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When a good investment is no longer the right investment

October 27, 2026•2 min read

Imagine you've owned an investment property for 15 years.

You bought it for $650,000. Today, it's worth $1.5 million.

It's been one of your most successful investments. So why would you ever consider selling it?

This is a question I think more property investors should ask, particularly as they approach retirement.

An investment that was right for building wealth isn't necessarily the right one for enjoying it.

Consider a couple in their early 50s who own an investment property worth $1.5 million, with $350,000 owing on it.

They also have a $600,000 mortgage on their family home.

On paper, they're doing well. But the investment property generates relatively little spare cash after expenses, and they'd love to start working less over the next few years.

Selling the property could potentially allow them to pay off their home mortgage and free up money for other purposes, after accounting for tax and selling costs.

Of course, they'd be giving up future rental income and potential capital growth.

So which is the better decision?

I wouldn't start by trying to predict where property prices are heading.

Instead, I'd explore three possibilities: keeping the property, selling it now, or selling it in five years.

Then I'd look at how each choice could affect their ability to reduce work, their retirement income, their debt and their financial security.

The interesting thing is that the option that produces the most wealth isn't necessarily the one that gives them the best life.

And that's really the point.

Building wealth is important. But knowing when and how to use it is just as important.

I've explored this example in more detail in my latest article, including the questions and trade-offs I'd consider before making such a significant decision.

[Read the full article: Should you sell an investment property that's made you wealthy?]

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