Connecticut taxes pension income, IRA distributions, and Social Security above certain thresholds. Florida taxes none of it. Here is what that saves — and what the property tax comparison actually looks like.
Connecticut retirees face a tax picture that has improved modestly in recent years but remains meaningfully burdensome compared to Florida. Connecticut taxes pension income and IRA distributions at rates up to 6.99%, partially taxes Social Security above income thresholds, and carries property taxes that are among the highest in New England. Moving to St. Augustine eliminates the state income tax burden entirely and typically reduces property tax as well — though the exact property tax comparison depends heavily on which Connecticut town you are leaving.
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Talk to a Specialist →| Annual Taxable Retirement Income | Est. CT Tax (at ~5.5% blended) | Florida Tax | Annual Savings |
|---|---|---|---|
| $40,000 (above CT exemption threshold) | ~$2,200 | $0 | ~$2,200 |
| $60,000 | ~$3,300 | $0 | ~$3,300 |
| $80,000 | ~$4,400 | $0 | ~$4,400 |
| $100,000 | ~$5,500 | $0 | ~$5,500 |
CT buyers who fall under the income exemption thresholds — $75,000 single / $100,000 MFJ — may already be paying little or no Connecticut income tax on pension and Social Security income. For those buyers, the income tax savings from moving to Florida are smaller. For buyers above those thresholds, the combined income and Social Security tax is meaningful.
Connecticut property taxes are assessed by town and are among the highest in the country by mill rate, though assessed values are set at 70% of market value in most towns (the "assessment ratio"). Effective rates in Fairfield County, Hartford, and New Haven commonly run 1.5%–2.5% on market value. Smaller towns in Litchfield and Windham counties run lower.
| Home Value | CT Property Tax (est. 1.9% effective) | St. Johns County Year-1 Tax | Annual Savings |
|---|---|---|---|
| $375,000 | $7,125 | $4,385 | $2,740 |
| $450,000 | $8,550 | $5,388 | $3,162 |
| $550,000 | $10,450 | $6,735 | $3,715 |
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| Savings Category | Annual | 10-Year Total |
|---|---|---|
| Income tax (on $65K taxable retirement income) | ~$3,575 | ~$35,750 |
| Property tax savings (on $450K home) | ~$3,162 | ~$31,620 (grows as CT taxes rise) |
| Combined estimate | ~$6,737 | ~$67,370 |
This is before accounting for community-specific CDD fees in St. Augustine. At Reverie at Silverleaf (no CDD), the 10-year savings hold. At Parkland Preserve (CDD $23,900–$39,240 over 10 years), the net savings narrow but remain positive in most scenarios.
Connecticut buyers — particularly from Fairfield County, Hartford suburbs, and the shore communities — tend to expect quality finishes, active community programming, and cultural access. The historic character of St. Augustine resonates with buyers from historically dense New England towns. Drive time to Jacksonville International from St. Johns County communities is 30–35 minutes, with nonstop service to Bradley/Hartford and regular connections to all New England airports.
Reverie at Silverleaf — transparent cost structure, active new construction. WaterSong at RiverTown — community scale and waterfront character that translates well for buyers leaving Connecticut shore towns.
CT buyers above the income exemption thresholds see some of the strongest combined income + property tax savings in this market. An agent can help you run the full comparison for your specific situation.
Connect with a Local Agent →CT income tax rates 2025: 3.0%–6.99%. Pension and Social Security exemption thresholds from CT DRS — verify current limits at portal.ct.gov/DRS. Property tax effective rates approximate — vary significantly by town. St. Johns County millage 13.47 mills. Consult a CPA for your specific situation. This page is for research purposes only.
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