I think the answer is it depends on the ride. I just did a couple quick comparisons of two vastly different rides.
22 miles time trial race (C-130, Dover DE) - completely flat
Strava power estimate: 231W
Wired Powertap: 233W (not in the Strava file)
34.5 mile group ride (9 guys working mostly together), rolling terrain, 20.5 mph ave.
Strava power estimate: 201W
Wired Powertap: 161W (not in the Strava file)
Looks like Strava over estimates when there is any drafting involved. I've found it to be 10-15% high on most of my solo rides... 20% or higher if I'm riding with a group.