This study explored children’s area estimation performance. Two groups of fourth grade children completed area estimation tasks with rectangles ranging from 5 to 200 square units. A randomly assigned treatment group completed instructional sessions that involved a conceptual area measurement strategy along with numerical feedback. Children tended to underestimate areas of rectangles. Furthermore, rectangle size was related to performance such that estimation error and variability increased as rectangle size increased. The treatment group exhibited significantly improved area estimation performance in terms of accuracy, as well as reduced variability and instances of extreme responses. Area measurement estimation findings are related to a Hypothetical Learning Trajectory for area measurement.