“I bought a private island for under $20K with my buddies”

Mike Cossette is the proud owner of a one-acre island off the Gulf Coast of Florida, which he bought five years ago with two friends (entrepreneur Adam Miller and public relations specialist Dominic Forth) by pitching in around $20,000. They started out using the island for family camping and fishing trips, but as word of their island grew and led to media appearances, it became clear that this purchase might pay off in other ways. Today, the island is worth $200,000 to $400,000, with discussions underway with a university to turn it into a research base. Here’s how Cossette and his buddies ended up with this dreamy yet challenging out-of-the-box investment.

How did you end up buying a private island? “It started as a random conversation with a buddy who crashed at my Airbnb during Covid. I mentioned the idea of renting raw land to campers for proof of concept, then borrowing against that income to develop. The next morning, he said, ‘Let’s buy an island.’ He had one picked out. That weekend, he went out to the island, and within a week, we were under contract. It was just weird enough, he asked me to come in as a partner, since banks wouldn’t finance any of it, and I knew I’d regret not doing it more than doing it. So I agreed.”

Please tell me more! “It’s off the Gulf Coast of Florida near Crystal River. About 1.2 acres total, with one acre above water, and technically two islands connected by mangroves. It’s wild, overgrown, and has zero infrastructure, which is part of the charm and the challenge. I love the raw nature and uniqueness … I don’t love the red tape and hurricane risk.”

What do you hope or plan to do with it? “The original idea was to rent it to off-grid campers on Hipcamp.com, show some income, then finance development. We still plan to do something along those lines—maybe glamping, events, probably nothing for a while since we have small kids and our own businesses. Every plan hit a permitting wall, so we’re leaning into creative, light-footprint ideas and patience.”

What are the main challenges of owning an island? “Everything’s harder than you might think. You’re dealing with environmental agencies, wetlands, protected species, no utilities, barge access, tide levels, wind patterns, and then throw in hurricanes. Building anything permanent is a logistical and regulatory maze. We’ve talked about underground containers or collapsible structures to survive storms. It’s basically the opposite of buying a city lot and pulling a permit.”

Can you ballpark how many private islands exist in the US, and how many are currently available to purchase? “There are hundreds of private islands in the US; at any given time, there are 100–200 privately owned islands listed for sale across the country. I know there are clusters off Florida’s Gulf Coast where ours is and others off the Eastern seaboard, the Great Lakes, and even the ‘third coast’ of Texas. Many are in rivers or lakes, not just oceans.”

What was your background in real estate investing before buying this island? “I’ve been in real estate for 20+ years as a broker/owner of a RE/MAX office in Austin [TX]. I’ve done residential flips, STRs, LTRs, built an Airbnb duplex, own a 12-unit apartment complex that I self-manage, and I’ve even used seller financing and subject-to creative financing to scale. I’ve always been about pairing cash flow with creativity, but the island’s probably the most eccentric play and one of the more outside-the-box things I’ve done.”

Got any advice for investors or regular folks who might want to try buying a private island? “Unless you love weird problems or want to use the land for your own enjoyment purposes, I wouldn’t do it if you want to try and develop anything. If it’s already been developed or there’s infrastructure on there, it’s going to be a lot more expensive. At least you can avoid all the red tape and agency interference. But definitely have a strategy, even a loose one, don’t overpay for fantasy, and talk to locals before you close. What surprised me most was how little most people actually do with their islands. You’ve got to get scrappy and creative if you want to monetize it.”

Craving more sandy eye candy? See more photos of Mike’s dreamy island paradise below.