$30,000,000 Lottery Winner…

I just did something I have never (okay, maybe twice…) done before:  I bought a lottery ticket.

I went for coffee and in front of the Tim Hortons/Esso was a big sign: 6/49 Jackpot: $30 Million!

Let’s assume I have to spend all $30,000,000 on real estate.  What would I buy?


What would you do if you won the lottery?

This is a question people ask eachother over and over again, and thus the lottery companies across the world have capitalized on this pipe-dream and incorporated it into their various marketing ploys.

I always used to answer, “I would do nothing,” and assume that I would just go about my daily routine as if none of this had ever happened, except I would eat prime rib every night for dinner…

But evidently, lottery winners in Ontario MUST allow for their name and photo to be published and MUST accept one of those oversized cheques in person.  So my plan to remain anonymous and never inform my family and friends of my new-found riches simply won’t work.

There are downsides to winning the lottery.  For example, will you ever feel joy finding money in the street again?  Okay, lame example…

People always ask, “Would you quit your job,” and I honestly think I would keep working in the real estate industry.  It’s truly a “come and go as you please” type business, so really, what would change?

The next question becomes: “What would you buy?”  The possibilities are endless!  Cars, houses, toys, gadgets, professional sports teams!  I wouldn’t know where to begin, and even for the sake of a fun exercise, I would lost my mind trying to think of what I would buy.  So I’m going to limit my response to real estate.

My knowledge of international real estate is somewhat limited, but I do know of a few places I’d like to travel to on a regular basis, and thus purchasing a property there is a no-brainer.

Even if I had $30,000,000, I still would refuse to throw caution to the wind, so I’d have to not only ensure my investments were sound, but also ensure that my real estate portfolio was well diversified.

Okay, so I have $30,000,000 to spend.  And now, I’m on the clock…

1) Ski Chalet, Park City, Utah: $5,995,000


I had a very deprived childhood, clearly, as I was forced to ski the mountains of Park City, Utah from 1988 to 2002.  I have felt a large void ever since we sold our family home, and what better way to rekindle those modest childhood memories than to buy a monster $6M house?  I’ve always admired houses made from wood, with no brick or mortar.  This house is built on the mountain side and thus its two levels of living space are both at-grade.  The main level faces west with a huge floor-to-ceiling window and an 18-foot rise.  I can only dream about having my friends and/or family here for the ski vacation of a lifetime.

2) Summer Home, Ajijic, Mexico, $1,250,000


All it took was one week for me to fall in love with the city of Ajijic, Mexico after visiting the quiet, land-locked city for a wedding last summer.  As ridiculous as this may sound, $1,250,000 for this palatial estate is dirt cheap!  The weather in Ajijic is among the best in the world, as the precipitation is low, and the temperature is always in that reasonable 20 – 25 degree window, and never a 40-degree scorcher.  The city of Ajijic is essentially run by Americans & Canadians who have moved their lives south to this authentic Mexican town.

3) Cole Harbor, Nova Scotia, $515,000


What is more modest: the price, or the house itself?  This traditional 3-bedroom house is situated on a deceiving four acres of land!  I would leave this house exactly as it is, since I’d have my gawdy Park City, Utah home to visit, among others.  Cole Harbor would be my escape to simpler times when I wasn’t burdened with cash and a caviar-eating lifestyle.  I would wear sandals and jean-shorts 24/7, and ride my ATV or dirt bike through the surrounding miles and miles of trees.

4) Scottsdale, Arizona, $1,800,000


Combine the weak U.S. economy, the glut of houses for sale in “hot-spots” such as Scottsdale, and the $1,800,000 price tag of this home, and I’m gonna call it an even $1.5M.  This large ranch bungalow has two pools, a putting green and a fantastic three acre backyard full of cactus’s and tumbleweeds.  There is one reason I would own this house: GOLF!  With direct flights from Toronto to Scottsdale on a daily basis, this home away from home would be a simple jaunt southwest for the weekend.

5) Hvar, Croatia, $2,750,000


This is basically as close as I could come to having my own castle!  The Croatian coast is home to some of the most beautiful, and affordable real estate in the world.  Right on the Adriatic Sea, Hvar is an island just south of the mainland Croatia, and is quaint yet sophisticated, and relatively unknown as far as the globe is concerned.  I’d rather vacation here than Ibitha, Spain, or some other over-developed “hot spot” for richie-rich types.



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  1. Dan says:

    David – It’s too bad your Listing of the Day feature can’t be done anymore. It was refreshing to get some blunt commentary about some of the listings that are out there. Still, I enjoy reading most of the other stuff you write about – you have a talent for composition. Not sure if you’re taking requests, but I’d like to hear a balanced view about the pros and cons of the discounted (or flat fee) commission that’s being around in Toronto now for a few years? I personally have used them to sell my condo and it worked out fine – but then I knew what I was doing.

  2. David Fleming says:

    I’d like to think that when I rant and rave, I do so in a more orderly fashion than most. Perhaps the premise (winning the lottery) is outlandish, but the idea here is an attempt to balance the desire for domestic and international real estate while keeping in mind that no matter how rich you are, you have to be smart with your money.

    I should also note that “Listing Of The Day” used to comprise half my posts but this feature got me in trouble with RECO as well as my own managers. I’ve had to since re-tool my blog to some extent.

    There is a second part coming tomorrow, which may or may not be interesting depending on how you view the article. I’m always open to feedback, good or bad, and I thank you for posting your thoughts!

  3. Jess says:

    I enjoyed your blog more when you wrote about your actual dealings in the Toronto real estate market. Now you write about all kinds of things, some not even related to Toronto realty. It’s not as interesting. There are already enough people out there ranting about everything and anything.