Views output into multiple columns based on variable of results
not sure what you're asking is really possible just through the Views UI.

However, this should is reasonably simple with a views template file and a bit of PHP knowledge.

http://webpartners.es/en/drupal-7-views-templates-and-preprocess provides some info about how to override the output of the view. you'll need to apply a bit of logic on how to begin/close your columns/lists but that's just a bit of arrays in PHP.