman, day laborer, pool maintenance person, pest control...) does not possess an extended entry pass, they MUST be called into the gate: (863)-326-9496
Resident will need to supply the Vendor’s name, the address to which they are headed and the day they are expected. Failure to do this will result in the vendor, guest, etc... being turned away until the resident authorizes their entry. It is up to the resident to request extended passes for visitors or vendors requiring entry more than 1 day.
Authorized vehicles still require to provide photo ID for staff to scan.
Cypresswood Community Association Meeting
Time: TUESDAY, January 20, 2026 @ 6pm EST
Location: 1099 Clubhouse Rd, Winter Haven, FL 33884
Agenda:
1. Call to Order
2. Roll Call
3. Approval of meeting agenda
4. Approval of November 17, 2025 meeting minutes
5. Resident comments (3 min each)
6. President Report
A. Master Calendar – contract renewals
B. Committee Actions
1) Committee Chair/Vice Chair Appointments
2) Committee Meeting Minutes
C. Community Survey
D. CCA Policies – next two - Cypresswood Rules and Cypresswood Budgeting
E. President’s 2025 Annual Report – draft provided; review/comment by January 31, 2026.
7. Vice President and Traffic Control Committee Report
8. Treasurer Report
A. Financial Report
B. CCA Counsel
9. Committee Reports
A. Landscape
B. Drainage and Roads
1) 4022 Palma Ceia Circle ditch embankment erosion
2) Water Drainage on The 7th Green into Cypress Pond HOA
C. Amenities
1) Amenities Operator update – monthly statistics/challenges and update on amount of CGCS cost increase and impact to CCA 2026 Operations Support ($250,000)
2) Amenities Chair update
10. Old Business
A. Traffic Control Barrier Arm Padding
B. Traffic Control Building Renovation
C. Provision of Ward Cattle-Mowing contracts to the Board
D. Resolution of Board Question regarding new Kegerator and Liquor License
11. New Business
A. Committee Chair/Vice Chair Appointments
B. Delegated Board Authority for Purchasing – per 2026 detailed budget
12. Next Meeting – February or March, 2026?
13. Good of the Order – Around the table
14. Adjournment
2025 Community Survey II Results
A CCA Board Workshop was held on November 5, 2025 to discuss pub/venue improvements. The CCA Board members have been asked to pick their "top 3" improvements for the Amenities Committee and Operator to consider - these will be voted upon at the November CCA meeting.
The survey results are in! Follow the link above to read the results of the Amenities Committee Community Engagement Survey. The survey results will be used in planning for renovations to existing amenities, determining interest regarding new amenity offerings and providing information to our Cypresswood Community.
President: Chuck Georgo
Vice President: Dave Carter
Treasurer: Scott Shira
Secretary: Nora Ouellete
2026 CCA Board Meeting Dates
Congratulations to the Cypresswood Golf Course for winning the 2023 Best of Haven award for Best Golf Course in Winter Haven!
More information can be attained at the Traffic Control Center or clubhouse. The PDF applications can be found on the "Gate Access" page linked below.
Traffic Control 863-326-9496
Gate Access
Click on the link below for documents and information from the latest meetings.