This study examined students' accuracy of measurement estimation for linear distances, different units of measure, task context, and the relationship between accuracy estimation and logical thinking. Middle school students completed a series of tasks that included estimating the length of various objects in different contexts and completed a test of logical thinking ability. Results found that the students were not able to give accurate estimations for the lengths of familiar objects. Students were also less accurate in estimating in metric units as compared to English or novel units. Estimation accuracy was dependent on the task context. There were significant differences in estimation accuracy for two- versus three-dimensional estimation tasks. There were no significant differences for estimating objects with different orientations or embedded objects. For the tasks requiring the students to estimate in English units, the embedded task and the three-dimensional tasks were correlated with logical thinking. For estimation tasks with novel units, three-dimensional and two-dimensional estimation tasks were significantly correlated with the logical thinking.In order to interact effectively with our environment it is essential to possess an intuitive grasp of both dimension and scale and to be able to manipulate such information. Estimation, approximating and measuring are all components of such intuition (Forrester, Latham, & Shire, 1990, p. 283).