Everyone talks about New Jersey and New York buyers moving to Florida.
But here's what the relocation data is quietly showing: Connecticut and Massachusetts residents are leaving at some of the highest rates in the Northeast — and a growing number of them are landing in St. Johns County, Florida.
Fairfield County, CT. The Boston suburbs. The North Shore. MetroWest. These are high-earning, highly educated households who have spent decades building wealth — and are now asking a very simple question:
Why am I paying this much to live here?
This post answers that question with real numbers. Not estimates pulled from a generic cost-of-living website. Actual line-by-line comparisons that show what your Connecticut or Massachusetts dollar buys in St. Johns County — and what it's been costing you to stay.
The Big Picture First
According to 2025–2026 data from the Council for Community and Economic Research and the MIT Living Wage Calculator:
- Fairfield County, CT cost of living index: 148 (48% above national average)
- Greater Boston / Middlesex County, MA: 162 (62% above national average)
- St. Johns County, FL: 103 (just 3% above national average)
A household spending $130,000 per year in Fairfield County can maintain the same standard of living in St. Johns County for approximately $90,000. That's $40,000 back in your household every single year — before we even touch state income taxes.
In Boston's suburbs, that same gap is even wider.
STATE INCOME TAX: Where It Starts
Connecticut: CT has a state income tax with rates ranging from 3% to 6.99% on income over $500,000. For a household earning $150,000, expect to pay approximately $7,200–$8,800 in Connecticut state income taxes annually.
Massachusetts: MA has a flat income tax rate of 5% across all income — plus a new 4% surtax on income above $1 million (the "Millionaires Tax" passed in 2022). For a $150,000 household, annual MA state income tax: approximately $7,500.
Florida / St. Johns County: State income tax: $0. Always. On wages, salaries, bonuses, investment income, pension distributions, and Social Security.
Annual income tax savings for a $150K household: Moving from CT: $7,200–$8,800/year Moving from MA: $7,500/year
Over 10 years — before any investment growth — that's $72,000–$88,000 that stays in your family instead of going to Hartford or Boston.
PROPERTY TAXES: The Line Item That Changes Everything
This is the comparison that stops Connecticut and Massachusetts buyers cold — because both states carry some of the heaviest property tax burdens in the country.
On a $650,000 home:
| Location | Effective Tax Rate | Annual Property Tax |
|---|---|---|
| Fairfield County, CT | 1.83% | $11,895 |
| Middlesex County, MA (Boston suburbs) | 1.12% | $7,280 |
| Hartford County, CT | 2.20% | $14,300 |
| St. Johns County, FL | 0.86% | $5,590 |
| St. Johns County + Homestead Exemption | — | ~$5,040 |
Moving from Fairfield County to St. Johns County on a comparable home saves you $6,855 per year in property taxes alone.
Moving from Hartford County — one of the highest-taxed areas in the entire Northeast — the savings jump to over $9,000 per year.
And unlike Connecticut and Massachusetts, Florida's Save Our Homes cap limits your annual assessment increase to 3% or the rate of inflation — whichever is lower. Your tax bill cannot spiral the way it does in CT and MA when municipalities raise rates or reassessments come through.
WHAT DOES $650,000 BUY YOU?
This is the question that makes the comparison visceral.
$650,000 in Fairfield County, CT: A 3–4 bedroom colonial or cape, typically 1,800–2,400 sq ft, built in the 1970s–1990s. Older systems. Modest lot. Annual property taxes of $11,000–$14,000. Brutal winters. Likely a commuter-town location with highway dependence.
$650,000 in the Boston suburbs (Middlesex or Norfolk County, MA): A 3-bedroom ranch or split-level, approximately 1,600–2,200 sq ft. Tight lots. Aging infrastructure. Annual property taxes of $7,000–$9,000. Snow removal. High utility costs. Congested commutes.
$650,000 in St. Johns County, FL (Nocatee, Ponte Vedra, or St. Augustine area): A brand-new or near-new 4-bedroom, 3-bath single-family home. 2,400–3,200 sq ft. Open floor plan. Modern kitchen. Screened lanai or pool-ready backyard. Two-car garage. Located in a master-planned community with resort pools, fitness centers, pickleball courts, and miles of walking trails. Annual property taxes of $5,000–$5,800. HOA covering landscaping: $150–$350/month.
Same budget. Roughly 800–1,000 more square feet. A newer home. Lower taxes. A community designed around living well.
GROCERIES & EVERYDAY EXPENSES
The gap in daily spending is real and consistent.
| Item | Fairfield Co., CT | Greater Boston, MA | St. Johns Co., FL |
|---|---|---|---|
| Gallon of milk | $4.80–$6.20 | $4.60–$5.80 | $3.20–$3.80 |
| Dozen eggs | $5.20–$7.00 | $5.00–$6.80 | $3.50–$4.50 |
| Dinner for two, mid-range | $110–$170 | $100–$160 | $55–$90 |
| Monthly groceries (couple) | $950–$1,350 | $900–$1,250 | $550–$760 |
| Gas per gallon | $3.60–$4.30 | $3.50–$4.20 | $3.00–$3.40 |
| Monthly utilities (3BR home) | $280–$420 | $260–$400 | $160–$250 |
Monthly grocery and daily expense savings for a couple relocating from CT or MA to St. Johns County: approximately $350–$600/month — or $4,200–$7,200 per year.
HEALTHCARE COSTS
For retirees or near-retirees, this one matters enormously.
Medicare Supplement Plan G (monthly premium, per person):
- Connecticut: $195–$275
- Massachusetts: $210–$295 (MA has unique insurance regulations that often push premiums higher)
- St. Johns County, FL: $115–$168
Annual healthcare premium savings for a retired couple: Moving from CT: $1,920–$2,568/year Moving from MA: $2,280–$3,048/year
Same Plan G coverage. Same benefits. Simply a different state's insurance market — and Florida's competitive market drives premiums significantly lower.
CAR INSURANCE AND HOME INSURANCE: The Honest Numbers
Florida does cost more in these two categories — and any honest comparison has to say so.
Car insurance (two cars, clean record, couple): Connecticut: $2,400–$3,200/year Massachusetts: $2,600–$3,400/year St. Johns County, FL: $3,000–$4,400/year
Florida's car insurance runs $400–$1,200 more per year than CT or MA. Budget for it.
Home insurance: Connecticut ($650K older home): $1,800–$2,800/year Massachusetts ($650K older home): $2,000–$3,000/year St. Johns County ($650K new construction, non-coastal): $3,200–$5,200/year
Florida home insurance is higher — no sugarcoating it. New construction in a non-coastal St. Johns County community insures better than older coastal or flood-zone properties. An independent insurance broker who shops multiple Florida carriers is essential. Budget approximately $1,500–$2,500 more per year than what you paid in CT or MA.
THE COMPLETE ANNUAL SAVINGS PICTURE
For a household earning $150,000 moving from Fairfield County, CT to St. Johns County:
| Category | Annual Savings |
|---|---|
| State income tax | +$8,000 |
| Property taxes | +$6,855 |
| Groceries & daily expenses | +$5,400 |
| Healthcare premiums (retired couple) | +$2,200 |
| Car insurance | -$800 |
| Home insurance | -$2,000 |
| Net Annual Savings | $19,655 |
For a household earning $150,000 moving from Greater Boston, MA to St. Johns County:
| Category | Annual Savings |
|---|---|
| State income tax | +$7,500 |
| Property taxes | +$2,240 |
| Groceries & daily expenses | +$5,000 |
| Healthcare premiums (retired couple) | +$2,664 |
| Car insurance | -$700 |
| Home insurance | -$1,800 |
| Net Annual Savings | $14,904 |
Over 10 years: CT household saves approximately $196,000 MA household saves approximately $149,000
These are conservative estimates. They do not include investment growth on what you didn't spend, the equity typically freed up by right-sizing from a Northeast home to a Florida home, or the estate and inheritance tax advantages of Florida domicile.
THE CONNECTICUT EXIT TAX: One More Number
Connecticut homeowners planning to sell and leave should be aware of one additional cost: Connecticut imposes a real estate conveyance tax at the state and municipal level. On a $650,000 home sale, expect to pay approximately $8,000–$12,000 in Connecticut conveyance taxes at closing — before you even leave the state.
Florida has no equivalent exit tax. No real estate transfer tax at the state level. Your sale proceeds move with you.
WHY ST. JOHNS COUNTY SPECIFICALLY?
Connecticut and Massachusetts buyers tend to arrive with high standards — for schools, community quality, safety, and infrastructure. St. Johns County meets every one of them:
- Schools: #1 ranked school district in Florida by the Florida Department of Education. 95% of schools rated A or B. Graduation rates above 94%. For families with children, the academic quality is genuinely comparable to top CT and MA public school districts — at a fraction of the property tax cost.
- Safety: St. Johns County ranks consistently in the top 10 safest counties in Florida. The county's communities are well-maintained, well-lit, and actively managed.
- Infrastructure: Master-planned communities like Nocatee, RiverTown, Palencia, and the Del Webb communities were built in the last 10–20 years. The roads are new. The amenities are new. The utilities are new. You're not inheriting aging infrastructure the way you often do in established CT and MA towns.
- Proximity: Jacksonville International Airport offers direct flights to Boston, New York, Chicago, and Washington D.C. Staying connected to family and colleagues in the Northeast is genuinely manageable from St. Johns County.
- The lifestyle: Beaches, golf, boating, nature preserves, world-class dining, and a calendar of outdoor activities that functions year-round. From October through April, St. Johns County weather is something Connecticut and Massachusetts residents simply don't have a comparison for.
The Bottom Line
Connecticut and Massachusetts residents are among the most financially sophisticated households in the country. They run the numbers carefully before making major decisions.
So here are the numbers, plainly:
A $150,000 household moving from Fairfield County saves approximately $19,600 per year in St. Johns County. A Boston suburb household saves approximately $14,900 per year. Both savings persist and compound every year — for as long as you live here.
The weather gets better. The space gets bigger. The schools stay excellent. And the tax bill gets dramatically smaller.
The only question is how many more years you're willing to pay the Northeast premium before making the move.
Want to See What Your Specific Numbers Look Like?
Every household is different — your income sources, your home value, your retirement timeline all affect the real savings figure for your situation. I work with CT and MA relocating buyers regularly and can connect you with a local CPA to run your actual numbers.
No pressure. No pitch. Just the math.
Call or text Gail DeMarco: 904-640-8000 St. Johns County Relocation Specialist Serving Nocatee, Ponte Vedra, St. Augustine, RiverTown, Palencia, and all of St. Johns County, FL
All figures based on 2025–2026 data from the Tax Foundation, Council for Community and Economic Research, MIT Living Wage Calculator, Medicare.gov, Zillow, and local market data. Individual results vary. This article is for informational purposes only and does not constitute financial, tax, or legal advice. Consult a qualified CPA for guidance specific to your situation.