It doesn’t take a statistical analyst to know there are a lot of Key West homes for sale. After all, winter is high season real estate. Nothing new about that.

A glance up and down your street probably comes with half a dozen real estate signs. There are about 330 Key West homes for sale, including single-family homes, townhouses and condos and a handful of multi-family homes. Single-family homes represent about two-thirds of the listings. Every listing is written to entice buyers to come live like a local on an island that doesn’t require a passport.

From the descriptions you’d think all of us live “nestled in a tropical paradise” with nary a thing to do but wander the hidden lanes and snuggle on cozy porches, all the while being “mere minutes from all that Duval has to offer.” (I used to write those descriptions so I’m fluent in the cliches.)

I geek on Key West real estate in my spare time. I get a boatload of emails from Realtors and websites like Zillow about new listings, trends and sales.

I long ago bookmarked the Monroe County Property Appraiser’s search site, which means I can know almost as much about your house as I do mine, if I am so inclined. Folks are often shocked at the depth of public record information available, from who owns the property and its sales and price histories to your mailing address, taxes, exemptions and the status of your building permits. There’s even a floor plan for most homes.

A couple weeks ago I noticed something odd in those emails: price reductions. Price reductions in high selling season? Some of them big ones, too. Those usually come in late spring, say sometime after Easter or Mother’s Day, when visitors and snowbirds start to leave the island for places up north. The buyer market shrinks a little bit each day as heat and humidity increase.

I was curious. I took about 45 new Key West listings and compared them with their property records, looking specifically at owners and mailing addresses and at the sales histories. About half of those listings had off-island mailing addresses and most of those homes had been purchased sometime between 2020 and 2023.

Then I did a random sample of new single-family home listings and single-family homes not for sale and used Zillow to track their estimated market values over 10 years. The trend was conspicuous.

Key West homes for sale | Now we’re double, triple 2020 prices

Somewhere around June 2020, Key West home prices exploded. It wasn’t unusual to see a home valued under a million dollars in 2020 soar to double — and sometimes triple — over the following four years. You can quibble about Zillow’s valuation accuracy, but the fact remains that the upward trend line was consistent across the island.

In late 2024 and into 2025, that Zillow trajectory slowed and even fell for many properties. There are, of course, the irrationally exuberant who’ve got their homes listed for what might gently be termed “aspirational,” and there’s no way anyone is going to reduce a home price to its 2020 level. (I mean, who’s going to cut a home price by a million-plus dollars?) But we can’t discount the high-season price-cut alerts. They’re real.

We know what happened five years ago, in March 2020. Covid turned Key West into a haven for mainlanders escaping lock-down restrictions. And while Key West real estate, even pre-Covid, was out of reach for most locals, our 2020 home prices looked darned cheap to investors and off-island home buyers, so they started snapping up just about anything with walls.

With it came a bonanza for contractors and renovation specialists. You can see that from public-record building permits. There’s no doubt that the whirring, buzzing, jack-hammering, painting and planting frenzy spiffed up the island’s real estate. (I do quibble about the renovations that sandpapered away the slightly musty, halfheartedly shabby island charm, replacing it with an awful lot of glossy-surfaced, open-concept design choices more suited to, well, not here. But that’s me.)

The Covid boom is showing signs of stalling. If it does, the hardest hit will be the real estate agents; the folks who bought high in the early 2020s, renovated extensively and expensively and are now entertaining the prospect of not recouping their investments, and the hundreds of contractors, tradespeople and construction-adjacent businesses.

Key West’s real estate world has long been one of boom and bust and its historical trajectory has always been up. There’s an inherent and optimistic appetite for living on an island that needs no passport. But one thing’s for sure whether the Covid-fueled frenzy is over or not: Most locals can’t afford to buy a home and raise a family. Even if we lop a million dollars off every listing.