Estill began his career at Kentucky in 2000 after redshirting his first year because of a knee injury. Estill scored a total of 936 points, averaging 9.3 per the 100 games played in. For the 2002-03 season, Estill was named to the All-NCAA Regional Team, All-SEC (Second Team) and the All-SEC Tournament Team. Estill holds the record for the best career field-goal percentage in Kentucky basketball history. He records a percentage of .601 with 365 field goals made out of 607 attempted.
Estill declared for the NBA Draft following his junior season. After going undrafted in the 2003 NBA Draft, Estill decided to play basketball overseas.