86, 88, 88A and 90, Winner Street

Nos. 86, 88, 88A, and 90 Winner Street are two shops with accommodation above and a house, built around the 1820s. The buildings are finished in stucco, showing some signs of previous blocking out, and feature an asbestos slate roof, with a left-hand stack that has a brick shaft and cast-iron gutters.

The structure is located on the corner of Church Street and Winner Street, characterized by a curved corner. It is two storeys high, with No. 90 also having a cellar. The front is asymmetrical with five windows and two blind recesses on the first floor. No. 90, on the left, has a large late 19th or early 20th-century shop window, which includes a pair of two-pane sashes in the center, flanked by high-transomed nine-pane fixed windows. To the right, there is a half-glazed shop door with a two-pane overlight. No. 88 features a panelled recessed door with a plain overlight and two first-floor two-pane sashes. The remaining part of the range includes a 20th-century shopfront with plate glass windows and a central door, followed by another 20th-century door with a plain overlight, and at the far right, a window with an embrasure that is likely original but has unfortunate replacement plastic glazing. The first floor retains one probably original twelve-pane 19th-century sash and has blind recesses between two plastic windows, with the embrasures likely being original.

The interior has not been inspected. Historically, Winner Street was the main medieval thoroughfare in Paignton and is named after the bishop's vineyard. The buildings are included for their group value.