Sentinel Tax — CPA Tax Services for Retirees
Bonita Springs & Naples, Florida

Tax Planning
Built for
Retirement.

A year-round CPA relationship — proactive planning in the fall, professional tax preparation in the spring — all for a flat annual fee.

20+
Years of CPA Experience
CPA/PFS
Certified in Tax & Financial Planning
$749
All-inclusive Annual Fee
The Retirement Tax Plan
Annual Tax Package
$749
/ year — everything included
  • Fall Tax Planning Meeting — review income, Roth opportunities, and year-end moves before it's too late to act
  • Federal Tax Return Preparation — investment income, Social Security, itemized deductions, prepared by a CPA
  • State Tax Return — including your home state up north if applicable
  • Year-round CPA access — questions, estimated taxes, life changes
  • Secure document storage — your returns on file for 7 years
Get Started — Schedule a Free Call

No business returns required. Designed for personal retirement tax situations.

Is This Right for You?

Built for Retirees with Real Assets
and Real Tax Questions

If you've built a portfolio of $1 million or more, your tax situation in retirement is more complex than most people realize — and more full of opportunity than most CPAs take the time to find.

You're managing RMDs, investment distributions, Social Security income, and potentially a second home or seasonal residency. The decisions you make — and when you make them — have a meaningful impact on what you keep.

Sentinel Tax is a small, focused CPA firm in Bonita Springs designed specifically for retirees in this situation. We don't do bookkeeping or payroll. We do one thing: help retirees pay less tax through better planning.

Investment Portfolio Income Social Security Required Minimum Distributions Itemized Deductions Seasonal Florida Residents Multi-state Returns
🏦
$1M+ Investment Portfolio
You have a meaningful portfolio generating dividends, capital gains, and distributions. How and when you take income affects your tax bracket, Medicare premiums, and future flexibility.
📋
Itemized Deductions
Charitable giving, property taxes, mortgage interest — we'll make sure every deduction is captured.
🌎
Multi-State Situation
A home in the north and winters in Southwest Florida. We handle both states so nothing falls through the cracks.
The Annual Process

Two Key Moments.
Year-Round Relationship.

Most CPAs only talk to you in March or April. That's too late to change anything. Our model is built around working with you before year-end, when you can still act.

September — November

Fall Tax Planning Meeting

Before the year closes, we sit down together — virtually or in person here in Bonita Springs — to review your income picture and identify every available opportunity to reduce your tax bill before December 31st.

  • Review estimated income and projected tax liability
  • Identify Roth conversion opportunities in your current bracket
  • Time capital gains and losses strategically
  • Plan charitable giving (QCDs from IRA if applicable)
  • Review estimated tax payments and avoid penalties
  • IRMAA planning — protect your Medicare premiums for next year
February — April

Spring Tax Return Preparation

When your tax documents arrive, we take it from there. Your return is prepared by a CPA — not outsourced, not automated — with a thorough review to make sure everything from the fall plan was executed correctly.

  • Federal return: all investment income and Social Security
  • Itemized deductions reviewed and maximized
  • State return — Florida and your home state if needed
  • E-file with direct deposit for any refund
  • Secure storage of your completed return for 7 years
  • Review and set up next year's estimated tax payments
Why Proactive Planning Matters

Most Retirees Are Leaving
Real Money on the Table

A reactive CPA files your taxes accurately. A proactive one helps you pay significantly less — by identifying opportunities that disappear when the calendar turns.

🔄

Roth Conversion Windows

Early retirement — before Social Security and RMDs kick in — often creates a window to convert traditional IRA funds to Roth at historically low rates. Miss the window and it's gone.

🏥

IRMAA & Medicare Premiums

A single year of higher income can trigger a Medicare surcharge that costs thousands in extra premiums two years later. We plan around the thresholds before they become a problem.

📈

Capital Gains Timing

When you sell, how much you sell, and in which tax year are all choices. Strategic sequencing can keep you in the 0% long-term capital gains bracket — but only with advance planning.

🎁

Qualified Charitable Distributions

If you're over 70½ and charitably inclined, giving directly from your IRA can satisfy your RMD without increasing your taxable income — a meaningful tax advantage most taxpayers miss.

📅

RMD Planning

Required Minimum Distributions add to your taxable income whether you need the money or not. We help you plan around them — or use them wisely — before they start pushing you into higher brackets.

⚖️

Tax Bracket Management

Retirement gives you more control over your income than you may realize. We help you fill your bracket intentionally — taking just enough income each year to minimize taxes over your lifetime.

Seasonal Residents Welcome

Here for the Winter.
We'll Handle the Rest.

If you spend October through May in Southwest Florida, you're in the right place at the right time — and working with a local CPA while you're here just makes sense.

We're in Bonita Springs, minutes from Naples, and happy to meet in person during the season. During the summer months, we stay connected virtually — so your tax plan doesn't take a vacation when you head north.

We can also handle your home state return, so there's no need to juggle two accountants in two states.

Bonita Springs, FL Naples, FL Virtual — Year Round
October
Season Begins — You Arrive in Florida
Great time to schedule your fall planning meeting in person
Oct — Nov
Fall Tax Planning Meeting
Review year-end strategy, Roth opportunities, estimated taxes
December 31
Year-End Deadline
Last day for Roth conversions, charitable gifts, tax-loss harvesting
Feb — April
Spring Tax Preparation
We prepare and file your federal and state returns — you're still here for the season
May — September
Summer — You Head North
We stay in touch virtually. Questions, estimated payments, changes in circumstance — we're here
About Sentinel Tax

A CPA Who Has Spent 20 Years
Finding What Others Miss

I'm Chris, a CPA and Personal Financial Specialist based in Bonita Springs. After spending two decades helping business owners build and protect what they've earned, I've shifted my focus to what I find most meaningful — helping retirees keep more of what they've worked a lifetime to accumulate.

Most retirees I meet are working with a CPA who does an accurate job of filing their taxes. Accurate is fine. But in retirement, there are planning decisions — made before December 31st — that can save thousands of dollars a year. Those decisions don't happen in April; they happen in the fall. That's what we're here for.

Sentinel Tax is deliberately focused. We don't do bookkeeping, payroll, or business returns. We work exclusively with retirees and pre-retirees who have meaningful assets and want a CPA who thinks ahead alongside them — not just behind them.

Our office is in Bonita Springs, and we serve clients throughout the Naples area and beyond. For snowbirds, we're easy to meet in person during the season — and we stay connected virtually the rest of the year.

CPA PFS — Personal Financial Specialist 20+ Years Experience Bonita Springs, FL
Ready to Get Started?

A Free 20-Minute Call.
No Obligation. No Pressure.

We'll spend a few minutes getting to know your situation — your income sources, your goals, and whether our annual package is a good fit. If it is, we'll walk you through exactly how the process works and get you set up.

Schedule Your Free Intro Call →

Already have a CPA? Many clients switch to us after realizing how much proactive planning they've been missing.