Transit-oriented development (TOD) advocates sustainable development and the building of livable neighborhoods. Several measures are proposed to evaluate TOD principles; however, the suitability of these measures is not fully explored in the context of developing countries. This paper provides a systematic method for multivariate analysis of TOD measures in the context of developing countries. A bivariate analysis is conducted to simultaneously study all TOD measures against the distance to transit measure because of its essential role in TOD. A dynamic zoning system is introduced to capture a realistic reflection of neighborhood that is walkable for its residents. In the proposed zoning system, neighboring zones can overlap, as the walkable areas for the nearby residences may overlap. The adherence of Tehran’s Master Plan to TOD principles is examined with a focus on TOD measures and multidimensionality in assessment. The results highlight the curse and the blessing of the high-density urban sprawl in sustainable development.