If you ask anyone in Toronto to name their favourite real estate personality, you’ll likely hear the name “James in the City” come up. James Milonas, as he’s more formally known, has developed a major name for himself in the Canadian – and, increasingly, North American – luxury real estate and fashion scene. He’s known as much for his candid and unbashful social media real estate tips as he is for his often vibrant editorial-worthy style. Appearances in shows like HGTV’S Open House Overhaul and his viral TikTok videos only further amplify Milonas’ beloved (and growing) personal brand. A relentless voice and advocate for underrepresented communities, the openly (and proudly) queer realtor is not only a trailblazer for his industry peers, but also an impactful supporter of over 30 charities in Toronto. And he’s just getting started….
Where it all began
Milonas grew up in the Toronto suburb of Richmond Hill, where his childhood involved everything from sports and babysitting to attending charity events. The lifelong athlete excelled at sports as a child, playing everything from rep hockey and football to tennis and field sports like shot put. In fact, he had one of the longest throws in shot put in York Region.
“Sports was my life and has helped shaped who I am as an adult, in everything from mental health and leadership to discipline and scheduling,” says Milonas.
ADVERTISEMENT |
His current success comes as no surprise to anyone who knew Milonas as a kid. “From the time I was a little, I always knew I was going to be something in this world and take it by storm,” he says. “My dream as a child was to be an actor. But then I wanted to be a lawyer at some point, and a fashion designer at another. I just wanted to be in a position where I could help people. As much as I love the medical field, I faint at the sight of blood.”
So, real estate – helping people realize some of their life’s greatest dreams – grew more appealing to Milonas from a young age. “Plus, you could dress a certain way, make your own hours, and be influential,” says Milonas. “Then, I can use the money I earn to give back through charity.”
But the path there wasn’t without its hurdles. Two weeks before high school graduation, Milonas was struggling: his parents’ divorce had taken a toll on him to the point that he was heavily using narcotics and even considered ending his life. “I couldn’t handle the way my life was going, or to even be in school,” he says. Despite good grades, university acceptances, and a promising future, he dropped out just before the school year ended.
“I couldn’t handle the way my life was going, or to even be in school,”
James Milonas, also known as James in the City, Toronto-area Realtor and Content Creator
Editor's note: Suicide is never the answer. You deserve to be heard, and people are ready to listen. Speak to someone today either over text, by sending a message to 45645 (available from 4pm-midnight), or dialling, 1.833.456.4566 (available 24/7) for help via TalkSuicide.ca.A principal with faith in him, however, told Milonas that if he wrote and passed his exams, he could finish off his school year in the summer after taking a few weeks to reset. Soon after, Milonas quickly started working in fashion styling and fashion management. “That was sort of a stepping stone for getting into real estate,” says Milonas. “I knew I didn’t want to work for somebody else, but I also knew I didn’t want to sit in a classroom.”
ADVERTISEMENT |
So, Milonas did his first real estate course at home in his own time when he was 21-years-old. Then some health issues poised a temporary setback. “At that point, I just started dating my then life partner – who I was with for 11 years – and he really pushed me to finish off the second and third courses,” says Milonas. “Even though we’re no longer together, I admit, he helped me build my brand. If it wasn’t for him, I wouldn’t have gotten into the [real estate] industry. He literally signed me up for the phases and came home with a handful of books.” But surely, it wasn’t long before Milonas was a licensed realtor.
An early adopter
Once he was licensed, Milonas wasted no time utilising the latest tools to build his personal brand – including the then just-launched Instagram. “I got on Instagram in 2012, before realtors were really using it for business,” he says. “People had been using Facebook pages for a while, but Facebook wasn’t my target demographic. I thought, ‘Who is going to take me seriously in the business world with this baby face and gay voice, if someone is over 40 or 50?’ So, I got on Instagram to target my audience – millennials and first-time homebuyers, and people looking to get their first apartments – and I would market myself as that go-to person for Toronto.”
Milonas was living in Toronto but joined an office in Richmond Hill, where he had more roots and knew the neighbourhoods. “I wanted to work in that pocket, but knew I would never break in right away, and be selling $3 and $4-million-dollar homes off the bat,” says Milonas. “So, I started working in the city and building content – back when Blackberry devices were still a thing. James and the City became a brand and I became a go-to for colleagues in Vaughan, Richmond Hill, Markham, and Newmarket who didn’t want to travel south of Steeles for showings. My business was built on referrals from them.”
At the time, Milonas was busy building his personal brand, posting daily on social media. “I’ve always been ahead of the curve when it comes to new social media technology and updates,” says Milonas. “When Instagram Stories launched, I was on top of that; when Reels came out, I was on top of it; when IGTV came out, I was on top of it. I always wanted to make sure I was ahead of all the other realtors.”
@jamesinthecity It really is THAT simple! Thank you to @oreillyrealtygroup for the inspo! This is brilliant #torontorealtor #torontorealestate #realestatelife #rentalhacks #rentalhousing #torontorentals #torontorentalmarket #landlordtenantproblems #landlordtenantissues #jamesinthecity ♬ Feral Anthems pt 4 – DJ L BEATS
When TikTok took off right before the pandemic, it offered yet another highly influential platform for Milonas. “When the pandemic happened and I was no longer going to events or having my camera person follow me around, I knew I had to get in front of people in another way,” says Milonas. “What’s the best way to do it other than on the fastest growing platform? So, I would sit at home and film the content that would typically be a static Instagram post. And then my brand blew up.”
ADVERTISEMENT |
It blew up to the point that people didn’t even know him by his last name – just as “James in the City.” Like Cher, says Milonas with a laugh. Before long, he was even being recognized as ‘the real estate guy from TikTok’ in the streets or at Starbucks.
Not hiding behind a façade of a suit and tie
It’s no secret that the real estate industry hasn’t exactly been synonymous with queer professionals within it. “I don’t think we’ve come a long way; I think we’ve come a bit closer,” says Milonas of the prevalence and treatment of the 2SLGTBQIA+ community in the real estate industry. He recalls an incident in his early days of real estate when he picked up a client for an open house who was in the market for a $3 to-4-million-dollar home. “I remember one night, I mentioned my partner was a male and his whole attitude changed toward me,” says Milonas. “He told me that this working relationship wasn’t going to work and to terminate his contract immediately.”
It pains him to say, but Milonas says that queer people are still looked at as “freaks” in society. “I hate to say that, because we’re not; we’re just humans and we’re born this way,“ he says. “We are lovable humans. We express ourselves, and aren’t afraid to not hide behind a façade of a suit and tie.”
ADVERTISEMENT |
“we’re just humans and we’re born this way,“
James Milnowas, aka James in the CIty, Toronto-area realtor
A big problem, says James Milonas, is that there aren’t enough queer clients for queer realtors to feel comfortable. “I have very few gay clients,” says Milonas. “Mostly, it’s because I just don’t encounter a lot of gay individuals on a business level. It’s something I really have to work on and support the gay community as much as possible. I still have more work to do to be more accessible to the queer community and the struggles they face. A queer realtor with a voice and a platform, I need to be better at being more present with my community.”
One way he’s doing this is through a partnership with ProudFM. Starting this August through February, the radio channel will feature a campaign about queers buying and selling real estate, with Milonas front and centre. “It’s not something that’s spoken about because there hasn’t historically been enough representation in the real estate industry,” says Milonas. “And there hasn’t been a lot of exposure about the ongoing challenges and discrimination faced by the queer community when securing a home.”
ADVERTISEMENT |
Paving the way for young queer realtors
Milonas’ resonating piece of advice for young queer realtors is to be themselves in all of their glory.
“I don’t hide behind a typical suit or tie; I dress the way I want to dress,” says Milonas. “There are some days where I maybe look a little more feminine, if I’m wearing a silk shirt and skinny jeans. Other days, I may look more masculine in a tight t-shirt and khakis. I think some realtors are afraid to express who they are because they don’t want to turn people off. The way I look at it, if my appearance is offending you, you’re not the client for me. That’s a ‘you’ issue, not a ‘me’ issue.”
Milonas wants the challenges, lessons, and even hate he’s received as a realtor to pave the way for other queer realtors. “I have a platform and I don’t care about what people say about me,” he says. “I will challenge the [societal] norms so that others can feel comfortable.”
ADVERTISEMENT |
People approach him all the time, thanking him for this.
Giving back at every opportunity
Whether he’s volunteering at a shelter or lending his voice to an important campaign, philanthropy comes first for Milonas – and his platform helps with this.
“My mom always told my brother and I, ‘If you have $1, give $10. If you have $10, give $100,’” he says. “And she’d instill in us that it’s not about us; it’s about them. So, she brought us to events and taught us how to fundraise from a very early age.”
ADVERTISEMENT |
Milonas knew he wanted philanthropy to be a main pillar and core value of his real estate career – and something that went beyond simply buying a ticket and showing face at the city’s most sophisticated charity events. “Every Thanksgiving, I run a drive for Covenant House, where I fill a massive U-Haul with dried goods and drop it off,” says Milonas. “That could mean everything from packages of rice or tuna, to tampons and toothpaste and socks and hats – whatever Covenant House needs to fill their pantry.”
But his charity involvement doesn’t stop there. “Every charity event I am involved with is somehow tied to my personal life,” says Milonas. “For example, last night’s Butterfly Ball benefitted Boost for Kids; I was witness to child violence, and one in five children under the age of 18 will experience violence – that’s a horrible statistic. So, I’m involved in all of these children’s charities and women’s shelters. CANFAR is a big thing for me too as a gay man.”
After volunteering withHIV/AIDS charity CANFAR for years, in April, Milonas was able to co-chair CANFAR’s annual lunch, where the splashy affair surpassed its fundraising goal. “HIV/AIDS isn’t just an LGBTQ+ issue – it’s a human issue,” says Milonas. “We can all get infected. We need to end the stigma. You can live a long and healthy life with HIV, as long as you’re on medication. And, if you’re on medication, you can’t transmit the virus. Because, if you’re on medication, then you’re undetectable, and if you’re undetectable, then you’re untransmittable – something that, sadly, is not widely known or educated.”
Proudest moments
When it comes to his real estate career, Milonas is most proud of his personal brand. “I think realtors focus too much on their logo and on the actual name of their business,” says Milonas. “They don’t necessarily know how to brand because they’re afraid to do something outside of the norm. So, I do ‘James in the City,’ and everyone knows I sell real estate, but it doesn’t say anywhere that I’m a realtor. That’s my occupation, not a brand. They worry too much about their logo; my logo was the easiest thing. You need to be the realtor for those who connect with you. Not because you have a nice house in your logo.”
ADVERTISEMENT |
It’s tricky for Milonas to choose just one career highlight. Not to mention, the best are likely yet to come.
“I don’t have a specific sale that stands out to me, but every sale is so special,” says Milonas. “Every single one is a highlight. I just sold a townhome in Brockton Village, and on the call where I told the clients that their offer was accepted, I could hear the joy in their voice. That is what keeps me going. It’s little things like that, and helping other realtors with my advice – whether it’s on how to park their licence when they’re going through emotional turmoil, or on doing certain transactions. It all comes down to how I can give back. My career itself is a career highlight.”
What’s next?
“I think the world is ready for a ‘James in the City’ TV show,” says Milonas on his next steps. “The brand is getting so big that it’s being recognized outside of Toronto, which is amazing. I was in New York and got recognized and was in LA last week for the Beverley Hills White Party and got recognized at the airport. The brand is exploding and I’m very blessed.”
ADVERTISEMENT |
Milonas says he’s modelled his entire world after Kim Kardashian and Bethany Frankel. “They built their personal brand up – Kim Kardashian and Bethany Frankel with Skinny Girl – and it all evolved from there,” says Milonas. “So, I have my eye a number of things that I want to do, but it all comes down to my core loves.”
For example, this could mean a further foray into the fashion world. “It could be a fashion line,” says Milonas. “Or even a line of t-shirts. For example, I wear a lot of polos in the summer. So, maybe it’s a branded graphic tee with one of my sayings. I’m also known for my lips. I have big, natural, and voluptuous lips and always wanted to develop some kind of skincare line just for lips.”
Milonas is happily in another relationship at the moment and he and his partner have also discussed collaborating on a project. “He’s really big in the fitness world and I’ve been on this incredible fitness journey with him and he’s transformed by body and outlook on life,” says Milonas. “My views on life and family have changed since meeting him. So, a business collaboration with him in the fitness worlds is also in the cards.”
ADVERTISEMENT |
While the possibilities are endless, one thing is certain: we’re only going to see and hear more of James in the City – whether in real estate circles or not.
Credits
Shot by: Nick Merzetti; Fashion/Art/Editorial Direction and Production by: Steven Branco; Hair and Makeup by: Angela Lee /Judy Inc.; Lighting Assistant: Leah den Bok; Wardrobe Assistant: Sharad Mohan; Locations: 4 Douglas Crescent, Tennis courts at Trinity Bellwoods Park, and the Pool at Lavelle Rooftop Patio, recently featured in last month’s 20 Best VIBES in Toronto by View the VIBE and Living Luxe Magazine. A Stamina Group Production. Special thank you to Paul Greenberg of The Agency and his client for allowing us to use 4 Douglas Crescent, as the backdrop for a portion of the shoot. It takes a village, and it couldn’t have been done without everyone’s support.
