Wincheap is a road and suburb in Canterbury, Kent, England. The road forms part of the A28 road, stretching for around 1 mile (1.6 km) from the city wall, close by Canterbury East railway station, to the over-crossing of the A2 and the parish of Thanington.

There are two theories about the name: either it comes from the Saxon Wenchiape, a wine market, or from Weychep from the old English Waegnceap, indicating a wagon market.

Wincheap originated as an ancient trackway to the east of the River Stour. In Roman Britain it was used for communication between Canterbury and the iron works in the Weald. The modern street was established by the early 13th century; the name is recorded starting in 1226.

Wincheap Gate, since demolished, was one of the entrances in the city walls. A timber market was held halfway along Wincheap in the 13th century, while an annual cherry fair took place on Wincheap Green until the early 19th century. The green was destroyed during construction of the Canterbury Ring Road in the 1960s.

In the 16th century, the Canterbury Martyrs were burned at the stake for heresy in Wincheap. A monument marks the spot on Martyrs Field Road.

Since 1996, most of Wincheap from the railway bridge to the A2 bypass has been marked as a conservation area by the city council. There is a petrol station halfway along the road, which has been criticised for having a negative effect on the area.

At the end of 2021, the council announced plans to make Wincheap one-way southbound, sending northbound traffic via a different route. This plan has not been realised.

Nos. 50–52 were constructed in the 18th century and were originally a single house. They are three storeys high and constructed of red brick. They were Grade II listed in 1973.