The transition from a busy work life to a retired state entails a lot of adjustment, planning, and wise decision-making. While there have been numerous studies that elucidate retirement issues across the globe, the need to know about retirement preferences of middle-aged and older teachers remains a blank spot in the literature, hence this discrete choice estimation investigation. The overall purpose of this study is to explicate the utility and importance of retirement preferences of a select group of 40-70 year-old teachers (n = 152) from the northern part of the Philippines. Using the Statistical Package for the Social Sciences (SPSS) version 21, a set of 12 choice bundles with 4 holdouts were extracted from a pool 96 orthogonal array. Respondents were asked to sort and rank each card based on its importance and utility value using the Balanced Incomplete Block Design (BIBD). Results indicate that the most important attribute considered by Filipino teachers relative to their retirement preferences was investment. This was followed by pursuit of an old interest, travel, and part-time job as the least preferred. This utility study yielded empirical data that can be benchmarked by retirement planning policy makers in the academic setting to better address the uncertainty faced by aging teachers when it comes to their retirement decisions.