Current Letter
May 2026
Turn A Real Estate Sale Into A Tax-smart Strategy & Before You Shred: Know Which Tax Records To Keep
Strategies for structuring an installment sale and guidance on how long important tax and financial records should be retained.
Turn A Real Estate Sale Into A Tax-smart Strategy
Selling investment or commercial real estate can result in a substantial tax bill if the property has appreciated significantly. One strategy to help ease your tax burden is an installment sale.
What’s an installment sale?
In an installment sale, the seller gets at least one payment after the tax year in which the sale occurs. So, if you sell investment or commercial real estate, instead of receiving the full purchase price all at once, you get payments over time.
This allows you to defer recognition of gain and spread the tax liability over several years. Installment sales can also help attract more buyers because they won’t have to pay the entire price upfront and obtaining financing might be easier.
2 types of installment sales
There are a couple of ways to set up an installment sale:
1. Traditional. This generally involves the buyer making payments directly to the seller under the terms of a promissory note.
2. Structured. Here, a third-party assignment company or financial institution assists with the transaction and oversees the payment schedule. The third party typically assumes responsibility for future payments to the seller, which may reduce the seller’s risk.
Tax considerations
Gains from real estate held for more than one year are typically taxed at favorable long-term capital gains rates (15% for most taxpayers and 20% for higher-income taxpayers). For 2026, the 20% rate applies when taxable income exceeds $545,500 (singles), $579,600 (heads of household), $613,700 (married couples filing jointly) or $306,850 (married couples filing separately). With the gain spread over multiple years, an installment sale may help keep you below the 20% rate threshold.
Depending on your income level, it might also help prevent you from triggering the 3.8% net investment income tax (NIIT), or at least reduce your NIIT liability. The NIIT applies to net investment income to the extent that modified adjusted gross income exceeds $200,000 (singles and heads of household), $250,000 (joint filers) or $125,000 (separate filers).
However, several tax rules can complicate installment sales. For example, depreciation recapture must be reported as ordinary income in the year of sale, even if payments are received later. Only the remaining gain can be spread out under the installment method. The good news is that if your marginal ordinary rate is 32%, 35% or 37%, depreciation recapture is taxed at only 25%.
Additionally, installment agreements exceeding $5 million may trigger an IRS interest charge on the deferred tax. Special rules apply to related-party sales and may accelerate the remaining tax if the property is resold within two years.
Electing out
Installment reporting is generally automatic if you sell property and receive at least one payment after the tax year of the sale. However, you can choose to elect out of it and report the entire gain in the year of sale.
This might make sense if you expect higher tax rates in future years, have current-year losses or deductions that could offset the gain, or want to accelerate income for financial planning purposes. When you file your tax return for the year of the sale, you can decide whether to elect out.
Moving forward
Installment sales can be complex. If you’re thinking about selling investment or commercial real estate, contact us to determine whether an installment sale makes sense for your situation.
Before You Shred: Know Which Tax Records To Keep
Tax documents can accumulate quickly. While clearing out old files can feel productive, it’s important not to discard anything until you’ve reviewed some record-retention guidelines.
Why good recordkeeping is important
Well-organized records make it easier to prepare accurate tax returns and respond if the IRS requests additional information or examines your return. Documents such as receipts and bank statements should support the income, deductions and credits you report.
Good recordkeeping also helps you monitor financial activity throughout the year. And it can simplify preparing future tax returns or amended returns.
The general rule
Records that support a tax return should generally be kept until the statute of limitations expires for that return. In general, the IRS has three years to assess additional tax after a return is filed. Returns filed before the due date are considered filed on the due date.
This three-year window is why you should keep supporting documentation, such as W-2 and 1099 forms, receipts and charitable contribution records, for at least that long.
Situations that extend the timeframe
Certain circumstances allow the IRS additional time to review a return. For example, the statute of limitations increases to six years if more than 25% of gross income is omitted from a return.
If a taxpayer fails to file a return or files a fraudulent return, there’s no time limit on when the IRS can assess tax.
Additionally, the timeframe for claiming a refund generally extends to three years after filing the return or two years after paying the tax, whichever is later.
Don’t discard these records too soon
Some documents should be retained beyond the typical three-year period because they may affect multiple tax years or support future transactions. These include:
Property and investment records. You should keep records related to property (such as real estate) or investments (such as stocks or bonds) for as long as you own the asset, plus at least three years after it’s sold. When these assets are sold, these records are needed to calculate the basis, gain or loss.
Retirement plan records. Retain retirement and pension documents for as long as the accounts have funds and for at least three years after the accounts are closed or funds are withdrawn. Keep records of nondeductible IRA contributions indefinitely to prove taxes were already paid on those amounts.
Bad debt or worthless securities deductions. Records supporting these claims should generally be kept for seven years from the date the return was due.
Filed tax returns. Proof of filing should be kept for at least as long as the statute of limitations applies to that return; however, it’s a good idea to keep proof longer for your records.
Seek guidance
Don’t guess when it comes to tax records. If you’re unsure whether to keep or discard certain documents, contact us for guidance. We can help you determine appropriate retention periods so you have the documentation you need if questions arise.