Moving to Winter Park After December 31, 2026? What Amendment 3 Means for Your Homestead

If you are planning a move to Winter Park, the calendar just became part of the conversation. Florida voters approved Amendment 3 on November 3, 2026, and it changes the homestead exemption starting with the 2027 tax roll. For most people who already live here, that is good news. For people who are still living in New York, Chicago, Atlanta or anywhere else outside Florida on December 31, 2026, the rules are different, and the difference lasts for years.

I have been getting the question from relocating buyers almost every week: “Does it matter if I close in December or in February?” The honest answer is that it can matter, but not in the way most headlines suggest. Here is what the state has actually said, what is still unsettled, and how I would think about timing a Winter Park purchase right now.

What Amendment 3 changes, in the state’s own words

The best source on this is not a news recap. It is the Florida Department of Revenue’s Property Tax Oversight bulletin PTO 26-21, dated November 5, 2026. According to that bulletin, Amendment 3 (House Joint Resolution 1-F) does three main things:

• It reduces the annual cap on assessment increases for non-homestead property from 10 percent to 5 percent.
• It increases the homestead exemption for all non-school taxes, exempting assessed value up to $150,000 in 2027 and up to $250,000 in 2028, with inflation adjustments after that.
• It provides that people who are not Florida residents as of December 31, 2026, receive a $25,000 exemption on assessed value for school taxes and up to $50,000 for non-school taxes when they qualify, with eligibility for the larger exemption beginning with the fifth year of exemption.

The amendment takes effect January 1, 2027, and first applies to the 2027 tax roll. The enrolled text of HJR 1-F on the Florida Senate site spells out the same structure, and it also says the Legislature will set uniform procedures by general law to administer the newcomer rule. The Department says more rulemaking, updated forms and guidance are still coming.

The December 31, 2026 line, explained plainly

The dividing line is residency, and it can split neighbors on the same Orwin Manor street for years. If you already maintained a permanent residence in Florida as of December 31, 2026, and you qualify for homestead, the non-school portion of your exemption steps up to as much as $150,000 of assessed value in 2027 and $250,000 in 2028. The school-tax portion stays at $25,000.

If you had not maintained a permanent residence in Florida as of December 31, 2026, and you buy and homestead a Winter Park house in 2027 or later, the amendment gives you a smaller exemption to start: $25,000 for school taxes and up to $50,000 for everything else. That looks a lot like the exemption Florida homeowners have today. Beginning with your fifth year of exemption, you move up to the larger amount.

Notice what the text keys on. It is not when you close on a house. It is whether you maintained a permanent residence in Florida as of December 31, 2026. That is a residency question, and the state has not yet published the details of how it will be proven. I would not trust anyone, me included, who tells you today that a lease, a hotel stay or a closing date by itself settles it. Wait for the Department of Revenue and your county property appraiser to say so in writing.

Why the county matters before anything else

Homestead is filed with the property appraiser in the county where the house sits, not the one printed on your mail. Around Winter Park that is not always obvious. A Winter Park mailing address in 32789 or 32792 can be inside the city limits or in unincorporated Orange County, and homes around Maitland, Casselberry, Longwood and Howell Branch Road sit close to the Orange and Seminole county line. I walk through how that works in What a Winter Park Address Actually Means and Orlando Address vs. City Limits.

So step one, before you file anything, is a parcel lookup on the right site:

• Orange County: the Orange County Property Appraiser homestead page says applicants must be a Florida resident as of January 1 of the year they apply, and its key dates page lists March 1, 2027, as the exemption deadline, with online, email, mail and in-person filing.
• Seminole County: the Seminole County Property Appraiser exemptions page lists a March 1 deadline and says that as of January 1 you must have title, maintain the home as your permanent residence, and provide a Florida driver’s license showing the property address.

One caution: some county pages still describe the familiar “up to $50,000” exemption, because that is the law for 2026. When you read about 2027 amounts, rely on the Department of Revenue bulletin rather than an older county FAQ until the counties update their pages.

What this means for a Winter Park buyer timing a move

I am not a tax advisor, and nobody can promise you a dollar figure yet. But here is how I am helping relocating clients think it through.

If you are already moving this year. If your job, your family or your lease already has you settling in Winter Park before the end of December, talk with a tax professional about what establishing permanent residence actually involves for your situation. Do it now, not on December 30. A rushed closing on the wrong house is a far more expensive mistake than a smaller exemption for a few years.

If your move is really a 2027 move. Do not buy a house you do not love just to beat a date. Run your numbers using the newcomer exemption for the first four years and the larger one after that. Then decide whether the house still makes sense.

If you are a current Florida resident moving within the area. Selling a Longwood or Oviedo home and buying in Winter Park is a different conversation. Florida’s homestead portability rules still matter here, and I cover them in Downsizing and Florida Homestead Portability. Ask the property appraiser how portability and the new exemption amounts will interact for your specific move.

If you are buying a second home here. A Park Avenue condo or a lake cottage you are not homesteading is non-homestead property. Under the amendment, its annual assessment increases are capped at 5 percent instead of 10 percent starting in 2027. The assessed value can still reset after a sale, so the seller’s current tax bill is not your future tax bill.

The sale-year tax bill still surprises people

This part has not changed. When you buy a home in Winter Park, the seller’s exemption and their Save Our Homes cap do not transfer to you. The Seminole County Property Appraiser explains that once homestead is granted, the following year’s assessed value can rise no more than 3 percent, or the change in the Consumer Price Index if that is lower. It lists the 2026 CPI figure at 2.7 percent. That cap belongs to the owner, not the house.

So when a seller has owned a house on Lake Osceola or in Windsong for twenty years, their tax bill can be far below what yours will be once the parcel is reassessed after your purchase. Amendment 3 makes the exemption bigger, but it does not erase that reset. When I prepare a buyer’s numbers on an older Winter Park home, I estimate taxes from the purchase price, not the seller’s bill. I also cover the rest of the ownership costs in What an Older Winter Park Home Actually Costs to Own.

A short checklist for relocating buyers

1. Look up the parcel on the Orange or Seminole County Property Appraiser site and confirm which county and city the house is in.
2. Talk with a tax professional about your residency timeline before December 31, 2026, if that date could apply to you.
3. Plan to file homestead with the correct county by March 1 of the year after you qualify, and have your Florida driver’s license updated to the property address.
4. Budget taxes from your purchase price, not from the seller’s current bill.
5. Watch for updated forms and rules from the Department of Revenue and your county property appraiser. I will update this post when they publish.

For background on the exemption itself, see my Florida Homestead Exemption guide. If you are still deciding where to land, Moving to Winter Park, FL and Moving From New York to Orlando are good next reads.

Planning a move to Winter Park?

I have over 37 years in the real estate industry and have been local since 1978. RealTrends ranked me in the top 0.5 percent of Florida agents and #10 in Winter Park by transactions for 2026. If you are trying to figure out whether to buy this year or next, call or text me at 407-620-7785 or email will@irlhomes.com. I will help you look at the houses and the timing together.