Hi Mike and thanks for your post.
Frankly, only you can really decide for you and your family which of the two areas is "better" in terms of lifestyle. What I might like or prefer in a home and neighborhood environment may differ drastically from your own. The best way to "gauge" how you might like an area is to visit each area frequently and to talk with neighbors located next to or in the same area as the home in which your contemplating purchase. There are definitely "exterior" differences between Palo Alto and Cupertino in terms of the configuration of the town, the locations, and the styles of homes available in both price ranges--so consider these carefully with your Realtor to see what is most attractive to you.
As for schools, both schools are extremely highly rated (as you can see by their API scores). Both Gunn and Monta Vista have a history of excellence in academics, sports and extracurricular activities. And, both high schools are known for the achievements of their alumni. So, you can't go wrong with either Gunn or Monta Vista as a school.
As for resale, I'm going to give a slight edge at this time to Cupertino over Palo Alto for two reasons: 1) Cupertino is more centrally located to Silicon Valley and tech firms, so if you work in Santa Clara, then Cupertino is your town and 2) housing in Cupertino seems to be a tad more affordable than in Palo Alto--in other words, you get a little more home and little more lot size for the same price in Cupertino than in Palo Alto. Also, many of my buyers have expressed a desire for newer housing, and for this, I also give the edge to Cupertino over Palo Alto. I find a lot of great homes in Palo Alto that have been renovated and updated on the inside, but in Cupertino, a lot of homes have been completely torn down and rebuilt to be brand new.
So, Mike, there you go! Both are great cities and you can't go wrong with either! Just work with a great Realtor to help you find the best possible home for you and your family. If you are not working with a Realtor and need assistance, feel free to contact me.
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