There seem to have been a few different branches of Bowles in Chatham.  One or two lines go back to the 1200's in other parts of Kent and start to appear in the Chatham/Rochester area in the 1400's. 

The most famous Bowles line in this area though would be Charles Bowles' line which will be dealt with separately under Charles Bowles of Chatham.

I don't have a complete history to tell for the earliest years as the records are very incomplete and disjoint so I'll just summarize chronologically what I have been able to discover.

The 1422 Will of John Kent of Hoo St. Werburgh, just north of Chatham, refers to his "newly built tenement in Hoo St. Werburgh parish, which he recently bought of 'Dominus' John Bolle, chaplain, and Henry Hovell."  ref. 

There was a Chancery Court case heard in London in the late 1460's between John Rous, gentleman, and four parties including Thomas Batter and William Bole, clerk.  The dispute originally arose at an Assize arrayed in Rochester and involved unspecified lands in Kent.  ref.  William Bole was probably of Rochester if the issue originally came up here as the land in question is probably the land at Ifield and Northfleet, Kent which was referred to in an earlier Chancery Court case between Thomas Batter and William Bole.  ref. 

In 1471 Thomas Bole of Rochester was leasing "a piece of garden in Rochester 54' wide and 132' long southwards from the city wall; and a footpath adjoining the garden 9' wide and 105' long from the road on the south side to the garden" from the Prior and Convent of Rochester and sub-leased it to a tenant, William Nicolas for 26s a year.  ref. 

  (more to come, this area is still under construction)