Joe wasn’t planning to buy a home overseas, let alone one he hadn’t stepped inside. Yet a family trip to Europe planted a seed. This is his story of serendipity, caution and a house on Andros that changed everything.
Joe began his journey exactly where many cautious overseas buyers start: convinced he’d never actually go through with it. When he and his wife took a long-overdue trip in 2023, spending 10 days in Italy followed by 10 days in Greece, he found himself thinking, “I could do this.” The peaceful routines, the food, the surroundings… everything nudged him towards the idea that a different kind of life might be possible. But by his own admission, Joe is the type who can talk himself out of almost anything.
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How a holiday turned into a life-changing idea
The trip began as a straightforward holiday to spend time with family in Italy and Greece. They visited Joe’s cousins in Italy, spent time harvesting olives and sharing long lunches, then travelled to Andros – the Greek island where Joe’s father-in-law was born. With their daughters joining them, the holiday took on a different feeling: familiar yet new, relaxed yet comforting. Being surrounded by family, Greek conversation and homemade food created a sense of belonging that Joe hadn’t anticipated.
One evening over dinner, his wife and daughter looked at him and asked the question that would reroute their lives: “Why don’t we buy something here?” Joe didn’t give a firm yes or no. Instead, he kept things open and told them, “If you find something, we’ll consider it.”
Within days of returning home to Pennsylvania, Joe’s phone rang. His wife and daughter, still on Andros, had found something.
The first property: where caution took over
This is where Joe’s cautious instincts kicked in. The home seemed right – until he discovered that in Greece, the deposit doesn’t sit safely in escrow. It’s transferred directly to the seller. If something goes wrong, you rely on the contract stating that the seller must return double the deposit… and you hope you never end up arguing this in court.
For someone like Joe, who prefers everything clear and risk-free, this felt like a flashing red warning sign. He couldn’t shake the feeling that he might lose control of the process. And then everything fell apart anyway. The seller accepted an offer from someone else and, at the last moment, demanded €100,000 more if Joe still wanted the house. That confirmed every fear he’d ever had.
Yet this messy beginning was the twist that changed everything – because losing the first property opened the path to the home that truly was meant for them.
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The house he bought in 15 minutes –without seeing it
A week later, the agent called back. He’d kept a listing off the market because he believed it was perfect for them. If Joe’s family could fly back to Andros quickly, he’d hold it.
Joe stayed home, still wary. His wife and daughter went instead. They walked through the house for just 15 minutes before calling him. “Dad, this is it. This is even better than the first one.”
For a man who had hesitated over every detail of the buying process, the decision suddenly felt simple. He trusted them – and he trusted the feeling. They bought it.
He wouldn’t see the home in person until the day of closing.
What he found when he finally walked through the door
Joe remembers stepping inside and instantly knowing his family had chosen well. The house needed work, but his wife is an interior designer and former caterer, and Joe is a master gardener. The place was almost waiting for them. Between them, they renovated the entire ground floor, created a workspace for their daughter and built an outdoor kitchen for long meals with friends.
The land became Joe’s happy place. Today he tends to 30 olive trees, grapevines, apricot and persimmon trees – all the things he once admired in Italy but never imagined recreating.
The unexpected moments that make Andros feel like home
At closing, Joe was surprised to learn – moments after the paperwork was signed – that the electricity and water were off and could take weeks to reconnect. He turned to his lawyer and agent in frustration, thinking, “Why am I only finding this out now?”.
Joe had been told to expect bureaucracy at the electricity office and went armed with cookies and pastries to butter up the notoriously cranky clerk. “If you look at her the wrong way, she might not help you,” the seller had warned. But they needn’t have worried. The woman behind the desk recognised Joe’s wife’s surname and realised they were estranged cousins. After many hugs and tears, their electricity was connected in a matter of hours.
Experiences like this made Joe appreciate how tightly connected life is on Andros, and how important it is to treat people well. When they carried out renovations, they hired local workers, paid fairly and built relationships. “Bad news travels quickly on a small island,” Joe says. Doing things the right way means you can walk through the village with your head up – and be welcomed.
The parts that still worry him
Joe is honest about the challenges too. Andros doesn’t have an airport and doesn’t allow large cruise ships to dock, which is part of its charm. But it also means limited healthcare. Serious emergencies require helicopter transport to Athens, and Joe admits that’s a concern, especially as he gets older. It’s one reason he hasn’t committed to living there full time.
Still, he and a group of returning expats are working on this. They’re trying to bring refurbished medical equipment from the US to upgrade the island’s clinics – a small step towards making life easier for everyone who lives there.
Joe’s advice to anyone thinking about buying overseas
For readers who are cautious or nervous about making mistakes, Joe’s guidance is clear and reassuring.
1. Get a professional advisor – not just a general lawyer
Joe’s biggest hindsight lesson is the importance of having someone who specialises in overseas property, golden visas and local regulations. It saves time, stress and confusion, and makes the process smoother. He says it would have made their own journey much easier.
2. Don’t overthink it to the point of talking yourself out of your dream
Joe believes research is essential – but too much can stop you making a decision at all. At some point, you have to trust your instincts.
3. Build relationships with locals from day one
Hiring locally, paying fairly and being respectful goes a long way, especially on an island where everyone knows everyone.
4. Accept that you won’t control everything – and that’s OK
Joe never expected to buy a house without seeing it. But letting go of complete certainty allowed him to say yes to something life-changing.
Final thoughts
Joe never planned to buy abroad, let alone commit to a property he hadn’t seen. But a family trip, a lost first deal and a moment of instinct changed everything. Today he owns a renovated home on Andros and encourages cautious buyers to get professional help, trust their instincts and embrace the adventure.
