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Before you sell, it’s worth checking whether taxes will apply – and how much. This 2025 flowchart helps you understand when sales are taxed as short-term or long-term capital gains, when income levels trigger the 3.8% Net Investment Income Tax (NIIT), and how gains can affect other areas like Social Security taxation, IRMAA surcharges, or state taxes.

In short:

  • Investments in retirement accounts (like IRAs or 401(k)s) aren’t taxed until you withdraw.

  • Short-term gains (held less than a year) are taxed at your regular income rate.

  • Long-term gains (held more than a year) may qualify for 0%, 15%, or 20% rates depending on income.

  • High earners may owe the NIIT in addition to capital gains tax.

Understanding these thresholds before selling can help you plan smarter and avoid surprises at tax time.

CLICK HERE to download this flowchart.

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