I ran across this short statement and quote in C.S. Lewis’s The Allegory of Love:

Even the irregularity of a medieval street was an accident, and proceded from no ‘Gothic’ love of wildness. When the Middle Ages dreamed of an ideal town–of the town they would have built if they could–they saw its houses all of the same height:
And ther was non that other hath
surmounted
in the cite, but of on heght alyche

So people who are raised in cookie-cutter houses in cookie-cutter suburbs dream of the twisting, narrow streets and the chaotic mix of building styles of a medieval city, while people who were born in the twisting, narrow streets and the chaotic building styles of a medieval city dreamed of cookie-cutter houses in cookie-cutter suburbs.

Figures.