As 2025 winds down, most people start prepping for the holidays. But if you’re a Massachusetts business owner, freelancer, or high-earning individual, Q4 is tax season in disguise.
From state sales tax filings to estimated corporate payments and last-minute deductions, October through December is packed with essential tax deadlines. Miss one, and you could face steep penalties or lose out on strategic opportunities to lower your tax bill.
This guide covers the key Massachusetts tax deadlines in Q4 2025—and how to stay ahead with help from a proactive, strategic CPA team.
October 2025: Extended Returns and Payroll Reporting
October 15 – Final Deadline for Extended Individual Tax Returns
If you filed for an extension back in April, this is your final chance to file your 2024 federal and Massachusetts state tax returns. It’s non-negotiable.
This applies to individuals with:
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Complex investment or business income
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Delayed K-1s or 1099s
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Dual federal and state filing obligations
Tip: A CPA review at this stage can help identify any final tax-saving moves and ensure accuracy—especially if there have been changes since April.
October 31 – Q3 Payroll Filings
If you have employees, you’re required to file:
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Federal Form 941 (for withheld payroll taxes)
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Massachusetts Form M-941 (if you’re a quarterly state filer)
This deadline covers payroll taxes like Social Security, Medicare, and income tax withholdings. Missing it can result in penalties and additional scrutiny, which is why many clients choose to automate this process using payroll systems like Gusto—fully supported by our CPA team.
November 2025: Quiet but Critical
November 20 – Monthly Sales, Meals, and Room Tax Returns
Businesses with monthly filing obligations must submit their October sales tax returns by this date. This applies to:
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Restaurants and cafés (Meals Tax)
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Retailers selling taxable goods (Sales/Use Tax)
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Hotels or short-term rental operators (Room Occupancy Tax)
Even if you had little or no sales, Massachusetts still expects a return. Penalties can be assessed just for missing the filing—even if nothing is owed.
If you’re unsure whether your business is on a monthly or quarterly filing schedule, we can confirm your status with the DOR and help ensure you stay compliant.
December 2025: Final Payments and Strategic Planning
December 15 – Q4 Corporate Estimated Tax Payments
C-Corps and certain S-Corps operating on a calendar year must submit their final 2025 estimated payment by this date.
This is critical to:
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Avoid underpayment penalties
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Align your cash flow with upcoming tax obligations
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Manage your corporate tax liability before the year closes
If you’re unsure how much to pay, our Virtual CFO services offer accurate forecasting tools that eliminate guesswork and optimize your tax position.
December 31 – Deadline for Year-End Tax Strategies
This is the final day to make any financial moves that will affect your 2025 tax return. Smart year-end strategies may include:
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Purchasing eligible business equipment for a Section 179 deduction
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Distributing bonuses or making owner draws
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Making charitable contributions
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Funding employer-side retirement plans (e.g., SEP IRA or profit-sharing)
If you wait until January, those opportunities are gone. Year-end tax planning with a CPA ensures you don’t leave money on the table.
Ongoing Monthly and Quarterly Filing Reminders
If you’re a Massachusetts business owner, you’re likely responsible for at least one of these:
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Sales/Use tax returns (due by the 20th of each month if filing monthly)
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Meals tax filings (same schedule as sales tax)
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Withholding returns (due monthly or quarterly, depending on your DOR-assigned frequency)
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Federal Form 941 for payroll tax (filed quarterly)
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Massachusetts M-941 (filed quarterly for most employers)
Not sure what your filing frequency is? We routinely audit and adjust client filing statuses to match their revenue and compliance history. Staying aligned reduces risk and simplifies workflow.
How to Stay Ahead Without the Stress
Juggling client work, internal projects, and family obligations during Q4 can make it easy for tax obligations to slip through the cracks. But the penalties and missed planning opportunities add up fast.
That’s why so many of our clients rely on Peter Witts CPA for:
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Monthly and quarterly filing support
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Tax planning and entity-specific guidance
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DCAA-compliant services for government contractors
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Integrated tools like QuickBooks Online and Gusto for real-time insights
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Virtual CFO oversight for strategic forecasting and planning
We’ll even provide you with a custom 2025 tax deadline tracker so your business stays one step ahead every month.
Don’t Wait Until It’s Too Late
If you’re making year-end decisions the week after Christmas, you’ve already missed your window. Smart businesses plan in advance—and we’re here to help you do just that.
Schedule your year-end tax review with Peter Witts CPA before December 10 to ensure all your filings are on time and your strategy is optimized.
Because the best way to close the year strong is by planning ahead—while there’s still time to make it count.