This paper discusses how real estate education can benefit from applying a diary approach. A diary approach can enable a main driver of students’ motivation to learn: curiosity about their own real-world observation. The utilization of real-world observation by students seems to receive limited attention in existing real estate educational programmes. In general, educational programmes prepare students for professional involvement in property by providing them with a conceptual reference. This conceptual reference is, however, often built on a mere theoretical understanding of mechanisms that abstract from the real world. It appears useful that, in addition to abstract reasoning, students are taught to reflect on how real world developments fit to textbook theory. Such reflective skills could enlarge the public and private proceeds of their future professional actions in the field of real estate. With this in mind, we share experiences from a recent course in which students of the University of Groningen’s Master’s programme in Real Estate Studies were encouraged to keep diaries, which most of them did. In their diary entries, students described current real estate issues, projects, or policies which they somehow encountered or read about. Important is that each the subject of each entry somehow raised the student’s wonder, leading him or her to question something, or to explain their observation using theory. One or more entries of each student’s diary were discussed in the classroom. In so doing, students participated actively, under the teacher’s supervision, in group debates about their observations. This allowed students to share knowledge(claims) about their fellow students’ observations, debating how these can be framed by existing theory or by making slight alterations to theoretical models. We argue that a diary approach can be a useful supplement to the theoretical and methodological core of a real estate programme. The creation of a diary, and debate about its entries, develops both students’ reflective skills and their skills in combining real-world observation with the knowledge they are taught. As a result, the diary approach in this paper may support a sound professional involvement in property by university graduates.