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Most the best towns were already in existence by the mid-middle ages, but one interesting exception of a planned medieval town is Middelburg, founded in East Flanders in the 1450s, and painted by Rogier Van Der Weyden in his famous alterpiece. 
The town was founded by Pieter Bladelin, born Pieter de Leestemakere (1408-1472), the humble son of building crane operator, he probably had town building in his blood! Here he is, to the right in this painting, the Adoration of the Magi, with his castle visible on the top right.
By the 1450s nobody was rich or powerful enough to just build a new town, but Pieter whose perfect reputation for never wasting money and for being completely incorruptible allowed him to give it a go. Here is the story of Middleburg as told by Shirley Neilsen Blum:
Bladelin rose from humble origins to become one of the most trusted ministers of the Duke of Burgundy's government, and his town was supposed to be a model of good governance. Here is a close up of the fireproofed city built in brick, tile, and stone, with hidden timber frames.
Bladelin had his own castle built, as well as large church, a convent (public education), a public hospital, and many townhouses for the coppersmiths he relocated. One of their shops can be seen in the painting.
In addition to the later defensive walls, he also had a canal dug to make trade with the outside world cheap and easy, and a free annual market. He also had excellent connections with the English court and secured good trading deals for the craftsmen of his city. A model city!
Pieter Bladelin dies as piously and fruitfully as he had lived and his lavish funeral was a model of charity. After his death his wife inherited the town he had built. It was ultimately destroyed in 1581 by Dutch freedom fighters/Calvinist rebels/Murdering Pirates (pick a label).
