Casarena on the Lakes is a small, gated townhome community on Lake Cannon in Winter Haven, reached off Casarena Court near Havendale Boulevard and 21st Street NW, in Polk County (multiple Winter Haven real estate listing guides, 2026). Lake Cannon is part of the Winter Haven Chain of Lakes, which gives the community its lakeside identity and water access.
Listing and community guides describe the townhomes as built in roughly the 1983 to 1989 period, generally two and three bedroom plans in the range of about 2,000 to 2,500 square feet, so this is older, mid-size townhome stock rather than new construction (Winter Haven real estate listing guides, 2026). Confirm the exact build year, size, and bedroom count for any specific unit, since plans vary across the community.
Because this is a small association community, the money is made or lost on the HOA and the unit, not on the address. The drivers are the monthly dues, the reserve funding, the condition of the shared dock, pool, and tennis courts, and the age, roof, and systems of the specific townhome, all of which have to be read from the current association documents and an inspection of the exact unit.
The pitch is gated lakeside living with Chain of Lakes access: a community dock and gazebo on Lake Cannon, a pool and hot tub, and tennis courts, with downtown Winter Haven, Havendale, and the wider Polk County job and retail base a short drive away. The work is the diligence: read the budget and reserves, confirm what the dock and water access convey, check the flood zone, and inspect the older townhome before you buy the view.
