Does The “Sell One, Buy Two” Strategy Still Work In 2025? 3 Real Stories From Singapore Homeowners

After the government imposed the Additional Buyers Stamp Duty (ABSD) in 2011, a popular strategy for a time was the “Sell One, Buy Two.” This involved selling the existing property, while the couple would then purchase two more with the sale proceeds, under separate mortgages – most commonly one larger unit for a home, and a smaller one for rental gains (or in cases where the couple don’t need a big home, they can do the reverse.) It sounded good on paper, but did it really pan out? We spoke to some homeowners who, in previous years, tried the method:

1. Rental proved too troublesome, but no major regrets so far

YM’s parents sold their terrace house to purchase two condo units, in 2017. Part of the reason was the inaccessibility of the terrace house, which would be a problem for YM’s parents as they were getting too old to drive; it was quite a distance from the house to the nearest amenities. 

(By coincidence, we have covered the area where YM used to live in this article on Sea Breeze estate)

YM’s parents then purchased two resale condo projects: a three-bedder in the Simei area, and another two-bedder in the Tanah Merah area. This was for YM’s use at the time, as she works close to Tanah Merah. But the original plan, once YM moved out, was to rent out the two-bedder.

YM says that plan lasted all of two years: “After I moved out they did try to rent it, but it was a headache. The property agent really didn’t care after he got his commission*, and it was difficult for my parents because they don’t really know English. So I was always being called to deal with the tenants, which was not good as I was about to go abroad for a few years. So after around two years of renting, when I left Singapore, they stopped renting out the place also.”

YM says the two-bedder is now used by her uncle, who helps to maintain the unit rather than pay rent. When she returns to Singapore for good, which will be in a couple of years, she will move into it as her own home. 

YM says her parents don’t express any real regret, but they did say the idea to rent out a unit is much more difficult than the agent had claimed. She notes that tenants often had to be “chased” for rent, and that it’s impossible to really tell a good tenant from a bad one at the start. So the real benefit of the second property had ultimately been a place to stay for her and her uncle, and not really a financial gain.

*Some property agents help with managing tenants, as it’s in their interest to get lease renewals; but we should point out that technically, the agent’s responsibilities end after the tenancy is signed. 

2. Rental income is good, but they still wish they’d bought a larger unit 

YP and his wife sold their maisonette in 2016, and purchased a two-bedder and a three-bedder under separate names. YP says this was a “last minute” decision as the original intent was to buy a larger condo unit. 

At the time, the couple were eyeing a 1,600+ sq ft unit within the Katong area; instead their decision left them with an 800+ sq ft unit, which is their home, and a 668 sq ft unit instead in Katong, which is rented out. 

While he’d rather not disclose his home, YP says the two-bedder is actually just an apartment, not a condo (there are no facilities like pools or gyms), but it is freehold and within the desirable Joo Chiat area. Over the past 10 or so years, there have only been vacancies for four months, and YP says the rental income is “on the high side” for units in the area. 

Although the second property has performed quite well, YP still regrets the decision somewhat. When the couple had their second child, they felt their current home was too small; but they also found that the apartment unit was challenging to sell:

“Even though it is freehold, it is not so attractive because District 15 has a lot of condos that have a pool, BBQ, clubhouse, all those things. Also it’s very small, about 12 units with no sales for a long time, so it’s quite challenging to sell now.”

(As an aside, we also remarked to YP that a likely issue was the sheer number of freehold boutique condos in District 15, which makes his property’s freehold status less outstanding.) 

So even though the rental yield is high, YP does feel his family’s options were limited by his choice of the second property; and he recommends that other buyers “make an exit plan also” before going ahead with a second home. 

3. Living in the smaller unit to maximise their gains  

JN and her husband made the decision to purchase two properties back in 2019, after they finally moved out from a single larger home shared with their in-laws. The couple purchased a three-bedder condo unit in the Geylang / Aljunied area, and a 1+ Study unit that JN says is “around 12 minutes’ walk” from their three-bedder. 

Both were resale and in good condition, and the 1+Study unit was tenanted within weeks of the renovations being completed. The three-bedder also had renovations that were less than five years old. 

JN says they were pleasantly surprised when COVID-19 caused an increase in rental demand rather than vacancies, as the couple had expected the latter. When they agreed not to raise the rent, the tenant agreed to sign a longer lease. When the tenant eventually left in 2024 however, the couple’s child had already moved out, as he needed to stay closer to the CBD.

As they don’t need much space, JN and her husband made the decision to move to the 1+Study unit instead, saying there was “almost no difference because it’s just down the road anyway.” 

The larger unit was then rented out, and the agent found a tenant even before the couple moved. JN credits their stronger gains and ease of rental with the area as a whole: they had picked the Aljunied / Geylang area because they’ve worked in the area for over two decades, and her husband once owned a shop in the neighbourhood. As such, they were already familiar with the surrounding projects and amenities. This led her to turn down suggestions in other neighbourhoods, which she claims haven’t done as well the last time she checked. 

JN says they don’t have any regrets; but advises that anyone buying a second rental unit should look within an area they understand. Also, that it may be practical to rent out the larger unit, if your need for space is not so urgent.