Bracebridge Road in Newton was paved a few years before the Mason Rice school was built. The equipment used to build the school destroyed the pavement (or so I was told when I was a child living there). The road is private and the owners did not repave it. My parents lived on that road from 1966 to 2018, and it was unpaved during that entire time. It is still unpaved. Yes the bottom 30 or so feet at the intersection of Pleasant St still has pavement, and probably the top 20 feet with Hancock Avenue.
Yes it is a question designed to trick the AI that is not smart enough to interrogate Open Street Maps (which has its own errors on St Croix, an issue I am not sure I am willing to address). I developed that question about a year ago after asking the Microsquash Bing AI if a Westminster Road and West Princeton Road just west of Mt Wachusett was paved. I then rode that on my bicycle as part of a loop, and it was not paved. So I was looking for ways to determine whether an AI was smart enough to tell me, and I did that by asking it questions to which I knew the answer.