In Singapore’s competitive property market, where many buyers covet high-floor units in the latest condominium launches, Benjamin Chiang and Nai Kai Wei made a series of choices that might raise eyebrows.
The couple, both in the tech industry, now live in a ground-floor unit in a 99-year leasehold development that was completed nearly three decades ago.
The two-bedroom home, acquired for more than $1 million in a resale transaction a few years ago, houses Chiang, Nai, their energetic twin sons, a months-old infant, their domestic helper and a pet cat.
"The common Singaporean thinking is: must buy high floor, must buy new, must buy freehold. We’ve gone quite the opposite," says Chiang with a laugh.
The decisions behind this home run counter to what he dubs "folk knowledge" — the accumulated wisdom passed down by friends, family and property agents about what makes a good property buy in Singapore. But for Chiang and his family, these conventional preferences did not align with what mattered most to them.
Starting their search in 2022, they spent a few months hunting for the right home before inking the sale and purchase agreement. Instead of following the well-trodden path, they charted their own course, driven by practical needs and thorough research.
The children’s education was first and foremost a non-negotiable factor in their house-hunting equation. Their property search began a couple of years before the twins were due to start Primary One.
"We are the slightly kiasu parents,” Chiang admits. "We identified a primary school where we wanted them to go, then we moved to live near that school."
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This led them to Kentish Court, located in District 8 in the Rest of Central Region (RCR), or city fringe.
For the family, the neighbourhood’s appeal extends well beyond its proximity to schools.
The 24-hour Mustafa Centre is within walking distance, along with numerous hawker centres, food courts and wet markets. "I’ve systemically tried all the nasi biryani in this area," Chiang says with a grin.
City Square Mall sits nearby, and Little India — lively, colourful and always buzzing with activity — adds character to the locale. He also appreciates the rich heritage of the historic Pek Kio neighbourhood.
Proximity to the city was a secondary benefit. At his previous workplace, Chiang would sometimes walk the short 2km commute home. Nai, working remotely, had the flexibility to be based anywhere.
Space was a key factor in choosing an older development. "I really prefer older estates because the units are more spacious," Chiang notes. Spanning more than 1,200 sq ft, their apartment offers breathing room that is increasingly hard to find in newer condos, especially in the RCR and Core Central Region (CCR).
The 77-unit Kentish Court is relatively low-density, occupying a land area of 35,381 sq ft. Many residents are middle-aged 'empty nesters', with a few large or young families, Chiang observes.
"It's a friendlier estate. Most of them have stayed here for a long time. Everyone knows everyone, and we all hang out," he says.
Residents in smaller, older developments also tend to be less rigid about enforcement. "I think people are less uptight about condo rules in such estates," says Chiang. He is not a fan of the hyper-vigilant policing he has seen in newer developments, where everyday occurrences — such as shoes left outside the front door, or visitors and domestic helpers using the pool or gym — can spark petty complaints.
"We’re not living in military barracks, right? This is a residential estate, so let’s be mature and make it a place of residence, like an actual home," he says.
At Kentish Court, the mix of long-term residents and transient tenants has created a culture of give and take and a neighbourly atmosphere, with more empathy and understanding for the realities of communal living, Chiang notes.
Perhaps the most unconventional choice was living on the first storey, driven partly by convenience and partly by personal comfort.
"First of all, I want quick access out of my place. I don’t want to wait in the lift to go all the way down. Secondly, I don’t like to be in lifts, as I’ve got a bit of claustrophobia," Chiang says.
It is not without trade-offs — insects, for one — but they are manageable with practical solutions, such as mosquito nets and sealed openings to prevent cockroaches.
Living on the ground floor also brought something Chiang did not anticipate. "It’s very cosy, with café vibes," he says, describing how neighbours often stop to chat when passing by.
Moreover, because the development is gated, they have peace of mind letting their children play with friends within the estate. This freedom and easy community interaction have become integral to their daily life as a young family.
Data was a starting point when the couple began their property search in late 2022. After identifying a target location based on their desired school, they set a clear budget and jumped right into the legwork.
They studied recent transaction data of nearby condominiums via the URA Realis website, browsed listings on real estate platforms and Carousell to understand asking prices, walked the neighbourhood to get a feel for it, and viewed numerous units that caught their eye.
Their budget ceiling was firmly below $2 million. Landed properties were initially on their radar, but finding one within budget proved nearly impossible. Those available required extensive renovation, while maintenance concerns — including potential structural issues such as roof repairs — gave them pause.
"I thought we’re not ready for that," he says. "So it’s better to be a bit more prudent, a bit safer."
A real estate agent, a friend of Chiang's, also arranged many viewings for them. But the search later took an unconventional turn. "We actually drove into Kentish Court and put a little yellow sticky note in the lift, saying we want to buy and asking potential sellers to call us," Chiang recounts with a laugh.
That simple notice connected them with the eventual seller, although their actions ruffled feathers among the condo management.
The couple had set clear criteria: they wanted a unit in decent enough condition to avoid major renovation. This meant ruling out several properties they viewed — homes with rotting wooden cabinets, dilapidated fixtures and even overwhelming odours that made those homes unliveable.
Their renovation approach was hands-on and budget-conscious. They kept the flooring but hired handymen to strip out window grilles, cabinets and other fixtures, before replacing them with DIY installations they designed online. The most expensive item was the cat-proof netting throughout the apartment, costing about $2,000.
They also sourced furniture from online marketplaces and accepted hand-me-downs from friends. For instance, the dining table, chairs, bookshelves and the children’s double-decker bed came free. "Kudos to my wife. She’s very, very resourceful," Chiang says. A few pieces, such as the TV console, travelled with them from their previous homes.
Ask Chiang what advice he would give someone starting their property search today, and his answer is straightforward: Question conventional wisdom.
"Let’s not be too disturbed by the supposed must-dos for residential property," he says. "Things like, 'You should always buy EC (executive condominium), because EC sure will make money.'"
While not necessarily wrong, such thinking may not align with what actually matters to the buyer and their household.
For his family, that has meant finding value in options others typically overlook: low-floor units, older estates with generous square footage and leasehold properties in neighbourhoods they genuinely wanted to live in.
Living at Kentish Court has shifted their daily rhythms in meaningful ways. Now that they have a balcony, Chiang and his wife have taken up gardening, tending to edible and ornamental plants each morning. The central location means less driving, as hopping on a bus to the city or walking out for a meal has become routine.
As for concerns about resale value or rental yields — considerations that often drive others’ property decisions — Chiang is not losing sleep over them.
"If the price rises or stays the same, great! But even if it dips, I doubt Singapore property values or rents will fall very much anyway," he says. Should they need to rent the unit out, he is confident the location will also make it easy to find a tenant quickly. For now, the priority is a home that serves the family’s needs today, not maximising hypothetical future returns.
Pragmatism runs through their real estate journey. "We’re very practical creatures. We’re driven more by things like schools and price, than anything else," Chiang reflects.
He calls it a "bland" approach. But that practical mindset cuts through the noise. In a market saturated with hype about prestigious addresses and panoramic views, sometimes the best property decision is simply the one that works for you and your family.
Property Diaries is a new monthly series that goes behind the scenes of real estate transactions, featuring homebuyers and investors sharing their search journeys, decisions and lessons learnt.
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