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    Home EUROPE Greece

    Canadian real estate celebrity selling Greek islands

    The Analyst by The Analyst
    June 28, 2026
    in Greece
    Canadian real estate celebrity selling Greek islands


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    A celebrity of the private island market and owner of several of them – as he himself admits – Chris Crowlow every morning opens the his email. There, dozens of messages await him: some from pranksters and others from billionaires looking for their next private island. The hard part, he says, is distinguishing which are real business opportunities.

    “Our company attracts quite a few, shall we say, eccentric people,” the 53-year-old Canadian tells the Telegraph. As the founder and CEO of Private Islands Inc., he has set out to solve a problem that hardly concerns the average person: which private island best suits the needs of a zapluto who wants to isolate himself from the rest of the world.

    Canadian real estate celebrity selling Greek islands-1

    Crowlow and his team of five operate an online platform for buying and selling private islands. Today its website hosts around 800 listings, from tropical paradises in the Caribbean and rocky islets in the North Atlantic to Greek islands and man-made atolls in the Indian Ocean. Prices start at $49,900 and go up to $450 million.

    Canadian real estate celebrity selling Greek islands-2
    Chris Crowley on Island Hunters. Source: Youtube

    Although he had no experience in real estate, in 1999 he created a website that collected ads for the sale of islands. According to Crowlow, Private Islands Inc. has around 100,000 subscribers to its newsletter, a clientele that it admits is “unimaginably rich”.

    Crowlow, however, is not limited to sales. He is also a television personality. In Canada he starred in Island Hunters, a reality documentary where prospective buyers visit three different private islands before deciding which one to buy. Also coming soon is the new series Private Islands Inc., in which he will help millionaires and billionaires find the island of their dreams.

    However, he does not stay out of the game. He admits to having several private islands, although he avoids talking about them. “Everyone I know has an island, because I talk to island owners all day. I’m not saying this out of snobbery, but it goes something like this: “Where are you going on the weekend? Your island or mine?”, he laughs, admitting that he “lives in his own bubble”.

    Canadian real estate celebrity selling Greek islands-3
    Chris Crowley on Island Hunters. Source: Youtube

    The Greek ads

    On his website you can also find ads for Greek private islands. In their descriptions, in addition to the blue-green waters, private beaches and idyllic sunsets, Crowlow also makes sure to highlight the most… mundane issues: the current building ratio, the potential for tourism development and the prospects for the development of luxury infrastructure. In fact, he does not fail to point out that the increased demand for investments in Greece and the “Golden Visa” program further enhance the value of these properties.

    Canadian real estate celebrity selling Greek islands-4

    Skyros Island

    One of the ads for ‘Skyros Island’ mentions a 136-acre private island, which is being touted as one of the most attractive investment opportunities in the Mediterranean. According to the description, it falls under Law 4280/2014, which allows tourist development with a building factor of 0.05. As he mentions, this translates into the possibility of building up to 55,000 sq.m. facilities, above and below ground, for the development of a luxury resort, bungalow complex or large-scale private residence. The ad also emphasizes its increased investment value, due to the demand for tourist properties and the Golden Visa program, pointing out, however, that the illustrations are indicative and not binding.

    Canadian real estate celebrity selling Greek islands-5

    St. John Island

    The private island of Agios Ioannis, with an area of ​​750 acres, is presented on the website as one of the most important investment opportunities in the Mediterranean. According to the ad, it has approximately 300 acres of buildable land, a feature particularly rare for the Greek islands. This fact makes it suitable for the development of a luxury tourist complex, a high-end gated community or a large private mansion. The listing highlights the rarity of the property and the potential to develop into an iconic residential or tourist project, with the sale price available upon request.

    Canadian real estate celebrity selling Greek islands-6

    Kythnos Island parcel

    The “Kythnos Island parcel” is presented as a rare investment opportunity in the Cyclades, combining direct access from Athens with an unspoiled natural landscape. As mentioned, it remains unused and has a private sandy beach with crystal clear waters, while its relief includes elevated points that ensure an unobstructed view of the Aegean. According to the ad, the property is offered for the development of an eco-village with 20-25 traditional houses, a luxury private mansion or a boutique hotel, with an emphasis on sustainable development. The ad points out that the area retains its authentic Cycladic character, presenting the property as a rare opportunity for high-end private or tourist development.



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