The work readiness of property graduates is the subject of global discourse and is an increasingly critical gap as employers demand professionals with competencies in their fundamental roles and digital technologies. Although these issues have been explored from the perspectives of students, graduates, and employers, the insights of property academics remain unexplored. As such, this study delved into the challenges encountered by property academics in Australia concerning the training of property graduates for the digital age, as well as the efficacy of strategies used to achieve this. The opinions of 22 property academics were gathered through an online questionnaire survey and analysed through mean scores, relative importance index (RII), and exploratory factor analysis (EFA). The profile of respondents suggests that approximately half of them have no more than five years of industry experience, and only 54.5% currently engage with the industry. The most significant challenges include limited funding to procure bespoke software and insufficient time to achieve digital competency. Furthermore, academics cited limited support from the universities as a key challenge, but rated curriculum rigidity as non-pertinent. Regarding strategies, retraining academics for digital proficiency, increased technical support from universities, adopting active learning, and revising curricula to incorporate digital technology are critical. Collaboration with industry partners and increased funding for software procurement also emerged as key external factors. Variations in these perceptions also suggest that older academics are less receptive towards retraining, academics with more industry experience believe that a restructuring of the curricula is required, and smaller institutions require more funding and industry support. The core themes of the proposed strategies also indicate that holistic curricula integration is required to incorporate the perspectives of all stakeholders. Practically, these findings underscore the pivotal role of academics in bridging the skills gap and the interconnected roles of graduates, universities, and industry partners.