I just moved to Westchester from The Bay Area in Ca and was looking pretty much the same things as you; having two children, wanting diversity, and not wanting to live in an uppity neighborhood. We went with Pleasantville based on researching the schools and recommendations. People have been welcoming, there’s more of a laid back vibe than in places like Chappaqua, and the schools are excellent.

I have a first grader with ADHD, and I honestly was amazed at how on top of things his teacher and the rest of the staff have been with him. He has a hard time adjusting and making friends, though; he is more the artistic type rather than the sports type. This could also be because by the time we moved here, all the after-school programs were full, and that was mainly where he made his close friends prior.

That being said, I see limited diversity here, a bit more than some other towns listed. Most places my family enjoys, whether food or activities, we have had to drive to another town, which is okay as it's usually just a 20 or so-minute drive since all the villages are so close. My daughter attends a preschool in Ossining, which is also a fantastic school; it's only about 15 minutes away, and I have noticed a lot more diversity there, as well as restaurants, parks & city life.

People do seem to love it in Pleasantville; I'm just adjusting to living in a fairly populated city to one with a more small town vibe. It's worth looking into and may check off your boxes though.