2026 Real Estate Investor Tax Calendar

Critical Dates, Deadlines & Planning Strategies

📅 Never Miss a Tax Deadline Again

This calendar includes federal tax deadlines, quarterly estimated payments, strategic planning windows, and real estate-specific dates. Keep this handy throughout the year and schedule reminders for critical deadlines.

Pro Tip: Proactive planning beats reactive filing every time. Book your Strategic Tax Blueprint early in each quarter to stay ahead.

⚠️ 2026 Tax Law Updates

  • Bonus Depreciation: Now Permanent at 100%
Q1 2026 | January - March
January 2026
Jan 15

Q4 2025 Estimated Tax Payment Due

Final quarterly estimated tax payment for 2025 tax year. Covers income from October-December 2025.

CRITICAL PAYMENT
Jan 31

1099 Forms Distribution Deadline

Distribute 1099-NEC (contractor payments $600+) and 1099-MISC forms to recipients. Critical for landlords who paid contractors, property managers, or other vendors.

CRITICAL REAL ESTATE
Jan 31

W-2 Forms Distribution

If you have employees (including property managers you employ), distribute W-2 forms.

PAYROLL
Late Jan

Year-End Tax Planning Review

Review 2025 results and start gathering tax documents. Schedule your tax prep appointment early to avoid April rush.

PLANNING
February 2026
Feb 28

1099 Filing with IRS Deadline

File 1099-NEC and 1099-MISC forms with the IRS (if filing by paper). E-filing deadline is March 31.

CRITICAL
Mid-Feb

REPS Hours Documentation Review

If claiming Real Estate Professional Status, review and finalize your 2025 hours log. Document material participation for each property.

REAL ESTATE REPS
Late Feb

Cost Segregation Studies - Order Now

Acquired property in 2025? Order cost segregation studies now to maximize depreciation deductions on your 2025 return (100% now permanent for property acquired after January 19, 2025).

COST SEG
March 2026
Mar 15

S-Corp & Partnership Tax Returns Due (Form 1120-S, 1065)

Calendar-year S-Corporations and Partnerships must file or request extension. K-1s must be issued to partners/shareholders.

CRITICAL ENTITY
Mar 15

S-Corp Election Deadline (Form 2553) - 2026 Tax Year

Last day to file S-Corp election to be treated as an S-Corporation for 2026. Critical if you're converting from LLC or sole proprietorship.

CRITICAL ENTITY
Mar 31

1099 E-Filing Deadline

Electronic filing deadline for 1099 forms with the IRS.

CRITICAL
Late Mar

Q2 Tax Planning Session

Meet with your CPA to review Q1 results, adjust estimated payments, and discuss mid-year strategies (entity structuring, REPS qualification, STR conversions).

PLANNING

🎯 Q1 Key Strategies

  • Finalize 2025 REPS documentation before filing your return
  • Order cost segregation studies for 2025 acquisitions (100% now permanent for property acquired after January 19, 2025) to maximize Year 1 deductions
  • Review entity structure for multi-property owners (LLC vs S-Corp optimization)
  • File S-Corp election by March 15 if converting from sole proprietorship or LLC for 2026
  • Consider catch-up depreciation (Form 3115) for properties acquired in prior years
Q2 2026 | April - June
April 2026
Apr 15

Individual Tax Returns Due (Form 1040)

Personal income tax returns for calendar-year taxpayers. Includes Schedule E (rental income), Schedule C (self-employment), and all real estate activity.

CRITICAL FILING
Apr 15

Q1 2026 Estimated Tax Payment Due

First quarterly estimated payment for 2026 tax year (covers Jan-Mar income).

CRITICAL PAYMENT
Apr 15

IRA & SEP Contribution Deadline

Last day to make 2025 Traditional IRA, Roth IRA, and SEP-IRA contributions.

RETIREMENT
Apr 15

Extension Filing Deadline (Form 4868)

File extension to move personal tax deadline to October 15. Payment still due by April 15.

EXTENSION
May 2026
May 15

Q1 Payroll Tax Returns (Form 941)

If you have employees, quarterly payroll tax returns are due.

PAYROLL
Mid-May

Mid-Year Tax Projection

Review YTD income and expenses. Adjust estimated payments if needed. Evaluate new property acquisitions for cost segregation opportunities (100% bonus now permanent).

PLANNING
June 2026
Jun 15

Q2 2026 Estimated Tax Payment Due

Second quarterly estimated payment for 2026 (covers Apr-May income).

CRITICAL PAYMENT
Late Jun

Mid-Year REPS Hours Check

If qualifying for REPS in 2026, review hours log to ensure you're on track for 750+ hours and >50% participation.

REPS

🎯 Q2 Key Strategies

  • Mid-year tax projection to avoid surprises and adjust estimated payments
  • Entity optimization review: Should active rental income move to S-Corp?
  • STR conversion analysis: Can you qualify under the 7-day rule?
  • 1031 exchange planning if considering property sales later this year
  • Bonus depreciation alert: 100% bonus now permanent
Q3 2026 | July - September
July 2026
Jul 31

Q2 Payroll Tax Returns (Form 941)

Quarterly payroll tax returns due for employers.

PAYROLL
Mid-Jul

Year-End Planning Kickoff

Start thinking about year-end strategies. Review property acquisition plans, cost segregation opportunities (100% bonus now permanent), and REPS hours progress.

PLANNING
August 2026
Mid-Aug

Q3 Tax Planning Session

Review Q1-Q2 results. Discuss year-end tax strategies: accelerating expenses, deferring income, property acquisitions before 12/31.

PLANNING
September 2026
Sep 15

Q3 2026 Estimated Tax Payment Due

Third quarterly estimated payment for 2026 (covers Jun-Aug income).

CRITICAL PAYMENT
Sep 15

Extended S-Corp & Partnership Returns Due

If you filed extension in March, S-Corp and Partnership returns are now due.

CRITICAL ENTITY
Late Sep

Year-End Strategy Deep Dive

Final quarter to execute year-end moves: property acquisitions, repairs vs. improvements classification, retirement contributions, charitable giving.

PLANNING

🎯 Q3 Key Strategies

  • Begin year-end tax planning conversations (don't wait until December!)
  • Evaluate property acquisitions: Can you close before 12/31 for Year 1 depreciation (100% bonus now permanent)?
  • Review REPS hours: Are you on track? Can spouse qualify?
  • Plan 1031 exchanges if selling properties in Q4
  • Consider Form 3115 catch-up for higher bonus years (2024: 60%, 2025: 40%, 100% now permanent for property acquired after January 19, 2025)
Q4 2026 | October - December
October 2026
Oct 15

Extended Individual Tax Returns Due (Form 1040)

If you filed extension in April, personal tax returns are now due. Final deadline—no further extensions available.

CRITICAL FILING
Oct 31

Q3 Payroll Tax Returns (Form 941)

Quarterly payroll tax returns due for employers.

PAYROLL
Late Oct

Year-End Tax Playbook Execution

Execute planned strategies before year-end: accelerate repairs, purchase equipment, maximize retirement contributions, harvest losses.

PLANNING
November 2026
Early Nov

Property Acquisition Deadline Planning

If acquiring property in 2026, finalize closings by 12/31 to claim Year 1 depreciation (20% bonus + cost segregation benefits).

REAL ESTATE COST SEG
Mid-Nov

Estimated Tax True-Up

Calculate Q4 estimated payment to avoid underpayment penalties. Consider making final payment early if large income spike in Q4.

PAYMENT
December 2026
Dec 15

Safe Harbor Estimated Payment Option

Make single large estimated payment by 12/15 to satisfy safe harbor rules and avoid penalties (if you haven't made quarterly payments).

PAYMENT
Dec 31

All Year-End Actions Must Be Complete

Last day for: property acquisitions (depreciation), repairs & maintenance, equipment purchases (Section 179/bonus depreciation), retirement contributions (Solo 401k, SEP), charitable contributions, loss harvesting.

CRITICAL YEAR-END
Dec 31

REPS Hours Finalization

Finalize and document all real estate hours for 2026. Ensure you meet 750+ hours and >50% participation tests.

REPS
Late Dec

2027 Planning Session

Schedule January/February meeting to review 2026 results and set 2027 strategic goals. Bonus depreciation continues to phase out (0% in 2027 unless extended).

PLANNING

🎯 Q4 Key Strategies

  • Execute year-end tax playbook: repairs, equipment, retirement contributions
  • Close property acquisitions by 12/31 to maximize Year 1 depreciation (100% bonus now permanent)
  • Finalize REPS hours documentation for the full year
  • Review entity structure for 2027 optimization (S-Corp election must be filed by March 15, 2027)
  • Order cost segregation studies for 2026 acquisitions before tax season rush
  • URGENT: Bonus depreciation ends after 2026—this may be your last chance (unless Congress extends)

🚀 Bonus: Multi-Year Planning Calendar

  • Bonus Depreciation: 100% bonus now permanent
  • REPS Qualification: Plan 5+ years ahead to maintain qualification and maximize passive loss deductions
  • Cost Segregation Catch-Up: File Form 3115 to claim missed depreciation on properties acquired in prior years
  • 1031 Exchange Timeline: 45 days to identify replacement property; 180 days to close (from sale date)
  • S-Corp Election (Form 2553): Must be filed within 75 days of entity formation OR by March 15 for current-year election
  • Estate Planning: Review entity ownership structure annually for gifting, transfers, and succession planning

DISCLAIMER

This calendar is provided for educational purposes only. Tax laws and deadlines are subject to change. Consult with a qualified tax professional for advice specific to your situation.

Strategic Planning Advisors, LLC provides tax advisory, CFO, and IRS resolution services.

Information provided on this site is for educational purposes only and does not constitute formal tax, legal, or investment advice. Please consult your advisor before making financial decisions.

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