Cleanup broken glass and debris
You could have it scraped with a small excavator and apply fresh, clean topsoil.  The best time to do this would be early-spring.  Then you can plant grass seed right away.  When I've done this in the past, it took a couple months to grow and look nice.  Doing that for a half-acre will be expensive but if you only need to do it in the immediate area of the old shed it shouldn't break the bank.
Sod is another option depending on your budget.
If you don't care about getting rid of all the glass, sure, raking or whatever isn't a bad idea.  I'd start by using Roundup or similar to kill most of the existing vegetation to make that easier.  Then use a line trimmer &amp; lawn mower as low as you can.
After that, consider if the raking is doing as good a job as you want; if not, rent a tiller and turn the soil over then re-compact it with a lawn roller (also easy to rent.)