I have only one tool that I know for a fact came from my grandfather (my mother's father). He worked as a handyman in boatyards up the Massachusetts coast from Boston in the years after the First World War. He must have acquired the brace second hand: the tool is a model 102 10-inch sweep brace made by Peck, Stow, and Wilcox (latterly Pexto) around the time he was born (late 1880s).
It's the brace on the left in the photo
here.
I use it whenever I have need of a brace, which isn't always to bore a hole in something. I also have several screwdriver bits (some show in the photo at the link) and I'm collected many more, plus countersinks, bat-wing bits, and gimlets. I also have modern adapters that take Torx bits and others unheard of in 1880. (Skipper, as I called him, would be pleased to have known this.)
The brace collection has 10 in all, including a barebones (all-metal) Spofford brace and a North Bros (Bell System). I have also recfurbished a Peck Stow brace with a Samson chuck, disassembling it and replacing all the ball bearings. Works as good as new....