John Bolle was born in Chartham, co. Kent where the Bolles were known to be tanners but were also very wealthy. See The Bolles of Chartham, Kent   He, however, settled in London and apparently established himself as a very successful grocer.  Certainly he lived in a grand house on Great Tower Street which had previously been occupied by Sir Thomas de Salisbury.  ref. 

John Bolle's Will of 1449 is very informative regarding his family.  He mentions his birthplace as Chartham in a bequest of 5 pounds "for the work of the steeple of the church of Chartham, co. Kent where I was born".  He mentions his son John who will receive his 20 pounds and two silver cups when he reaches the age of 28 but until then he is to be supported by his wife, Blanche who is leaves the bulk of his estate to.  He leaves furred gowns to his brothers Richard and Thomas and foregives his sister Alice Redehode's debt to him.  He leaves a house to his nephew Thomas Redehode.  ref.   In 1459 he updated that Will to leave a little house in Chartham to his half-brother William and to his wife, the daughter of John Morley.  His son John now inherits directly so he must have become 28 within the 10 years since the first Will.  He also adds some remainders of his estate to his brother Henry's son John (but not to Henry).  He also mentions his "grete place in Shamelford" which is most likely the Bolle's great house at Shalmsford, Chartham.  Since it was not mentioned in the 1449 Will he probably inherited it in the 10 years since.  ref. 

There is also a Chancery Court pleading to the Archbishop of Canterbury involving a bond for a marriage in Kent.  The catalogue entry is undated so we don't yet know if it refers to John Bolle Sr. or Jr.'s marriage to a daughter of Richard Smyth's.  ref. 

John Bolle Sr., the grocer in London, lived in a very significant house as well. 

John Bolle's Family Tree

Based on the above mentioned Wills, his family tree would look like this: