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Duval Street in Key West may be short in length, but it's long on price tags. One of the most surprising facts is that commercial rent here can soar as high as $100 per square foot annually, rivaling or even surpassing costs in major cities like downtown Miami or Chicago. The sticker shock doesn’t stop there—tiny retail spaces and condos as small as 500 square feet regularly sell for over a million dollars, not because of luxurious finishes, but because of location, location, location. On Duval, you're paying for access to a constant stream of foot traffic, not for sprawling square footage or modern architecture. The charming conch cottages and historic homes lining the side streets just off Duval also command high prices. Even modest, weathered wooden homes—often no bigger than a two-bedroom apartment—can fetch anywhere from $800,000 to well over $1.5 million. What’s even more surprising is that these homes are rarely purchased as full-time residences. Many are scooped up by investors or second-home buyers, often paying cash, who see the properties as vacation rental goldmines. That steady Airbnb income has inflated property values dramatically in the area, making it even more competitive. Despite these high property values, homeowners enjoy a financial break thanks to Florida’s Homestead Exemption and the lack of state income tax. Even million-dollar homes come with relatively manageable property tax bills. But that doesn’t mean living here is cheap—insurance costs, especially for hurricane coverage, are steep, often adding $5,000 to $10,000 a year to your expenses. Utilities are more expensive than on the mainland, with higher rates for electricity and water, especially during hot, humid months when air conditioning is essential. Another hidden cost of living near Duval is tied to the island’s charm—historic preservation. Many buildings fall under strict historic district regulations, meaning renovations require special permits, materials, and approval processes that can delay projects and inflate costs. Meanwhile, basic goods and services—everything from groceries to gasoline to handyman labor—are marked up due to the logistics of getting supplies onto the island, a phenomenon locals refer to as paying “island prices.” Interestingly, even with high demand, some commercial spaces on Duval remain empty for long stretches. That’s because property owners can afford to wait for the perfect tenant who’s willing to meet their sky-high rent demands. And those rents are justifiable in many cases—some bars and restaurants make enough in a single week to cover their entire month’s rent thanks to relentless tourist traffic. Real estate turnover is fast and competitive, and unlike most places, the majority of sales happen with cash offers. Financing delays can cost you the deal. What's more, unlike other tourist cities where you might find a lower-cost neighborhood a few blocks away, Key West offers no such break. Every inch is valuable, and prices stay high even in the quietest corners. Simply put, there’s no such thing as a “cheap side” of Duval Street.