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Around 300 buildings in Chester centre are listed at Grade II, the lowest grade. The oldest Grade-II-listed buildings in central Chester date from the medieval era and retain some of their medieval fabric, for example, St Nicholas Chapel (1300). Early buildings are often timber framed, with some later encased in brick. Examples include the Old Custom House Inn, Nine Houses, Ye Olde Edgar and Stanley Palace. Many Georgian houses, in local sandstone or brick, are listed at this grade, including Park House and 10–28 Nicholas Street, as well as some Neoclassical buildings, such as Chester City Club.
From the mid-19th century, Chester was at the forefront of the Black-and-white Revival (example pictured), reintroducing timber-framed buildings into the city. Grade-II-listed examples include The Chester Grosvenor Hotel, St Werburgh's Mount, St Oswald's Chambers, 30 and 38 Bridge Street, and several houses on Northgate Street. A few modern structures have been listed, including Newgate (1937–38), and Modernist buildings such as the former Odeon Cinema (1936) and Addleshaw Tower (1973–75), a free-standing bell-tower. Unusual listed structures include a scale model of Grosvenor Bridge, the War Memorial, a Cenotaph to Matthew Henry, a tombstone commemorating a soldier, a sundial, a birdbath and two telephone kiosks.