Cypresswood Community Association

Welcome to Cypresswood

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:


Solicitor Prevention

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. 

Next Meeting

Cypresswood Community Association Meeting

Time: Monday, May 20, 2024 @ 6pm EST

Location: 1099 Clubhouse Rd, Winter Haven, FL 33884

March 2024 Meeting Presentation 

The survey results are in!

Follow the link below 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.

Your HOA President has been briefed on the results of the survey and can answer your questions or listen to your concerns. Look for video updates on a variety of survey topics in the coming weeks!

Community Survey Results

2024 Officers

Community Newsletter 

Best Golf Course in Winter Haven!

Congratulations to the Cypresswood Golf Course for winning the 2023 Best of Haven award for Best Golf Course in Winter Haven!

Gate Access

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

Minutes and Meeting Info

Click on the link below for documents and information from the latest meetings.