At first glance, Keong Saik Road, off New Bridge Road in Chinatown, appears overrun with trendy pubs and restaurants.
But some of its old-world charm remains. On weekends, snatches of opera singing drift down to street level from several decades-old clan associations housed on the upper floors of shophouses.
On weekdays, the click-clack of mahjong tiles can sometimes be heard as wrinkled hands swiftly shuffle tiles in serious games of mahjong.
And the kind of establishments Keong Saik is most notorious for have not all gone away. Brothels occupied at least half of more than 50 buildings there about a decade ago. Three continue to ply their trade so discreetly that many do not know they exist.
While some old ways do not change, new businesses, such as posh eateries, a Japanese hair salon and a co-working space, have rapidly taken over most of Keong Saik Road in the past five years.
At least eight new businesses have opened this year, including artisanal bread shop Bread & Hearth, vegan eatery Afterglow and edgy tailor business 1:1.618 x Leong T.
Two months ago, PTT Family, an Indonesian hospitality and entertainment group, opened Potato Head Folk in a 1939 three-storey building formerly occupied by the 75-year-old coffee and kaya toast shop Tong Ah Eating House.
Mr Dre Masso, 38, project opening manager of PTT Family, said: "Stepping into Keong Saik Road, we felt that it has a village feel to it with its iconic shophouses.
"Like many Chinatowns around the world, it is going through a gentrification process. The old KTV bars have cleared out, giving an indication that the street is going to be replaced by something better."
The area's reputation as an up and coming area, its proximity to the Central Business District and high foot traffic, attracted Mr Jonathan Yang, 29, to open Mexican eatery Muchachos last year.
He said: "Almost immediately after I moved in, rental prices in the area surged, but I had already signed on the dotted line and got a good deal."
Executive director Matt Cullen of creative agency Arcade, which opened at Keong Saik in 2011, said: "It is a wonderful address for creative people to be inspired by - some of the coolest restaurants, cafes and bars in Singapore are popping up everywhere."