Our NewsPress Releases October 4, 2023

Coldwell Banker Tailored Realty Builds Community in Windsor-Essex

Chuck Roy brings an impressive business resume, a deep sense of a community and a vibrant collection of contacts to Coldwell Banker Tailored Realty in Windsor, ON, one of the newest brokerages in the growing Coldwell Banker Canada network. He also brings a keen sense of the importance of a team mentality in real estate. And he can hit a golf ball! 

Chuck Roy’s golf game has always been about scoring the bigger number.  

Roy, the Broker-Owner of the new Coldwell Banker Tailored Realty office in Windsor, ON, remembered being on the links at a tournament in 2007 that raised money for the St. Vincent de Paul Society. The tournament brought in about $6,000. 

“I told the president at the time, I said, ‘Don, we could make a lot more money for this worthy cause if we did things just a little different,’” Roy said. “I mean, we could put a four-by-eight-foot piece of plywood at a hole and put 12 sponsor signs on it if we wanted to!”  

Chuck Roy’s “just a little different” meant a more liberal definition of a hole sponsor. It meant more levels of corporate sponsorship. And Roy’s “just a little different” meant leaning into his radio connections for on-air advertising.  

“Just a little different” turned into a significant difference when the tournament happened the following year. 

“We got a lot of different folks involved and we were able to clear $32,000,” said Roy. “The whole idea is to raise a good amount of money, right?” 


Chuck Roy foursome at 2023’s Society of St. Vincent de Paul Charity Golf Classic, Windsor, ON, included Roy, left, and Paul Abbott, V.P. Franchise Development (Ontario), right.


Windsor-Essex: very charitable 

Roy has answered that question the same way every year since. This year, with Roy again at the fundraising helm, the Society of St. Vincent de Paul Charity Golf Event netted $28,000 for its food bank programs. Since 2008, the tournament has raised $450,000 for the charity. 

Roy said the easiest thing to do is to ask someone for their money. 

“The worst thing they are going to do is say no, so, if that happens, you say thank you and move on to the next person,” Roy said.  

“When you are in a sales job, you get ‘no’ a lot. I feel every now and then that I am bothering people, but I’m really not. Besides, Windsor-Essex is very, very charitable, it’s unbelievable.”  


Subway years 

Doing business and supporting his community have been twin impulses for Chuck Roy since the very beginning. As a 20-year-old in 1987, he opened his first Subway shop. At the time, it was only the third or fourth franchise in the entire country. The shop at 300 Oullette Avenue in downtown Windsor was “10 or eleven feet wide and a hundred and some feet deep.”  

The tiny restaurant gave Roy a closeup view of the challenge of homelessness.  

He got involved with the Downtown Business Association and helped support outreach programs with food from his Subway franchise.  

“I feel that I have been fortunate,” he said.  

“I’ve always worked my butt off, but I’ve always been fortunate, too, and I appreciate the life I was able to build for myself and my family. I have tried to always give back to the people in the areas I lived and worked in.”  

Roy was able to do increasingly more for charities as his Subway career took off. And take off, it did. By the time he wrapped up his time with Subway in 2012, he had owned 18 restaurants—as many as 12 at one time. 

“When I started expanding, I was the first guy to go into all the little towns,” he said. “People thought it was the wrong move. But those stores ended up being the highest volume stores. There was no competition.”  


“Remember to be generous” 

Over the better part of two decades, Roy also served as global chair of the Subway Franchise Advertising Trust Fund, the first non-U.S. born official to achieve the top post that came with a healthy marketing budget. Along the way, he sat on or led Subway’s local, regional and national advertising boards.  

“As other franchisees got on board in the market, and as we got bigger and more funding was available, I tried to remind us all to be generous,” he said. 

“Contribute and give and do what you can. If you do good things, good things come back.” 

Yes, Roy still supports the company that supported him and his charity initiatives over the years. Yes, he still eats at Subway.  

“Once or twice a month,” he said. “My wife doesn’t like me eating the cold cuts, but I like the BMT and they’ve got this new Italian one, I forget its name, it’s the No. 13.”  


Windor, ON, waterfront.



Amazing waterfront in Windsor 

Chuck Roy was born in Campbelltown, NB. When he was five years of age, his father moved the family to Windsor after getting a job at Champion Spark Plugs. Chuck met his future wife, Marla, in Windsor, where they worked at a Burger King restaurant together. 

“She worked the specialty board,” Roy said, “where they make the different non-hamburger sandwiches, the chicken sandwiches.”  

The fast-food romance stuck. They’ve been married for 36 years and have two grown children.  

Windsor is home for the Roys. The land and the people are beautiful, he said.  

“We are surrounded by water and the waterfront is amazing,” he said. “Not everyone knows about all the wineries on the South Shore. It’s a lovely drive. Very peaceful.”  

Windsor-Essex, population 342,000, is just across the river from Detroit, population 4.3 million, a metro region that offers all the entertainment, shopping, sporting and dining draws that come with being the 14th largest city in the United States.  

The enduring attraction of the region, though, is its people. And their generosity. 

“People always reach into their pockets here,” Roy said. “The money that comes out of the auto workers’ pockets every month is impressive. The charity in the people here is what you get to know when you live here.”  


The next chapter: real estate 

“What do you want me to do with these briefcases that you haven’t opened yet?” Marla Roy asked her retired husband one day a few years ago. 

The couple were downsizing and moving to a new home. What to take, what to keep were the big questions. The fate of five briefcases was up for negotiation. Each briefcase was identical. Each contained real estate licence course material. There were five briefcases because, for five straight years, Roy had ordered the course material, and for five straight years he had let the briefcases sit without opening them or cracking a book. 

“I bought the first course five times,” he laughed. “Back then it was the old system where you had to get your first course done within the first year. If you didn’t, they’d call you up after a year and ask, same last four digits on your Visa, sir? and send you the material again.” 

Eventually, Roy stopped ordering the course material, actually opened a briefcase, dug in, enrolled in a class in London, ON, and, after a year of study, got his real estate licence and his broker’s licence.  

“Real estate was always interesting to me—all the different types of real estate,” he said. “I was close to the commercial side of things over the years. I did a lot of the legwork myself, getting appraisals done and stuff like that.” 

Roy started as an independent realtor in 2015. He made a splashy entrance. He wrapped his SUV with an image of his face, he bought billboards.  

“You name it, I did it,” Roy said. “There weren’t many people in Windsor who didn’t know I was in the business.”  


Coldwell Banker enters picture 

Over time, he realized that the realtors in his brokerage needed more support.  

“I wanted to find a global brand because I just didn’t have the ability to give the realtors the resources they need—website, training, social media, that kind of important stuff.”  


Chuck Roy, right, with William Nelson, Broker-Owner, Coldwell Banker WIN Realty, at Coldwell Banker Gen Blue conference, Vancouver, June 2023.


In brand shopping mode, Roy ran into a Coldwell Banker franchisee at a networking event. From there, he filled out the fields of information in the online Coldwell Banker Canada franchise inquiry form. Then, Vice-President, Franchise Development, Paul Abbott “got in the car and drove up here,” said Roy. They had dinner. Abbott suggested that Roy attend the Gen Blue Canada conference in Vancouver to get a feel for the people of brand.  

“I was tremendously impressed with everything I saw there and got back and made the decision to move forward with Coldwell Banker,” Roy said. “It’s a big benefit to align yourself with a global brand.  


Chuck Roy’s brand shopping took him to Coldwell Banker Canada’s online franchise information page. Illustration.



Coldwell Banker Tailored Realty 

Roy’s Tailored Realty has joined Coldwell Banker Essential Realty (Owen Crampsie, Broker-Owner) and Urban Realty (Joane and Frank Urbanski, Broker-Owners) in serving clients in the Windsor-Essex region.  

Abbott said the addition of Tailored Realty to the Coldwell Banker landscape in Windsor-Essex is a great development for the brand and for buyers and sellers.  

“Coldwell Banker Canada continues to attract high-quality leaders with experience and vision, and that is what is available, both for agents and consumers, in Windsor-Essex,” said Abbott. 



“I wanted to find a global brand because I just didn’t have the ability to give the realtors the resources they need—website, training, social media, that kind of important stuff,” Roy says.

Roy said he wants to grow the brokerage to 15 agents or so.

“What I love about Coldwell Banker is they’re more concerned with quality, not quantity,” he said.

Coldwell Banker Tailored Realty takes its name from the sense of concierge or boutique service it offers its clients, a kind of attention and care that has long animated Chuck Roy.  

“We work like a team,” he said. “We help. We don’t let anybody fall down. We keep people picked up.”