The Real Estate Investor's Tax Calendar: Every Deadline, Filing, and Estimated Payment Month by Month

Missing a tax deadline as a real estate investor isn't just an inconvenience — it can be catastrophic. Miss the 45-day 1031 exchange identification window by a single day and you're paying six figures in capital gains tax. File estimated payments late and the IRS charges underpayment penalties regardless of your reason. Fail to elect S-Corp status by March 15 and you wait another year.

Most tax guides for real estate investors focus on strategies. This one focuses on timing — the specific deadlines, filing requirements, and proactive planning actions that should happen each month.

Print this. Save it. Set calendar reminders. Your future self (and your CPA) will thank you.

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Quick Reference: Critical Dates at a Glance

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January: Year-End Closeout and Contractor Reporting

Key Deadlines

• January 15 — Q4 estimated tax payment due (for prior tax year)
• January 31 — Issue Form 1099-NEC to every contractor you paid $600+ during the prior year
• January 31 — Issue Form 1099-MISC for rent payments of $600+ (if applicable)
• January 31 — W-2s due to employees (property managers with W-2 staff)

Action Items

Financial closeout:

• Reconcile all rental property income and expenses for the prior year
• Finalize December bank and credit card statements
• Ensure all property manager year-end statements are received
• Compile total mortgage interest paid (verify against 1098 forms when received)
• Tally total property taxes paid across all properties
• Calculate total depreciation for the year (or confirm with CPA)

1099 preparation:

• Review all contractor payments: handymen, plumbers, electricians, landscapers, cleaning crews
• Any individual or non-corporate entity you paid $600+ gets a 1099-NEC
• You do NOT need to issue 1099s to: corporations (C-Corp or S-Corp), payments made via credit card (payment processor handles it), or incorporated property management companies
• Use a service like Track1099, Tax1099, or your accounting software to e-file

REPS hour tracking:

• If claiming Real Estate Professional Status: finalize your hour log for the prior year
• Minimum: 750 hours in real property trades or businesses
• Must be more than half of all personal services performed
• Document should include: date, activity, hours, property address
• Keep this log permanently — it's your primary audit defense

Pro tip: January is when your CPA is least busy. Schedule a tax planning call now for the current year, not just a filing discussion for last year.

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February: Document Collection and Entity Review

Key Deadlines

• No major federal deadlines
• State-specific: Some states have annual LLC report deadlines in February (check your state)

Action Items

Collect tax documents:

• 1098 (mortgage interest) from each lender
• 1099-INT (interest income)
• 1099-DIV (dividend income from REITs or brokerage accounts)
• 1099-B (capital gains from securities sales)
• K-1s from any partnerships or syndications (these often arrive late — follow up)
• Property tax statements from each county
• Insurance premium summaries
• Property manager annual statements (income/expense by property)

Entity maintenance:

• File annual reports for all LLCs (deadlines vary by state; some are due in February)
• Verify registered agent status is current
• Confirm operating agreements are up to date
• Review entity structure — does it still serve your portfolio size and strategy?

Estimated tax review:

• Calculate whether prior year estimated payments covered your liability
• If you owed > $1,000 at filing, you likely need to increase current year estimates
• Safe harbor rule: Pay at least 100% of prior year tax (110% if AGI > $150K) to avoid underpayment penalties

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March: Entity Tax Returns and S-Corp Elections

Key Deadlines

• March 15 — S-Corp (Form 1120-S) and Partnership (Form 1065) tax returns due
• March 15 — Deadline to elect S-Corp status (Form 2553) for the current tax year
• March 15 — File extension (Form 7004) if S-Corp/Partnership returns aren't ready

Action Items

Entity return filing:

• S-Corps and Partnerships must file by March 15 — one month before individual returns
• K-1s are generated from these returns and flow to your individual 1040
• If your entity return isn't filed, you can't complete your individual return
• Late filing penalty: $235 per partner/shareholder per month (2026 rate) — a 4-member LLC that's 3 months late = $2,820

S-Corp election considerations:

• If converting an LLC to S-Corp taxation, Form 2553 must be filed by March 15 of the year you want the election to take effect
• S-Corp election benefits investors who earn active income through their RE business (property management company, flipping company) — saves self-employment tax on profits above reasonable salary
• S-Corp election typically doesn't help for passive rental income
• Discuss with CPA: the breakeven is usually around $40,000+ in net active RE income

Extension strategy:

• Filing an extension is free and gives you until September 15
• Extensions extend the time to file, NOT the time to pay
• If you owe tax, estimate and pay by March 15 to avoid interest
• Many experienced investors file extensions routinely to ensure accuracy

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April: Individual Returns and Q1 Estimated Payments

Key Deadlines

• April 15 — Individual tax return (Form 1040) due (or extension Form 4868)
• April 15 — Q1 estimated tax payment due for current year
• April 15 — Last day to make prior-year IRA contributions (Traditional or Roth)
• April 15 — Last day to make prior-year HSA contributions
• April 15 — Last day to fund Solo 401(k) employee contributions for prior year (if not on extension)

Action Items

Tax return filing:

• Schedule E is where rental income/loss is reported
• Each property should have a separate Schedule E entry
• Verify depreciation schedules are correct — standard residential depreciation is 27.5 years for the building (not land)
• If you did a cost segregation study, verify the accelerated depreciation is properly reflected
• Review passive activity loss limitations — passive losses can only offset passive income unless REPS qualifies

Key Schedule E deductions to verify:

Estimated tax payments:

• Q1 payment due April 15 for current year income
• Calculate based on projected annual tax liability ÷ 4
• Use IRS Form 1040-ES worksheet or ask your CPA
• Pay via IRS Direct Pay (irs.gov/payments) or EFTPS

Retirement account strategy:

• Fund prior-year IRA by April 15 ($7,000 limit for 2026, $8,000 if 50+)
• If self-employed through RE: Solo 401(k) employee contribution deadline is April 15 (employer contribution deadline is the tax filing deadline, including extensions)
• Self-directed IRA for RE investing: can hold rental properties, tax liens, notes

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May: Mid-Year Review and Cost Segregation Planning

Key Deadlines

• No major federal deadlines
• State-specific: Some states have property tax deadlines in May

Action Items

Mid-year financial review:

• Pull Q1 actual income/expense for each property
• Compare actual vs. budget — are you on track?
• Review rent roll — any leases expiring mid-year that need renewal or rent increase?
• Assess capital improvement needs — any repairs that should be classified as improvements?

Cost segregation study timing:

• If you purchased or placed in service a property in the current year (or prior years without a study), May is a good time to engage a cost segregation firm
• Studies take 4–8 weeks to complete
• Starting now ensures results are ready well before year-end tax planning
• Rule of thumb: cost segregation is worthwhile on properties valued at $300,000+ (building value, not including land)
• Typical study cost: $3,000–$7,000 depending on property size
• Typical first-year benefit: $20,000–$200,000+ in accelerated depreciation

1031 exchange awareness:

• If you're considering selling a property this year, NOW is when to plan the 1031 exchange
• Don't wait until you have a buyer — identify your qualified intermediary (QI) in advance
• The QI must be engaged before closing on the relinquished (sold) property
• You cannot use your own attorney, CPA, or agent as the QI

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June: Q2 Estimated Payment and Insurance Review

Key Deadlines

• June 15 — Q2 estimated tax payment due
• June 15 — Tax return deadline for U.S. citizens living abroad (automatic extension)

Action Items

Estimated payment:

• Q2 estimated tax payment covers income earned April–May
• If you sold a property or had a large capital event, adjust your estimate upward
• Underpayment penalty is calculated quarterly — you can't "make up" a missed quarter with a larger Q3 payment

Insurance audit:

• Review all landlord policies for adequate coverage
• Confirm replacement cost values are current (construction costs have increased significantly)
• Verify all properties are on landlord/dwelling policies, NOT homeowner policies
• Check umbrella policy limits — recommended minimum $1M per $1M in assets
• If you acquired new properties, ensure they're added to your portfolio policy

Property tax appeals:

• Many jurisdictions allow property tax assessment appeals in June–August
• If your assessed value is significantly above market value (or comparable sales), file an appeal
• Gather 3–5 comparable sales as evidence
• Potential savings: 10–30% reduction in property tax bill
• Some jurisdictions allow hiring a property tax appeal firm on contingency (they take 25–40% of savings)

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July: Mid-Year Tax Planning and REPS Check-in

Key Deadlines

• No major federal deadlines

Action Items

REPS mid-year audit:

• If pursuing Real Estate Professional Status, you should have 375+ hours logged by June 30
• If you're behind, assess whether you can realistically hit 750 hours
• Activities that count: property management, maintenance, tenant relations, deal analysis, property inspections, continuing education in RE, development/redevelopment
• Activities that don't count: investor education (reading books), commuting to your W-2 job, general financial planning
• If your spouse is claiming REPS, their hours count — one spouse can qualify

Mid-year tax projection:

• Ask your CPA for a mid-year tax projection
• Compare projected liability to estimated payments already made
• Adjust Q3 and Q4 estimates if needed
• Identify tax-saving opportunities to execute before December 31:
  • Accelerate deductible expenses
  • Defer income if possible
  • Plan property acquisitions for maximum first-year depreciation
  • Consider bonus depreciation on short-lived assets (appliances, carpeting, landscaping)

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August: State Deadlines and Portfolio Analysis

Key Deadlines

• State-specific: Various property tax deadlines
• State-specific: Some states have second-half property tax installments due

Action Items

Portfolio performance review:

• Calculate year-to-date cash-on-cash return for each property
• Identify underperformers — is it a management issue, market issue, or capital improvement need?
• Review rent comps — are your rents at market? Below market rents are the most common drag on returns.
• Assess: should you sell any properties before year-end? (If so, begin 1031 exchange planning now)

State and local tax planning:

• Review state income tax implications for properties in multiple states
• Some states (CA, NY, NJ) have high state taxes on rental income
• States with no income tax (TX, FL, NV, WA, TN, WY, SD) offer significant savings
• If investing across state lines, ensure you're filing required state returns

Depreciation schedule review:

• Verify remaining depreciable basis on each property
• If properties are fully depreciated or nearly so, consider:
  • Cost segregation study to reclassify remaining components
  • 1031 exchange into higher-value property with new depreciable basis
  • Sale if the property no longer serves your portfolio strategy

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September: Extended Returns and Q3 Estimated Payment

Key Deadlines

• September 15 — Extended S-Corp (1120-S) and Partnership (1065) returns due
• September 15 — Q3 estimated tax payment due
• September 15 — Solo 401(k) and SEP-IRA employer contribution deadline (if S-Corp, and on extension)

Action Items

Extended entity returns:

• If you filed a March 15 extension, S-Corp and Partnership returns are now due
• K-1s will be generated — ensure they're transmitted to all partners/shareholders
• File even if you're still waiting on some information — amend later if needed
• Late filing penalties continue to accrue at $235/partner/month

Estimated payment assessment:

• Q3 payment is your second-to-last chance to catch up on underpayments
• Recalculate year-to-date tax liability vs. payments made
• If you're substantially under, increase Q3 and Q4 payments to avoid penalties
• Consider the annualized income installment method if income is uneven (common for investors with large capital events)

Retirement funding:

• SEP-IRA contribution deadline matches your tax filing deadline (including extensions)
• Solo 401(k) employer contribution also follows the filing deadline
• Maximum 2026 contributions:
  • SEP-IRA: 25% of net self-employment income, up to $70,000
  • Solo 401(k): $23,500 employee + 25% employer, total up to $70,000 ($77,500 if 50+)
• These contributions reduce taxable income dollar-for-dollar

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October: Extended Individual Returns and Year-End Planning

Key Deadlines

• October 15 — Extended individual tax returns (Form 1040) due
• October 15 — Last day to recharacterize or undo a Roth IRA conversion (for some prior-year conversions — verify with CPA)

Action Items

File extended returns:

• No further extensions available — October 15 is the hard deadline
• Interest on any unpaid tax has been accruing since April 15
• Verify all K-1s are incorporated
• Double-check passive activity loss carryforwards from prior years

Begin year-end tax planning:

• You have ~75 days to implement tax strategies for the current year
• Key levers to pull:

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November: Pre-Year-End Execution

Key Deadlines

• No major federal deadlines
• State-specific: Some property tax deadlines

Action Items

Execute year-end tax strategies:

• If purchasing a property for current-year depreciation, it must be placed in service (available and ready for rental) by December 31 — "placed in service" is not the same as "closed on"
• Accelerate deductible repairs: complete any needed maintenance, painting, appliance replacement before year-end
• Review accounts payable — are there deductible expenses you can pay before 12/31?

1031 exchange deadline awareness:

• If you sold a property and are in a 1031 exchange:
  • 45-day identification period: you must identify replacement properties within 45 days of closing
  • 180-day closing period: you must close on the replacement property within 180 days
  • These deadlines are absolute — no extensions, no exceptions, not even for weekends (unless the 45th/180th day falls on a weekend or federal holiday)
  • Calendar the dates and work backward

Estimated tax true-up:

• Project final-year income with reasonable accuracy
• Calculate total estimated payments made vs. projected liability
• If you'll owe, make an additional estimated payment in December
• Q4 estimated payment isn't due until January 15, but paying early stops interest accrual

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December: Year-End Close and Future Planning

Key Deadlines

• December 31 — Last day to place assets in service for current-year depreciation
• December 31 — Last day to close on 1031 exchange properties (if 180-day window ends 12/31)
• December 31 — Last day to make current-year charitable contributions
• December 31 — Last day to harvest capital losses
• December 31 — Solo 401(k) employee contribution deadline (for W-2 employees of their own S-Corp)

Action Items

Financial closeout preparation:

• Reconcile all bank accounts and credit cards
• Ensure all rental income is deposited and recorded
• Verify security deposit accounting is accurate and compliant
• Confirm all contractor payments are recorded (for January 1099 preparation)
• Back up all financial records

Asset-in-service verification:

• If you acquired property in Q4, document the "placed in service" date
• Take photos showing the property is available for rent
• Keep listing screenshots, lease agreements, or other evidence of availability
• This documentation prevents IRS challenges to your depreciation start date

Next-year planning meeting with CPA:

• Schedule a January tax planning call
• Discuss:
  • Entity structure changes needed
  • Estimated tax payment schedule for next year
  • Planned acquisitions/dispositions and their tax impact
  • REPS qualification strategy
  • Cost segregation opportunities on new acquisitions
  • Retirement contribution strategy

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Special Timelines: 1031 Exchange Calendar

A 1031 exchange has the most unforgiving deadlines in real estate investing. Here's the timeline:

Critical rules:

• The 45 and 180 day counts include weekends and holidays (except if day 45 or 180 falls on a weekend/holiday, it extends to the next business day)
• You cannot receive the proceeds at any point — QI holds them
• The replacement property must be "like-kind" (any real property for any real property in the U.S.)
• Boot (cash or non-like-kind property received) is taxable
• Reverse exchanges (buy replacement first, sell relinquished after) are possible but more complex and expensive

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Estimated Tax Payment Quick Calculator

Most real estate investors should make quarterly estimated tax payments. Here's a simplified approach:

Safe Harbor Method (Simplest)

1. Look at your total tax liability from last year's return (Form 1040, line 24)
2. Divide by 4
3. Pay that amount each quarter
4. If your AGI was > $150K, multiply the total by 110% before dividing by 4

This guarantees no underpayment penalty regardless of what you actually owe.

Current-Year Projection Method (More Accurate)

1. Estimate total current-year income (rental, W-2, capital gains, etc.)
2. Subtract estimated deductions (depreciation, interest, expenses, etc.)
3. Calculate projected tax liability
4. Subtract withholding from W-2 jobs
5. Divide the remaining liability by 4 (or adjust quarterly based on when income is earned)

When to Use Which Method

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Record-Keeping Requirements: What to Keep and For How Long

Digital storage: Use cloud backup (Google Drive, Dropbox, or dedicated accounting software) with redundancy. Physical receipts should be scanned and stored digitally with a logical folder structure: Year > Property > Category.

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Annual Tax Planning Checklist

Use this checklist every December to ensure nothing falls through the cracks:

• All rental income reconciled
• All expenses categorized (repairs vs. improvements)
• Depreciation schedules current
• 1099s prepared for all contractors paid $600+
• Estimated tax payments calculated for next year
• REPS hours documented (if applicable)
• Cost segregation studies ordered (if applicable)
• 1031 exchange deadlines calendared (if applicable)
• Entity annual reports filed/scheduled
• Insurance policies reviewed and updated
• Retirement account contributions maximized
• Tax planning meeting scheduled with CPA
• All records backed up digitally

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The Bottom Line

Real estate tax strategy isn't a once-a-year exercise. It's a 12-month cycle of deadlines, planning, and proactive execution. The investors who save the most in taxes are the ones who plan in January, execute throughout the year, and show up to their CPA with organized records in March — not the ones who dump a shoebox of receipts on their accountant's desk in April.

Set these dates in your calendar. Review this guide quarterly. And work with a CPA who specializes in real estate — the combination of proper timing and expert strategy is worth tens of thousands of dollars per year as your portfolio grows.