The Winchester Engineering and Planning Office is located on the lower level of Town Hall. The office maintains all plans and engineering records for the town. It is also involved in studies that deal with drainage, traffic, water, sewage and other pubic works and planning projects.

The department oversees the design and construction of various municipal improvements. It also conducts engineering-related plan reviews and field inspections, site plan approvals and new or redeveloped commercial and residential properties.

The department also handles parking permits for Aberjona, Waterfield and Jenks parking lots.