Daperis CPASelling a Home and Leaving New York: A Client's Move to Florida
The situation
A longtime New York homeowner decided to relocate to Florida, selling their primary residence as part of the move. They were a former NYC school teacher and like many, decided they wanted to move south for retirement. On the surface, it looked simple: sell the house, move, done. In practice, three separate tax questions were riding on getting this right.
The problem
First, the home sale itself. The client qualified for the Section 121 exclusion on the sale of a primary residence, but qualifying isn't automatic. It has to be confirmed: ownership and use tests met, gain calculated correctly, exclusion applied properly.
Second, the year of the move was a part-year tax year, which meant every dollar of income (wages, interest, dividends, whatever else was in play) had to be allocated to either the New York-resident period or the Florida-resident period. Get this wrong and you either overpay New York or underpay it, and New York does not forgive the second one quietly.
Third, and by far the hardest part: proving the move was real. New York taxes high earners aggressively when they leave for a no-income-tax state, and residency isn't a checklist, it's a case you build. Switching a driver's license or joining a gym in Florida doesn't settle it on its own. No single action does. New York looks at the whole pattern: where you actually live your life, where your doctor is, where you bank, how your days are actually spent. If that pattern doesn't hold together, New York can still tax you as a resident no matter what your paperwork says. And "no income tax" is only one part of the real comparison. It doesn't automatically mean cheaper. Sales tax, property tax, and cost of living all factor into what a move actually saves, which is really its own conversation.
What we did
We confirmed the home sale qualified cleanly for the exclusion and filed it correctly. We allocated the client's income between their New York-resident period and their Florida-resident period, matching each income type to the correct state and the correct dates. We made sure the client understood, before the move, not after, what actually establishing Florida residency required, so their day-to-day life matched the return they'd eventually file.
The result
A clean part-year return, a properly excluded home sale, and a residency position built to hold up if New York ever looked at it, not assembled after the fact.
Keep It Simple / Key Takeaway 🍕
Leaving New York for tax purposes isn't about the paperwork you file when you go, it's about whether your actual life matches that paperwork. Build the case while you're living it, not after New York comes asking.
Client details have been changed to protect confidentiality. Some of these case studies are composites drawn from more than one engagement. Every situation is different, and the results described here are not a guarantee of similar outcomes.