Home Owners Association Information About
Cypresswood, Winter Haven, FL 33884

Community Overview

Cypresswood is a master-planned community in Winter Haven, FL, governed by the Cypresswood Community Association (CCA), a nonprofit formed in 1981 that oversees 14 sub-associations and maintains community-wide infrastructure including roads, drainage, landscaping, and recreational amenities. The CCA is not a traditional HOA but coordinates the sub-HOAs.

HOA Fees

Fees vary significantly by sub-association (e.g., Plantations HOA 2026 assessment $1,790 annually; Golf Villas $295 monthly; Enclave $435 monthly; Cypress Pond $1,700 annually). CCA dues are collected through the sub-HOAs. Specific master CCA fees and transfer/capital contribution details are unavailable in public sources.

HOA Rules & Regulations

Resident rules include no soliciting, no overnight street parking of RVs/boats/trailers (must be garaged), pets on leash with waste pickup required, no garage/yard sales (estate sales permitted under conditions), no farm animals, no portable buildings, limited satellite dishes, no advertising signs except realtor signs, and quiet hours/no noisy gatherings. Fishing restricted to specific ponds; all signage must be obeyed. Enforcement involves Polk County Sheriff. Architectural review required for modifications via sub-HOAs.

Community Amenities

Amenities include an 18-hole championship golf course, junior Olympic-sized swimming pool, four lighted tennis/pickleball courts, wellness center/fitness facilities, clubhouse with restaurant and lounge, pro shop, driving range, and green spaces. The golf course and restaurant are open to the public.

Lifestyle

Residents enjoy a tranquil country club lifestyle in a gated setting with year-round or seasonal living options, emphasizing recreation, social events, and maintenance of common areas by the CCA and sub-HOAs.

Contact Information

Cypresswood Community Association (Master): Website cypresswoodcommunityassociation.com; Gate/Traffic Control (863) 326-9496; Clubhouse 1099 Clubhouse Rd, Winter Haven, FL 33884.
Plantations HOA: Stambaugh, Inc., (863) 324-5100, gm@stambaughinc.com, 500 Orchid Springs Dr, Winter Haven, FL 33884.
Golf & Country Club: (863) 324-6174, cypresswoodcc@gmail.com, cypresswoodcc.com.
Other sub-HOAs: Contact details vary; refer to cypresswoodcommunityassociation.com for neighborhood-specific boards (e.g., Garden Patio Homes, Eagle Pond). Office hours and mailing addresses available on sub-HOA pages.

Notable Aspects

600-acre development with ~1,063 homes; 18-hole golf course designed by Ron Garl (voted best in Winter Haven); 50-year lease on amenities signed in 2017; no-soliciting policy; proximity to US-27 and central Florida attractions; diverse housing including estates, villas, and condos.

Conclusion

Cypresswood offers resort-style living through its master association and sub-HOAs, with strong emphasis on amenities, security, and community standards in a desirable Central Florida location.