I work in St Johns Wood. It's not gritty in any sense, but it's right next to Regents Park, has a nice High Street (what we call a main street for shopping) and is very international. As someone who also lived in Boston (Watertown), I wouldn't say it's like Back Bay, but you won't find that here really anyway - it's not Boston. It's not sleepy per se, and it's all of 5 minutes into central London by the Jubilee line.
The question is - are you going to have a driver, going to drive to the school, take a bus or the tube? That will really determine where you should live. Have you thought about Belsize Park? It's on the Northern line so easy for Hampstead & Euston, and the other kids (if taking the tube) will be able to get to their areas reasonably easily via tube. Belsize has some great shopping/eating, near the Heath and has a lot of row houses. Also easy to get into central London.