The world of real estate sales is often intense, stressful, fast and strategic, however there are moments of comedic relief that I find myself smiling and laughing about over the years. I thought today, instead of a typical “How to ______ in Real Estate” article, I would share with you my top 8 Most Entertaining Moments In Real Estate.

8.  The Donkeys. 

One of my favourite types of properties to show & sell are acreages.  One of my clients (a couple), many years ago, were looking to purchase a quiet acreage with the possibility of having animals on the land.  After searching for a short while, we found the perfect property! The home was beautiful, the land was flat, surrounded by trees and there was a nicely penned area which enclosed the two rescue donkeys that lived on the property.  These were no ordinary donkeys.  They were highly intelligent and constantly showcasing their ability to outwit their humans by escaping their enclosed pasture no matter what was placed in their way to keep them in. They were often seen wandering the property together and would make a game out of dodging their human’s recapture efforts. My clients fell in love with the donkeys and were ultimately able to work out an agreement with the seller such that the donkeys would remain onsite until a new barn and enclosed pasture on the sellers new property could be built (approximately 1 year after the closing of the sale). The Donkeys were visited by their owners and doted on by their new caretakers over that year.


7.  The Kissing Girls.

While showing a triplex, I opened a bedroom door of the second unit and found two twenty something girls ‘making-out’ on the bed. No one was supposed to be home! I apologized to the girls and they didn’t seem to even really notice that we were there and kept on…To this day my clients have a little chuckle to themselves and still remember that property as the kissing girls’ house.

6. The Couch Snooze.

Once each week in any given area, there is typically a local MLS tour where the realtors all congregate, carpool and view the latest homes on the market. This one particular home was supposed to be unoccupied for the MLS tour…however, we (realtors) were all surprised to find a 40 something man snoring, mouth open and oozing a little drool and having a great snooze on the couch. He slept through the entire tour of 40+ agents roaming in and out of his house.

5. The Old Man & The Chocolates.

I once sold a condo bellonging to an older man who was hovering around 80 years old and who was finding that his life was slowing down. He was preparing to move into a seniors home where he could still have freedom, yet he would also have support ready when he needed it.  He had a theory in life that ”Chocolates make everything better”. Each week he would walk to the local Zellers (remember Zellers?) and buy several boxes of mixed chocolates so that he could give them to the people he appreciated (he would always save himself one box to enjoy).  Over the course of the listing and sale, I accumulated nearly a dozen boxes of chocolates from him. It was how he said thank you for a job well done, or whatever emotion needed to be expressed as he wasn’t good with expressing himself. Just as his sale was about to be finalized he nearly stopped the entire deal. It turns out he wasn’t so ready to let go of his home, his life, or succumbing to the reality of living in a seniors home. Yet his rationale mind knew that the move was in his long-term best interest and ultimately decided to move. The day that he signed the paperwork with the lawyers I visited him and brought with me two boxes of Purdy’s chocolates. He beamed ear to ear and gave me a big hug.  Just before I left him that day, he gave me yet another box of chocolates and a thank you card. I felt so lucky to have helped him.


4. The Comic Book House.

I’ve seen nearly every style of home and in nearly every condition. However until a few years back, I hadn’t ever been in a house quite as colourful as the one I’m about to tell you about. The walls were professionally yet brightly coloured with a different colour in every room. Within the walls of these rooms lived every superhero and villain you could think of! Large Batman, Joker, etc… paintings on every wall, floor to ceiling glass cases filled with figurines (which I’m sure cost a small fortune), an entire room consisting of thousands of mint condition comic books all stored very carefully in boxes, toys, themed kitchenware & bedding, etc. The entire home had been engulfed! I had never been so entranced.  Unfortunately, to get the high price tag that my clients wanted, we had to carefully have nearly everything packed away and put into storage.  My client negotiated with me to keep a few of the figurines out and one painting, to which I agreed. We staged the rest of their home and sold it for their full price!

3. The Ex-Drug homes. 

I unfortunately have shown hundreds of ex-drug operation homes.  These homes are completely destroyed by these operations and have a smell that permeates everything. They typically all have some sort of dog on site warning signs, video cameras everywhere (or signs of dismantled cameras), exposed mass drainage systems, basements where the drywall is missing and the studs are exposed, hundreds of little black empty potting plant pots (likely hiding somewhere on the land), sketchy interior and exterior electrical hookups, a brand new electrical box, secret & locked rooms within the home, smaller camouflaged buildings a few acres away from the main home with sketchy wiring and drainage, a nearly vacant home where furniture, food & clothing is sparse. The most interesting of the ex-drug homes however are the ex-drug operations that took place inside of a detached workshop.  Most of these detached shops have a false exterior that blend with the home (as to not appear suspicious).  The interior, however, tells another story. Double steel walls, entrance doors with locks similar to those found in a bank vault, layers, hidden rooms, strategic water and electrical systems. The remains of an ex-drug operation always give me ‘creepy’ feelings and make me feel sad for the properties.

2. The Snakes on Acreages. 

One of my favourite parts of showing or selling an acreage home is taking a stroll around the property.  I find it entertaining when a realtor shows up in impractical shoes to show an acreage property. There is no way they can properly walk around the property in stilettos or loafers. Typically gumboots are needed. A true acreage in the country will be home to many wild animals such as Snakes.  Snakes love following along on a walking tour of an acreage because as we walk through the grass, we rustle up the little insects hiding within the grass and the snakes can enjoy a feast! Folks who are used to walking acreages understand that this happens and are accustomed to seeing them or having them accidentally ‘running’ over their boots. If you don’t know what to look for, you likely won’t see the snakes as they are fast. I see them now nearly every time I show a grassy acreage property. But the buyers and the other realtors don’t ever notice and I usually don’t say anything for fear of upsetting them!


1. The Naked Man. 

Within a few short moments of entering the bedroom level of a beautiful home, my clients and I heard the ‘squeakings’ of a bed. I was told no one would be home while I was showing the home and it had thus far been vacant.  I called out “hello?”, to which I received a reply from a man whom was obviously quite startled as he sprung from his bed, lacking any sort of clothing, saying he forgot the showing was that day! I remember my clients and I quickly turning our heads in embarrassment and shock. As we did so, the Seller realized he was dressed in his birthday suit and scrambled to cover himself. We continued to look at the house as per his request and as it turned out my clients loved the house.  After a few more weeks of looking, they purchased the naked man’s house and now have fun story to tell their friends.  Throughout my career there have been 3 similar moments of startled naked people.

Real Estate sales are never dull! It can be highly challenging, demanding and is always full of surprises.  That’s why I absolutely love my job and the people I have the pleasure of working with.