Bordered by funeral parlours in the east and lighting shops to the west, the wedge of land between Lavender Street and Jalan Besar has previously not drawn much attention.
It is a working man's district, home to hardware merchants and machinery repair shops.
But as more trendy cafes move into the area and bring with them a youthful following, the neighbourhood's hard industrial image is softening up.
In Horne Road opposite the Jalan Besar Stadium, pop music can be heard through the red and gold acrylic frontage of The Bravery, a year-old cafe, on an otherwise quiet weekday.
On weekends, the space fills up with hipsters and cafe-hoppers, drawn by the 10 or so cafes opened in the past two years.
The area is also home to unique businesses such as a one-man appeals writing service and "pop-up shops", whose owners rent premises to sell wares for a short spell - a month in the case of online design marketplace Naiise.
"The crowd flow is a bit unpredictable, it is a growing estate," said Mr Aaron Lim, 26, who manages Windowsill Pies. "FairPrice just opened down the road, so I'm guessing there will be a surge in clientele in the next few months."
Mr Louis Ching, who chairs Kwong Soon Engineering, a ship building and repair firm just round the corner in Cavan Road, also senses a change in the wind.
The 75-year-old was born across the street from where he works. His father set up shop in the area in 1928.
"Back in my time, the Cantonese worked in machinery, the Hokkien worked in hardware, and the Hainanese ran coffee shops," he explained in Mandarin.
"We all knew one another and would help one another out, if we worked in the same line. You can say it was like a kampung," said Mr Ching. "Now my neighbours have changed, I'm not even sure who they are."
Many hardware shops have shuttered or relocated in the last few years, often replaced by hotels and backpacker inns.
Mr Ong Kah Seng, director of consultancy R'ST Research, said the selling point for the hostels is that "they are in a central location yet they offer a very real glimpse into Singapore" where character is preserved.
Real estate agents said monthly rent for a two-storey shophouse ranges from $5,000 to $10,000, if the shophouse is in an "up-and- coming" area, near other cafes.
Hotel 81 and Fragrance Hotel were the mainstays, until over 10 backpacker hostels opened in the last four years. The newest arrival this June was Parc Sovereign Hotel Tyrwhitt, behind Tibetan Buddhist temple Thekchen Choling.
"Whenever the rainy season comes, flies fly into our temple. Now that they have built a hotel, the area is newer and I find there's new energy," said Ms Ng Yizhen, 45, senior manager at the temple.
Over in Hamilton Road, Mr Jay Khong, 36, manages the Lofi Inn, a backpackers' hostel, and the Encore pub. He planned to take over the hardware store next door, "but they say they want to rent out to only hardware owners".
Many old-timers worry that in a few years, they might not have a place in the neighbourhood.
At lunch, four men sit down to have tea in the Hamilton Road alley beside a carpentry shop and behind Ding Le Food Court, after a morning at construction sites.
"It's getting harder to get government approval for foreign workers and the locals don't want to ply this trade," said Mr Chong Sai Kao, 54, director of SM Foundation Machinery, against the drone of a power drill.
Mr Steven Ong, 58, managing director of FAV Engineering, remembers a neighbourhood with friendlier policies.
"In the past, you were allowed to repair cars in the back lanes here, not any more," he said, pointing to concrete barriers to keep cars out of the alley.
The men prefer their alley and the 90 cent coffee they get there.
But old and new do meet in Jalan Besar, as Mr Alex Lian, 42, manager of recently opened vegetarian eatery 7 Sensations, has learnt. Among his regulars is an elderly couple. "They have lived here since young and studied just across the road. The People's Association building was formerly Victoria School."
Meanwhile, Ms Celia Chen, 31, administrative manager of Shun Zhou Hardware, has discovered another side to the area.
When she first signed on, female colleagues advised her not to work too late - for "after 7pm, it is dark when you go out and people will see you differently".
Men sometimes come by in posh cars to pick up girls, she said. The area is home to many pubs and karaoke lounges.
But this no longer bothers her. After all, the rough and tumble is part of the charm of Jalan Besar, a place where worlds meet.