The houses on the North side of the High Street are probably on the site of the original settlement. From around 1300, people on the South side could vote for the MPs that the borough began sending to Parliament, and therefore the Lord of the Manor took a great deal of Interest in that side because he wanted a family member to be an MP and he wanted contacts with the court. So there were advantageous rents, which would attract well-to-do traders who would also boost the income from the market. But the borough did not extend to the North side, where the land from Turpins Row to the Red Lion belonged not to the Manor but to the Rectory. Here, the land and the plots backed higgledy-piggledy on to the River Misbourne. Thus it was that Amersham acquired its beautiful, wide High Street laid out by mediaeval planners.
An interesting article about plans for the town lighting appeared in a local paper in 1859:
Listen to Gerald Lee talking in 2004 to Diana Goodbody about the shops on the North side of the High Street in the 1940s and 1950s
R1_0011 – you can hear many other audio clips by Gerald Lee by putting his name into the search box at the bottom of the column on the left (or below on mobile devices)