The Great Wealth Transfer Has a Real-Estate Problem Hiding Inside It

An August 31, 2026 LendingTree study included one of those numbers so large it’s hard to fathom its sheer size: Americans age 65 and older who own homes could transfer roughly $17.2 trillion of wealth to younger generations over the next twenty years.¹

We have been hearing about the “Great Wealth Transfer” for years now, and usually the conversation revolves around the sheer size of it. Trillions of dollars moving from Baby Boomers to their children and grandchildren. What happens to markets? What happens to charitable giving? What happens when younger generations suddenly have more capital available to buy homes, start businesses or retire earlier?

Those are all interesting questions, but as I was reading the study, I kept coming back to something much more basic. A lot of families have done a pretty good job deciding who gets their assets someday, but I am not sure they have spent nearly enough time talking about what their kids are actually supposed to do with them when they arrive.

Real estate is probably the best example.

For example, imagine Mom and Dad have three adult children. They have a $2 million investment account and a house worth $1.5 million. Their estate documents say that everything gets divided equally among the three kids, which sounds completely reasonable. Most parents want to treat their children fairly, and “one-third to each” feels about as fair as you can get.

The investment account is easy enough. You divide it three ways and everyone moves on with their life, but the house is where things get interesting.

Maybe the oldest daughter lives ten minutes away and still brings her children over for Sunday dinner. She would love to keep the house because she cannot imagine someone else living there. The middle child moved to Texas fifteen years ago, already has a house, and would much rather have his share of the money. The youngest loves the house too, but not enough to sign up for the property taxes, insurance, roof replacement and whatever exciting surprise the HVAC system has planned for next July.  Nobody is being difficult or greedy, and nobody needs to be the villain in this story.  They simply have three different lives.

And there is another dynamic here that I think gets overlooked. In plenty of families, one of the siblings decides that keeping the peace matters more than getting their fair share. They may say, “She wants the house more than I do, just let her have it,” or “I don’t want this to turn into a fight, so I’m fine walking away from it.”

That may sound generous, and sometimes it is. But parents may not want to build an estate plan that depends on one child being willing to disinherit themselves in order to keep everyone cordial. If one sibling gives up a meaningful asset simply because they are the person least interested in conflict, that may preserve the family dinner table, but it does not necessarily produce a fair result.

That is why I think the conversation has to come before the solution.

Too often, estate planning starts with the mechanics. Should the property go into a trust? Should one child get the house and the others get more of the investment assets? Should there be a buyout provision? Should life insurance create liquidity? Those can all be potential solutions to discuss with the right professionals, but they are answers to questions we may not have asked yet. Before we get there, we need to understand how everyone actually feels about the property.

Now take that same conversation and replace the primary residence with the family lake house.

A lake house is rarely just a line on a balance sheet. It is where the kids learned to swim. It is Fourth of July weekends, old family photographs, grandchildren running around barefoot and forty years of memories packed into the same property. Mom and Dad may naturally look at that and think, “We want the kids to have this forever.”

And the kids may feel exactly the same way… right up until somebody has to pay for a new dock.

Emotional value and financial value are not always the same thing, and inherited real estate has a way of forcing families to figure out the difference.

This is one of the reasons another finding from the same LendingTree study caught my attention. Among people who expect to receive an inheritance, only 57% said they had clearly discussed the amount, timing or likelihood of that inheritance with the person they expect to receive it from. Another 16% had not discussed it at all.1

That is a pretty significant communication gap considering how much money and property we’re talking about.

And I do not think the answer is that parents need to sit everyone down at Thanksgiving and distribute copies of their balance sheet between the turkey and pumpkin pie. There are plenty of good reasons not to share every dollar amount with your children.  But I do think there is a very useful conversation parents can have, and it does not need to be complicated.

A useful place to start is attachment.

Ask each child how they actually feel about the property. Not what they think they are supposed to say, and not what they think Mom and Dad want to hear. Do they see the house as something they would genuinely want to own someday, or do they simply have fond memories of it? Those are not the same thing. Loving the house you grew up in does not necessarily mean you want to own it at age 50.

Then, consider practicality.

If someone does want the property, what would ownership realistically look like? Would they live there? Use it as a second home? Rent it? Could they afford the taxes, insurance, maintenance and repairs without creating financial strain? If multiple children want it, would they genuinely want to own it together? Shared ownership can sound wonderful when everyone is sitting around the kitchen table. It can feel very different when the roof needs replacing and three siblings have three different ideas about what should be spent.

Next, consider fairness.

This is the part families sometimes avoid because they worry that talking about money will create conflict. In my experience, avoiding the conversation is much more likely to create it later. If one child wants the property and another does not, how would everyone feel about a buyout? If one child receives the house, should the others receive more of the investment assets? If one sibling has been living in the property or helping care for Mom and Dad, does that change how the family thinks about what is fair?

You do not need to settle every issue in the first conversation. The point is to surface the differences while everyone is still able to talk about them openly.