Connecticut taxes retirement income and has some of the highest property taxes in the country. Florida taxes neither. Here's what that actually means in dollars for CT retirees.
Connecticut retirees moving to Sun City Center are typically coming from one of the highest tax environments in the country. Connecticut taxes most retirement income, levies an estate tax, and carries some of the highest property tax rates in the Northeast. The financial case for Florida is among the clearest of any state — but the details matter, particularly around CT's phased retirement income exemptions.
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Talk to a Specialist →Connecticut has a graduated income tax with rates from 3% to 6.99%. It taxes most retirement income, though it has partial exemptions for Social Security and pensions that phase in based on income level.
| Income Source | Connecticut Treatment | Florida Treatment |
|---|---|---|
| Social Security | Exempt if income below $75K (single) / $100K (joint); taxed above those thresholds | No state tax |
| CT state / local pension | Exempt for most state employees | No state tax |
| Federal / military pension | Exempt | No state tax |
| Private pension / annuity | Taxed; 50% exemption for income under $75K (single) / $100K (joint) | No state tax |
| IRA / 401(k) distributions | Taxed at graduated rates | No state tax |
| Investment income | Taxed at graduated rates | No state tax |
Connecticut has the third-highest effective property tax rate in the country. Fairfield County (Greenwich, Westport, Darien, New Canaan, Stamford) carries extraordinarily high home values and significant tax bills. But even Hartford, New Haven, and mid-state communities pay rates well above Florida's Hillsborough County.
| Connecticut Market | Home Value | Annual Tax (est.) | Hillsborough FL (w/ homestead) |
|---|---|---|---|
| Fairfield County (Westport, Darien) | $1,100,000 | ~$19,800 (1.8%) | ~$4,475 on $340K FL home |
| Fairfield County (Stamford) | $650,000 | ~$11,700 (1.8%) | ~$4,475 on $340K FL home |
| Hartford County suburbs | $380,000 | ~$7,980 (2.1%) | ~$3,850 on $300K FL home |
| New Haven County | $340,000 | ~$7,140 (2.1%) | ~$3,850 on $300K FL home |
A Fairfield County retiree paying $19,800/year in property taxes who purchases a $340,000 Sun City Center home pays $4,475/year with homestead — a savings of $15,325 per year on property taxes alone. Over 20 years, that's more than $300,000, even without accounting for investment of the difference.
Connecticut levies an estate tax on estates over $13.61 million (as of 2024), with a top rate of 12%. Florida has no estate tax. For CT retirees with significant assets — real estate, investment portfolios, business interests — establishing Florida domicile before death eliminates Connecticut estate tax exposure on worldwide assets. This is a planning consideration worth discussing with an estate attorney during the move process.
Fairfield County, Connecticut is one of the wealthiest counties in the country. Home values in Greenwich, Darien, New Canaan, Westport, and Wilton commonly exceed $1 million. Even more modest Stamford and Norwalk homes have appreciated dramatically. CT retirees are often working with some of the largest equity positions of any group moving to Sun City Center.
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