Takahara was born in Mishima in June 4, 1979. After graduating from high school, he joined Júbilo Iwata in 1998. In 1998, the club won J.League Cup and he was selected New Hero awards. In 1999, the club won J1 League and Asian Club Championship. The club also won the 2nd place 1999–00 and 2000–01 Asian Club Championship. In August 2001, he moved to Boca Juniors on loan.
In 2002, he returned to Júbilo Iwata. The club went on to win the J1 League, while Takahara became the top scorer and was elected Most Valuable Player of the year. End of 2002 season, he moved to Hamburger SV. On December 3, 2006, he scored his first hat-trick in the German Bundesliga in a league game against Alemannia Aachen.
In January 2008 he moved to Urawa Reds for a transfer fee of around ¥180 million (around $1.7 million). Due to a disagreement with the style of coach Volker Finke, who had taken over as coach of Urawa in 2009, Takahara was leased to Suwon Samsung Bluewings of the South Korean K League 1 in July of the following year. On July 31, 2010, he made his debut as a substitute for the 39th minute of the match against Gwangju FC. On 29 August, he scored a goal in the 39th minute of the second half of the game against FC Seoul. He helped victorious game 4-2 and won the MVP in this game.
In 2011, he returned to Japan and signed with Shimizu S-Pulse. After that, he played for J2 League club Tokyo Verdy (2013–14) and J3 League club SC Sagamihara (2014–15). In December 2015, along with legendary Japanese judoka Tadahiro Nomura, Takahara founded Okinawa SV. He served as president as well as playing manager for the club.