Cypresswood Tennis Villas is a maintenance-included villa enclave inside Cypresswood Golf and Country Club, a gated, guard-attended master-planned community in Winter Haven, in Polk County (multiple Winter Haven real estate guides and the Cypresswood community materials, 2026). The wider community is described as an established, exclusive community of estate homes, patio homes, villas, and condominiums with a 24-hour manned gate.
The villas here are generally two bedroom, two bath units where the association handles exterior maintenance such as the roof, lawn, paint, and building exterior, which is the appeal of a lock-and-leave villa; confirm the exact maintenance scope and the bedroom count for any specific unit. The community is presented as a 55-plus active lifestyle community, so a buyer should treat it as 55-plus and age-restricted (HOPA) and verify the current age-restriction rules with the association before relying on them.
Because this is a small enclave inside a larger gated community, the money is made or lost on the villa association and the unit, not on the address alone. The drivers are the monthly dues, what the exterior maintenance and any master or club dues cover, the reserve funding under Florida current condo and association rules, and the specific unit condition and exposure, all of which have to be read from the current association documents.
The pitch is gated, resort-style golf-community living: the community sits inside Cypresswood Golf and Country Club with its 18-hole golf course, pool, lighted tennis courts, wellness center, and clubhouse, off US 27 south of Interstate 4 in Winter Haven, with Polk County destinations and the wider Central Florida corridor a manageable drive. The work is the diligence: read the dues, confirm what they include, verify the age restriction, and read the reserves before you buy the lifestyle.
