Some of the oldest models, 70s-80s, will. Some models immediately after that could be forced in if the tires
were taken off the trailer and it was rolled in on its rims. Some have jack hammered, trenched and recessed the garage floor to make it happen. Others have modified their structure to accomodate a taller door. A lot of folks create a dedicated parking pad or build a separate garage or shed. The newer the trailer, the heavier and taller it will be.