169 AND 171, WINNER STREET (See details for further address information)

Nos. 169 and 171 Winner Street is a house that has been converted into a shop with accommodation above and at the rear. It is likely from the late 18th century or early 19th century. The building is roughcast with a slate roof that is hipped at the left end, featuring a stack with a rendered shaft and a platband. The structure is double-depth and two rooms wide, built into the slope of Winner Hill Road, with rear entrances at first-floor level.

The exterior consists of three storeys and a cellar, with two storeys visible from Winner Hill Road. The front has three windows, with a shopfront dating from around 1900 on the left. This shopfront includes a panelled pilaster at the left end and a three-light shop window with louvred overlights that angle towards the shop door. To the right, there is a 20th-century door with an overlight, and at the far right end, there is a second shop window with three lights. The first and second floors each feature three 12-pane sash windows.

The interior has been partially inspected; the shop interior is modern, but other interesting features may still exist elsewhere in the house. Historically, Winner Street was the main medieval thoroughfare in Paignton, named after the bishops' vineyard.