Mass Migration to Southwest Florida: Why New Yorkers, Chicagoans & High-Earners Are Moving South

Over the past year alone, 51,967 New Yorkers relocated to Florida—more than double the number from any other state. Illinois, New Jersey, and California aren’t far behind.

This isn’t a coincidence, and it’s not just about sunshine.

I’m John Garuti, and after working with hundreds of buyers relocating to Southwest Florida, I can tell you this migration is driven by money, policy, and long-term lifestyle strategy. If you’re considering making the same move, understanding the real reasons—and the trade-offs—can save you tens of thousands of dollars.

The Real Reason People Are Leaving New York, Chicago & Major Cities

Let’s get something straight:
This is not a weather story. It’s a financial shift.

Imagine dropping your kids off at school in New York and realizing you’ve just handed over $26,000 a year in state and local income taxes. In Florida, that money stays in your pocket.

When I talk with families relocating from New York or Chicago, taxes come up every single time. New leadership in major metro areas continues to push higher taxes on income, investments, and businesses. Smart money sees where this is heading.

Florida’s Tax Advantage

• Zero state income tax
  
  
• No city or county income tax
  
  
• Favorable estate and retirement tax treatment
  
  

If you earn $250,000 a year in New York City, you could pay up to 14% in combined state and local income taxes—before federal taxes even enter the picture. In Florida? Zero.

That said, these savings can disappear quickly if you don’t understand the full cost picture. Insurance, HOA fees, and location matter more than most people realize—and we’ll get to that shortly.

Housing Costs, Policy & Predictability

Housing policy also plays a major role in this migration.

In cities like New York, aggressive tenant regulations, rezoning mandates, and shifting rules create uncertainty. When builders don’t know what regulations will look like next year, construction costs rise, resale values become unpredictable, and buyers lose confidence.

Compare that to Southwest Florida:

• Median home price: ~$410,000
  
  
• Manhattan median price: ~$1.2 million
  
  

This price gap alone explains why families feel they can finally breathe again financially.

Lifestyle Isn’t Marketing—It’s Reality

Yes, the lifestyle matters—but not in the way most ads portray it.

I played golf yesterday. In November. Shot a 99 (not thrilled), but the point is this: year-round outdoor living is real here.

• Southwest Florida averages 271 sunny days per year
  
  
• New York averages 107 clear days
  
  

This translates into daily quality-of-life improvements that go far beyond beaches and palm trees.

What Buyers Actually Find When They Arrive

Here’s where expectations often collide with reality.

The Southwest Florida housing market is stable, not slow. We currently have around 7.5 months of inventory, which is considered balanced. But competition still exists for well-priced homes in desirable areas.

One key metric tells the real story:

• Pending sales jumped 57% year-over-year in October
  
  

Buyers are active again—and when the right home appears, it doesn’t sit.

Insurance Costs: The Reality Check

Homeowners insurance in Southwest Florida is higher than most northern buyers expect:

• Typical range: $4,300 to $11,000 per year
  
  
• Coastal homes carry the highest premiums due to hurricane exposure
  
  

Yes, insurance offsets some tax savings—but for many high-income households, the math still strongly favors Florida.

Infrastructure & Economic Growth

One reason Southwest Florida continues to attract long-term residents is that infrastructure is keeping pace with growth.

• Southwest Florida International Airport is expanding flight options
  
  
• Lee County is projected to reach 585,000 jobs by 2045
  
  
• The region needs approximately 200,000 new workers in the next three years
  
  

For professionals, entrepreneurs, and families, this signals economic momentum, not speculation.

Naples, Fort Myers & Key Southwest Florida Submarkets

Southwest Florida is not a single market—it’s a collection of distinct communities, each attracting different buyers.

Naples

• Median home price: ~$847,000
  
  
• Luxury-focused lifestyle
  
  
• World-class golf, dining, and beaches
  
  
• Higher insurance and hurricane exposure in certain zones
  
  

Naples appeals to buyers prioritizing refinement, exclusivity, and long-term property stewardship.

Fort Myers

• Median home price: ~$361,000
  
  
• Family-friendly and relaxed
  
  
• Cultural attractions like the Edison & Ford Winter Estates
  
  
• Strong value relative to lifestyle
  
  

Cape Coral, Bonita Springs & Estero

These are not “suburbs”—they’re fully formed communities:

• Cape Coral: waterfront living and vibrant local events
  
  
• Bonita Springs: blends Naples luxury with Fort Myers accessibility
  
  
• Estero: newer developments and master-planned communities
  
  

Choosing the right area is often the difference between loving your move and regretting it.

The Trade-Offs Most Agents Skip

Hurricane risk is real. Insurance reflects that reality. Some years are calm; others are not.

However, Florida’s building codes are among the strictest in the country, and newer homes are designed to withstand severe weather.

Growth also brings short-term inconveniences:

• Increased traffic
  
  
• Ongoing construction
  
  
• Temporary service strain in high-growth corridors
  
  

Some buyers thrive in evolving areas. Others prefer established neighborhoods. The key is knowing which environment matches your tolerance and goals.

Is the Migration Slowing Down?

Yes—and that’s actually good news.

Florida is no longer seeing the explosive surge of 2021–2022. However, the state is still adding approximately 320,000 residents per year, which is enormous by any standard.

For buyers, this means:

• Fewer bidding wars
  
  
• More balanced negotiations
  
  
• Better due diligence opportunities
  
  

You’re entering the market during a rational phase, not a frenzy.

Final Thoughts & Next Steps

Families moving to Southwest Florida aren’t chasing sunshine—they’re making deliberate financial and lifestyle decisions. Right now, with balanced inventory and stable pricing, the window of opportunity remains open.

If you’re considering relocating, buying, or investing in Southwest Florida, I’d be happy to walk through your goals and help you avoid costly mistakes.

Call: (239) 456-3711
Email: hello@swfloridarealestate.com

One final piece of advice: the best opportunities rarely appear during the next wave of hype. They happen before competition heats up.

If you want to do this right, now is the time.