59 and 61, Fortuneswell

59 and 61 Fortuneswell is a house with shops located at the junction with High Street in Portland. It dates from the 18th century and has been modified in the 19th and 20th centuries. The building is a large square block, painted at the front, with plain block or rubble on the sides and slate roofs. It features a twin-gabled front that is slightly canted, with lower buildings behind it on High Street, stepping down the hill.

The structure has two storeys, a basement, and an attic. Each gable has a small 9-pane sash window above a continuous moulded string course. Below this, there are two sets of 2+2 four-pane sashes with stone cills, and full-width plate-glass shop fronts that include a small central stone pier and a small section of stone at the right end.

On the left side of the building, there are two brick eaves stacks on stone bases, with three and two linked flues respectively. There is one plain casement window on the first floor and a small plank door leading to the cellar at the centre. The plinth here continues to an adjoining flush unit that is two storeys and lower than the front, featuring a small 2-light early casement window, a 12-pane casement window, and a plank door. Beyond this, there is a slightly lower hipped single bay unit. The rear gables also have coped verges.

The interior is not accessible but may contain items of interest. This building is situated on an important corner site and is one of the earliest structures in the area.