No need to apologize for your questions. That's what “The Dean" is here for, and the college admission process is so confusing that it raises questions galore.
There's really no downside to notifying your colleges about the new award, even with your verdicts looming. But only send the news if you feel that you've won an important award, and “important" will be defined differently depending on where you're applying. At the most hyper-competitive places (like the Ivies and any school with an acceptance rate in single digits or teens), only a major award (national, best in state, etc.) would move the needle at this late date. But at most other colleges, if you feel that the honor you just received is a significant one, then email your regional admissions rep today. If you can't decide what qualifies as “significant" write back to explain your award and name the colleges. And if you do send the news to your colleges, be sure to explain the award to the admission folks, too, if the honor isn't well known or self-explanatory. It's also useful for them to know about your competition (e.g., “10 winners were selected from 5,000 entries"). However, don't send the award info if you won it as part of a team or group of more than two.
Although it's possible that your admission decision has already been made, it won't hurt you to submit this eleventh-hour update. You won't annoy admission officials, and — should you be wait-listed — it might even help push you toward the front of the line in May if the college is still accepting applicants.
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