The beautiful girl, who grew up between the courts of Rimini and that of Pesaro, was Ungaro’s only legitimate daughter. Well educated, she always stood out for her bizarre character and was not inclined to obedience; for this reason her father decided to guarantee her a dowry of 50,000 ducats in order to make her "more attractive" on the market of marriage strategies of the time. In 1363, in order to consolidate the alliance with the D'Este family, it was decided that there was to be a marriage between blood relatives and she married her young uncle Ugo D'Este. He died at the age of 26 during a fight, after only 7 years of marriage, leaving Costanza Malatesta, perhaps not yet twenty, a widow and with a rich inheritance. The girl then returned to Romagna to the court of her uncle Galeotto the Bold and her father Malatesta IV. Her love story with Ormanno, a German duke in the service of Malatesta with his army of fifty squires on horseback started then; it is said that the two met for the first time and fell madly in love with each other.
“Messer Galeotto had one of his soldiers, who was a corporal of fifty squires; his name was Ormanno, and he was German [...] Now it happened that the said Ormanno, passing several times by the palace of Madonna Costanza, the woman being at the windows, their gazes fell on each other in such a way that Ormanno fell deeply in love with this woman, and knew how to keep such ways, that the woman became aware of it, and began to fall in love with him. […]
(Taken from: “Il pecorone” (The large sheep) by Giovanni Fiorentino
Their love story was lived in secret but, after the death of her father, her uncle Galeotto decided to lay his hand on the girl's conspicuous inheritance and to do this he obviously had to look for a pretext. And he found it ...
He discovered this love story and accused his niece of being shameless, as her behavior tarnished the reputation of the Malatesta family, and all of this was unacceptable to him. So, he decided to punish her ruthlessly. On the night of October 15th, 1378, the two lovers were discovered lying together and were barbarously killed by an assassin hired by her uncle...
Nothing more was ever heard of the two unfortunate lovers but, legend has it, that on October nights, the girl’s weeping can still be heard in the rooms of the castle.
Numerous studies have been carried out involving ghost hunters and researchers on the so-called paranormal phenomena (by the specialized group called "Research Company") which seem to take place inside the fortress.
The love story of Costanza and Ormanno was told in a small book: "Il Biancospino" (The Hawthorn).
Another interesting legend involving the castle is the one that tells of Sigismondo's treasure. There has always been talk of this treasure so well hidden as to make the countless attempts to find it useless.
The origin of this belief derives from an event of April 7th, 1464. In that year Sigismondo Pandolfo Malatesta was engaged as captain of the Venetian troops in Morea and some criminals took advantage of his absence and attempted a conspiracy. However, this was discovered and during the investigations a witness revealed that, in addition to taking over the government of the town, the traitors wanted to take possession of Sigismondo's "treasure" which was hidden somewhere within the walls of Montefiore Conca.
But which of the castle’s walls are those mysterious walls? In the external walls erected to defend the Fortress of Montefiore, in the area called "Fratta", there is a tower that the inhabitants of Montefiore have always called "The Tower of the Treasure". This is a peculiar tower, completely filled with a pouring of stones and white lime to make it impossible for anyone to access it. It was struck several times by lightning. These facts immediately made people think that inside the tower there was some kind of metallic material, the material that was believed to represent the Treasure of the Malatesta family, and for this reason it was called the "Tower of the Treasure". To ward off those with bad intentions, it was later dubbed "The Devil's Tower".