Today, dining complex Chijmes is the province of champagne-swilling tourists and well-heeled diners.
But until 1983, it housed a convent school run by a Roman Catholic order of French religious sisters.
The space - 1.3ha today but originally 3.3ha - encompassed the Convent of the Holy Infant Jesus (CHIJ) English-language primary and secondary schools, the Chinese-medium St Nicholas Girls' School, nuns' quarters, a chapel and an orphanage. Abandoned children used to be left at the convent's "Gate of Hope" in Victoria Street.
Sister Celine Low, 80, a former student who was CHIJ schools supervisor from 1979 to 1984 and the order's provincial from 1991 to 1997, noted that the chapel - a place for hymns, masses and silent prayer - was the school's "centre of life".
"The chapel is special to me," she said. "My mother was educated in this school, fell in love with the chapel and was later baptised as a Catholic."
The chapel and the nearby Caldwell House - formerly the nuns' quarters - were collectively gazetted as a national monument in 1990. They are now used mainly for events such as weddings.
The space behind the chapel, which now contains basement restaurants, was once a playing field at ground level.
"The school was bustling with life, very vibrant. We had three schools, and the field was shared by all," said Sister Low. "We were wild. We screamed, we played, we let our hair down."
The CHIJ school in Victoria Street, also known as the Town Convent, was Singapore's oldest Catholic girls' school, founded by the French sisters of the Congregation of the Holy Infant Jesus in 1854.
It mostly took in girls, but some boys - including David Marshall, Singapore's first chief minister - were educated there between the 1910s and 1930s.
In 1851, Father Jean-Marie Beurel travelled to France to recruit teachers to set up mission schools here. Three years later, four religious sisters - led by Mother St Mathilde Raclot - arrived in Singapore from Penang.
They moved into Caldwell House, a neoclassical bungalow designed by George D. Coleman, the architect behind theOld Parliament House. Built between 1840 and 1841, it is the oldest building in the compound.
Father Beurel bought Caldwell House and, over the years, acquired more plots of land until the convent's property extended from Bras Basah Road to Stamford Road.
Mrs Ellen Louis, 94, a day student and boarder at CHIJ between 1932 and 1938, saw the convent as a sanctuary. "It was a happy time," she said. "I felt very safe, without a qualm in the world."
The nuns, mostly from Ireland and France, were strict disciplinarians dressed all in black, she recalled. "Silence had to be maintained in most places, unless it was recreation time. We moved in rows of two, a nun leading us from the dormitory to the chapel, from the chapel to the refectory."
Mrs Louis added: "The nuns were so beautiful, I wondered why they became nuns."
When World War II broke out, heavy bombing in the city damaged the convent's main gate, orphanage, chapel and school field.
Two months after the Japanese Occupation began, the school reopened under Japanese authority, having been renamed the Victoria Street Girls' School.
The European nuns had to wear armbands to show they were not British, and learnt Japanese to teach a Japanese curriculum.
The present Anglo-French Gothic chapel, with a spire five storeys high, was designed by Father Charles B. Nain. It was completed in 1903 and consecrated in 1904, replacing a smaller chapel.
The interior's main and side naves are divided by arcaded parapets with colonnettes joined to a plaster cross-vaulted ceiling.
Pews were imported from Toulouse, in France, while stained glass windows depicting the Twelve Apostles and the life of Jesus Christ were made in Bruges, in Belgium.
Mrs Louis' daughter Wendy, 65, studied at CHIJ from 1959 to 1968.
She said that she would often go to the chapel with friends to reflect and "play at being pious".
"It was a place to simply sit and absorb the light and quiet. Often, I was asking for help for exams or some kind of heartache."
Students were also fond of the spiral staircases near the chapel. Sister Low said: "We would climb up and down, with books on our heads to protect us from the dust."
Ms Margaret Connolly-Tan, 64, a boarder at the convent from 1957 to 1960, has not forgotten the stories that the nuns told. In one tale, a French architect who worked on the chapel's steeple had a lame leg but, armed with his faith, managed to climb it to put up a cross.
A Gothic walkway, supported by columns with flora and fauna motifs, links the chapel and Caldwell House.
Sister Low recalled that Caldwell House had a parlour, a music room, a refectory, an infirmary and an upstairs lounge for the nuns.
Still visible on one wall of the lounge is a line from the Bible, in French: "Marche en ma presence et sois parfait", which means "Walk before me and be perfect".
The nuns would sit around a large octagonal wooden table, where they chatted, marked homework, knitted or darned.
The lounge was also where they taught one another to dance the foxtrot, waltz and Irish jig and played games such as mahjong. The French nuns were very good at mahjong, said Sister Low.
In 1983, the convent moved to Toa Payoh, partly to make way for the Mass Rapid Transit Corporation headquarters in the city, and was renamed the Convent of the Holy Infant Jesus (Toa Payoh).
The last mass was celebrated in the chapel on Nov 3 that year, before the space was deconsecrated.
After extensive restoration and development works to the tune of $100 million, the area reopened in 1996 as Chijmes.
Many former students lament that the convent is now an echo of its old self, but Sister Low feels that its spirit lives on.
She said: "We can look at itand relive what we experienced. Peace still reigns here."