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The Truth About Downsizing in Retirement

Phil’s Tax Hacks · September 11, 2025

Here’s some of what we discuss in this episode:

🏠 Downsizing isn’t always cheaper than staying put

💰 Property taxes can jump when you reset your tax base

📉 Transaction costs (commissions, moving, new furniture) cut into equity

👨‍👩‍👧 Family dynamics and emotional ties play a big role

🧭 Lead with lifestyle goals, not just financial ones

Today’s Hack

Downsizing in retirement seems like a no-brainer, but it’s not that simple. In this episode, Phil tests some of the most common beliefs about downsizing and whether they really hold up. Is moving to a smaller home always cheaper? Does it automatically lower your taxes? Will it actually simplify your life, or just trade one set of challenges for another?

Phil explains how property taxes, equity swaps, and transaction costs can turn “downsizing” into an unexpectedly expensive move. Beyond the financials, the discussion explores the emotional weight of leaving the family home, how proximity to children and grandchildren factors into the decision, and why lifestyle goals must play just as big a role as the math. Downsizing isn’t just a real estate decision. It’s a financial, emotional, and family decision, and the right move depends on what you want your retirement years to look like.

0:00 – Intro

1:01 – Why People Downsize

2:23 – Equity & Property Taxes

6:33 – Are Rates Dropping Soon?

8:45 – Estate Planning

10:43 – Emotional Factors

14:23 – Financial vs Emotional

If you have any questions about what we discussed in this episode, reach out and we’ll be happy to set up a time to talk.

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