Casarena on the Lakes is a gated townhome and single-family home community on the shore of Lake Cannon in northwest Winter Haven, part of the renowned Winter Haven Chain of Lakes in Polk County (Homes by Marco subdivision guide, 2026). It was built between 1983 and 1989, making it an established 1980s community rather than new construction.
Homes here range broadly in size, with listing guides citing roughly 2,025 to 3,439 square feet across the townhomes and single-family homes, and addresses sit along Casarena Court off Lake Cannon (Homes by Marco, 2026). Confirm the exact square footage, bedroom and bath count, and whether a given home is a townhome or detached for any specific listing.
Because this is a small gated community, the money is made or lost on the HOA and the home, not on the citywide average. The drivers are the monthly association dues, the reserve funding, the condition of the shared waterfront amenities, and the specific home, lot, and lake access, all of which have to be read from the current association documents and a real inspection.
The pitch is a quiet, gated lakeside address with Chain of Lakes access: the community offers a heated pool and hot tub, tennis courts, and a private boat dock and gazebo on Lake Cannon, with downtown Winter Haven, Legoland Florida, and the Polk Parkway all a manageable drive. The work is the diligence: read the budget and reserves, inspect the home and the amenities, and check the flood zone before you buy the view.