Cypresswood Golf & Country Club is a gated, master planned golf community in Winter Haven, Polk County, on roughly 600 acres with about 1,063 developed homes and homesites organized under the Cypresswood Community Association (Cypresswood Community Association, 2026). It is an established community marketed for both year round and seasonal residents, built around its golf course and clubhouse rather than a single home style.
The centerpiece is an 18 hole championship golf course designed by Ron Garl that opened in 1973, with the broader amenity set including a pro shop, a junior Olympic sized swimming pool, lighted tennis and pickleball courts, a wellness center, and a clubhouse with a restaurant and lounge (Polk County Golf Courses, 2026; Cypresswood Community Association, 2026). Access is through a guarded gate with traffic control, and the community is a no soliciting neighborhood.
Because this is a master community with many neighborhood associations, the money is made or lost on the layered association picture and the specific enclave, not on the address alone. The home styles span estate homes, patio homes, villas, and condominiums, so the dues, the rules, and the maintenance responsibilities differ by sub-association and have to be read from the current documents for the exact parcel.
The pitch is a country club lifestyle inside one gate in Central Florida, close to Winter Haven, with regional draws such as Legoland nearby and the Orlando attractions corridor within reach. The work is the diligence: match the home style to your budget, read the master and sub-association budgets and reserves, and confirm the golf and amenity terms before you buy the gate and the green.
