Sure. In this case Windows is already a TM so Windows + anything is already on shakey ground, especially if you try to use it for a site about Windows.
If it were something else where the trademark was completely unknown at the time when you registered it then you'd have a lot better chance, but if when the new product comes out you try to make money off of that instead of whatever you got the name for in the first place you'd still be trading off their TM.
Here's an example. Where I went to college there was an Unos Pizzeria that was started before the Pizzeria Uno chain (or is that the other way around?). Same basic name, but the local one had it first, so could continue to use it in that area for pizza. But if it had been Unos Carwash and then Unos Pizzeria tried to come to town, Unos Carwash could still wash cars but not be able to open a pizza restaurant using the same name.