What a Naples home costs to own, what is drawing buyers from the Naperville area, and how to tell if the move fits the next stage of your life
If Naples is on your short list, you are almost certainly not the first person in your circle to look at it. Over a recent two-year span, 282 households from DuPage County moved to the Naples area. That is a big enough number that you probably already know one of them.
Moving is easier when connections are already in place. Many Naples buyers have friends, former neighbors, golf partners, or family members who made the move first.
Naples may already be familiar to you. Plenty of buyers spend years visiting before they think about living in the area full time. The decision now is whether the place you know as a visitor should become home. We will cover who makes the move, what drives it, and what to weigh before you decide.
Key Takeaways
- The Chicago metro, led by Cook, DuPage, Lake, and Will counties, is the single largest source of out-of-state Naples buyers.
- The decision usually turns on life stage: grown children, a coming retirement or business sale, and a house with more room than it needs.
- Right now Naples gives buyers more time than the tighter Naperville market, with 7.0 months of supply against weeks of inventory back home, even as closed sales have risen year over year for twelve straight months.
- The May 2026 median sale price in Naples is $620,000. Pricing is tightest from $400,000 to $750,000 and loosest above $3 million.
- Florida has no state income tax. Insurance, flood, and HOA costs are the other half of the math.
Who is making this move
The IRS tracks county-to-county moves from actual tax returns, and the Chicago metro leads every origin market for Naples. Cook County sends the most. DuPage, Lake, and Will counties add to it. Across all four, no metro in the country sends more buyers to Naples. These are usually deliberate moves. They are planned around retirement, a home sale, and a hard look at what Naples costs to own. The full county-by-county breakdown is in Who Is Moving to Southwest Florida?. It shows how Naples and Fort Myers draw different buyers from the same suburbs.
What usually drives the move
For many households, the reasons show up at a similar point in life. The children are grown and on their own. Retirement may be getting closer, or a business sale may be ahead. The house that fit a family of five is now a lot to keep up. Naples offers more time outdoors, a lower tax burden, and more control over your calendar. The question is whether the place that fit one season of life still fits the next one.
Taxes open the conversation
Florida has no state income tax. Illinois layers income tax on top of some of the highest property tax bills in the country. For a lot of Naperville households, that yearly difference is large enough to start the search south.
Taxes are often the reason people start looking, but rarely the only reason they move. There is a fuller cost picture too, including the assessed-value reset that moves your tax bill to market value when you buy. Add up the tax savings, but get real insurance and HOA numbers before you set a budget, because they change the picture.
One change worth watching is on the 2026 ballot. Florida voters decide on November 3 whether to raise the homestead exemption. If approved, it would lower the non-school part of many property tax bills. Timing may matter for new residents, especially if Florida residency is established after December 31, 2026. Our explainer on the Florida property tax amendment walks through who qualifies and when. If your move is already close, ask your tax professional how the timing could affect your eligibility.
What changes after the move
The best outdoor months run October through May, and summer becomes the season you plan around. Water and golf move to the center of daily life. Golf becomes a weekday activity rather than a summer one.
Insurance and flood preparedness become part of owning a home in Florida. They are the local version of snow load and frost lines back in Illinois. FEMA frames it as a year-round homeownership responsibility, built into how you choose and maintain a property. The Southwest Florida insurance market has steadied since 2022, with rates flattening and carriers returning. High-exposure coastal homes can still run higher. Our Southwest Florida homeowners insurance guide shows how to estimate the cost. It also explains how to weigh wind and flood together before you make an offer. Two homes at the same price can carry very different annual costs. Elevation, roof age, wind mitigation, flood zone, distance from the Gulf, and HOA dues all move the number.
A drive that looks short on the map can take far longer in season, once the winter residents arrive and the roads fill. Healthcare access in Collier County is strong, and worth checking against your needs. Travel back to Naperville is easy, with RSW a short drive from most of Naples and direct service to Chicago. You will also meet plenty of former Illinois and Midwest residents, which can make settling in easier.
Right now, Naples gives you more time to choose
You have spent years in a tight market. Naperville runs on weeks of inventory, and well-located homes still move quickly, often selling at or above asking. Buyers learn to move before someone else does.
Naples is the slower of the two at the moment, though it is far from quiet. Closed sales have risen year over year for twelve straight months, and pending sales were up 9.9 percent in May. Even so, a well-priced Naples home still takes a median of 57 days to sell. The city carries 7.0 months of supply, far more than Naperville, with about 2.1 months of competitive inventory. May’s median sale price was $620,000, with the full figures in the Naples market report for May 2026.
Price behavior depends on the range. From $400,000 to $750,000, asking prices sit within about 3.6 percent of recent sales. There is little room to negotiate. Above $3 million, asks run around 15 percent above recent sales. That is where buyers have the most room to negotiate. A move-up buyer from Naperville usually lands where pricing is fairly aligned. The discipline is simple. Anchor to what has actually sold.
The slower pace changes the question you get to ask. In Naperville, the pressure is to win the house. In Naples, for now at least, you have time to confirm that the house, the location, and the long-term cost of ownership are right before you commit.
Naples is several different places to live
Naples holds several different lifestyles. Waterfront, golf, and a walkable downtown are three ways to live. Choosing among them is most of the decision. Each carries its own price range, its own insurance picture, and its own daily routine.
See what the current Naples market looks like
To see how those differences show up in real listings, browse current Naples homes below.
These six communities are the ones Worthington tracks and reports on by name every month, each with its own search page: Lely Resort, The Vineyards, Esplanade Golf and Country Club, Isles of Collier Preserve, Pelican Bay, and Grey Oaks.
When you want to search the whole market and read more about living in each area, our Naples page is the place to do it.
Common questions about moving from Naperville to Naples
It is worth it if your reasons are time, climate, lower taxes, and a lifestyle that fits this next stage. It is a harder call if your family is in the Midwest or you want four real seasons. A few days in Naples is the surest way to tell.
Over a recent two-year span, DuPage County sent 282 households to the Naples area. With the rest of the Chicago metro, it is the largest source of out-of-state Naples buyers in the country.
Right now Naples gives buyers more time than Naperville. It carries 7.0 months of supply and a 57-day median for well-priced homes. The May 2026 median sale price was $620,000.
Beyond the price, plan for property taxes, homeowners and flood insurance, and HOA dues. Two similar homes can run very different annual costs, depending on elevation, roof age, wind mitigation, flood zone, and distance from the Gulf. Buying also resets the assessed value to market, which moves your tax bill.
Start with how you want to spend a normal week. The community sets the price range, the insurance profile, and the daily pace as much as the house does. A few days in the area in season is the fastest way to tell which one fits.
The path forward
The decision comes down to three steps:
- Get your real numbers. Know what a Naples home costs to own, including insurance, flood, and HOA, not just the purchase price.
- See what fits. Weigh communities and lifestyles against how you want to spend your days.
- Walk it as a resident. Spend a few days on the ground, seeing how the place works day to day.
In Naples, Kim Dolniak and Susana Alvarez Davis handle all of this together, before you come down and once you arrive. Reach Kim at 314.368.6713 or Susana at 239.770.0997.
The visit is the step that usually makes the decision clear. It is where you find out whether Naples works as well to live in as it does to visit. If it does, you get more time outside, less house to keep up, and winters you look forward to. We will help you plan it and point you toward communities that fit your stage and budget.
Plan your Naples scouting trip.
Not ready to talk yet? You can see every listing without creating an account. If you want to keep an eye on the market while you decide, create a free account. It will save your searches and send alerts.
For the full migration picture, see Who Is Moving to Southwest Florida?
