Yes, it will fit, even with the wide tires. The wide turf tires are not as wide as a Woods 59 mower, obviously, around 60-inches or 5-feet wide. If you do not have the mower deck on it, the turf tires are only about 50-inches wide. Lenghth should be right at 8-feet, as I know I've hauled two lo-boys on a 16-foot trailer.
If you do have the mower deck on it, it will not fit between the rails on a 5-foot trailer. The mower deck cut is 59-inches, but the actual deck is more like 63-inches.
1951 Farmall Cub, Cub Cadets 102, 104, 1811, 1864, Simplicity Legacy XL 4x4 Diesel with FEL, 60" mower, 50" Tiller