Eastgate forms an imposing sight at the entrance to the top of the street and was reconstructed in the 15th century when the chapel of St. Peter was above it. Much of the chapel was rebuilt around 1788 in a gothic style. Clustered around Eastgate are three interesting features - a drinking fountain given to the town in 1859 by a Wilmcote quarry owner; a red telephone box of circa 1935 now listed; and a Greek Doric pillar box dating from Victoria's reign.
Fortunately, the great fire of 1694 which destroyed 450 houses in the town largely missed Smith Street and as such Landor House, built in 1692 and one time home of the poet Walter Savage Landor, is worthy of note at the top of the street.
Opposite Landor House are several interesting old houses, both timbered and stone, built before the Great Fire.
Further down Smith Street Venetian windows can be found at numbers 27 and 29 and there are 16th Century houses at the bottom of the street, partly disguised by plaster and paint.