Until recently Singapore’s Duxton Hill, a cluster of pre-Second World War buildings in the British colonial style known as ‘shophouses’ (narrow walk- ups of two or three storeys connected by a walkway) wasn’t best known for its architectural frontage. It was an unofficial red-light district, home to raucous karaoke and hostess bars. But things are changing quickly here, with an injection of creative, independent businesses taking over spaces vacated by the girlie bars, enticed by the relatively low rents and eye-catching digs.

Take Deborah Oh, a psychologist turned Pilates and spinning instructor who also owns and runs an events space called Group Therapy. “Despite the negative connotations associated with Duxton Hill, we just saw the potential here of a space that was a little bit different and a little bit out of the way,” she says.

Of course, few things in Singapore happen by accident. Bars have left mainly because the Urban Redevelopment Authority has designated the area a historic district within Chinatown and police are no longer renewing their licences. In many cases, rents that exceeded S$20,000 (€11,500) a month two years ago have halved.

Where a seedy bar once stood, Oh got a sunny, lofted upper floor of two shophouses. Designing the space and furniture herself to create a raw, earthy aesthetic, she opened Group Therapy in May. The venue now hosts an eclectic mixture of events including TEDxSingapore, the island’s offshoot of the annual ideas conference.

It’s a similar story with Rayner Tan and Aveline Chan, owners of The Pigeonhole, a live-music venue that also sells books, single malts, coffee and now hot meals. The two quit their jobs as a video editor and lawyer to open the space, which occupies two ground-floor units and is distinguishable by its scarlet floor. The area’s revival is helping with business, they say, as The Pigeonhole has seen a steady uptick in customers since it opened in March.

Near the top of the hill are the two most glamorous newcomers. First there’s Buyan, a Russian haute cuisine and caviar restaurant, and five doors away is Sabio, a tapas bar with a serious spread of jamon and a punchy sangria. A cosmopolitan crowd gathers at both establishments after sunset.

Flor Patisserie, a Japanese bakery that prides itself on using only the freshest organic ingredients, is another novel enterprise. With his bakery and cafe, Chef Yamashita was one of the first of the new wave of Duxton Hill tenants to set up shop.

But it’s not just restaurants and cafes that are establishing themselves on the hill; an eclectic array of independent businesses are also injecting life into the enclave. Vocanic, for instance, is a fast- growing young company that advises clients such as Nokia and Topshop on how to use social media. It has already taken up three lots and opened new offices in Hong Kong and Kuala Lumpur.

Pivotal Labs, a software engineering company that resolves technical issues for companies such as Twitter and Google, has also opened a spacious shophouse office on the hill after it outgrew its old premises in the more traditional Central Business District.

Nearby, there is the independent bookseller Littered With Books – a rarity in chain store-dominated Singapore – which sells fiction, children’s titles and travel literature. Divers Outfitter, just down the street, is one of the island’s best sources of scuba-diving equipment. Just underneath it, the dance school En Motion sees a steady stream of students passing through its doors late into the night.

With these new tenants, the hill is starting to resemble the long-since gentrified enclave of Ann Siang Hill, a few hundred metres away. To complete the transformation, all it needs is a couple of boutique hotels, a retailer stocking Scandinavian furniture and a few investment funds looking for a fashionable address. Wong Joon Ian