137 and 139 with Front Boundary Wall

137 and 139 are a pair of houses located on the south side of High Street in Fortuneswell, Portland. They were probably built in the mid-18th century but were re-fenestrated in the early 19th century. The houses are constructed from Portland ashlar and have a slate roof. They likely started as one house, featuring mullioned windows similar to the adjoining No. 135, but are now divided into two small properties.

The buildings are two storeys tall with an attic, each having one window. The windows are set within flush plaster band surrounds; No. 137 has 6-pane windows, while No. 139 has 15-pane sash windows. Only No. 139 features a raking dormer with a 12-pane sash window. There are central paired doors beneath the remains of a moulded architrave from the former entrance: No. 137 has a 19th-century four-panel moulded door, and No. 139 has a 6-panel part-glazed door.

To the right of the houses is a stone stack with a skirt and capping, and a brick stack is located to the left. The interior has not been inspected. A notable feature of the property is a boundary wall made of large stone blocks, approximately 1.3 meters high, which runs forward to a low front boundary. This pair of houses is considered one of the best remaining groups in the Underhill area.