Meet Chester, who was born and raised in Singapore, and later took a bold leap across the globe to pursue his ambitions in one of the world’s most iconic cities—New York. Armed with determination and a passion for real estate, Chester made his mark in the competitive Manhattan property scene, closing over US$400 million in transactions and even appearing on the hit show Million Dollar Listing New York. His journey from a Singaporean student on the West Coast to a recognised name in luxury real estate is nothing short of inspiring.
Today, Chester leads a high-performing team at Serhant, one of New York’s top brokerages, where his multilingual abilities and cultural fluency help him connect seamlessly with clients from all over the world. Whether it’s advising international investors or managing multimillion-dollar developments, Chester brings a blend of precision, charisma, and professionalism that sets him apart. His story is a powerful reminder that with vision, hard work, and the right mindset, Singaporeans can make a global impact.
You have built an incredible career in the competitive New York real estate market. What initially inspired your journey from Singapore to the Big Apple?
I went to do my undergraduate on the West Coast, and then I graduated and I wanted to work in the US for some time. I wanted to experience the US work life and culture. New York City is very similar to Singapore in a lot of ways. It’s a finance hub, very diverse, a small city, and fast-paced—very much like Singapore.
In New York City, if you work hard and work smart, you can really make a name for yourself. That was what excited me to move to New York. It’s still part of the US, but it has its own culture and way of living. It’s really an international hub for many countries.
How is the real estate landscape in New York different from that in Singapore?
Real estate is expensive in both places. New York City doesn’t have the government HDB housing or balloting system that Singapore has. Singapore provides those to encourage citizens to purchase homes and offers grants to Singaporeans. Here in New York, everything is free market—whether you’re a local, domestic, or foreign buyer or seller.
It’s very diverse in terms of the number of countries and people that invest, buy, and sell in New York City. The product here is also different—you have new construction, lofts, townhouses—it varies a lot. But demand is very active because everyone wants a piece of Manhattan in their portfolio.
You have closed over $400 million in transactions and appeared on Million Dollar Listing New York. What do you think sets your approach apart in the luxury real estate world?
At Serhant, we are very focused on media—television, press, social media, any form of media that allows us to advertise, promote, and showcase our brand and listings. Our recent Netflix show Owning Manhattan was a good example of that. Our website traffic jumped over 10,000 times when the show aired. I had friends and family in Singapore who watched the show as well. In today’s market, you have to be everywhere.
My CEO, Ryan Serhant, always emphasise that he appears on platforms CNBC, NBC, LinkedIn to appeal to the older generation, parents, assistants of families, etc. And we’re also big on platforms such as Instagram, YouTube, and TikTok—for the younger audience, the child or teenager who is watching it at home or on the way to school. Everyone is your audience now.
It’s important to understand what they value, for example their time is money so communicating efficiently and productively is key, but they do value your service as well.
Having been involved in multiple new development projects from pre-construction to sell-out, what do you think is the secret to understanding what buyers really want?
Buyers today are more savvy and knowledgeable, thanks to the internet and social media. The key to selling new construction is understanding the culture of the neighbourhood, the quality of the finishes, the developer, and the architect—and being able to explain all of that. You need to be able to talk about the product, the appliances, amenities, and so forth. And having a good pricing model, and market strategy depending on the neighbourhood.
The secret is having the patience and knowledge to explain all this to consumers and give them a positive experience when they tour the building or sales gallery. Most buyers today can tell if something is cheap or if you don’t know your stuff. You have to be on top of your game if you want to sell new developments.
How do you leverage your multilingual abilities and cultural fluency to connect with international investors and clients in cities like New York, LA, and Miami?
My team at Serhant is very multilingual—we have agents who speak Mandarin, Cantonese, Thai, Hindi, Spanish. When working with international clients, you must understand that wealth transfers from certain city to city—New York City, Miami, LA, the Hamptons, Singapore, London, Monaco and others.
At a certain price point, many clients want investments or homes in multiple cities. It’s important to understand what they value, for example their time is money so communicating efficiently and productively is key, but they do value your service as well. Just speaking their language and knowing how to communicate helps a lot—you know when to push and when to pull to get deals across the table.
What advice would you give to aspiring realtors from Singapore or any parts of the world who want to break into luxury global markets like New York?
First, you have to be in the country. You have to come to New York and be able to work here. Understand the real estate culture here, and understand the people. But the most important thing is hard work. You can’t take that away. Work hard, work smart, find a mentor or team leader who can help you grow your database and experience exponentially. That’s vital.
Beyond your career, how do your passions like caring for your dogs or serving during Hurricane Sandy keep you grounded and connected to your community?
Aside from work, there’s personal life too. That helps me stay grounded and humble. We’re in the service business, so it’s always good to give back to the community. My dogs, friends, and family remind me of my purpose and why I work so hard.
Sometimes in this line of work, you can get carried away and forget who you are or why you even started in the first place. Service helps me stay connected to what really makes me happy. Not everything is about success or money.
What is one Singaporean dish you really miss?
Very difficult question! There are a lot. The staple is definitely chicken rice. You can’t find any really good ones here. There are some, but they’re very Malaysian-focused. In terms of pure Singaporean flavour, it’s very hard. I also miss things like roti-prata—those are impossible to find good versions here.
Where do you see yourself in the next five years?
I haven’t thought that far yet. Right now, I’m focused on making sure my team at Serhant is successful. Over the next five years, I hope to grow as a person, take care of the people I love—my family, my friends. I just want to wake up every day, do my best, be the best version of myself, and hope that everything flows—work is great, family is great, life is great.
Do you have anything you’d like to say to your family and friends currently based in Singapore?
Sure, I miss them. From Singapore to New York is one of the longest flights—about 19 hours on Singapore Airlines. I understand that flying here or me flying back is tiring, and the time difference is tough too. But when I do get to see them, it’s really special. I don’t take that time for granted.
Connect with Chester: LinkedIn, Instagram and Facebook.
