Flavell, who has led Connells for seven years, started working for estate agents Shakespeare, McTurk and Graham in the 1970s which was then acquired by Connells in 1987.
He then rose through the ranks until he was tasked with leading the group through the turbulence of the credit crunch in 2008.
Under Flavell’s tenure Connells has doubled the size of its Mortgage Services broker arm, while he also oversaw the acquisition and development of estate agents Burchell Edwards.
He will see the number of lettings branches rocket from six in Kent in 2008 to 139 by the end of this year.
Stephen Shipperley, Connells Group executive chairman, said: “On behalf of the group, I would like to thank Stuart for his outstanding service and contribution to the business.
“Stuart has been a strong leader managing the company through challenging times and market transitions.
“We are grateful for his many contributions to the company over almost 38 years and his distinguished tenure as chief executive. We wish him a very long, healthy and happy retirement.”