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A couple of things come to mind: Why don't you want the product pages to be in the index? Why is there concern of a penalty? As to your question: Are you signed into Google when you are searching? Google will show you these types of results in the SERP's, but they are not necessarily shown to customers. If you have Google desktop installed it will also show you documents on your machine in SERPs if they find them relevant to what you are looking for. * Do the URL's have parameters? If so you can set those in GWT and inform Google what they should do when they encounter them as they crawl the site. *Canonical the pages you don't want in the index if possible to the static pages.

Yes - indeed. The 301 need to be relevant. You can not redirect www.domain.com/red-pantss to www.domain.com/blue-sweaters /red-pantss --> /pants or even better /red-pants