The oldest housing estates in Singapore and their histories

This hipster enclave is one of Singapore's oldest housing estates. Developed in the 1920s by the Singapore Improvement Trust (SIT), Tiong Bahru sits on former Chinese burial grounds – a history that can be guessed from its name, which means 'new cemetery' in a mix of Hokkien and Malay. Besides being the site for farming and military use, Tiong Bahru was also infamous for being a 'mei ren wo' or 'den of beauties', as rich businessmen often kept their mistresses in these flats. Other beauties also lived here: glamourous cabaret dancers from the nearby Great World Amusement Park, and pippa girls (or prostitutes) with their minders. 

What to see today: Head down to Tiong Bahru to admire the Art Deco architecture of the pre-war flats. Particularly appealing are the exterior spiral staircases, courtyards and kitchen stairwells, where neighbours used to pass goodies across to each other with bamboo poles. For more to see and do, read our ultimate guide to Tiong Bahru. 

Ever heard of The Quests? They're only the most successful local band of the 1960s, or so considered by many. The Quests derived their name from the school magazine of Queenstown Secondary Technical School, where two band members used to study. The school itself is one of the many pioneering landmarks of Queenstown. As Singapore's first satellite town, Queenstown was also home to the island's first polyclinic and first branch library. Like many other parts of Singapore, this estate was built on swampy land flanked by two hills – one a Chinese cemetery and the other an orchard and rubber plantation. In the old days, a village called Bo Beh Kang and the British Buller Camp had to be cleared to make way for Queenstown's development. 

What to see today Museum @ My Queenstown displays artefacts from Queenstown's past. Situated in the soon-to-be-redeveloped Tanglin Halt, you can check out old signages, relics from old factories, and even an outfit worn by The Quests. Wait, there's more in our ultimate guide to Clementi and Buona Vista. 

Swamps are a bit of a theme here, and Toa Payoh is the 'big swamp' (in Hokkien). This mature estate has a bit of a seedy past, being the battleground of some of Singapore's largest crime syndicates, gangs and secret societies. It was notorious as the "Chicago of the East", so fearsome that even policemen avoided entering the district come nightfall. Nevertheless, the National Heritage Board documented the strong kampong spirit among the villagers in Toa Payoh. The closely-knit communities put up a huge fight against the government's relocation efforts at the time – after all, they also relied on the land to farm for a living. With major incentives to move, the villagers and squatters eventually made way for Toa Payoh new town, Singapore's first MRT station, first cooperative supermarket and first Residents' Association, among others. 

What to see today This heritage neighbourhood glitters with hidden gems, the most famous being the dragon playground. Check out our ultimate guide to Toa Payoh for a full list of things to eat, drink and do.

Bedok's history is closely tied to the sea. Before land reclamation in the East, communities living in Bedok had easy access to the beaches to carry out fishing activities, and run the coconut plantations as their main livelihoods. The Orang Laut were the early inhabitants of this area, but settlers from Indonesia and Malaya eventually streamed in. On another note, piracy was said to be rampant in the waters off these shores. Records speak of fierce battles that resulted in much death and injury. These marks of old Bedok were eventually cleared for development in the 1960s, resulting in one of Singapore's densest planning areas. 

What to see today If you can't get close to the water at the beach, you can do so at Bedok Reservoir. This neighbourhood is also famous for some of the best food on the island – get in the know with our ultimate guide to Bedok. 

Marine Parade has the distinct honour of being the first housing project built entirely on reclaimed land. It has the hills in Bedok and Upper Changi to thank – these were blasted for sand to fill the seas. Before reclamation works began in 1966 however, Marine Parade was a hub of activity. This former beachfront attracted groups of people out for a picnic and a splash, and many patronised the hawker stalls dotting the sand. In a situation similar to Sentosa today, Marine Parade was also a popular location for wealthy families to settle down, perhaps to make the most of the cool sea breeze. 

What to see today Marine Parade today maintains much of its breezy, seaside character of the old days. Take a jaunt to this laidback town for sport and water activities, seafood and more you can find in our ultimate guide to Marine Parade and East Coast Park.