He completed his early education in Nassau and graduated from Prince William High School in 1982.
He worked at Barclay’s Bank in Nassau before and after pursuing university studies at St. John’s University in Collegeville, Minnesota where he completed his Bachelor’s Degree in 1989.
He was awarded an LL.B. (Hons) Degree from the University of the West Indies (Barbados) in 1994 and completed his Legal Education Certificate at the Norman Manley Law School in Kingston, Jamaica in 1996. Raymond was admitted to The Bahamas Bar in October, 1996.
Raymond has been engaged by leading legal firms in The Bahamas; namely Bannister & Co. between 1996 and 2001 and Evans & Co. between 2001 and 2003. In 2003 he opened his legal practice Raymond A. Rolle & Co. where he continues in private practice.
Raymond was the F.N.M. Candidate for the Englerston Constituency in 2007 and served as Chairman of the New Providence Port Authority between 2007 and 2012.
Raymond is married to Latina Rolle nee Ferguson. Raymond is the father of three children.