Key West, a laid back Florida island famous for Hemingway and Jimmy Buffett, was recently named one of the top luxury real estate markets in the nation by Realtor.com®.
Located in the southernmost point in the continental U.S., it averages 867 listings priced at $1 million or more annually, and the median listing price is $1,307,500.
“The Key West-Key Largo area is one of just two micropolitan markets to qualify for our December luxury ranking list,” says Anthony Smith, senior economist at Realtor.com. “With a population just under 82,000, it has more million-dollar listings than the Philadelphia metro, which is home to more than 6.3 million people. It’s a market that consistently punches well above its weight class.”
In Key West, the average entry price for a luxury home—defined as the top 10% of the market—starts at $4,996,500, the second-highest in the nation.
“Prices rose steadily following COVID and, unlike many other markets that experienced sharp corrections after the post-pandemic boom, have largely held those elevated levels,” says Smith. “Limited coastal inventory has kept luxury prices hovering near all-time highs.”
Scarcity sets Key West apart
According to Smith, what truly separates Key West from other warm-weather coastal markets is scarcity. “Strict development limits and a finite supply of waterfront land constrain new inventory, while demand continues to broaden,” he says.
“Waterfront and views matter a lot to luxury buyers here. In Key West and throughout the Keys, open or protected view corridors are limited, and you can’t easily recreate them, so they consistently command a premium,” Lisa Swanson, owner of The Agency Florida Keys, tells Realtor.com.
“Open water homes with deep-water boating access and ocean views command the highest prices, followed closely by historic homes in Old Town Key West,” adds Jimmy Lane, principal broker of Island Life Realty Experts in Key West.
What luxury buyers value most
Location isn’t the only factor influencing price in Key West.
Swanson says, “Luxury buyers want turnkey, move in ready, newly updated, and are willing to pay a premium for these properties.”
And it’s precisely this mindset that is reshaping Key West into a rarefied, enduring luxury enclave.
“The market attracts a growing base of luxury buyers seeking privacy, uniqueness, and lifestyle over scale, often viewing Key West as a destination or legacy market rather than a traditional second-home play,” says Smith.
“As a result, Key West luxury behaves less like a typical U.S. resort market and more like a globally constrained enclave, where exclusivity and permanence underpin long-term pricing strength.”
Swanson also says Key West buyers aren’t just purchasing a house—”they’re buying walkability, culture, boating access, and a globally recognizable island brand, with far fewer new-build alternatives than most coastal cities.”
Lane says another thing that sets Key West apart from other coastal cities is the culture. “We are located closer to Havana than we are to Miami, so you really get that laid-back, island vibe,” he says.
“Key West only has a full-time population of 25,000, but during peak season, that number can more than double, which supports our amazing restaurants, theaters, and attractions.”
Larger price gaps and slower sales
Key West-Key Largo and Crestview-Fort Walton Beach-Destin, FL metros both show substantial gaps between median and luxury prices.
In Key West-Key Largo, the luxury threshold is 3.8 times the local median.
Meanwhile, in Crestview-Fort Walton Beach-Destin, the median listing price is $583,500, while the entry point to luxury (the top 10% of homes) sits at $2,837,322—meaning the luxury threshold is 4.9 times the local median.
“A common thread across many of these metros is proximity to the coastline, where access to waterfronts, views, and limited developable land creates sharp price stratification within the same market,” writes Smith. “Lifestyle-driven demand in these areas tends to concentrate luxury housing into narrow corridors, widening the gap between typical homes and the top of the market.”
In both of these markets, luxury homes also take longer to sell.
In Key West-Key Largo, the median is 68 days, and in Crestview-Fort Walton Beach-Destin, the median stretches to 117 days.
Swanson says, “We are seeing longer timelines to go under contract, which is normal as buyers take more time and become more discerning.”
Swanson notes that, on average, trophy homes over $4.9 million tend to stay on the market longer.
“That’s mainly because the buyer pool is smaller, and due diligence is more intense,” she explains. “But properties over $4.9 million can still sell quickly when they check the ‘scarcity’ boxes: irreplaceable location, strong views, boating utility, privacy, turnkey condition, and/or priced correctly for today’s market.”
Swanson adds, “If any of those are off—especially pricing or condition—time on market tends to stretch.”
Celebrities flocking to the Florida Keys
Key West and the Florida Keys have long been a playground for the rich and famous.
Actress Sydney Sweeney bought a $13.5 million retreat in the Florida Keys in 2024.
Last year, Barstool Sports founder Dave Portnoy snapped up a Florida Keys compound for $27.8 million.
And NASCAR legend Dale Earnhardt Jr. and his wife Amy owned a house in Old Town Key West for more than a decade. The 2018 DIY Network show “Renovation Realities: Dale Jr. & Amy” followed the couple as they lovingly restored their Key West home.
