Powers Realty Group, Inc.
Relocation
For Chicago and Wisconsin families making the move to the Gulf Coast.
Naples Boutique Broker®

Second Home and Retirement Relocation to Naples, Florida

Buying a Second Home in Naples from Chicago or Wisconsin

Many of the families we help moving to Naples come from Chicago, Milwaukee, and across the Midwest. Some want a winter home to escape the cold, some want a vacation home the whole family can enjoy, and others are planning the retirement home they will eventually live in full time. Powers Realty Group, Inc. has offices in Naples, Florida and Shorewood, Wisconsin, so one team guides you from your first question to your first sunset on the Gulf.

We Made the Same Move

Suzanne Powers' family has spent time in Naples and Marco Island since 2010, and she bought her own Florida home in Fiddler's Creek in 2022. She knows firsthand what Midwestern buyers want to understand before buying a second home in Florida: insurance, HOA rules, seasonal living, and which communities feel like home. That experience is built into how our team guides every client.
  • Initial Consultation. We begin with a private conversation about your timeline, goals, budget, and lifestyle. We also walk you through how buying in Florida works, including the written buyer agreement required before touring.
  • Community Matching. We narrow Naples and Marco Island neighborhoods to the ones that fit how you want to live, from walkable Olde Naples to resort-style Fiddler's Creek.
  • Private and Virtual Tours. You can tour in person on a scheduled visit or remotely through live video walkthroughs led by your Powers agent.
  • Due Diligence and Negotiation. We review flood zone, insurance, year built, and association finances before you commit, then negotiate with a clear view of the true cost of ownership.
  • Closing and Settling In. We coordinate closings across both states and connect you with trusted local professionals. We also point you to the steps for establishing Florida residency.

Neighborhood Real Estate Guides

We're ready to provide you with the latest neighborhood and community information and easy-to-use search tools to explore the finest homes through our Florida Gulf Coast neighborhood real estate guide and Milwaukee's North Shore neighborhood real estate guide.

Powers Realty Group Inc.

FLORIDA GUIDES

Powers Realty Group Inc.

WISCONSIN GUIDES

Gretchen Keating, Suzanne Powers, and Donna Powers

A concierge-level experience

Gretchen Keating is Powers Realty Group’s distinguished Relocation Specialist, dedicated to curating seamless transitions into Naples’ most coveted communities. With refined expertise and an insider’s knowledge of both national and local markets, Gretchen delivers a concierge-level experience tailored to discerning buyers and sellers. Whether orchestrating a private listing, guiding the acquisition of a luxury estate, or structuring complex equity and buyout solutions, she ensures every detail is executed with discretion, precision, and elegance hallmarks of the Powers brand.

Want to learn more about relocating to a new community? Gretchen Keating would love to help get you moving!

Frequently Asked Questions About Relocating to Naples

Florida residency is built through a series of steps, including filing a Declaration of Domicile with the county clerk, obtaining a Florida driver's license, registering to vote, and filing for the homestead exemption by March 1. Our guide to becoming a permanent resident of Florida walks through each step.

Not always. Some clients buy first and sell second, while others sell first to buy with cash in hand. Because our team works in both Wisconsin and Florida, we can map out the timing, financing, and closing sequence that fits your situation.

Absolutely. Suzanne Powers Relocation Services supports local businesses moving employees to the Milwaukee and Naples markets, and we hold preferred vendor status with numerous global organizations and their third-party relocation providers. We work within your company's relocation program guidelines from start to finish.

Many of our clients purchase remotely. We provide live video tours, detailed property walkthroughs, neighborhood insights, and trusted local referrals for inspections, insurance, and closing. Florida also permits remote online notarization, which can allow you to close without traveling.

It depends on your lifestyle. Olde Naples and Aqualane Shores offer walkable, in-town living; Port Royal and Park Shore deliver waterfront luxury; Pelican Bay and Fiddler's Creek offer resort-style amenities; and Marco Island provides a relaxed island setting. We match communities to your priorities during our initial consultation.

The region offers everything from custom luxury estates and waterfront homes to golf course properties, gated communities, country club residences, condominiums, townhomes, and age-restricted active adult communities.

Insurance is a key part of any Florida purchase and should be reviewed early. Coverage and costs vary with a property's flood zone, elevation, construction year, and wind mitigation features. We connect you with experienced local insurance professionals so you can factor accurate costs into your decision before you commit.

Florida's condominium safety laws now require milestone structural inspections for condo buildings three stories or taller and structural integrity reserve studies for key building components. Before you buy, we help you review the association's inspection reports, reserve funding, budget, and any pending or planned special assessments so there are no surprises after closing.

Naples' busiest real estate season generally runs from January through April, when seasonal residents are in town and inventory and competition are at their peak. Summer and fall often bring more negotiating room. We'll help you time your search around your goals and your move date.

Start with a no-obligation consultation with Suzanne Powers or Gretchen Keating. We'll discuss your timeline, goals, and preferred communities, then build a custom relocation plan for your move. Call 239.682.7476 or use the Let's Get Moving form on this page.

RECENT BLOG POSTS ON Relocating

Real Estate Perspectives

September 29, 2026 | Suzanne Powers | Powers Realty Group, Inc.

Selling Your Isles of Collier Home? Why Gretchen Keating Is the Agent to Call

Real Estate Perspectives

September 28, 2026 | Suzanne Powers | Powers Realty Group, Inc.

Marco Island vs. Naples: Which One Fits Your Life?

Real Estate Perspectives

September 21, 2026 | Suzanne Powers | Powers Realty Group, Inc.

Living in the Isles of Collier Preserve: HOA Fees, Neighborhoods, and What Life Is Really Like