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James Milonas Realtor® | Founder, James In The City - Luxury Toronto Real Estate


“Your Luxury Real Estate Partner”

REALTOR® and FOUNDER of Toronto Luxury Real Estate Brand “James In the City,” James Milonas – wants to be your real estate partner. A natural born salesperson with a creative spirit and an eye for luxury, this Toronto native has always had a drive for helping others and a passion for entrepreneurial success.

“I’ve always been interested in being my own boss,” says James. “Even as far back as when I was 9 or 10 years old when my younger brother played competitive hockey, I spotted an opportunity to create a small business with some of the other older siblings. We created a babysitting club to watch younger kids for spectator parents and were paid for keeping track of the little ones so that these parents could watch their other children play on the ice. By the time I was 14 I had shifted my attention to a new venture called “Second Hand” where I literally provided an extra set of hands to people in my neighborhood. I did everything from cutting the grass to walking the dog and picking up the kids from school. It wasn’t until I was 16 that I discovered sales and started working in the retail industry.”

James enjoyed working for himself and helping others, but he decided that if he was interested in sales and retail it was time to experience “corporate America” firsthand and applied for a job with retail giant Walmart. Working as a sales associate, he learned as much as he could about business management while developing practical skills and gaining valuable real-world experience.

“I wanted to learn more from my retail experience than simply how to fold T shirts and I did,” says James. “I specifically chose and loved working at Walmart, and I ran one of the most profitable garden centres in my region. I would have continued to work in retail while pursuing a post-secondary education, but I fell ill and dropped out of school. When I did eventually return to work, I decided against University and started working in retail fashion – specifically visual merchandising.”

James found an outlet for his creativity and was able to thrive in his new role. However, his work-life balance was not quite what he was hoping for and dreams of a more flexible career in real-estate began to manifest for him.

“I lived in Richmond Hill where I was fortunate to witness the evolution of a few real estate powerhouses,” explains James. “I looked up to these realtors and considered them mentors. I love working in real estate because it allows me to have everything that I have in my life today but it’s also interesting and dynamic. I can be charitable, I can make my own money, set my own hours, and have structure while being my own boss. I still get to be creative with things like staging a home and I feel as if all of the parts of my life are balanced now, fitting neatly into one little envelope.”

Today, James has even been featured on television including HGTV’s Open House Overhaul.

Finding the Path to Success

James started out in real estate when he was just 21 years old. He was very young and admits that he made his share of mistakes but was fortunate to get his start in a brokerage that had strong, influential people who he could look up to and learn the ropes from.

“I learned a lot from my broker of record Vivian,” explains James. “We’ve always had a great relationship and I’ve learned so much from her. I owe much of my real estate business to her because of the doors that she opened for me and the opportunities she provided that I wouldn’t necessarily have had elsewhere.”

Mapping the path to success began for James when he was a child. He explains that both sides of his family immigrated to Canada in the 1960s, bringing a strong work ethic with them – which was instilled in him at a young age. Family has always been a priority for James, but it’s also from family that he first learned the importance of hard work.

“I looked at my parents and saw how they operated their businesses,” says James. “My father was an entrepreneur who ran a very successful business. My parents ran a multilevel marketing company that was new to Canada in the 1990s. Through their example I learned that relationships are essential to any successful business venture.”

Philanthropy with Roots

James subscribes to the mantra that “you can’t change the whole world” but you can have an impact on a “small part of it.” While he learned the importance of strength in business relationships from his family, he also learned a lot about the nature of personal relationships. His life at home as a teenager was not without turbulence and ended with his parent’s divorce when he was about 18 years old. His mother is credited as an important figure in his life and a role model for his philanthropic endeavours.

“We weren’t without our family issues while my parents were together,” explains James. “I credit my upbringing as the primary motivation behind a lot of the charitable work that I do today. I believe that when you are privileged it is your duty to give back. You don’t have to be worth millions of dollars to be charitable. If you have five extra dollars in your pocket that you don’t need and you give that money to someone who really needs it, I believe that money will come back to you and it will multiply.”

James is an active supporter of over 30 charities in the GTA including CANFAR, The Covenant House, CNIB and The Royal LePage Shelter Foundation. James donates to charities that are close to his heart. He supports women’s shelters and shelters for abused children. He also donates to Sick Kids hospital but is most passionate about working with the youth homeless shelter Covenant House.

“Covenant House does so much for at-risk, homeless youths in Toronto,” says James. “I really feel for kids living on the streets. I can relate to kids who have been rejected after coming out to their parents as gay, lesbian, bisexual, transgender. Whatever the reason is these kids don’t choose to be on the street. In some cases, they are told that they no longer live under their parents’ roof if they’re not “straight. Supporting Covenant House allows me to help the organization grow and build more facilities to house homeless youths. Sadly, as more kids are forced to be on the streets it takes more and more to help end the cycle.”

Today’s Demands and The Importance of Support

As a millennial James has grown up with technology and is very comfortable navigating today’s paperless (and contactless) ways of doing business. Social media, email, online document signing, and virtual showings are second nature to James. While the pandemic has placed a lot of pressure on businesses to go online, James has made the transition with ease.

“It can be challenging when you work with a client who is older and chooses to lead more of an offline life,” says James. “If we do need to meet in person during the pandemic, we take all of the necessary precautions. I don’t do open houses and haven’t done them for many years, I think they’re a waste of time. I think Covid-19 has reinforced the idea that you don’t need to host an open house to sell a home.”

James explains that even before the pandemic many buyers have benefitted from online viewings because it can be hard to take time away from a busy schedule to view properties in person.

“A fantastic virtual tour that showcases a property in the right light with professional photos is a must for every listing,” says James. “An interactive floor plan where you can actually sit in the living room, take your mouse, drag and click to explore. You can literally do a 360-degree scan of every single room in a house or condo. Potential buyers can go up and down the stairs, visit the backyard, and all without leaving the comfort of home. I’ve been doing this for years, but I think it’s starting to catch on with other agents. The pandemic is forcing realtors to embrace technology and really step up their marketing game.”

James also credits his life partner Scott for supporting him in today’s uncertain market.

“I have to give credit to my life partner Scott,” says James. “Times are tough and it’s important to have someone in your corner who will support you financially and emotionally when you’re getting started as an entrepreneur. When I was first starting out and building my business, I was fortunate to be able to rely on my partner to keep things afloat during times when income wasn’t rolling in. I was able to get on my feet without worrying about paying the bills and I’m really lucky to have that kind of support. I’m not sure that most agents have that and, in a business, where income fluctuates throughout the year, a lack of understanding and support can lead to resentment and even divorce for some couples.”

The Little Things and the Value of a Handshake

What sets James apart from other agents is his attention to detail and an understanding of what motivates people to buy.

“I listen to my clients,” explains James. “When I show a home, I hang around in the background and listen. I watch how my buyers enter a home and listen to how they react to what they see. I read between the lines because I want to adapt and show them places that best suit what they’re looking for – even if they haven’t quite figured out what that is yet. Finding the right place for someone to live has a lot to do with understanding people and while we may start off looking at places that fit a client’s general description of what they want – by the second or third appointment we start looking at the places that I think they should see.”

James says that meeting and exceeding a client’s expectations instead of worrying about his own bottom line maintains a consistently high level of service.

“At the end of the day, whether I'm selling a $300,000 studio on the Lower East Side or a seven or eight figure penthouse in Yorkville, my clients are getting the same treatment regardless of their postal code,” says James. “It is because I don’t place my commission before the needs of my clients that I am able to focus on providing consistent service across the board.”

James says that part of maintaining that high level of service is about creating unique experiences for buyers and sellers alike.

“It’s about the little things you can do to enhance a client’s experience,” explains James. “For example, before the pandemic, if an out-of-town buyer was referred to me and didn’t know the city very well, I would hire a driver and show them around in my “mobile office” for the day. Because I wasn’t behind the wheel myself, I could highlight points of interest for my clients.”

Trust is also essential to the work that James does. Even though he sells real estate and relies on contracts, he still believes in the value of a “handshake.”

“Traditionally, most of my deals have been done over a handshake – because I trust my people,” says James. “Since I’m not as concerned about sales as I am about providing great service, I’ve discovered that great service builds trust. My buyers and sellers need to know that I’m acting in their best interest and if I’m focused more on their happiness than my own commission cheque, it shows and that means a lot.”

April Potter is a veteran writer with expertise in financial services including nearly 15 years in debt restructuring. April has written for multiple online publications on a variety of subjects and offers a range of social media. Also a painter, her background in finance is balanced by her artistic endeavors.

James Milonas


Johnston & Daniel, A Division of Royal LePage 416 580 0573


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