Headmasters House to Merchant Taylors School (Boys)

The Headmaster's House to Merchant Taylors School (Boys) is a building likely constructed in 1878 by Lockwood and Mawson. Originally serving as the headmaster's residence, it is now used as offices. The structure is made of red brick in English bond, featuring sandstone and terracotta dressings, and has a graduated green slate roof with blue slate fishscale bands. The design is eclectic, incorporating both Gothic and Tudor elements, and has a modified square plan with projecting gabled bays.

The exterior consists of two storeys with a two-to-one window arrangement and a short gabled wing to the right. It has a chamfered plinth and a first-floor string course that wraps around the building. A gabled porch is located at the angle, featuring a two-centred arched doorway with set-in colonnettes topped with foliated caps, divided doors, and oversailing verges supported by wooden brackets. The porch also has panelled bargeboards and a cut-down finial. To the left, there is a tall cross-window, with one and two-light windows above, while a large six-light transomed window is present at the ground floor of the gabled wing to the right, with a stepped three-light window above. The building has short ridge chimneys with swept stone caps, likely the bases of former tall shafts that are now missing. The left return features a similar two-to-one window arrangement, with two gables; the right gable projects and includes a storeyed canted bay window adorned with crocketed cornices on both levels, with other windows matching the front.

The interior has not been inspected. This building forms a group with the main school building.