[2] Since 1996, most of Wincheap from the railway bridge to the A2 bypass has been marked as a conservation area by the city council.

[5] There is a petrol station halfway along the road, which has been criticised for having a negative effect on the area.

[6] At the end of 2021, the council announced plans to make Wincheap one-way southbound, sending northbound traffic via a different route.

Originally a timber-framed building, it was extensively rebuilt in the 18th century, though the overhang of the top two floors was retained, as was the 16-panelled front door.

96–116 date from the early 18th century, and are a group of two-storey brick houses that are a mixture of painted, stuccoed and roughcast, included hipped tiled roofs.

198–204 Wincheap was established around the early 15th century and was believed to be the city's oldest continuously trading inn.

[5] The Hospital of St James by Canterbury was based at the southern edge of Wincheap where the road meets Thanington.

[17][18] The Thanington Pumping Station was based at the edge of the conservation area at the southeast part of Wincheap.

[5] A telephone box at the north end of Wincheap by the railway bridge was Grade II listed in 1989.

It was built in 1935 by Sir Giles Gilbert Scott and constructed from cast iron.