By SGN | 7 Jan 2025
The word “luxury real estate” often invokes images of glitzy condos and sprawling penthouses a la Selling Sunset. And to some extent, the stereotypes are true – just ask Chester Yow.
As a Singaporean luxury real estate agent whose client base is predominantly in The City That Never Sleeps, he has seen his fair share of glamorous parties and celebrity gatherings. However, a high-calibre role like Chester’s comes with its fair share of hard work, rejections, and hurdles.
Besides navigating a new industry, Chester faced unique challenges in terms of socio-cultural adjustments in the U.S. These early obstacles shaped his survival mindset, especially in a field where success is never guaranteed.
“In real estate, you don’t get a salary. Everything is commission-based,” he shares. “You don’t celebrate until you get your cheque. This is a tough, tough industry to be in, where only a few can make it.”
A Singaporean childhood
Chester enjoyed a typical Singaporean childhood. He was the middle sibling to an older brother and younger sister, attended public school throughout his pre-university days, and was on the rugby team. After completing his national service, he set his sights on attending university in Hawaii.
While Hawaii might not feature on the list of top study destinations for most Singaporeans, Chester’s decision to study in the picturesque island state was far from arbitrary. Both his parents studied and were married in Hawaii, and they spent time there with Chester and his siblings in tow.
“I spent many holidays in the U.S., reconnecting with friends and family,” he recalls. Chester and his family visited so frequently that even after returning to Singapore, they continued to celebrate American holidays, such as Thanksgiving.
“My mum would prepare turkey, along with traditional Thanksgiving dishes like cranberry sauce and pumpkin pie,” he says. “We’d gather with family and friends, much like Americans do, to give thanks and enjoy a feast.”
As such, it hardly came as a surprise to Chester’s parents when he decided to follow in their footsteps, and attend university in Hawaii, where he studied Political Science and Government.
An American education
At the time Chester attended university in the early 2010s, Singapore was still relatively unknown outside of Asia. This lack of familiarity often led to misconceptions.
“People living outside of major cities like California and New York didn’t know much about Singapore,” Chester reflects. “Before F1 or the release of Crazy Rich Asians, many people didn’t even know where Singapore was; some assumed it was a developing country.”
For Chester, studying in the U.S. was both mind- and eye-opening. “People cared not only about academics, but also about building character and personality,” he recalls.
As an ethnic Chinese person, Chester often faced misguided assumptions about his background and language skills. “I would get comments like, ‘Your English is so good!’” he shares. “Ironically, I even had to take an ESL test to prove my English proficiency because my A Levels weren’t recognised in the U.S.”
People also struggled to understand his Singaporean accent. “I had to learn to speak more slowly and enunciate clearly,” Chester reflects.
Despite these challenges, he eventually adapted, taking on a variety of hands-on roles during his university days. “I worked as a lifeguard, in the campus bakery, as a junior accountant, and also as a teaching assistant,” he shares.
Each job provided its own set of experiences and lessons. “I made sure I wanted to experience all types of jobs,” Chester explains. “Some paid more than others, but it was great to be able to work and study at the same time. It helped me build relationships and make new friends.”
These roles also gave him a deeper understanding of the work culture in the U.S. “Overall, they were very rewarding experiences in terms of learning about the work and study culture in the U.S,” he adds.
Academically, Chester found significant differences between the U.S and Singapore as well. “In the U.S, students are celebrated for all grades, whereas in Singapore, poor performance is often met with disappointment,” he notes.
On the flip side, Chester appreciated the sense of independence in American culture. Many of his American friends left home at 18 and worked multiple jobs to support themselves through college, while entrepreneurship and starting one’s own business were highly encouraged.
“There’s a strong emphasis on being your own boss and doing your own thing, rather than following a ‘regular’ life path,” he comments. “While a degree is still important for many things, qualities like who you are as a person, how driven you are, your mental toughness, and the support system you have in place, all matter. There’s room for both growth and failure.”
Living independently in a foreign place, without the safety net of his parents’ home or funds, propelled Chester to figure things out on his own. Inspired by his experiences and the vibrant opportunities that lay ahead, he decided to remain in the U.S after graduation.
Pursuing a real estate career in the Big Apple
Chester’s next move took him to New York, initially motivated by a romantic relationship that ultimately didn’t work out. Nevertheless, he remained in the city, drawn to its fast-paced environment, reminiscent of Singapore, particularly in the finance and tech sectors. But there was one significant hurdle.
“The high cost of living made me realise I needed a more stable income. I had originally planned to attend law school, but after speaking with several Singaporean lawyers, I learned about the tough work-life balance, unforgiving hours, and heavy student loan burdens they faced,” he shares.
This led Chester to explore alternative career paths. At first, he dabbled in supply chain management roles. After a couple of years, a friend suggested he try real estate. “Back in 2014, there was this influx of investment from China. And I could speak Mandarin Chinese, which was in demand,” Chester explains.
“So, I decided to give real estate a shot. I still remember my first sale – a Singaporean family found me online and needed an apartment for their daughter attending New York University (NYU),” he recalls.
Appearances are deceptive, especially in the NYC luxury market. “Someone could walk by you in the street, and you wouldn’t even know they’re worth millions. So, you never want to stereotype someone you just met,” he advises.
Chester’s New York clientele, which includes the ultra-wealthy, celebrities, and people of importance. “A lot of them are low-key. Not everyone turns up in a Rolls-Royce or a Ferrari,” he comments. “There are clients who are dressed to the nines. But I also have clients wearing flip flops and jeans, who have a lot of money.”
Developing a niche in luxury real estate with Serhant
Although Chester entered the real estate market in 2014, it wasn’t until 2016 that he joined celebrity broker Ryan Serhant’s team. In the interim, he worked in various sales roles, building his network, getting to know different neighbourhoods, and honing his skills in real estate.
Chester spent his time hustling and networking, immersing himself in New York City’s competitive real estate market. His efforts soon led to a key opportunity.
“I was working on a sales listing with Ryan and one of his team members, and they were both impressed with my work ethic,” he recalls. “That’s when Ryan invited me to join his team.”
At the time, Chester was on a different team at the same firm, but the collaboration allowed him to demonstrate his skills and commitment. “It was a turning point,” Chester adds. “The opportunity to work closely with Ryan gave me the chance to prove myself and eventually join his team.”
Of course, his early days with Ryan and the Serhant Team weren’t without disruptions. Chester rarely took holidays and spent most weekends working on projects and listings, closely shadowing Ryan.
Adapting to the high-pressure, fast-paced real estate market while handling multimillion-dollar deals pushed his limits. But Chester quickly found his stride, carving out a solid niche in luxury real estate.
For those unfamiliar with the sector, Chester offers a brief explanation. “The U.S. luxury property market is unique. Each state has its own rules and requires separate real estate licences,” he says.
“In New York, where public housing options are limited, property is in high demand. Studio apartments can start at US$670,000, with larger ones exceeding US$40 million. Manhattan is highly coveted; after all, it’s the heart of the financial world and a symbol of exclusivity.”
A standout moment was his work on a building with a total sell-out of over US$400 million. “One weekend, Ryan called me unexpectedly and told me to meet at a specific spot. When I got there, he was waiting for me with a new suit, which he gave to me as a present. We went on a helicopter ride around the building, with a photographer taking pictures of it,” he recalls.
Chester describes his time working alongside Ryan as akin to “getting a master’s degree.” “I learned so much from him, after he took me under his wing. I observed how he spoke, negotiated, learned his trades and techniques,” he shares.
“I was like a sponge. Just being around him, soaking up his energy and picking up on the words and phrases he used – it was invaluable to me.”
Launching his own real estate team and rejoining Serhant
After three rewarding years at Serhant, Chester decided to launch his own team, the Yow Team in 2019, touting it as the next logical step.
He describes transitioning from the Serhant team to leading his own five-person team as a significant milestone in his career, attributing much of his growth to Ryan’s mentorship. “He’s very business-oriented and laser-focused on his goals. I learned how to be an efficient team leader from him,” Chester says.
He also touts managing people as one of his strong suits. “In real estate, people want two things: to be valued, and to make a name for themselves. Helping my team achieve this has been important for my success too,” he mentions.
When Ryan launched his own firm, Serhant, Chester rejoined him, bringing his team along and continuing to grow it.
To date, his team has secured over US$400 million in sales, attracting attention from major publications like the New York Post and Wall Street Journal. “I’m proud to represent Singapore in New York City,” Chester adds.
Life in the public eye
Besides being a real estate agent, Chester has also appeared and featured on several reality shows like Bravo’s Million Dollar Listing and Netflix’s Owning Manhattan. “Being a part of Million Dollar Listing was an incredible experience,” he recalls. “The days were a mix of parties, glitzy events, and nonstop filming. Agents would flock to the penthouses we were showing, just to be on TV, and join in on the fun.”
On the back of the global reach of these shows, Chester’s popularity soared. “I’ve received heartfelt support from many Singaporeans,” he says. “Friends and family back home who know I’m in real estate, watch the show and constantly talk about it.”
Besides his television appearances, Chester is actively involved in public speaking. He has appeared on various podcasts, such as How He Does It and Stacked Homes, and has mentored other agents in both the U.S. and Singapore.
He is also deeply involved in entrepreneurship and angel investing. “As an entrepreneur, I spend my time meeting people, and forging friendships,” he shares. “As an investor, I have supported several up-and-coming tech and AI companies.”
Home is where the heart is
While Chester helps people find their dream homes in vibrant locations like NYC, Los Angeles, Miami, and the Hamptons, he never forgets his own.
Even when he’s miles away, Chester makes it a point to surround himself with fellow Singaporeans in the U.S. “I’ve connected with many Singaporeans here, especially in NYC. I met most of them through community events, social media groups, and networking gatherings,” he says. “It’s been wonderful to share experiences and maintain that connection to home.”
For those planning to move to the U.S. and navigate the real estate market for the first time, Chester offers some valuable advice.
“The U.S. housing system can be daunting,” he explains. “Start by familiarising yourself with the local rental market. Key factors to consider include rental requirements, especially if you don’t have a U.S. credit score or tax returns. In such cases, you might need a third-party guarantor.”
For those who already have the necessary documents, Chester highlights the importance of ensuring your income meets the building’s approval criteria. “Research online listings carefully, work with reputable real estate agents who understand your needs, and stay vigilant to avoid common scams,” he advises.
Chester is also passionate about giving back to the community. In October, together with Singapore Global Network, he co-hosted an event at the Serhant office, where he shared insights and strategies with aspiring entrepreneurs navigating NYC’s competitive landscape.
Through such initiatives, Chester highlights the importance of building a sense of belonging in a new environment. “Find your community,” he advises. “Whether it’s in the arts, sports, fashion, or another passion, connecting with like-minded people through shared interests can make a big difference.” He also notes that networking with locals offers invaluable insights and practical tips for settling into a new city.
Finally, Chester encourages newcomers to be proactive about seeking help. “Don’t hesitate to ask questions and reach out. There are plenty of resources and communities ready to support you during this transition,” he assures.
Meet Chester
Chester Yow is one of NYC’s top Singaporean real estate agents, and the founder of the Chester Yow Team, with over $300 million in closed deals. He specialises in luxury condos, co-ops, multi- and single-family homes, and investment sales, while also being an entrepreneur, public speaker, and angel investor in U.S. start-ups.
Connect with him here.
