Checking directly with the Cupertino planning department is best.
You should contact the City of Cupertino directly to get the latest guidelines. They are very responsive. Just call and you will get a live person usually right away. Or you can go in person. Lots of parking. Not much wait. They have pamphlets with good information that you can read if a couple people are in line ahead of you.
Cupertino does allow R2 zones on lots over 8500 but that is not the same as allowing a simple conversion to R2 for any lot over 8500. Also building on a R2 zoned lot "requires the review of the Design Review Committe". See http://www.cupertino.org/index.aspx?page=502
Always check with the city planning department before making a purchase.
Cupertino real estate information at http://julianalee.com/cupertino.htm
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This is a big question which only the LG building/planning dept could answer. Sounds like something they may consider based on the size of the lot, but it would also depend on many other variables... Have a Marvelous Monday! Your Friend & Realtor, Henry Brooks
This is a question only the Building/Planning dept at City Hall would be able to answer for you........I also think that this would perhaps only be a case by case consideration.....depending on the neighborhood zoning in place. If you have a Lot in mind, check directly with the City, as they lay down the zoning regulations.......I worked on the City's General Plan as a appointed Volunteer few years ago.
I am a Public Safety commissioner with the City of Cupertino, and have done contract jobs and tons of volunteer work with the City......worked closely with all the depts there....tone of us have the authority to answer this question......
Wishing you the Best, Do get in touch with me if I can help with any Real Estate needs.
Be well and Safe, Regards,