Get to Know the Broker: Matthew Lesser of Leslie Garfield

New York City native Matthew Lesser, 43, has a passion for townhouses, so much so that he’s made them the focus of his career in real estate. Having joined Leslie Garfield in 2005, he was named senior partner at the firm in 2014, and is responsible for leading a team on some of the biggest townhouse deals in the city. 

Lesser has represented more than $2.5 billion in residential, commercial and institutional real estate during his career, and has been responsible for the sale and leasing of over 350 properties. 

Some of his most notable deals include the $75 million sale of a six-story townhouse at 105-107 Bank Street in Manhattan’s West Village, the $65 million sale of a seven-story mansion at 12 East 63rd Street in Lenox Hill, and the $79.5 million sale of a five-story townhouse at 34-36 East 63rd Street, also in Lenox Hill.

Commercial Observer caught up with Lesser, a married father of two, in August for “Get to Know the Broker,” a series where we connect with residential brokers to learn more about what makes them tick. 

This conversation has been edited for length and clarity. 

Commercial Observer: What has been the biggest deal of your career? 

Matthew Lesser: Price or most meaningful? I’ve been fortunate to be part of several commercial transactions north of $100 million, but, for me, the most rewarding deals are the ones where I get to see an entire project through from purchase to sale. 

Identifying the opportunity, advising on the layout and finishes, helping shape the product, and ultimately selling it successfully is incredibly rewarding. 

The recent sale of 105-107 Bank Street was one of those projects. It sold for $70 million, making it the most expensive townhouse sale in New York City in 2026 to date and the second-highest Downtown townhouse sale ever. And we achieved a sale entirely off-market.

What’s your career Everest? 

Everest keeps moving. 

Early in my career, it was getting my first listing. Then it was my first $10 million deal, then $20 million, then $100 million. Today, it’s much bigger than a number. 

Being an owner and watching Leslie Garfield grow from a five-person family business into a 30-person company and, in my very biased opinion, the world’s leading townhouse brokerage, has been incredibly rewarding. Building something that lasts is probably the biggest mountain of all.

Who has been your biggest influence?  

No doubt, Leslie and Jed Garfield have both been pillars of my success. Although they’re both Garfields, they each had a very different influence on how I learned, grew and ultimately built my career. 

And, as cliché as it sounds, watching my father’s work ethic has been one of the biggest drivers in my professional life. At 81, he still might be the first one in at the Merrill Lynch office each day. 

What’s your go-to Grubhub order? 

More UberEats than Grubhub for my household. Moving to the suburbs has accelerated this use. For the kids, Chipotle seems to have become a household fixture. For me, it’s usually Greek. It delivers well.  

What TV show are you currently binging? 

I just finished “Death by Lightning,” which was excellent. Before that, “Paradise.” I’m almost done with “The Righteous Gemstones.” They’re all completely different, which is probably why I like them. I have a very short attention span. 

What is your silliest pet peeve? 

It’s silly, but I have a serious aversion to loud chewing. My wife, Erin, thinks I’m nuts. I also hate when people say, “To be honest.” 

What’s on your Spotify playlist? 

Morgan Wallen, Rufus Del Sol, Goose, Drake, Ripe, and always some `90s hip-hop artists. 

Who is your favorite architect/interior designer? 

I don’t really have one favorite. It depends on the project, the neighborhood and the personality of the house. I enjoy working with RAMSA, Drew Lang and Joseph Vance. Banda, out of London, consistently impresses me, as does GRADE. I also have a real passion for landscape architecture and design. Lots of inspiration from Hollander Design. Maybe that will be my next career. 

What is your most entertaining story from a deal? 

Fair to say that some buyers occasionally think they’re God’s gift to real estate and have a slightly loose relationship with market realities. 

We were once negotiating with a very famous actor who was considering purchasing two side-by-side townhouses. Ultimately, they decided to buy only one; which, in retrospect, was probably the easier part of the deal.

During contract negotiations, they demanded that the adjacent townhouse they weren’t buying be subject to a specific decibel-level cap. And not just a general “please keep it quiet” provision. They wanted an actual maximum decibel level written into the agreement, with pre-negotiated financial penalties if the neighboring house ever exceeded it.

At that point, we all realized we had probably entered a different kind of real estate transaction. Needless to say, the deal died pretty quickly. I still think about what the sound meter would have looked like at closing!

Amanda Schiavo can be reached at aschiavo@commercialobserver.com.

If you’d like to be featured in our Get to Know the Broker Spotlight, please email Amanda Schiavo at aschiavo@commercialobserver.com.