Lee Hsien Yang, the late prime minister's younger son, announced on Tuesday via Facebook his intention to apply for demolition permits.
"It is my duty to carry out my father's wishes within the limits of the law," he wrote.
The house at 38 Oxley Road, built in the late 1890s and occupied by the Lee family since the 1950s, holds significant historical value as the birthplace of the People's Action Party.
However, it has been a source of family conflict since Lee Kuan Yew's death in 2015, with siblings Lee Hsien Loong, Lee Wei Ling, and Lee Hsien Yang disagreeing over its fate.
The dispute, which previously led to public accusations between the siblings, has resurfaced following Lee Wei Ling's death on Sept. 9.
Lee Hsien Yang's move to demolish the house reignites the "siblings' feud" and puts pressure on the new government to make a decision.
In 2018, a ministerial committee presented options including national monument status, partial preservation, or demolition and redevelopment.
The government now faces the challenge of balancing historical preservation with respecting Lee Kuan Yew's reported wish for the house to be demolished after his daughter's departure.