The family is divided over whether to demolish the family home at 38 Oxley Road, or allow the government to decide if it should become a heritage site.
Singapore is one of Asia's most important financial hubs. It's wealthy and has a reputation for order and control.
But now a family that turned the island into a global model of efficiency is feuding, threatening its future.
Around 400 protesters gathered at Singapore's Speakers' Corner calling for an independent inquiry into whether Prime Minister Lee Hsien Loong abused his power in a feud with his siblings.
38 Oxley Road was the home of Singapore's founding father, Lee Kuan Yew and it was his wish for it to be demolished after he died two years ago. But a ministerial committee is now considering turning it into a heritage landmark.
The public row in a family that stands at the heart of Singapore's establishment raised uncomfortable questions in a city-state that prides itself on being a rock of stability in Southeast Asia.
TRT World's Melanie Ralph reports.