What Wisconsin Homeowners Need to Know Before Buying a Home in Florida

Every winter, I talk with clients who are done with Milwaukee winters. They want a place in Florida to escape the cold, maybe rent it out when they are not there, and build something for retirement. I get it completely. We have helped dozens of Wisconsin and Illinois families navigate Florida real estate and insurance, and I will tell you right now: Florida is not like buying a home in Waukesha County. The rules are different. The risks are different. And the costs can knock you sideways if you are not prepared.

This post is for anyone who is thinking about buying a second home or third home in Florida. Read it before you make an offer.

Florida Insurance Is Not Like Anything You Have Seen in the Midwest

Back home, you can buy a solid three-bedroom house and pay $1,200 to $1,800 a year for homeowners insurance. Florida does not work that way, especially on the coast.

According to MoneyGeek's 2026 data, the average annual homeowners insurance premium for a home with $250,000 in dwelling coverage in coastal Florida cities runs like this:

• Cape Coral: $9,147 per year

• Fort Myers: $8,798 per year

• Naples: $10,909 per year

• Fort Lauderdale: $15,680 per year

• Miami: $16,123 per year

These numbers are not outliers. They are the average. Your specific premium depends on the age of your roof, the type of construction, how close you are to the water, and what wind zone the home sits in. Two homes on the same street can carry very different premiums.

On top of homeowners insurance, if you are in a flood zone and you have a mortgage, your lender will require flood insurance. There is no option. In Cape Coral, the average NFIP flood insurance policy runs about $1,709 per year. Add it up and a coastal home in Cape Coral might easily run $10,000 to $12,000 a year in insurance alone before you pay a dollar of property taxes.

The Florida insurance market has also been in crisis. Since 2020, more than ten major carriers have exited the state entirely, including Farmers, Bankers Insurance, FedNat, Progressive (for new homeowner policies), and AAA. When big carriers leave, the remaining ones can charge more. Some homeowners have ended up with Citizens Insurance, which is the state-run carrier of last resort. That is not necessarily bad, but it is a different situation than most Midwest buyers expect.

Cape Coral: The Area Hit Hardest in the Last Hurricane

If you are looking at Cape Coral, Fort Myers, or any of the surrounding communities in Lee County, you need to know what happened in September 2022.

Hurricane Ian made landfall as a Category 4 storm on Florida's southwest coast. According to NOAA's official report, Ian caused an estimated $112.9 billion in total damage in the United States, with $109.5 billion of that in Florida alone. It is the costliest hurricane in Florida's history and the third-costliest in U.S. history. At least 156 people died.

Cape Coral took a direct hit. Storm surge of 6 to 9 feet above ground level flooded neighborhoods near the Caloosahatchee River. Water sensors in Matlacha and Cape Coral were destroyed outright. Thousands of homes were damaged or destroyed.

What happened to the market after? It is complicated. A flood of damaged homes pushed inventory up, which slowed price growth. At the same time, FEMA announced it would revoke Cape Coral's Community Rating System discount, which immediately raised flood insurance premiums by about $300 a year for approximately 125,000 policyholders in Lee County. The city fought back and FEMA issued a pause, but it shows exactly how real the risk is and how it directly affects the cost of owning.

If you are looking in Cape Coral today, do not assume that because prices have moderated, the risk has too. The risk is still there. The insurance market is just catching up to it.

The Rental Income Math Does Not Always Work the Way You Think

I hear this all the time: "Toby, I will buy a place in Cape Coral and rent it out on Airbnb. By the time I pay for insurance and taxes, the renters will basically cover it."

Here is what the actual data says.

According to AirDNA, the average active Airbnb listing in Cape Coral earns about $23,200 per year in gross revenue, with an average occupancy rate of 55% and an average daily rate of around $266. Some higher-performing listings earn closer to $50,000 annually.

Now let's do a quick back-of-the-napkin on a $450,000 home in Cape Coral:

• Homeowners insurance: $9,000 per year (mid-range estimate)

• Flood insurance: $1,700 per year

• Property taxes (Lee County, approx. 1% non-homestead): $4,500 per year

• Property management (20% of gross if you use a manager): $4,640 per year on $23,200 revenue

• Maintenance and repairs: $3,000 to $5,000 per year is realistic

• Mortgage (if financed at 7%, 30-year, 20% down): approximately $23,900 per year

Total annual costs without mortgage: roughly $22,840 to $24,840. Gross rental revenue: $23,200.

You can see the math. At average occupancy and average rates, you are roughly breaking even on operating costs before the mortgage. Rental income in Florida can subsidize the cost of owning, but it is not going to fully cover it the way a traditional rental property in Milwaukee or Chicago might. Rents in Wisconsin and Illinois are often high relative to insurance and tax costs. Florida flips that equation.

That does not mean it is a bad investment. It means you should go in with realistic expectations. You are paying to own a place in Florida, and the rental income helps offset that cost.

What to Check Before You Make an Offer: Single-Family Homes

If you are buying a single-family home, here are the things that matter most from an insurance and risk standpoint.

Roof Age and Condition

In Florida, a roof over 15 to 20 years old can trigger surcharges or even make the home uninsurable with standard carriers. Always ask for the roof documentation and factor replacement cost into your offer if needed.

Wind Mitigation Report

This is a nine-point inspection that evaluates how hurricane-resistant the home is. Things like the type of roof-to-wall connection, roof shape, roof covering, and whether the windows and doors are impact-rated all matter. A home with a strong wind mitigation report can qualify for significant insurance discounts, sometimes cutting your premium by 30% to 50%. Make your offer contingent on receiving a wind mitigation inspection. It costs around $100 to $150 and can save you thousands.

Elevation Certificate

This tells you the elevation of the home relative to the Base Flood Elevation in that area. The lower the home relative to the flood zone, the higher your flood insurance will be. A lender will absolutely require flood insurance if the home is in a Special Flood Hazard Area (Zone A or Zone V). But even outside mandatory flood zones, I strongly recommend flood coverage in southwest Florida. History has shown that storm surge does not always stay inside the lines on a map.

Year Built

Homes built after 2002 comply with Florida's post-Hurricane Andrew building code, which dramatically improved construction standards. Homes built before 2002 may qualify for fewer wind mitigation discounts and can be harder to insure.

What to Check Before You Make an Offer: Condos

Condos add a layer of complexity that catches a lot of buyers off guard.

Year Built and the New Florida Milestone Inspection Law

Following the 2021 collapse of the Champlain Towers South condominium in Surfside, Florida, which killed 98 people, Florida passed Senate Bill 4D in May 2022. This law requires condo buildings three stories or taller to undergo structural milestone inspections, beginning at 25 years for coastal buildings and 30 years for inland buildings. Buildings must also complete a Structural Integrity Reserve Study and fully fund reserves for major structural repairs. Associations that had previously been deferring maintenance through reserve waivers can no longer do that.

What this means for buyers is significant. If the building you are buying into has deferred maintenance and now must fund a reserve study, there may be special assessments coming. I have seen buyers blindsided by five-figure special assessments after closing. Always ask for the most recent milestone inspection report, the SIRS, and any pending special assessment documentation before you close.

Buildings Built Before 1981

I tell every client the same thing: be extremely cautious with older concrete structures. The Champlain Towers collapse was a sobering reminder that aging reinforced concrete in a salt-air coastal environment deteriorates in ways that are not always visible from the outside. The risk is real. Newer construction with modern building codes is far safer from both a structural and an insurance standpoint.

Flood Insurance: Your Lender Will Not Give You a Choice

If you use a mortgage to buy in a FEMA-designated flood zone in Florida, flood insurance is mandatory. Period. And even if your lender does not require it, I am going to tell you to buy it anyway.

In Fort Myers Beach, Marco Island, Cape Coral, and the surrounding coastal communities of Lee and Collier counties, the flood risk is not theoretical. Hurricane Ian proved that. Entire neighborhoods that had never flooded before were underwater.

The average NFIP flood policy in Cape Coral costs about $1,709 per year. That is actually a reasonable price for what it covers. Private flood insurance is available and can sometimes offer broader coverage at competitive rates. Give our office a call and we can help you compare options before you buy.

Real Estate Values: The Case for Playing the Long Game

Despite everything I have laid out here, Florida real estate has been one of the strongest long-term appreciation stories in the country. According to NeighborhoodScout data, Florida home values have appreciated roughly 307% since the year 2000, averaging about 5.7% per year. Over the last 10 years, appreciation has averaged 8.8% annually. Southwest Florida specifically, including Lee, Collier, and Charlotte counties, has averaged roughly 6% to 7% per year over the last 20 years.

The current market in Cape Coral and Fort Myers is softer following Hurricane Ian and rising interest rates. Zillow data as of mid-2026 shows Florida statewide values down about 3.3% over the past year. Inventory is elevated in some coastal markets. For long-term buyers, this is actually an opportunity to buy at more reasonable prices.

But here is the key word: long-term. If you are buying with a 5-year-plus horizon and you are buying something well-built, well-located, and properly insured, Florida can be a very strong investment. If you are buying hoping to flip it or exit quickly after a hurricane, you may find yourself in a tough spot. Following Ian, property values in some parts of Cape Coral softened as supply flooded the market from damaged and displaced homeowners.

My advice is always the same: buy for the lifestyle first. If you genuinely want to escape Wisconsin winters, spend time with family, and have a place to call your own in the sun, that is a perfectly sound reason to buy. The appreciation is a bonus. The rental income is a subsidy. But buy for the right reasons and give it time.

One More Thing: Nobody Wants to Be in Florida in July

I say this with love, but it is true. Florida summer is relentless. Heat indexes regularly top 105 degrees from June through September. Hurricane season runs June 1 through November 30, with peak season from mid-August through mid-October. Most Wisconsin snowbirds head south in November and are back home by April or May. That leaves your property sitting vacant during the hottest, most hurricane-prone months of the year, which means you need to think about property management, hurricane shutters, and what happens if a storm hits while you are 1,200 miles away in Wisconsin.

These are all things we help our clients work through before they buy, not after.

Call Us Before You Buy

We have been helping Wisconsin families buy and insure second homes in Florida for years. We know the carriers, we know the questions to ask, and we know where the traps are. Before you make an offer, give us a call at (262) 754-4736. A 20-minute conversation can save you from a very expensive mistake.

A Taste of Florida