Can Powers Realty Group, Inc. sell my Milwaukee home and help me purchase in Naples?

Yes. Suzanne Powers is a licensed broker-owner in both Wisconsin and Florida. Our team can coordinate your Milwaukee home sale and Naples purchase, offering consistent representation and service across both markets.

Where did Suzanne Powers purchase her Naples home?

Suzanne purchased her Florida home in Fiddler's Creek in 2022 after spending years vacationing in Naples and Marco Island. Her personal buying experience helped shape Powers Realty Group's buyer-focused approach in Southwest Florida.

Does Gretchen Keating live in Naples?

Gretchen Keating, Vice President and Director of Corporate Relocation at Powers Realty Group, owns a home in Isles of Collier Preserve in Naples. Her experience as a local homeowner provides valuable insight for clients exploring Southwest Florida communities.

How do I establish Florida residency after moving from Wisconsin?

Establishing Florida residency requires more than owning a home. You should document your Florida domicile, update relevant registrations, and review your tax obligations with qualified advisors. Our Wisconsin residency guide explains important considerations.

Moving From Chicago to Naples, FL

Q: Is there a nonstop flight from Milwaukee to Naples?

Seasonal nonstop flights connect Milwaukee Mitchell International Airport with Southwest Florida International Airport in Fort Myers, approximately 35–45 minutes from Downtown Naples. Flight schedules vary by season.

From the Lakefront to the Gulf Coast, with a Team that Knows Both

Midwest Values, Naples Expertise

Chicago has always been part of our story. For years, Chicago families have chosen Milwaukee's North Shore with Powers Realty Group, Inc. as their guide. When those same clients, and their friends and families, began spending winters in Naples and Marco Island, they asked us to follow them south. They wanted the team they already trusted.

In 2025, we answered that call and opened our office at 780 Fifth Avenue South in Downtown Naples.

Suzanne Powers owns a home in Fiddler's Creek, and Vice President Gretchen Keating owns a home in the Isles of Collier Preserve. We know these communities as homeowners, not visitors.

Chicago and Naples share more than flight paths. Much of Southwest Florida's seasonal community comes from the Midwest, and Chicago buyers find a familiar rhythm here: polished, unhurried, and close to the water.

Finding Your Place

From Your Chicago Neighborhood to Your Naples Community

One of our first conversations is about what you love most about home. Naples, Florida has a match for nearly every Chicago lifestyle.

For those who appreciate the high-rise living of the Gold Coast and Streeterville, complete with doormen and lake views, the Park Shore and Pelican Bay Gulf-front towers in Naples are ideal. If you enjoy the walkable streets, dining, and boutiques of Lincoln Park and Old Town, Olde Naples offers proximity to Fifth Avenue South, Third Street South, and the beach. For the privacy and estates reminiscent of Winnetka, Kenilworth, and Lake Forest, consider Port Royal, Aqualane Shores, and The Moorings. Those who favor the club life, golf, and manicured landscapes of Hinsdale and Oak Brook will find Fiddler's Creek, Isles of Collier Preserve, and Naples' private golf clubs appealing. For weekend boating enthusiasts, Marco Island and its canal homes with Gulf access provide the perfect retreat.

Every community has its own personality. Our job is to help you discover which one feels like home.

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MAKING THE MOVE

Getting From Chicago to Naples

One of the reasons Naples has become such a popular destination for Illinois homeowners is how easily the two locations can be connected.

Flying to Southwest Florida

Nonstop flights connect Chicago to Southwest Florida International Airport (RSW) in Fort Myers year-round. From O'Hare, American and United fly the route several times a day. From Midway, Southwest flies nonstop daily. Flights take about three hours, and Downtown Naples is about 35 to 45 minutes from RSW.

Driving to Naples, Florida

The trip from Chicago is approximately 1,300 miles and takes roughly 19.5 hours of pure driving time in normal traffic. Many homeowners divide the journey into two extended driving days.

Visiting During Season

January through April is the best time to tour homes. Plan ahead and we will build a showing schedule around your visit so you see several communities in one trip.

Whether you're purchasing a seasonal residence or planning a permanent move, we can help organize your property search so your time in Naples is well spent.

Changing Residency

Leaving Illinois: What to Know About Florida Residency

For many Chicago families, Naples starts as a winter home and becomes a permanent one.

Florida has no state income tax and no estate tax. Illinois has a flat 4.95% income tax and its own estate tax, with an exemption of $4 million per person.

Keeping property in Illinois matters too. Illinois can apply its estate tax to Illinois real estate even after you become a Florida resident.

Establishing Florida domicile takes more than buying a home: a Florida driver's license, voter and vehicle registration, a Declaration of Domicile, and a homestead exemption application. We encourage every client to work with their accountant and estate planning attorney.

We encourage our clients to work closely with their accountants and estate planning attorneys to make sure the transition is handled properly.

Coordinating the Sale of Your Chicago Home with a More Personal Experience.

One of the greatest advantages of working with Powers Realty Group, Inc. is our ability to serve you in both markets.

Powers Realty Group, Inc. is licensed in Wisconsin and Florida. If you are selling a home in Chicago, we will introduce you to a trusted Chicago broker and coordinate timing so your sale and your Naples purchase work together

We also know how different a Florida purchase can be.

The Naples market has its own property considerations, neighborhood distinctions, insurance requirements, and transaction practices. Having an experienced team with firsthand knowledge of both locations provides continuity throughout the process.

Whether you're selling your home in Hinsdale, Oak Brook, Lincoln Park, and Old Town, our team can coordinate your sale while our Florida team helps you identify your next property.

We will help you decide whether to buy first or sell first, plan around closing dates, and keep both sides moving.

You don't have to start over with a new real estate company when you arrive in Naples, Florida. You can continue with the people you already know and trust at Powers Realty Group, Inc.

We Know the Journey Because We've Taken It Ourselves.

Gretchen Keating & Suzanne Powers

Fifteen years ago, Powers Realty Group began at Suzanne's dining room table in Milwaukee's North Shore. Today, we've brought that same commitment to personal service to our office on Fifth Avenue South in Naples.

Our business has grown, but the reason our clients choose us has never changed.

We believe real estate is about relationships, trust, and having the right people in your corner during life's important transitions.

For Suzanne and Gretchen, Southwest Florida is more than another real estate market. It's where they've chosen to own homes, build connections, and enjoy the lifestyle they now help their clients discover.

From Chicago's Lakefront to Naples' Gulf Shore, We'd Be Honored to Help You Make the Move.

LET'S GET MOVING

HAVE QUESTIONS?

Frequently Asked Questions About Moving From Chicago to Naples

Can Powers Realty Group, Inc. sell my Chicago home?

Powers Realty Group, Inc. is licensed in Wisconsin and Florida. For a Chicago sale, we introduce you to a trusted Chicago broker and coordinate timing with your Naples purchase.

Can you help me sell my Naples home?

Yes. Our Naples office lists homes throughout Naples and Marco Island with the same boutique marketing, staging, and project management that built our reputation in Wisconsin.

Are there nonstop flights from Chicago to Naples?

Yes. Nonstop flights run year-round from O'Hare on American and United and from Midway on Southwest to Southwest Florida International Airport in Fort Myers. The flight takes about three hours, and Downtown Naples is about 35 to 45 minutes from the airport.

Which Naples neighborhoods feel most like Chicago?

Gold Coast buyers often like the Gulf-front towers of Park Shore and Pelican Bay. Lincoln Park buyers often prefer walkable Olde Naples. Buyers from the North Shore suburbs often choose Port Royal, Aqualane Shores, or The Moorings.

When is the best time to visit Naples to look at homes?

January through April, when the most homes are on the market and seasonal residents are in town. We plan showings around your visit.

Does Florida have an estate tax?

No. Florida has no state income tax and no estate tax. Illinois has its own estate tax, which can still apply to Illinois real estate you own after moving. Review your plan with your estate attorney.

How do I become a Florida resident after leaving Illinois?

Get a Florida driver's license, update your voter and vehicle registration, file a Declaration of Domicile, and apply for the homestead exemption. Work with your accountant to make sure Illinois residency ends properly.