As others have said here, and some do seem quite knowledgeable on the subject, i would take financial and legal advice first, as its a large sum, also you need it for retirement, and if you do end up needing it for care of any sort, its quite a minefield how they charge/ make you pay for it, also if he's hoping to 'pass it off ' as a gift to tax man I'm sure its not that simple and he would be 'sussed out' somehow on that? He cant AFFORD to buy or invest in any property by his own means, so why should you just dish it out to him? Also if hes no other cash, whats he going to use if this property needs repairs?either now or in the future? Is he going to expect that from you too? Also im sure he still has to pay some kind of taxes as a house owner himself anyway wont he,if its not to be lived in by himself,but as an 'investment'- this sounds like a 'pie in the sky' idea to me!- id also ask- how big WAS other sons wedding exactly? If you gave him a chunk for that, yet this son wants to buy a HOUSE? citing what you gave his brother as a reason to tip up to him too? Surely it cant have been same as a house costs these days? It looks to me like THIS son is the 'favourite'- not the other- so then your other son would be left feeling miffed? You cant hand out large chunks to one just because hes 'got no savings& needs something for his future"? We ALL need that- few of us are lucky enough to be in the position to have it- whose fault is it that he has not? His own? Not yours im sure- he needs to find work, if hes physically/mentally able and make his own future as your other adult children presumably have done? What about your other children anyway?you mention other son, what about others? Did they have a monetary gift also? Or do they expect one? If not now, maybe upon your passing? What then? You put cat among pigeons when you gave money for first sons wedding, but also when you got this sons 'help' to deal with your finances! You should have taken proper legal/financial help then, not from family.You WILL need your money for your own future, this is clear- you could live very many happy years yet- you need to have the cash for that- who knows what little there will be for state pensions after this covid situation has cost government so much.Dont rely on a cushy (or even comfortable) retirement unless you have your own money for that, just say you cant afford to give him money for what he wants right now, but of course if he marries you could offer him same towards a wedding as his brother if you wished- that seems fairer to all than, 'i paid for a wedding, so ill buy you a house' doesnt it?