Meet the father-son team guiding today’s Midwest buyers through one of the biggest moves of their lives. The Agency Naples’ Dominick Clarizio and his son John Clarizio, represent two generations, two skill sets, and one proven approach. Dominick, a top-producing luxury real estate advisor and former Chicago Stock Exchange member, and John, a licensed agent with a finance degree from Florida Gulf Coast University, together produced roughly $51 million across Florida and Illinois in 2025. But there’s nuance beneath these big numbers.

The Clarizios are watching the Midwest-to-Naples buyer evolve in real time—and adjusting to serve them better. Here, we explore those shifts and unpack how their multi-faceted, generation-spanning partnership comes together to meet the moment.

A Buyer Who’s Staying Past Winter

Ten years ago, the typical Chicago or Midwest buyer heading to Naples wanted a seasonal escape. A months-long reprieve from the cold. That’s no longer the primary driver.

“Today, a large share are relocating full-time or establishing Florida as their primary residence,” Dominick says. “The drivers have shifted from lifestyle-only to lifestyle plus financial strategy.”

Florida’s 0% state income tax, paired with rising tax and cost-of-living pressure in Illinois, has turned the move into as much a financial decision as a personal one, and the advent of remote work removed what used to be the biggest obstacle.

John sees the same shift from the ground in Naples. “There are so many Midwesterners down here now that it feels like you’re back home — that sense of community eases the leap of relocating.”

He also points to a trend buyers should have on their radar. There is growing discussion in Florida around putting forth an amendment to reduce or eliminate property taxes in 2027, along with the long-standing advantage of establishing residency by January 1st for tax-year purposes. “If that moves forward,” John says, ”I think it could bring an even bigger wave of buyers looking to make Naples their permanent residence.”

It’s a harmony of insights and instincts. Dominick answers “Is this a smart investment, and how does it fit the bigger picture?” John answers “How do we actually get you here and make it feel like home?”

As for why Naples calls to Midwesterners specifically, Dominick frames it as the Gulf Coast’s answer to the East Coast, with white-sand beaches and the walkability of Old Naples, without Miami’s congestion. “It’s more private and relationship-driven here, which is the balance most Midwest families are after — a place that’s sophisticated but still feels like home.”

Seeing Clients More Clearly, Through Two Lenses

The Clarizio’s success is strategic. Mindful of their differences, they split the work to play to their own strengths.

“We approach it as two complementary lenses on the same client,” Dominick explains. His financial-markets background shapes how he evaluates a home as a strategic asset. Dominick weighs timing, value retention, and the tax and domicile implications of a move.

“The luxury inventory here moves differently than the Midwest market. Having local guidance on timing, pricing, and new construction versus resale makes a real difference in what you ultimately pay and what you get.”

Dominick Clarizio

John picks up where that analysis ends. Having guided family and friends through the Midwest-to-Naples transition himself, he handles the logistics, the lifestyle adjustment, and helps connect clients into the community. A true digital native, John uses a modern, data- and social-media-driven approach to find the right property, applying SEO and generative engine optimization (GEO) to reach today’s luxury buyer more effectively.

It’s a harmony of insights and instincts. Dominick answers: “Is this a smart investment, and how does it fit the bigger picture?” John answers: “How do we actually get you here and make it feel like home?”

What Midwest Buyers Still Get Wrong

Even sophisticated buyers underestimate how different the Naples luxury market is from what they’re used to. “The luxury inventory here moves differently than the Midwest market,” Dominick says. “Having local guidance on timing, pricing, and new construction versus resale makes a real difference in what you ultimately pay and what you get.”

For Midwest families weighing the move, that’s the Clarizio pitch in a nutshell. One generation reads the market like a portfolio, the other translates it into a life.

Considering a Move to Naples?

Take a look at two of the Clarizio Team’s current Naples listings below. Both are newly completed estates in Naples’ exclusive Livingston Woods community, designed by Stock Custom Homes, listed alongside Chris and Kara Resop.