The Downtown Winter Haven Historic District contains several blocks of early 20th-century commercial architecture along Central Avenue and the surrounding streets, listed on the National Register of Historic Places. The district reflects the 1920s Florida land boom at its most optimistic: brick storefronts, decorative cornices, and the occasional Mediterranean Revival building.
The district has seen gradual revitalisation and now has independent restaurants, coffee shops, and small businesses occupying the historic storefronts. It is a pleasant place to walk, small enough to cover in an hour, and offers a more authentic glimpse of old Florida than anything in the nearby theme park corridor.