On a trip to Lisbon he encountered D. Maria de Vilhena (widow of D. Fernão Teles de Meneses, the Donatary of the islands of Flores and Corvo, then administratively one fiefdom) and his son Rui Teles. After some negotiation, D. Maria would cede the rights to the exploration of the islands to Van der Haegen, in exchange for monthly payments. Around 1478, he settled in Ribeira da Cruz, where he built homes, developed agriculture (primarily wheat), collected more woad species for export, and explored for tin, silver or other minerals (under the assumption that the islands were part of the mythic "Ilhas Cassterides", "the islands of silver and tin"). Owing to the island's isolation and difficulties in communication his crops became difficult to export. After several years, he decided to leave the island and return to Terceira. But his return was brief; after seven years he left Quatro Ribeiras and settled in the area of Topo, São Jorge Island, effectively establishing the community with other Flemish citizens. He died there on December 21, 1507/09, and was buried in the chapel-annex of the Solar dos Tiagos, in the villa of Topo, today in ruins.