The real estate agent who utilizes a boots-on-the-ground strategy for his sellers, buyers, and builders

Douglas Elliman’s Tom Cavallo

Independent/Ty Wenzel

The Cavallo name evokes stunning homes on the East End, in part, because of Cavallo Building, the family enterprise that began constructing homes in 1977 with Tom Cavallo Sr. Now, Doug Cavallo has taken the firm to the next level, creating a solid foundation for his family’s building legacy.

Recently, the firm expanded with Tom Cavallo Jr. joining the team. It was a natural fit and for Tom; real estate was in his blood. Since college graduation, Tom has been active in buying, remodeling, and selling properties with an attention to detail that has seen his star rise at Douglas Elliman even through the current Hamptons real estate slump.

Cavallo has utilized his own kind of guerilla marketing know-how in finding underutilized properties, which most agents do not spend enough time on. He matches homes and plots with buyers and builders who transform them into what the modern East End buyer is looking for. Finding the diamond in the rough is a rare talent, not an easy feat in this region, where properties are at the very high-end of the price pyramid. And because of his family experience that is entrenched in building, he is especially valuable for builders who are looking for affordable plots to build their specs or custom builds.

He has a deep knowledge of the Hamptons real estate market, as well as building parameters and what is available for a wide range of buyers. To better serve his clients, Tom is constantly searching for new opportunities in real estate investing and where there are still strong values in the Hamptons. He won’t tell us his secret sauce, but his conversion rate in a slow market saw him closing homes where not many were succeeding.

Prior to his career in real estate, Tom worked with children with special needs, including teaching at BOCES.

When did you join the real estate market?

I’ve been in real estate for more than a decade and have been with Douglas Elliman for six years. I became interested in real estate at a young age because it was always a big part of my life — my family has been building homes on Long Island for decades. So, I suppose it was a natural career path for me. I love the challenges of the real estate business and have a knack for finding off-market opportunities and a keen eye for development opportunities.

Are you local to the area?

I’m a native Long Islander, but I grew up a bit farther west, in Northport. I’m not a stranger to the area though — I spent summers in Montauk and the Hamptons growing up. I now live here in Southampton with my wife. We love it out here.

You’re part of a family that is well-versed in Hamptons real estate. Can you talk about that?

I grew up learning the ins and outs of the industry due to my family’s business. My father, and now, brother, own a building and contracting company, Cavallo Building. Learning from my father and watching him work definitely helped inspire me to make my own mark on the industry.

Independent/Ty Wenzel

Why Douglas Elliman?

Even though there are so many amazing brokerages on the East End, I chose Elliman for the company’s national reach and considerable NYC presence. Douglas Elliman affords their brokers the marketing power needed to reach an exclusive network of buyers and investors — not to mention sellers — because homes on the East End are so coveted by a global market.

You’re in the top three percent of all Elliman agents. What’s your secret?

I’m so honored and grateful for this recognition. I don’t think there is a secret, per se. I think it’s really all about having a passion for what you do and feeling excited to go to work every day. And because I truly enjoy what I do, it doesn’t feel like work. I guess that’s the secret.

How are you feeling about the market for 2020 after the big slump we’ve been in? Are you optimistic?

I think that the great low interest rates have helped tremendously. They’ve helped to build up demand for both my buyers and my builders, which has resulted in a strong start for 2020. So yes, I’m super optimistic.

Do you have any advice for buyers in this market?

At the moment, renters and buyers are out in the market in full force. The homes that are priced appropriately are selling, and the ones that are sitting are sitting for a reason. My advice would be to shop smart. Take both the particulars of the home (rent roll/size, any possible renovations needed) and the home’s location into consideration. For both investment and re-sale purposes, it’s smart to buy a home that will yield a high rent roll.

If a home requires expansion or extensive renovations, it sometimes makes more sense for buyer to build a new home instead. It’s important to take a location’s potential into consideration as well, with regard to what’s going to be the next up-and-coming area. A home could be in an underrated location or close to an area that’s becoming more popular, and those things are important to note.

What about sellers?

There are definitely some uncertainties in the market right now that might have some people worried. One big recent concern is the coronavirus, which is obviously a big wild card. However, I think this will actually affect the housing market in some positive ways. The recent push and drop in mortgage rates will boost home sales. Mortgage rates are already at three-year lows. There are a lot of investors who are more inclined to invest in real estate than the stock market, especially in the Hamptons, since it’s an international market with historically high rent rolls and low taxes.

A lot of people want to get their houses sold, so there are great deals to be made. Pre-construction homes are hot with the builders I support. I sold quite a few this spring before they even hit the market.

You’ve worked with special needs kids, can you tell us a little about that?

Absolutely. A fun fact about me: I was born with only one hand. I’ve never considered it a disability or let it keep me from accomplishing anything I’ve set my sights on. I’ve always enjoyed working with children, and my own experiences drove me to want to help inspire confidence in kids who might need a little extra support to achieve their own goals.

I worked as a one-on-one tutor with kids at BOCES, and found the experience to be really rewarding. At one point, I was actually considering pursuing a career in special education, before I found my passion for real estate. However, I still enjoy being part of the special needs community and I make sure to support local kids and try to serve as a mentor. I think it’s important to give back.

What do you do for fun?

Aside from the aforementioned work with the community, I really enjoy the outdoors. I like to be active and tend to spend my free time outside. Depending on the season, you can find me fishing, playing tennis, or snowboarding.

Anything you’d like to add?

I’ve found that most buyers prefer new homes if they can afford the product. I specialize in that type of product and have excelled in a very difficult market, with 2019 marking one of my best years. My reach has grown exponentially with builders, so if you’re a builder and need someone very experienced in finding properties to take it to the next level, I’m your man!

For home buyers, I have an arsenal of inventory for every price point. Just give me a call, and I’ll show you all of the possibilities — and maybe even my favorite fishing spots.

To inquire about Cavallo’s properties or to sell your home, call 631-871-1401 or email