Blog
6 min read

A Learning Experience in Home Buying in Japan

Written by
Derek Cirillo
Published on
August 17, 2025

I mean check out this view….

Recently, I came across a home in Izu that seemed too good to be true, a stunning mountainside retreat with a giant bay window offering panoramic mountain views, and onsen water already piped into the house. Just a short ride up a steep road from the nearest train station, and only an hour and 45 minutes to Tokyo Station. It was listed at 9.7 million JPY. A steal.

Immediately, I started running numbers in my head, imagining the renovations, the Airbnb potential, and of course, how amazing it would be as a personal getaway. It checked all the boxes.

We jumped on it. Reached out to the seller. Tried to figure out why a gem like this was even on the market. According to the seller’s agent, the house was "too popular on Airbnb," they couldn’t keep up with the volume. That was red flag #1.

Still, I figured if we could lock down a solid management team and get a structural inspection, it could be worth it. So we moved forward and submitted an intent to purchase.

One of our team members visited the property in person. Their report? Not great. The house was in rough shape, and the access road was steep. But from experience, I know many Japanese people are hyper-cautious about older homes, so I took it with a grain of salt and kept focusing on the potential.

Then things started to spiral.

After submitting our intent to purchase, with a clause requiring an inspection, the seller’s side began pressuring our agent to sign the contract ASAP. Red flag #2.

Still, I reasoned if the inspection was clean and i had a solid property manager I could make this work. My vision of this home was just too strong to see what was right in front of me.

But things just kept popping up.

Before we could even schedule the inspection, the seller offered our agent the full commission, both the buyer and seller sides. Clearly a move designed to entice him to rush this deal forward at the expense of me.

Luckily, our partners at YukiHomes are honest and transparent. They came straight to me and said:

“To be perfectly frank, all of this raises serious red flags. It looks like the seller may be trying to cover up some hidden defect or legal issue to rush the deal through. Based on my experience, I’d estimate there’s a 90% chance this property is either violating regulations or has serious hidden defects.”

Finally the red flags caught my attention.

I’m sharing this as a cautionary tale. Japan is an amazing country, and yes, there’s more societal trust here than in many other places, but that doesn’t mean every deal is clean. There are still bad actors, and it’s easy to get swept away imagining what a place could be, instead of seeing what’s right in front of you.

I’m lucky to have a great partner in Japan who truly looks out for my best interests and would do the same for you if you choose to work with us.

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Derek Cirillo
August 4, 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.