Please ensure Javascript is enabled for purposes of website accessibility

$3.5B real estate brokerage, in a digital world, keeps opening offices

Naples-based John R. Wood Properties shows no signs of slowing down as it surpasses 65 years in business. Neither does its president and CEO.

John R. Wood Properties President and CEO Phil Wood says "my dad was a big jokester, and I kind of try to do the same thing in the office. I walk around trying to get people to laugh."
John R. Wood Properties President and CEO Phil Wood says "my dad was a big jokester, and I kind of try to do the same thing in the office. I walk around trying to get people to laugh."
Photo by Stefania Pifferi
  • Charlotte–Lee–Collier
  • Share

Naples was just a fishing village when John R. Wood Properties was founded in 1958, a far cry from the high-end retiree and vacation haven it is today. In those 65 years, both the real estate brokerage and the area it serves have grown tremendously, and the firm’s almost $3.5 billion in sales volume as of the end of November 2023 puts it about $1 billion ahead of its closest area competitor.

Phil Wood, current president and CEO of John R. Wood Properties, joined the family firm, founded by his father, John R. Wood, in 1976. Back then he was just the ninth agent at the company. (He became president of the company in 1986 and CEO in 2010.) Today some 850 John R. Wood agents and about 90 other staff members work with buyers and sellers all over Southwest Florida.

Under Wood’s leadership, the company has carried on longstanding traditions while also embarking on new endeavors, like joining Christie’s International Real Estate in 2022 — a move that has given the company access to new technology and marketing tools. In a recent interview with the Business Observer, Wood, 68, talked about John R. Wood Properties’ commanding presence in the local market, his outlook for 2024, why he’s opening up physical offices when some other real estate companies are closing branches and more. Edited excerpts:

Why do you think you are so far ahead of everybody in sales volume? What makes John R. Wood Properties the leader?

Well, we’ve been very fortunate in the past couple of years to really bring aboard a lot of agents from other companies, and these are really good agents. I mean, a lot of them do $30, $40, $50 million a year. So it’s been a great addition to our agent group. We have a strong staff and management team that provides all the support for the agents, and they do a great job.

The company's guiding principles, established in 1958, have mostly remained the same over time. Things like hard work, kindness and respect, helping others and dreaming big. Why has that culture been so important to maintain?

The culture has been very important, and that’s attributable to my parents. I was an only child. I grew up totally immersed in the real estate company. I would hang out there; I knew all the agents when I was a kid. I did some work around the office, which I generally hated, because it was usually pulling weeds. I think the culture was embedded in me from a very early age, and when I did decide to come back here after college and join the company, I pretty well knew what to expect and that’s the way it was.

We have worked at it too; I don’t mean to just say it fell in our laps. We’ve worked at maintaining that culture, and we try to structure our philanthropy program and make sure that we’re doing plenty of that and make sure that we spread the dollars and the efforts to a lot of different organizations. And we try to support the organizations that the staff and management are involved in. That’s one of the most important things, since we consider ourselves a big family.

What have you learned over the years when it comes to things like employee recruitment and retention?

I guess it goes back to that culture thing again. My dad was a big jokester, and I kind of try to do the same thing in the office. I walk around trying to get people to laugh. I want them to have a good time while they’re at work. We’ll have luncheons, we’ll have parties, we laugh and kid and do things like that. But we also get the job done, and it’s a professional atmosphere while we’re having fun. And we do things to take care of the people, too. We help them buy their first home, because we want all of them to own real estate. That’s such an important part of building your investment portfolio. For most people, the biggest savings account that they’ll ever have is their home.

Over the years, has there been anything that the company used to do that just doesn’t work today or that you’ve had to change or give up?

A lot. We’ve been in HOA management and appraisals. We got out of both of those. We were in the rental business and then sold it and now as of one year ago, we’re back in the rental business doing luxury vacation rentals. So yeah, things come and go, and they change in the market over time. So we try to adapt to that. 

What made you decide to go back into the rental business?

It was in such demand. I think that was the biggest reason; the agents kept saying, ‘Hey, will you start up another rental department? We really would like to have that.’ We have a lot of customers who come down and quite often they want to rent for a few weeks or a few months before they buy just to get the feel of the area and everything. So having a rental department is a big help in that regard.

Phil Wood was named president of John R. Wood in 1986 and CEO in 2010.
Photo by Stefania Pifferi
Why was affiliating with Christie’s a step you wanted to take?

When they first came to us, we kind of said to ourselves, ‘Are you crazy? Why do we need Christie’s? We’re doing great. We’re really moving up in the luxury market and doing everything fine.’ But we got to talking to these people and they were very, very impressive….We’ve just had a great relationship with them and they really provide some great materials and assistance in all kinds of things, whether it be marketing a very high-end home or helping recruit some of the local agents. They’re a very well-known international brand and they do some great things with the artwork and real estate both.

One of the most interesting things about Christie’s, and we didn’t know this when we started, but they have what they call content where we can refer content to them, which is things in an owner’s home that they might want to sell that are of value. Even down to something like a sneaker collection. There are all kinds of things that get auctioned off to Christie’s, and that’s a great relationship to have for the real estate and for the other things.

What’s the Southwest Florida residential real estate market looking like these days, and what’s your outlook for 2024? 

We’re pretty optimistic about the coming season for a couple of different reasons. One is that the stock market has done pretty well in the last month or so, and that’s always a leading indicator of luxury sales in Southwest Florida. Our typical client has $10 or $20 million in the stock market, or more. So when it goes up 10% or 20%, they suddenly have a lot of extra dollars that they can invest in a second home down in Southwest Florida. In addition, we expect the interest rates to come down a little bit next year. I think when they get down to around 6%, we’re going to see more activity, for sure. Even though many of our buyers are cash buyers; about 70% of our sales are cash.

Do you expect any impact from 2024 being a presidential election year? 

I do see it having an impact. Based on the previous presidential elections, what usually happens is that sales kind of slow down for two or three months right around that November date when the election is going to occur. And then no matter who gets elected, it’s okay. They go ahead and buy. I will say that we have plenty of buyers. We have a shortage of inventory here, just like in the rest of the country.

What are some of the other challenges or issues unique to the Southwest Florida market?

I’ve lived here since I was two years old, and we’ve never had a hurricane that did damage like Ian did. It was just a perfect storm…And I think it’s going to change our building heights. I think that most of the coastal areas will have to address that. I know that Sanibel and Captiva and some other areas are already talking about it, but I would eventually see that all of our building heights go up quite a bit in order to prevent as much damage from occurring in the future, even though it’s unlikely that we’ll get such a heavy flood for many, many years. 

What about the current issues with insurance pricing and availability?

Insurance will be more expensive, there’s no question about that. But it will kind of balance out also. Always after some big losses, the insurance companies kind of go into panic mode and raise their prices like crazy. And then things don’t happen for a while and the prices settle back down and there’s new competitors that come in and create a more balanced market. So we’ll see that all over again; we’ve seen it multiple times in the past.

John R. Wood Properties has been buying brick-and-mortar locations throughout its footprint and converting them to brokerage offices. Why is the firm doing that? 

It is definitely bucking the national trend. I go to these national meetings, and I’ve been hearing for the last 10 or 15 years so many of our fellow brokers around the country trying to close up brick and mortar locations and go to more virtual type of operations. But we found that they can actually be a pretty good competitive advantage. We have 23 offices in the Collier-Lee County area, which is more than any of our competitors. And we’ve found it to be an advantage in a number of ways. One is that, of course, it’s a great billboard as customers drive by, because most of these are located on good, heavily traveled roads. So it helps attract customers and keeps our name in front of them. But it also helps attract the agents; they like to see all the offices that we have, and they’re pretty prominent offices for the most part. So it helps build our brand and helps keep that image out there.

One other aspect of that is that we feel it’s so important that in the last 10 years, we’ve made a real effort to try to buy our offices rather than just rent them. So we now own about eight of our 23, and all of our large ones are owned by us. So that helps really create some stability.



Beth Luberecki

Nokomis-based freelance writer Beth Luberecki, a Business Observer contributor, writes about business, travel and lifestyle topics for a variety of Florida and national publications. Her work has appeared in publications and on websites including Washington Post’s Express, USA Today, Florida Trend, and Learn more about her at

Latest News


Special Offer: Only $1 Per Week For 1 Year!

Your free article limit has been reached this month.
Subscribe now for unlimited digital access to our award-winning business news.
Join thousands of executives who rely on us for insights spanning Tampa Bay to Naples.