Taking Jardines Lookout as an approximate starting point, I was able to look at 1963 aerial images and it appears that the building in the background was part of a residential development that has since disappeared and been replaced by Cavendish Heights. In fact Blocks 6 & 7 of Cavendish Heights now occupy exactly the same space as that older block in the screencaps.
The road the car is driving along appears to be an earlier version of what became Moorsom Road. Back in the 1960s the road actually joined up with Clementi Road on the other side of the hill (behind the camera position) but the link between the two has since been pedestrianised and turned into a walking path whereas the modern route of Moorsom Road now curves the other way back down to join with Perkins Road. If anyone knows the name of this older development, it would be great iof you could let me know via email or comments.
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