Castle Hill House was built in 1760 by the Stringer family in classical style. It is in a brown brick in Flemish bond with red brick details and stone bands and a cornice. It has a symmetrical north-east entrance front of seven bays, the central three bays projecting slightly under a pediment containing an oval window in the tympanum. There is a parapet with a stone bracket cornice, a stone band under the ground and first floor windows and a wider stone band above the ground floor windows. The central entrance is pedimented with a bracket cornice and Ionic half-columns with panelled reveals. The south-east side has end chimneystacks, a small first floor extension and an attached section of garden wall enclosing a forecourt, ramped up near the house, incorporating a blocked carriage entrance with square brick gate piers with stone caps. The south-west side has at the south end a full-height curved bay over two storeys. Adjoining is a three bay section with a mansard roof, three flat-roofed dormers and three sash windows on both the first and second floor. Beyond it is a section of two bays under a roof hipped at the north end with similar six-over-six sash windows and a further section of two bays with six-over-six sash windows. Several modern gutter down pipes cross this rear elevation, giving it an untidy appearance. The north-west side is rendered. There are some cracks to the brickwork and several areas where the brickwork is stained. Despite this the building appears to be structurally sound and in a good condition.

On the interior the entrance into Castle Hill House from the north-east leads directly into the central staircase hall. This has a staircase with mahogany handrail, alternate spiral and plain turned balusters, finely carved tread ends and column newel posts. The walls of this central room are panelled with a bracket cornice, moulded dado rail, a deep skirting board and six-panelled door. The adjoining room to the north has a cornice with alternate brackets and paterae, panelling with a dado rail and a plastered rococo ceiling. This has a central moulded ceiling rose and four corner panels with wheat ear drops, cornucopiae, caduceus (the staff of Hermes who gave protection to merchants), and incorporates grapes in the design (symbolising the source of the wealth of the Stringer family, who were wine merchants). The wooden Gibbs surround fireplace is finely carved with a central shallow basket of flowers, and has a Delft tiled interior. Above is a finely carved wooden surround, now containing a mirror but probably originally designed for a painting. The original window shutters survive. The ground floor south-east reception room has early C19 panelled double connecting doors into the large south-west reception room with curved bay, which has a mid-C19 marble fireplace and a dumb waiter. The central first floor staircase-hall has a moulded cornice and a series of early C19 reeded door architraves with paterae to panelled doors. A short early C19 flight of stairs, with three slender turned balusters, finely carved scrolled tread ends and a column newel post, leads to the large south-west reception room. This has a curved bay window, and is called the Churchill Room after one of its most notable speakers. It has an early C19 fireplace of three colours of marble, with paterae, pilasters and a cast iron fire grate, a moulded cornice, dado rail and skirting board. The first floor south-east room has a plastered rococo ceiling with a ceiling rose and four panels of similar character to the ground floor north room; also a moulded cornice, dado rail and skirting board. There is a powder closet leading off on the south side. The staircase flight between the first and second floors has plainer turned balusters and scrolled tread ends. On the south-east side of the second floor is an early C19 fireplace with a reeded surround and paterae. The north-east room, possibly originally a housekeeper's room, has a dentil cornice, panelling, dado rail, a built-in picture surround, two-panelled doors to cupboards either side of the central fireplace and a corner laundry cupboard with shelves. A number of smaller rooms on this floor were probably used for servants' accommodation. The cellar has stone steps and contains original stone wine bins, a larger barrel store and a Second World War air raid shelter.

The ground floor door, which is within a decorative pedimented surround (discussed above) is original and in timber painted light green with eight moulded panels. All of the windows apart from the oval attic window are sashes with horns; three-over-three to the second floor and six-over-six to the ground and first floors. The attic window appears to be in a fixed timber frame and is divided into four panes. The large bowed bay to the rear of the property, on its south eastern side of three has three windows on each floor, with six-over-six sash windows on the first floor. It originally had identical windows on the ground floor but these were shortened probably in the second half of the C20 leaving the upper half of six panes. To the west of this bay there are three windows on both the first and second floors, all are six-over-six sash windows and there are three flat-roofed dormers within the roof level above. Two further windows on both the first and second floors are located on the north western end of the building, again these are six over six sashes. All the timber frames are painted white, this paintwork is in a relatively poor conditions on some of the windows, particularly on the windows to the rear of the property. Despite this all windows and the door are in a good condition with all panes present and in tact.

The roof structure is in a mix of different styles, the main portion is mansard in tile, with metallic flashing at the join between the angles. The north western end is hipped. The roof over the C19th north eastern extension was not clearly seen. There are tall brick chimneystacks located over both the eastern and western party walls. Overall the roof structure appears to be in a good condition with few slipped tiles and no major bowing. (1)

<1> Kent County Council, 2019, Historic building condition asseesment and photographic survey of Dover Town Centre (Unpublished document). SKE52120.