Advice about filing a 1040ES for the first time during your first year of retirement with living off of $55,000 of Capital gains and no IRA withdrawals

More information would be needed to correctly answer this for you. Your age, filing status and if you are collecting social security would all effect this out come. For now I will assume that this is the only income you have and that you are single. You would get to deduct the standard deduction for a single person (Single Filers and Married Persons Filing Separately: $15,750) and then would be taxed on the remaining amount ($39,250). It also matters if these are short term or long term capital gains. The tax rates are different for each. Assuming these are short term gains the tax would be about $4700. Here is a link for our calculator (https://turbotax.intuit.com/tax-tools/investment-tax-calculators/), so that you can put in your specific information to figure your tax. The final amount would be split between the estimated payments that you are making.

1. Greetings JR
   
    If you are a single taxpayer and your only income is the capital gain if it is long term. 
   Consider the $50,000 gain less the standard deduction $15,750 = $34,250.
   Applying the 0% capital gains rate, your $34,250 is less that the maximum of the bracket for long term gains ($48,350 single filers in 2025).
   If the gain is short term you will be looking at ordinary taxable income.
   
   We have a capital gains calculator that you may use for changes in your situation.
   https://blog.turbotax.intuit.com/income-and-investments/capital-gains-tax-calculator-48615/ 
   And there are other calculators that you may use including one for the most recent tax changes.
   https://blog.turbotax.intuit.com/collection/calculators/
   
   Thanks for the question!! Hope this helps!

It is possible you would get bumped up into a higher capital gains tax bracket since the IRA distribution will increase your taxable income.  The best way to estimate it would be to use the calculators provided by Mark_5.  These calculators would help you determine what your potential tax liability would be based upon your actual circumstances.  While we can provide rough estimates based upon hypothetical situations, we cannot ensure we know the entire "tax" picture.  

Please see this link for the actual tax calculator to use to help you determine your estimated tax liability.  Be sure to account for all of your sources of income and deductions you expect for 2025.

As for the IRA withdrawal, you will need to ask your financial broker to withhold federal (and state if applicable) taxes from the distributions.  If you use this option and are able to withhold enough tax to cover your anticipated tax due when filing, you may not need to make estimated tax payments.  The IRS has a tax withholding estimator that you can use to determine how much you should have withheld from your IRA distributions.

If instead you still want to make estimated tax payments, those amounts would be due quarterly as you earn the income.  The next estimated tax payment dates are September 15, 2025 and January 15, 2026.