A CPA for The Villages.
Retirement tax planning, RMDs, Roth conversions, Social Security, IRMAA, and monthly bookkeeping for the businesses that serve America’s largest retirement community. Mount Dora-based, about 35 minutes via US 441. Florida-licensed CPA. Books and return, year-round.
The Villages at a glance
America’s largest retirement community, and a serious small-business economy.
The Villages is a master-planned, age-restricted community spanning Sumter, Lake, and Marion counties 79,077 residents in the CDP at the 2020 census and one of the fastest-growing metro areas in the country, famous for its golf-cart road network and the nightly life of its town squares. The median age is 73.2 and 84.7% of residents are 65 or older, which makes this the densest concentration of retirement-tax questions in America, and the businesses serving those residents form an economy of their own.
79,077
CDP Residents (2020)
73.2
Median Age
3
Counties
84.7%
Age 65+
Accounting services
For the household planning its RMDs, and the golf-cart shop that keeps the community moving.
Two very different clients live at the same address here: retirees whose tax picture is distributions, brokerage accounts, and Medicare brackets, and the owners of the service businesses this community runs on. I work with both.
Retirement tax planning
Plan the year, not just the return.
RMD timing, Roth conversion windows, Social Security taxation, IRMAA-aware Medicare planning, qualified charitable distributions, and estate-and-gifting strategy, decided before December 31, when they still count.
Tax preparation
Retirement returns done right.
1099-Rs, brokerage consolidated statements, K-1s, rental schedules, part-year state returns for the moving year, prepared and signed by a licensed CPA.
Monthly bookkeeping
For Villages-area businesses.
Golf-cart sales and service, home services, landscaping, medical vendors, restaurants near the squares, CPA-managed books, with the same firm on the return. Scoped to your operation on a discovery call.
The short answer
I’m a Florida CPA serving The Villages from my Mount Dora office, about 35 minutes southeast via US 441. I handle retirement returns, year-round tax planning, and bookkeeping for the businesses that serve the community. Every engagement is custom-built, scoped on a discovery call. Secure portal for the paperwork; a short drive when you’d rather talk in person.
Why local matters
Four things The Villages gets wrong at tax time.
84.7% of residents are 65+
The most concentrated retirement-tax market in America.
Median age 73.2. That means the tax questions here aren't payroll and inventory. They're RMD timing, Roth conversion windows, Social Security taxation, IRMAA cliffs, qualified charitable distributions, and estate strategy. This is planning work, and it pays for itself when it's done before December 31, not after.
Sumter · Lake · Marion
One community, three counties.
The Villages CDP spans three counties, and the Lake County corner is my home county. Property appraisers, tax collectors, homestead filings, and local rates all change at lines most residents never notice until a filing goes to the wrong office. I keep the addresses, exemptions, and county filings straight.
The business ecosystem
Eighty thousand residents need a lot of service businesses.
Golf-cart dealers and service shops, home-services companies, landscapers, medical and home-health vendors, restaurants and retail around the town squares, The Villages supports a dense ecosystem of recurring-revenue small businesses. Those are precisely the operations where a monthly CPA close beats a year-end scramble.
35 minutes via US 441
Close enough to shake hands. Remote enough to be easy.
My office is in Mount Dora, about 35 minutes southeast through Leesburg and Lady Lake. The secure portal handles documents, dashboards, and signatures; the drive handles the first meeting or the complicated conversation. You get a local CPA without leaving the bubble more than you want to.
Rooted in the tri-county area
Built around town squares and cart paths.
The town squares
Spanish Springs, Lake Sumter Landing, and Brownwood Paddock Square anchor the community’s daily life, nightly entertainment, restaurants, and the retail rows that make up a real Main Street economy, three times over.
The golf-cart economy
An entire road network built for golf carts, and with it, an industry: cart dealers, customizers, battery and service shops, and the home-services businesses that navigate the same paths. Recurring-revenue operations that deserve monthly books.
Still growing
Repeatedly among the fastest-growing metro areas in the United States, with new villages pushing south into Sumter County. Every expansion bringing new residents with moving-year tax questions and new businesses to serve them.
What makes me different
Most area firms still run on paper. I built something different.
Most accounting offices in the area still operate on paper forms, phone calls, and once-a-year check-ins. I built a modern platform from scratch, and I use it with every client.
Secure client portal
Upload, view, track, from anywhere.
Documents, reports, and real-time financials accessible from any device. No email attachments, no fax machines, no lost paperwork.
Bank integrations
Transactions sync automatically.
Plaid-powered connections pull transactions nightly, so business books stay current without a shoebox of receipts or a manual data-entry pass at year-end.
Real-time dashboards
See your numbers whenever you want.
P&L, cash flow, and expense breakdowns available any day of the month, not just when I send a PDF. Curious in the middle of July? Log in.
Free financial tools
Calculators for the questions you ask yourself.
S-Corp savings, quarterly estimated tax, 1099 vs W-2 comparison, all free, no signup required. Run the numbers before you call me.
No other CPA firm serving The Villages combines this caliber of CPA work with this level of modern client tooling.
Services & pricing
Custom engagements, priced on a call.
Book a discovery call and I’ll quote your situation on the phone, or explore the core services below.
Every engagement
Custom-built
scoped on your discovery call
Retirement taxes in The Villages
The expensive mistakes here happen in November, not April.
A Roth conversion that should have happened in a low-income year, an RMD taken without charitable planning, an income spike that tripped an IRMAA bracket and raised two years of Medicare premiums, by the time those show up on a return, the window to fix them closed on December 31. Planning is the product; the return is the receipt.
That’s why I work year-round rather than just at filing time. Start with the tax services page or run the free calculators to see where you stand.
“We needed our taxes completed on a very tight timeline, and he delivered an incredibly fast turnaround without sacrificing accuracy or professionalism. We travel full-time, and Timothy went out of his way to meet us and personally pick up our documents.”
Shonda DePue, Google Review
Questions I hear from The Villages
Frequently asked questions.
Do you do retirement tax planning for The Villages?
Yes. It's core work for me, not a sideline. Required minimum distributions, Roth conversion windows in the years before RMDs begin, Social Security taxation, IRMAA brackets that quietly raise Medicare premiums when income crosses a threshold, qualified charitable distributions, and estate-and-gifting strategy. I plan those moves with you across the year, not just file the result in April.
How much does a CPA cost in The Villages?
I scope each return individually. A retirement return with brokerage activity, K-1s, or rental property is a different job from a plain 1040, and the engagement should reflect that. Book a discovery call at timcpa.com/contact and I'll walk you through what the engagement would look like.
Do you come to The Villages, or is everything remote?
Both work. My office is in Mount Dora, about 35 minutes southeast via US 441 through Leesburg and Lady Lake. Most clients run everything through my secure portal, upload documents from the lanai, see the return before signing, pay online. When a face-to-face meeting matters, the drive is short.
The Villages spans three counties, does that change my taxes?
Your federal return doesn't care which county you're in, but plenty of practical things do: Sumter, Lake, and Marion counties each have their own property appraiser, tax collector, homestead filing, and local rates. When you move within The Villages or own property across the lines, I make sure the homestead exemption, the tangible-tax filings, and the addresses on every return line up correctly.
I run a business that serves The Villages, do you handle bookkeeping?
Yes. The businesses serving this community, golf-cart sales and service, home services, landscaping, medical and home-health vendors, restaurants near the squares, are exactly the recurring-revenue operations that benefit from a monthly CPA close. The same firm keeps the books and files the business return, and the engagement is scoped on a discovery call.
We just moved to The Villages from up north, what changes on our taxes?
Usually a lot, in your favor. Florida has no state income tax, but the moving year takes care: establishing Florida domicile properly (declaration of domicile, driver license, voter registration, homestead), filing the final part-year return in your old state, and re-checking withholding and estimated payments against the new picture. I handle the transition year and the cleaner years after it.
What's the difference between a bookkeeper and a CPA in The Villages?
A bookkeeper records and categorizes transactions; a Certified Public Accountant (CPA) is a state-licensed accountant who can also sign tax returns, represent you before the IRS, and provide tax strategy. For a Villages-area business, my clients get one continuous engagement, the same license (#AC62625) on the ledger and on the return.
Do I still need to pay quarterly estimated taxes in retirement?
Often, yes, retirement income rarely has enough withholding by default. IRA distributions, brokerage gains, and Social Security can add up to a balance due plus an underpayment penalty if nothing is paid in during the year. I set a safe-harbor plan: either withholding on the IRA distributions (often the cleanest fix) or quarterly estimates sized to your actual picture.
Ready for a CPA who plans the year, not just the return?
Book a discovery call and we’ll plan the year together. If I’m not the right fit, I’ll say so, and point you somewhere better.
Tim
More reading
Still earning self-employment income in retirement? Compare retirement plans in Solo 401(k) vs SEP IRA and see how estimated payments work in my quarterly estimated tax guide.
Curious about costs? Read my complete guide: How Much Does a CPA Cost?
Nearby? I also have a page for Leesburg.