Singapore is a tiny country, geographically. The 999-year land lease was a compromise for Singaporeans who attained a bit more success and wealth and wanted to leave something (usually a house) for their later generations. The compromise was that the Government wanted to ensure that at some point in the far future, they could always get it back for future redevelopment. In the case of Freehold (Fee-in-Simple) Land, the Government can only get it back in a few ways: The Compulsory Land Acquisition Act. Not a popular move, historically. The owner dies without any beneficiaries and no valid Will. If the owner had no spouse or kids, but there’s a valid Will, it goes to the new beneficiary. Hence, Freehold is excellent (for a handful of wealthy citizens), but not so good for a The government whose charter is to benefit the masses, e.g., the land could be used for a school or a community club. === I think it is a leftover from the British era, and the British have this as a carryover from its historical common-law roots where 999-year lease are assumed to be “permanent” in nature. Do remember Hong Kong was leased for 99-years, and the reason for that was back then they think it is “as good as forever.” For practical purposes within Singapore, a 999-year lease are currently assumed to be freehold (permanent leasehold) for valuation purposes and generally will fetch a fair value with freehold. This is partly because most 999 year leases in Singapore have about 850 years more to go. Singapore does not have new 999 year leases for now.