Decreasing energy consumption and adapting to environments have become the mainstream architectural design concepts in response to the recent urban heat island effect and climate changes. The Passivhaus (i.e., passive house) concept, which was developed in Germany, has been promoted in Europe and North America. Similarly, green building policies have been implemented in Taiwan to promote resource efficiency in constructions and to reduce their impact on the environment and human health. Passivhaus are also being promoted in Taiwan. In urban planning, considering the relationships between buildings and the environment before implementing Passivhaus and green building policies enhances energy efficiency and environmental adaptation. Typically, natural ventilation is inadequate in urban environments. In addition to building layouts, natural indoor ventilation is affected by outdoor street environments. In street and indoor environments with poor ventilation, exhaust gas and pollutants can persist and jeopardize human health and comfort. This paper discusses the effect of building layouts on indoor ventilation performance. The findings indicated that the efficacy of indoor ventilation would be optimized if the direction of the main building layout and that of the main wind lie at an angle of 45 degrees; that the higher the street canyon aspect ratio (H/W) was, the better the efficacy of indoor ventilation was, but compared to the circulation zone in the street it was also higher, and therefore, other related measures or designs should be introduced to solve a lower ventilation efficacy; and that considering different building layouts, the ventilation efficacies of a parallel layout and a intertwined one were similar but led to distinct circulation situations in the street canyon, namely, the parallel layout generating a relatively stable and regulatory circulation however with a marked Venturi effect under a high H/W, and the intertwined one leading to a relatively unstable circulation with a lower Venturi effect.