Uppingham School New School House

Uppingham School New School House is a school boarding house built in 1889 by T G Jackson. It is constructed of coursed squared stone with ashlar dressings, featuring a slate roof and coped gables. The building includes a leaded cupola with a clock and two large stone stacks on the south slope of the roof, and it is designed in the Jacobean revival style. The structure has two storeys and attics, comprising a main block, an east wing, and a long range projecting to the north.

On the south front, the main block features central and east end projecting gables, with mullioned and transomed windows that have casement openings. The east end includes a canted bay window topped with a leaded ogee semi-dome. The east wing is two storeys in an L shape, with windows similar to those of the main block. The projecting gable at the east end has two first-floor windows, each with three cusped-headed lights, two transoms, and hoodmoulds.

The north front is treated asymmetrically, showcasing gables, two two-storey porches, and irregularly spaced mullioned and transomed windows, including one partly-blocked window, which may suggest an impression of growth over time. The two-storey wing to the north features a central arched entrance with a four-centred design, along with twenty single-light rectangular first-floor windows and similar but larger ground-floor windows, mostly arranged in pairs. This building forms two sides of a quadrangle, which is completed by the School Room and Science Block.