10 min read

Our Story

Written by
Derek Cirillo
Published on
June 3, 2025

A lot of clients and people on social media often ask us the same question. How did you get into selling homes in Japan?

So, I figured I’d write this to give you the full story. How we ended up selling Japanese homes, what drew us in and why.

Traveling to Japan to go snowboarding has always been a dream of mine. Growing up on the east coast of the US, I’m used to boilerplate conditions. I’m talking icy, Bone-chilling wind and a scheduled Christmas thaw with rain just to kill any hopes you had of a good season. Shout out to Jay peak though for being the only semi-reliable place on the east coast. Growing up on the “Ice-coast” as we call it will keep you from getting Jaded and keep your edges sharp.

Then came along Japan. I grew up watching snow board videos in the early 2000’s and you would hear whispers about Japan’s bottomless pow, but it wasn’t really on people’s radars as a snowboarding destination. There were a few videos out there though, like Analogs Trouble in Japan, which is burned into my mind. I’ve probably watched it a thousand times. It painted this almost mythical picture of weaving through white birch forests in waist-deep powder like some kind of snowboarding samurai.

After years of trying (and failing) to convince my friends to plan a Japan with me, the stars finally aligned in February 2023. We split our time between Tokyo and Nagano. The second we stepped off the Shinkansen in Nagano, it was already snowing. By the time we got to Shiga Kogen, it was absolutely nuking. Four feet overnight. I’m talking full-on snorkel conditions. That first run? It was everything I imagined, bottomless turns and smiles all around. We couldn’t strap our bindings fast enough to run another lap. I was immediately hooked.

While I expected snowboarding to live up to the hype, I really didn’t give much thought to Tokyo. I was so hyper focused on snow forecasts and living my snowboarding fantasy that the first part of the trip was almost background noise. My wife planned the entire week for us in Tokyo; I didn’t give it a bit of attention. But Tokyo absolutely blew my mind. I almost considered skipping the mountains and spending 2-weeks in Tokyo running around Golden Gai (Okay not really). Me, my wife and a few of our friends have spent our post college life trying to see and do as much as we can before life inevitably settles us down, so we’ve seen our fair share of places. But nothing has hit quite like Tokyo. I spent last summer surfing in Madeira and Ericeira, two beautiful places, but the whole time I couldn’t help but compare these places to Japan. And how much more i like Japan. Sorry Portugal.

Before this trip, I’d vaguely heard that homes in Japan were cheap, but I never gave it much thought. It felt like one of those too-good-to-be-true things people say online and then forget about. I’ve always dreamed of owning a ski home, but in the U.S. that’s a seven-figure dream. After getting completely mind-melted by that first day riding at Shiga Kogen, I started seriously thinking… Could I actually own a place here? So I started digging around. And what I found kind of blew my mind: homes, actual live able, albeit dated homes, for $20,000 to $30,000 USD. Not huts or sheds or mold filled junkers, real houses. It felt like a secret the world hadn’t caught onto yet.

Snowy Streets of Otaru

Since that first trip we’ve gone back every year, choosing new locations and exploring different ski resorts. One year we decided to give Otaru a shot. A small coastal city with 4 resorts within driving distance and one of those resort, Kiroro, holds the title as the snowiest resort on the planet. Otaru is situated in a perfect place to receive a never-ending stream of snow all winter. All it takes is cold winds from Siberia to blow over the Sea of Japan and pick up moisture. When the cold moisture rich winds hit the coast of Japan the first place they hit is the mountains above Otaru. Which means it absolutely dumps snow pretty much nonstop all winter.

We knew right away this was the spot we wanted to be. It was affordable, it was authentic, it had a plethora of resorts to choose from and importantly it was a cool place it’s own right. It wasn’t just a ski resort town, it’s a proper city.

After that trip to Otaru, I flew back to New York and immediately went into research mode. I started reaching out to consulting services, thinking I’d get some clear answers. But honestly, I kept getting let down. Most of them didn’t have a clue whether a property was properly zoned for minpaku (short-term rentals), and their whole vibe was basically “buy it and hope for the best.” I’m all for taking risks, but not blind ones, $25K might not be life-changing money, but it’s still a solid chunk, and I needed some kind of rental income to offset the cost. I talked to service after service, and none of them could help me figure out zoning or offer management support in the area. Until I met our current partner, Jacob.

Jacob turned out to be the missing piece. He’s a bilingual expat who runs a property management company across the entire island of Hokkaido and has boots on the ground. He’s partnered with a local real estate agent and a licensed contractor, so everything you would need. He helped us navigate the whole process: setting up utilities, coordinating renovations, and even getting us on track for a full Ryokan license so we can legally rent the place 365 days a year. No guesswork and no “hope it works out.”

Snow outside the first Airbnb we stayed in Otaru

After working with Jacob and seeing how seamless he made the whole process, we had a conversation: What if we brought this to more people? He didn’t have much access to foreign clients, and after experiencing how frustrating the other services were, I knew his setup was on another level. So we teamed up. That’s how Yuki Homes was born, a partnership built to give foreigners the same smooth, stress-free path we had. Whether you’re chasing powder, looking for a peaceful countryside retreat, or trying to build something new in Japan, we built this for you. A full-service, boots-on-the-ground team to help you actually make it happen. No guesswork. No language barrier. No broken promises. Just your dream life in Japan, one key turn away.

Derek Cirillo
June 2, 2025

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Our team

Meet the founders.

Derek Cirillo
Co-founder

Derek has been working in the Airbnb space for the past 10+ years and recently purchased a home in Japan. He is excited to bring this investment opportunity to others in the States & abroad.

Nick McLoota
Co-founder

Nick has a passion for adventure and has always dreamed of owning a property in Japan. His dreams finally came true when Derek brought him in on a deal of a lifetime in Hokkaido, Japan - one of Nick's favorite places on Earth.