Oakleigh on Glencrutchery Road was built in 1893 to a design by M. H. Baillie Scott, an early and characterful example of his work on the island blending the American Shingle style with Tudor Revival details. Its exterior combines red brick with half-timbered gables, vertically hung red tile cladding to the sides and rear, a red tile roof with dormer windows and Jacobean-style chimneys, and a distinctive two-storey octagonal bay window. Inside, the entrance hall is notable for a carved stone fireplace in a French medieval style, a striking interior feature for a Douglas house of this date.