This study clarifies relationships between residential development and the transformation of wind environment in a residential area on seaside reclaimed land. We first investigate the effects of buildings surrounding the site on the wind environment within the site, with regard to southerly summer winds, using both field measurement and CFD analysis, in order to clarify how geographic and climatic factors affect wind system formation. Next, we investigate the transformation of the wind environment as the residential development by measuring wind direction and velocity at six points within the site for a period of one year and three months. We then clarify the influences of outdoor wind environment on the natural ventilation of a house, built on the developed area, in the summer.