№ 10102. Типовая задача

from ipaddress import ip_network, ip_address

ip_net = ip_address('44.44.224.0')
ip_host = ip_address('44.44.229.28')

prefixlen = []

for mask in range(17, 32):
    net = ip_network(f'{ip_host}/{mask}', False)

    if ip_host in net.hosts() and net.network_address == ip_net:
        prefixlen.append(net.prefixlen)

print(max(prefixlen))