Boomers are not downsizing in retirement — they are buying bigger homes. Wealthy older Americans are ripping up the traditional retirement script, with many upsizing rather than downsizing.
Ben reports that wealthy boomers are increasingly buying larger homes in retirement, driven by desires for space for grandchildren and the financial means to do so, further tightening housing supply for younger generations. ✦ AI generated
Ben · The Compound · 2026-07-22 · original ↗
starts at this moment · 45:02
Wealthy older Americans are ripping up the traditional script for aging. The script is you have to buy a home because it's your biggest and best investment. And then when you retire, you downsize and then young people will move into those homes because boomers don't need bigger houses anymore. And they say, especially for wealthy people who have a lot of money, that's just not the case.
verbatim transcript · starts at 45:02
44:52the funny thing is though, he ran on a platform of full employment. And I wanted to be like, Dave, if you run on a platform of full employment, it's going to be high inflation. People are going to hate it. Right. Anyway, all right. Boomers were supposed to downsize. They're buying bigger homes instead. Story from the Wall Street Journal. Wealthy older Americans are ripping up the traditional script for aging. So the
45:12script is you have to buy a home because it's your biggest and best investment. And then when you retire, you downsize. and then young people will move into those homes because boomers don't need bigger houses anymore. And they say, especially for wealthy people who have a lot of money. That's just not the case. Uh, eight of the clients for Maril Lynch Financial Advisor uh this year retired.
45:31Every single one of them upsized. Only one client has downsized in the past year. This guy, this financial advisor says the historic retirement play of sell your home and buy a smaller one just isn't happening. Um, they say the new demand for even bigger properties is another way boomers dominate the housing market. They account for 42% of home buyers, the largest share of any generation. They're often cash buyers,
45:49giving them an advantage over younger purchase. Now, they they they ask these people, "Why are you buying a bigger home?" And one woman's like, "Listen, we have all these grandchildren and we want a bigger home. We" And so, it's like, you can't get mad at these people for doing what's in their best interest or what they want to do, obviously. But this seems like a script that was
46:05something people thought would happen. And for a lot of people, it's like, "No, I have a lot of wealth. I'm going to buy." And they interview this couple that went from like a 2500T house to a 5,000t house. And again, this is just wealthy individuals. Here's something from Kyla Scanland. She wrote this in the um New York Times. Empty nesters now own about 28% of large homes in the US.
46:25Millennials with children own about 16%. So, there is something where the baby boomers are holding on to their big houses. They're not. They saying, "No, no, we like this. We're happy where we are." And again, you can't fault them for this, but this was a big thing that like, no, no, no, this is the next step. This is supposed to happen. >> Yeah. I this is supposed to make me mad. I
46:44Right. Like this is >> obviously does make some people mad. >> Yeah. I think listen this is not an awesome situation, but who are you getting mad at? Like I think these >> people acting in their own self-interest. Like they're >> Yeah. >> Well, >> they want bigger houses for their to have their families over and Yeah. This is uh >> this is what it I made the point last