They were once home to Chinese clan associations and private social clubs, and for decades, the rows of shophouses lining the streets of Ann Siang Hill would bustle with activity every night.
Between the 1950s and 1970s, scores of Chinese immigrants residing in nearby Chinatown would stroll up the hill to these associations to socialise over mahjong and opera performances.
These nights, a different sort of crowd winds up the sloping road. And the clack of mahjong tiles and the high-pitched nasal tones of opera singers have progressively given way to the clink of glasses and the babble of chatter of office workers from the nearby Central Business District.
Over the last two decades, many of the 20 or so Chinese clan associations along Ann Siang Road have sold their properties to eateries and watering holes.
Only a handful of associations, such as Fa Yun Wui Kwun and Ching Yoon Wooi Kwoon, are left. But with dwindling membership numbers and rising costs, they are barely holding on.
Change is inevitable, admits Mr James Lee, chairman of the Kwong Wai Siew Li Si She Shut clan association at 25 Ann Siang Road. The Cantonese clan has slightly more than a hundred members, down from about 600 about 50 years ago.
"We can't remain like it was 50 years ago," says the 61-year-old retiree, adding that some of the existing associations have chosen to rent out the ground floor to restaurants and bars, and moved to the upper floors. "We need the funds to keep our operations going."
Next year, the 140-year-old association, which has been in Ann Siang Road since 1954, will lease out its second floor to an IT services company. Since last year, the space had been taken up by an abstract artist.
"We have no intention of selling this place. We have many good memories here," says Mr Lee, adding that he has been approached by three businesses wanting to buy over the building.
Named after Malacca-born Hokkien merchant Chia Ann Siang, who used to own the land, Ann Siang Hill was formerly a nutmeg and clove estate, but saw the introduction of clan associations in the late 19th century as the Chinese population in the area rose.
Today, the hill, and the streets leading up to it, including Ann Siang Road, Erskine Road and Club Street, are taking in a new breed of businesses - mostly eateries and bars - such as gentleman speakeasy Manor Bar, and Oxwell and Co, a rustic multi-concept restaurant and bar.
They join long-time Ann Siang stalwarts like luxury boutique hotel The Scarlet Hotel, and The Screening Room, a food and beverage venue cum film theatre.
As an indication of the area's popularity with drinkers and revellers, on Friday and Saturday evenings, Ann Siang Road and the adjacent Club Street are closed from 7pm to 2am. Dining tables are brought out and revellers pour out onto the two-way streets.
"The road closures create a really cool street party vibe that is hard to come by in a lot of other areas," says British chef and restaurateur Ryan Clift, who heads restaurant and bar Ding Dong.
Quaint shophouses, first restored in 1993, now boast colourful shopfronts and painted-over timber window shutters. Most of them, constructed between 1903 and 1941, have retained pre-war features such as mosaic-tiled floors, double-leafed doors, and five-foot walkways.
However, many businesses have had to undergo extensive and often expensive restoration works to rewire cables, fix up roofs and reconfigure water pipes.
"Due to age, rainwater can sometimes seep through," says Mr Zedy Ng, marketing manager of boutique hostel 5footway.inn in South Bridge Road.
"We have to identify these problems and patch them up to minimise inconvenience."
But for shops in the former hipster enclave, a hit with the indie crowd in the late 2000s, a leaky roof is the least of their problems. Their very popularity was their own undoing.
With rising rental costs, some of the smaller stores and boutiques selling a variety of products, such as patisserie cake shop Kki and design-inspired shop The Little Drom Store, have been priced out and had to relocate out of Ann Siang.
In fact, most of the quirky little shops and boutiques have disappeared, leaving just a bunch of bars and restaurants, says Ms Samia Ahad, founder of The Screening Room.
In the last 10 years, rent has increased by 30 per cent to 50 per cent.
Mr Marc Nicholson, chief executive officer of the local franchise of old-style barbershop Truefitt and Hill, said: "Many of the buildings nearby have been bought over recently. The higher value is going to put even more pressure on rents."
For some, the area has lost its magic.
"It is not as quirky and charming as it used to be. It is just rowdy with drinking crowds," says Kki co-owner Delphine Liau. The cake shop operated out of its 990 sq ft unit for four years till it moved to its current space at the School of the Arts last year.
"It is getting more tourists for sure, but for locals, it is losing its charm as the quaint Ann Siang Hill we used to know."