10 Winstedt has an interesting history that many may not know of. The story of the neighbourhood begins with Sir Richard Olaf Winstedt, an accomplished colonial administrator who was a strong advocator of, and an instrumental figure in the educational development of Malaya in the 1920s. Key achievements during his tenure include the drafting of Malaya's first Education Code, a widened curriculum for girls, reinforcement of new education standards, and the implementation of a centralised supply of textbooks.

Having been named after an esteemed educator, it is only fitting that, in the past decades, 10 Winstedt has housed many young minds engaged in learning at educational institutions such as Monk's Hill Secondary School and Outram Secondary School. Founded in 1958, Monk's Hill Secondary School presented its first batch of candidates for the national School Certificate Examination in 1961. The school was also well known for its sports achievements in cricket, track and field, swimming, and cross-country races and, especially in inter-school rugby.

Today, 10 Winstedt is poised to play a new role in history with its contemporary transformation into a place of business. To preserve an aspect of Singapore's history, LLS Facilities Management has kept the façade of the newly revamped buildings instantly recognisable as the well-loved school in the fond memories of many ex-students during their formative years. Years after the last student stepped off campus, 10 Winstedt continues to purposefully accompany its occupants throughout their life journey, with a shift towards entrepreneurial excellence, in contrast to the educational success of the past.

The refreshed facilities and enhancements breathe new life into the old compound, comprising five blocks of modernised commercial spaces. LLS Facilities Management welcomes a diverse mix of businesses to 10 Winstedt, giving rise to a vibrant social community flourishing in a green and tranquil environment spanning 74,000 square feet. Lush greenery embrace professional work spaces, offering a relaxing, yet productive, atmosphere that encourages inspiration, innovation and creation, and fruitful collaborations.