Good input here all-round! I got my boy a used Yamaha dtxpress2 kit this year for his birthday at around your budget. Came with a seat, a pair of sticks, and a high-hat stand. Roland's gear is comparable in most ways but Yamaha is apparently easier to upgrade separate components or the computer of.
Note! Floor-transferred noise is still a PITA if upstairs on wooden floorbeams. If the kit isn't going to sit on concrete/in the basement or whatever, look in to building a tennis ball platform. Fun to make and worth a days DIY.
With all the cautions out of the way, it's fun to have a kit around the place. The kids love it, their pals love it, even the Mrs had a go once or twice! I got Samson SR850 headphones as they are cheap and do a great job. Sometimes I connect to our electronic piano through headphones out > aux in to play a bit amplified, it doesn't need much to sound o.k.
As with most instruments but with drums especially, the real value is in lessons. Learning to play along with hits and favourite songs at any level is fun and gives great energy. We haven't regretted it for a moment.