The Landlord Tax Calendar: Every Deadline in One Place

By Tom, CPA · Updated October 27, 2026

Part of: Rental Property Taxes

TL;DR: Landlords juggle four kinds of dates: January information returns, quarterly estimated taxes, the annual return in April (or October with an extension), and local property tax due dates. Put them on one calendar and most penalties disappear.

Educational only, not tax, legal, or investment advice. Examples are illustrations, not predictions. Rules and limits change; verify current figures and talk to a qualified professional about your situation.

Your tenant pays the mortgage; the IRS pays for the roof, eventually, over 27.5 years. In exchange, the IRS would like a few forms on time. Landlord tax trouble is rarely about exotic strategy; it is usually about a 1099 that was due January 31 or an estimated payment that was never made because rent income quietly grew.

Here is the full calendar for a typical individual landlord filing Schedule E, using tax year 2026 dates (returns filed in 2027). When a date falls on a weekend or legal holiday, the deadline moves to the next business day.

CPA Warning Label: An extension extends the time to file, not the time to pay. Interest and penalties on unpaid tax start at the original April deadline.

January 1099s

January 15, 2027: fourth-quarter 2026 estimated tax payment due (Publication 505).

February 1, 2027 (January 31 falls on a Sunday): furnish Form 1099-NEC to contractors and file it with the IRS, if your rental activity is a trade or business and you paid a contractor $2,000 or more for services during 2026. For payments made before 2026 the threshold was $600; the $2,000 threshold applies to payments made in 2026 and is scheduled to be adjusted for inflation starting in 2027 (IRS Publication 1099). Payments to corporations are generally exempt, except attorneys.

Also in January: collect Forms 1098 (mortgage interest) from lenders and property tax statements, and expect any Form 1099-MISC or 1099-K you received, for example from a property manager or payment platform.

Electronic filing is required if you file 10 or more information returns in aggregate during the year.

Quarterly estimates

Rental profit has no withholding, so estimated payments may be needed. For tax year 2026, the federal due dates are April 15, 2026; June 15, 2026; September 15, 2026; and January 15, 2027 (Publication 505).

You generally avoid an underpayment penalty if withholding plus estimates cover the smaller of 90% of this year's tax or 100% of last year's tax (110% if last year's AGI was over $150,000, or $75,000 married filing separately). W-2 earners can instead increase paycheck withholding, which is treated as paid evenly through the year, a handy fix for a forgotten quarter.

Illustration: A couple's 2025 tax was $30,000 and their 2025 AGI was $180,000. To use the prior-year safe harbor for 2026 they need $33,000 (110%) paid through withholding and estimates. Their withholding is $27,000. Paying $1,500 on each of the four dates, $6,000 total, reaches $33,000 even if a big rental gain or sale arrives late in the year.

April return

April 15, 2027: 2026 Form 1040 with Schedule E, plus Form 4562 for property placed in service during the year, Form 8582 for passive activity loss limits, and Form 4797 if you sold a rental. This is also the deadline for the first 2027 estimated payment.

Extension: Form 4868 extends the filing deadline to October 15, 2027, but not the payment deadline. Pay your estimated balance with the extension.

Elections ride with the timely filed return (including extensions), so the calendar matters here too: the de minimis safe harbor election, the small taxpayer safe harbor election, the grouping or REPS aggregation election and any Form 3115 catch-up are all attached to the return. Miss the return date, and some elections are lost for the year.

Partnerships and multi-member LLCs filing Form 1065 for calendar year 2026 are due March 15, 2027, with K-1s to partners by the same date.

Property tax dates

Property tax is local, so dates vary by county and city, often billed in one, two or four installments. Many states also set an annual window to appeal an assessment, often only weeks after the notice is mailed. Your mortgage servicer may pay from escrow, but you still want the dates on your calendar to verify payment and to catch the appeal window.

For short-term rentals, many states and cities require monthly or quarterly lodging tax returns, sometimes filed even when a platform collects on your behalf. Rental license renewals are usually annual. Check the county treasurer, assessor and city websites for each property.

Year-end moves

• By December 31: finish and place in service any improvements you want depreciated for 2026; pay deductible repairs you want in 2026 (cash-basis landlords deduct when paid).
• By December 31: collect Forms W-9 from every contractor paid this year.
• Mid-December: project your 2026 tax and adjust the January 15 estimate or W-2 withholding.
• Before year end: decide whether a cost segregation study is worth ordering for a property bought this year.
• December: review the mileage log and rental day counts, especially for vacation homes where personal use days matter.

Records to gather, month by month

• January: Forms 1098, property tax statements, platform 1099-Ks, prior-year depreciation schedule.
• February to March: receipts sorted into repairs versus improvements; mileage log totals; rent roll reconciled to bank deposits.
• April: copies of the filed return and every election statement, stored with the property file.
• Mid-year: a quick profit check to see whether estimates need to rise.
• Fall: insurance renewals and property tax notices, a good time to check the assessment for appeal.

A landlord who touches the records monthly spends far less time in April than one who discovers a shoebox.

The one-page calendar

2027 information return thresholds may change with inflation indexing; check Publication 1099 for the 2027 figure once published.