Château de Saint-Sauveur-le-Vicomte was built in the 11th and 12th centuries. It was besieged twice during the Hundred Years War. The city walls were breached by cannon in 1374. This is believed to have been among the first successful uses of guns against city walls in history. Today it is partially ruined, but still a notable castle with massive 14th century towers and a 12-15th century abbey.
References:The Walls of Constantinople are a series of defensive stone walls that have surrounded and protected the city of Constantinople (today Istanbul) since its founding as the new capital of the Roman Empire by Constantine the Great. With numerous additions and modifications during their history, they were the last great fortification system of antiquity, and one of the most complex and elaborate systems ever built. They were also the largest and strongest fortification in both the ancient and medieval world.
Initially built by Constantine the Great, the walls surrounded the new city on all sides, protecting it against attack from both sea and land. As the city grew, the famous double line of the Theodosian Walls was built in the 5th century. Although the other sections of the walls were less elaborate, they were, when well-manned, almost impregnable for any medieval besieger.