Winsland House II consists of a pair of Edwardian-era semi-detached houses that were built in the 1910s, along with a new office development built in the early 2000s. It sits on a former 173-acre nutmeg estate that was first developed by Dr Thomas Oxley.
Besides serving as residences, these properties have housed the Singapore Tong San Association, a clan association, and the Orchard School of Arts and Commerce, a private college.
In the 1990s, the land was sold for redevelopment and the new corporate owner offered the building for conservation. Restoration works, which took place in 1996-97, retained aspects such as the open verandahs in their original condition. The airy and shady verandah spaces are an example of how European building aesthetics were adapted to the tropics. The restored building was conferred the URA Architectural Heritage Awards in 2002.