Massachusetts to Florida
By Dewey Kopenga and Travis Penny. updated June 2026
TL;DR
Massachusetts taxes retirement income at 5%, and the 4% surtax on income above $1 million can hit one-time events like a home sale. Florida zeroes that out and removes Massachusetts's estate tax, which has one of the lowest exemptions in the country. Add milder winters and the case is strong.
MA income tax
5% flat (+4% over $1M)
Florida income tax
0%
MA estate tax
Yes, $2M exemption (FL: none)
Drive from Boston
~1,300 mi (2 to 3 days)
Massachusetts applies its 5% flat tax to most retirement income, and the voter-approved 4% surtax on income over $1 million can catch a big capital gain from selling a long-held home. Florida charges nothing on income. Just as important, Massachusetts has a state estate tax with only a $2 million exemption, so many ordinary estates owe; Florida has none.
New England winters are long and icy. Sun City Center offers winter highs in the 60s and 70s with year-round golf, pools, and clubs in a true 55+ community.
Medicare transfers cleanly. Switch Medicare Advantage during open enrollment to a Florida plan. HCA Florida South Bay Hospital serves Sun City Center, with Tampa General and Moffitt nearby.
Frequently Asked
Start your move
Tell us a bit about your timeline and we'll put together a Massachusetts-to-Sun City Center plan. Dewey and Travis both get a copy.
Ready when you are
One 30-minute call covers property strategy and financing. Dewey and Travis on the line together.
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