I am 55 this year and will be retiring next year. Let me share my story. I first started with a HDB flat and then upgraded to a condo and finally upgraded to a landed property in 2006. My landed property then appreciated so much and became very overvalued. I sold it last year and made a lot of money. I then downgraded to a 4 room HDB flat. I told my children that it will be our retirement home. They understood and they don't mind as they have enjoyed staying in a condo and landed before. Since they too will be moving to a HDB flat when they get married, it is no big deal for them. My wife likes the flat as it is smaller and therefore easier and cheaper to maintain. In the past we spent a lot more maintaining our landed.

I paid the 5 year old flat in cash and have lots of cash balance. I invested my cash. I now earn a good passive income. My kids are working and contributes to the family expenses. We are managing well financially.