ALL trees flower, otherwise they couldn't reproduce :-) Sometimes the flowers are extremely inconspicuous and unnoticeable but they ARE there. And yes, all Cleveland pears flower. The flowers are quite showy in spring.

You may want to do some further research on this tree before opting to plant more. Ornamental pears tend to be rather problematic, often developing structural issues that make them very prone to wind and weather damage. Cleveland (or more correctly 'Cleveland Select', aka 'Chanticleer') is less prone to these problems than some other cultivars but it can still develop structural issues. The greater concern is that this and all other ornamental or flowering pears have rather aggressive invasive issues - since they are so widely planted, the trees cross pollinate with each other, develop fruits that are carried by birds and wildlife and seed themselves around freely. In some parts of the country, this is a huge issue, with flowering pears covering the countryside. In fact, the species Pyrus calleryana or Callery pears, to which all flowering ornamental pears including Cleveland Select belong, is rapidly becoming a classic textbook case for plant invasivenss.

Ditto gardengal's statement. I would highly recommend looking at another tree. Despite the showiness of the Callery pears for a couple weeks in the spring (and the flowers often have a foul scent), they have so many issues that it's simply not worth planting. Try one of the flowering cherry trees usually available at Lowe's, or a crabapple tree for a similar looks without the problems.

P.S.--Even if you decide to plant the Cleveland Select after all, DON'T plant it anywhere near your house! A large branch WILL fall from this tree in a wind/ice storm at some point....be safe.

Callery pears vary in susceptibility to breakage, they are not all 'Bradford'. However, I would not plant any of them either, for other reasons - starting with the unpleasant floral odor.