Nos. 1-2 Upton Fort (Former Caretaker'S Quarters), Former Artillery Store, And Former Smith'S And Fitter'S Shops, Upton Fort

Military support buildings at the western end of Upton Fort, a coastal artillery battery constructed in 1901–03. The buildings comprise the former Caretaker's Quarters (Nos. 1–2 Upton Fort), a former artillery store with attached paint store, former Smith's and Fitter's shops, and a generator room. Minor mid-twentieth century alterations have been made. There was also a latrine block to the south east which has been partly demolished. Further to the east are two additional contemporary buildings: a former cookhouse and a shelter, now dwellings.

The group occupies a single-storey arrangement within an area defined by a protective earthen bank and a blast wall on the south side. All buildings are constructed of brick with concrete dressings, flat concrete roofs, and rendered brick stacks. Windows throughout are timber sashes with glazing bars. Many windows have been replaced in later alterations, and the buildings do not currently meet the criteria for listing.

Nos. 1–2 Upton Fort form a pair of semi-detached dwellings with an H-shaped plan. The front (north) elevation is symmetrical, comprising a central section with four windows and a veranda supported on cast-iron columns, flanked by bays that break forwards. Each bay has a pair of sash windows to the front and an entrance door in the return. A small late-twentieth century extension to the north west side of No. 1 is not of architectural interest. A small extension added to the north west side of No. 1 in the later twentieth century is not of interest.

The former artillery store, marked as such on a 1905 plan, is an L-shaped building located immediately to the west of the Caretaker's Quarters. It comprises a rectangular range with a smaller block at its south east end that was originally a paint store. The building was converted to a cookhouse during World War II. It is built in English Bond with sash windows throughout, all fitted with iron bars. The north east elevation has an off-centre timber door flanked by small windows with ventilators above, and a larger sash window to the far right. The east and west sides have matching windows each with a ventilator above. The south elevation is blank but has two ventilators set high in the wall. The former paint store is accessed by a door in its north wall.

The former Smith's and Fitter's shops, located to the north of Nos. 1–2, is a rectangular building with a flat concrete roof and a louvered lantern to the western half. The main elevation faces south with three sash windows and two entrances; the left entrance has been widened but retains its glazed light above the doorway. A conservatory clad in plastic corrugated sheeting, not of architectural interest, links this building to a roughly square structure to the east used as a generator room (now a dwelling) during World War II. The generator room has double doors to the east elevation and single sash windows in the south and north walls. A building is shown here on the 1905 plan, marked as an Armament Office.

The interior of the Caretaker's Quarters, although not inspected, is indicated by the 1905 plan to have comprised two bedrooms, a living room and scullery in each dwelling, with toilets and coal stores to the rear. The former artillery store contains a large principal room with three smaller rooms leading off it, and formerly had a large cast iron range against its west wall, though this is not in situ. The Smith's and Fitter's shops was originally divided into two parts with a Smith's Shop in the western half and a Fitter's Shop to the east, though the internal partition has been removed.

By the mid-nineteenth century Portland had become an important naval port, home to the Royal Navy's Channel and Home Fleets. Towards the end of the nineteenth century a programme was established to strengthen England's coastal defences against possible French aggression and to protect the British fleet, which was vulnerable to torpedo attack. A battery for long-range breech-loading guns was built at Upton in 1903, strategically placed above Weymouth Bay to protect the eastern approaches to Portland Harbour. Upton's first weapons—two 6-inch breech-loading guns—were mounted in February 1903, followed by two 9.2-inch guns between July and September that year. After World War I the 9.2-inch guns were removed and the battery was left in the charge of a caretaker.

Upton Fort was updated and re-armed in 1940 to operate as an emergency battery. The defences were strengthened, 6-inch naval-type guns were installed, and two Coastal Artillery Search Lights were added. The battery was manned by the 522nd (Dorset) Coastal Regiment, and men were accommodated in Nissen huts at the northern end of the site. All ancillary buildings were re-used during World War II, though the functions of some changed: the Caretaker's Quarters became an officers' and sergeants' mess, and the artillery store was converted to a cookhouse. Upton Fort was the first of the Portland defences to enter care and maintenance following reorganisation of defences in November 1943, and was finally taken out of service in 1956.