Use the Python Imaging Library (PIL). Something like that:
from PIL import Image
filenames = ['/home/you/Desktop/chstamp.jpg', '/home/you/Desktop/something.jpg']
sizes = [Image.open(f, 'r').size for f in filenames]
max(sizes)
Update (thanks delnan ):
Replace the last two lines of the above snippet as follows:
max(Image.open(f, 'r').size for f in filenames)
Update 2
OP , . numpy. . :
from numpy import array
image_array = array([Image.open(f, 'r').size for f in filenames])
print image_array.argmax()