I don't really like to point fingers but I feel the reason why SG properties shot up in price so quickly in the last 5 years or so has to do with the SG government.
You know this government, they like to plan. And they are usually very systematic. I don't think it was ever their intention to cause so much oversupply of properties in Singapore. My guess is, somewhere in 2006 or 2007, under the leadership of the greedy LHL, his government went too far and lost sight of the commoners. I think they had intended to bring in lots and lots of foreigners. That was probably why they sold so many lands to the private developers and expected the rich foreigners to buy them.
In 2007 to 2012, there was also a huge shortage of BTO flats, despite the data showing that there was a long queue of people, especially young couples failing more than 5 times balloting. Remember those days when there is this COV thingy? And sellers of resale HDB flats were sometimes asking for ridiculous amounts like S$100k. It baffled me why the government became so short-sighted and didn't plan to build more BTO flats. Due to the lack of supply, that was why HDB flat prices also shot up suddenly. The government opened the floodgates to so many immigrants and new SGporeans, of course they too need a place to live in.
But too bad for LHL and his greedy party. In 2011, their popularity dropped drastically as shown by their poor showing in the GE2011. It was only then that the jokers woke up and realized the greed and irresponsible way they were running the country. They knew they could not allow foreigners in so freely like they had done so in the past.
That explains why now there are so many BTO flats being released suddenly in the last 1-2 years to cater to the commoners, while so many private properties are unsold due to fewer foreigners turned Singaporeans buying them. It's like the lazy student who didn't want to study before the exams and then last minute cram everything to make things right.
However, despite the high prices of the private condos, you'll be surprised people are still snapping them up. The cooling measures have little effect for most of them! I really don't know who they are. My guess is that there are too many damn rich people in SG. So I don't think the cooling measures will be removed any time soon. Singapore will just get more and more expensive to live in. If you look at the condo layout of today, you can see how ridiculous it is. Now super small 800 sq ft and below they can even squeeze out 3 tiny bedrooms and always a large balcony. Price? As high as S$1.2-1.5 mil for non-prime area. Crazy.
