The Philippines’ real estate (RE) market vis à vis its government’s collective efforts to accelerate its digital transformation faces prevalent illegal RE practices online on top of limited publicly accessible data for decision-making and decentralized and highly regional RE markets. As the middle-income millennials’ and Gen Zs’ purchasing power rises, these increasingly important consumer groups might fall prey to online RE colorums or make bad RE investment decisions. In anticipation of big data, ML, and AI becoming integral to the Philippine RE industry, this study extends the theory of the planned behavior model to account for RE investment and illegal practice and to build a theoretical basis for foundational models. A total of 400 Filipinos aged 15 to 42 from different regions in the country responded to a self-administered online survey questionnaire. The model was assessed using partial least squares structural equation modeling (PLS-SEM) and was proven to be sufficient to explain the proposed model. Results from the partial least squares structural equation modeling (PLS-SEM) revealed that during inflation, risk tolerance (RT), perceived property value (PPV), and aversion from illegal practice (IP) significantly influence millennials’ and Gen Zs’ intention to invest in the RE market, implying that they would consider prioritizing profitability at the expense of sustainability. Thus, a collective commitment to provide transparent and real-time data on RE KPIs and projects is necessary for safer and optimized operations while ensuring the sustainability of current and future projects.