Moving to Southwest Florida from the Northeast works out for most people who plan ahead, but five things often catch buyers late. The seller’s tax bill isn’t yours. The roof decides your insurance quote. The Gulf Coast is nothing like Boca. Golf communities keep much of their cost in the club. And CDD and HOA fees stack on top of the tax bill.
I covered all five in the June 2026 video above. This post includes the sources, what has changed since then and what to check on a specific house.
Is property tax in Southwest Florida lower than up north?
Usually, and often by a lot. But the seller’s bill is not the one you’ll pay.
Florida has no personal income tax (state constitution, Art. VII), and property tax on a comparable house tends to be well below what you’d pay in New Jersey or Connecticut.
My ballpark in the June 2026 video: a $750,000 house in Bergen County, New Jersey, pays around $15,000 to $20,000 a year. A house at the same price in Estero runs roughly $7,500 to $9,000, depending on the community.
The catch is the reset. When a Florida home sells, its assessed value returns to market value and the seller’s homestead exemption drops off (Lee County Property Appraiser). I’ve watched buyers write offers based on a $4,200 tax bill shown on Zillow, only to learn their bill would be closer to $8,000.
Plan for the post-sale number. After that, these rules limit increases for the 2026 tax year:
| Rule | What it does | Who gets it |
|---|---|---|
| Homestead exemption | Up to $51,411 off assessed value ($25,000 against school taxes) | Permanent residents who own the home on January 1 and file by March 1 |
| Save Our Homes cap | Assessed value rises at most 2.7% in 2026 | Homesteaded homes, from the year after the exemption starts |
| Non-homestead cap | Assessed value rises at most 10% a year, school taxes excluded | Second homes and other non-homestead property |
Sources: Lee County Property Appraiser, Florida Department of Revenue.
Is Florida getting rid of property taxes?
Not yet. The Florida House passed HJR 203 on February 19, 2026, by a vote of 80 to 30. It would have phased out non-school homestead taxes over ten years, but it died in the Senate when the session ended March 13 (Florida House). Anyone telling you to move for a tax elimination is selling a future that doesn’t exist yet.
Since the video, a June special session produced a different plan. It’s on the November 3, 2026 ballot as Amendment 3 and needs 60% of the vote to pass. As written, it would raise the non-school homestead exemption to $150,000 in 2027 and $250,000 in 2028 for people who were permanent Florida residents by December 31, 2026.
Later arrivals would stay near today’s exemption until their fifth year of exemption. The cap on second homes would fall from 10% to 5% (Florida Senate). After the election, the Florida Division of Elections will have the result. Talk to a CPA or tax attorney before planning around it.
Why is Florida homeowners insurance so expensive, and is it getting better?
The market is improving from a bad peak, but the house you choose still matters more than the headlines.
Lawsuits were a major part of Florida’s problem. NAIC figures in the state’s July 2026 stability report show that Florida had 12.3% of U.S. homeowners claims in 2024 but 73.2% of homeowners lawsuits. After the 2022–2023 reforms ended one-way attorney fees and assignment of benefits, Florida’s preliminary share of those lawsuits fell to 41.3% in 2025 (Florida OIR).
Citizens, the state-backed insurer, cut homeowners multiperil rates by an average of 8.8% for 2026 (Citizens). By May 2026, 20 new insurers had entered the state (Florida OIR). And since January 2024, 48 companies have filed for rate decreases (Florida OIR).
It’s still expensive.
In the video, I used a statewide average of about $11,700 a year for a $300,000 dwelling, compared with roughly $1,400 in New Jersey. Insurance.com’s September 2026 survey put Florida at $8,471 for that coverage, the highest of any state, versus $1,449 in New Jersey (Insurance.com).
The methods differ, but the advice doesn’t: budget several times what you pay now. A flood zone pushes the cost higher. An inland house outside one can come in well below the average.
What drives the quote on a specific house?
The home you choose decides the insurance bill, and the roof comes first. Most Florida carriers won’t write a policy on a shingle roof older than about 15 years.
The law offers some protection. Since 2022, an insurer can’t refuse a home solely because its roof is under 15 years old. An older roof can still qualify if an inspection shows at least five years of useful life remaining (SB 2-D).
Next, look at the build year. Florida’s statewide building code took effect on March 1, 2002, and its 6th edition took effect on December 31, 2017 (Highlands County).
A 1985 house with its original roof is a hard insurance story. A post-2017 house with a hip roof and proper wind mitigation can cost half or a third of what the headlines suggest. Insurers must offer discounts for features such as roof-to-wall connections and impact glass (s. 627.0629).
If the home won’t be your primary residence and lands on Citizens, renewals can rise by as much as 50% a year (Citizens).
Should you choose the Gulf Coast or the East Coast?
East for city energy. Gulf for water and a slower pace.
Every week, someone from New York or New Jersey tells me they’re looking at Boca or Delray. I ask if they’ve been to the Gulf Coast. Nine times out of ten, they haven’t.
| East Coast (Miami to Palm Beach) | Gulf Coast (Cape Coral to Marco Island) | |
|---|---|---|
| Water | Atlantic surf, deeper blue | White sand and water that’s often flat as a lake |
| Feel | Dense and fast, with high-rises and heavier traffic | Slower; season traffic is real, but it still feels local |
| Evenings | Louder restaurants and nightlife | Outdoor patios, seafood, golf clubhouses, long sunsets |
Boats are everywhere on this side. Lee County had 49,452 registered vessels in 2024, and that doesn’t include kayaks (Lee County).
I don’t pick a coast for anyone. I ask whether they want energy or water. My family chose water.
What do golf communities in Southwest Florida really cost?
Often more than the house price suggests.
Golf communities are our specialty, and most buyers looking for a golf home don’t understand what they’re buying. There are two basic models:
| Bundled | Equity or private | |
|---|---|---|
| How it works | Membership comes with the home and can’t be separated from it | Membership is separate: you’re invited to join, pay an initiation fee, then annual dues |
| My June 2026 ballpark | $700–$1,500 a month in fees; about $1,200 a month all-in at places like Heritage Bay or Esplanade | About $300 a month HOA at places like Quail West or Bonita Bay, plus a $150,000–$400,000 initiation and $25,000–$50,000 a year in dues |
| When you sell | Membership goes with the house | Membership doesn’t transfer |
Initiations run from about $50,000, which is rare here, to more than $500,000. Neither model wins outright. A big bundled community can make tee times hard to get, while an equity club caps memberships.
The number I build our golf guide around is the member-to-home ratio. A club with 700 homes and 350 memberships plays half full. One with 1,200 homes and 800 memberships means waiting for tee times on a course that gets hammered.
Before you fall for the clubhouse, get the initiation, dues, food minimum, capital reserve contribution, member-to-home ratio, and what happens to the membership when you sell. Our golf fees video breaks down the costs, and golf properties lists homes by community.
What is a CDD, and what do HOA fees run?
A community development district borrows to build a new community’s infrastructure and amenities. Owners repay that debt on the property tax bill.
We don’t have these up north. And “Joe, what is a CDD?” is a question I hear constantly.
The debt can be spread over up to 30 annual installments and collected with county taxes as a non-ad valorem assessment (Chapter 190, Florida Statutes). Homestead doesn’t reduce it. The August TRIM notice leaves it out, so the November bill runs higher (Lee County Tax Collector).
In June 2026, I put a typical CDD at $1,500 to $4,000 a year. Lee County’s special-district list includes CDDs for WildBlue, Miromar Lakes, Verandah and the Brooks of Bonita Springs, among others.
HOA fees for single-family homes in master-planned communities ran about $200 to $1,500 a month when I recorded, depending on what’s included (see HOA and amenity communities).
What should condo buyers ask for first?
The reserve study and three years of association financials. Get both before you write an offer.
After Surfside, Florida required milestone inspections and structural integrity reserve studies (SIRS) for condo buildings with three or more habitable stories. Reserves for SIRS items can no longer be waived (HB 913 analysis).
I’ve seen assessments of $40,000, $60,000 and even six figures hit owners with little warning as associations catch up. If a seller can’t produce a clean reserve study and three years of financials within 48 hours, walk away. Resale buyers also get 7 days to cancel after receiving the condo documents (s. 718.503).
Which Southwest Florida city fits you?
Start with how you want to live. Buyers often default to Naples because they’ve heard of it. That’s almost never the right reason.
| City | My short take | Permanent population, April 2025 |
|---|---|---|
| Cape Coral | Start here if you boat and want water access without Naples prices | 222,862 |
| Fort Myers | A walkable, historic River District downtown on the river | 102,060 |
| Bonita Springs | Beach and dining between Fort Myers and Naples, plus golf without the Naples premium | 55,801 |
| Estero | Newer gated, master-planned communities, plenty of bundled golf and about a 10-minute drive to the airport | 38,033 |
| Naples | The region’s polished, priciest option, with Fifth Avenue South and high-end golf | 19,089 (city limits) |
| Marco Island | Island living with a premium beach; bridge in, bridge out | 16,194 |
The population figures are the state’s official estimates from UF BEBR and don’t include seasonal residents. Cape Coral has more than 400 miles of canals (City of Cape Coral).
Bonita is where a lot of the Northeast buyers I work with land once they figure out what they want. Choose the wrong city and you could be moving again in 18 months.
Is moving to Southwest Florida worth it?
With the right plan, yes. My partner Jarrett and I both relocated from the Northeast. When customers ask me off the record what I really think, I tell them it’s real, and we wish we’d done it sooner.
Coffee on the lanai in February, in shorts. Golf two days a week without using a vacation day. And no shovel or ice scraper. The January normal high at Southwest Florida International Airport is 74.7°F (NOAA).
It isn’t perfect. Hurricane season runs from June 1 to November 30 (NOAA), and Hurricane Ian hit Lee County as a Category 4 storm in 2022 (National Hurricane Center). But I’ve never had a customer tell me they wish they’d stayed where it’s gray six months a year.
Want to run your own numbers? Reach out to me, or start with homes for sale.
