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What’s it like selling Derek Jeter’s Tampa house while Tom Brady lives in it?

A Q&A with a local Realtor who’s handling the $29 million Davis Islands listing
New York Yankee Derek Jeter's home on Davis Islands has been on the market since September. [Times]
New York Yankee Derek Jeter's home on Davis Islands has been on the market since September. [Times] [ Times ]
Published Jan. 26
Updated Jan. 26

Last fall, the doubly star-studded property of baseball star Derek Jeter — which is being rented by Buccaneers quarterback Tom Brady — was put on the market, culminating in a story that’s fascinated real estate buffs and sports fans alike.

Despite rumors that Brady was buying a Clearwater house, the supposed sale of that mansion hasn’t materialized, and his family remains in Jeter’s estate. The home has seven bedrooms, eight full bathrooms and eight half-baths, as well as a clubroom with a full-service bar, a billiards and game table with a glass corner wall overlooking the water.

It also features a wine cellar, movie theater, gym, in-law suite, au-pair wing, air-conditioned six-car garage, scullery and a full-home generator. Its expansive outdoor area includes 9,000 square feet of covered porches and balconies, a dock with two boat lifts, a heated spa and an 80-foot saltwater lap pool.

So what’s it like selling a home with a massive $29 million price tag, not to mention coordinating showing times with the house’s extremely famous residents?

Related: Derek Jeter lists Tampa home, residence of Tom Brady, for $29 million

Tampa Realtor Stephen Gay, who works for Smith & Associates, is the listing agent on the property, along with colleague Katherine Glaser. Gay spoke with the Tampa Bay Times about how the first few months have gone. The following interview has been edited for length and clarity:

Stephen Gay
Stephen Gay [ Joe Sale Photography, Courtesy of Smith & Associates Real Estate ]

How did you come to have this listing?

We competed with several agents both locally and also from the whole state of Florida, that have nationwide brands. Out of that they still liked our presentation the best.

Smith (& Associates), even though we’re a locally owned company, we are a global network of similar locally owned and operated boutique luxury firms across the world. The network we’re a part of is the leading real estate company in the world. In 2019, we sold $254 billion.

Have you always specialized in luxury real estate?

No, I would say that it’s something that you build up to over the years — I’ve been selling for 15 years now. But even though we have a $29 million listing we sold a $200,000 house last year. In the market as diverse as Tampa Bay is you can’t pigeonhole yourself. It all pays the bills.

An interior room of Derek Jeter's house features waterfront views and a fireplace.
An interior room of Derek Jeter's house features waterfront views and a fireplace. [ Courtesy of Uneek Image ]

What sort of things do you do to market an ultra-luxury listing like this?

It is obviously a little different than, say, a $200,000 condo. We’ve marketed to that network that I was just talking about, letting them know. A lot of people don’t think of Tampa as being a luxury market. We did a marketing push to that network and a lot of people that were in New York or in Chicago or even out in California said, ‘Oh wow, we didn’t know Tampa had houses like this.’ So it’s kind of education to those other brokerages, especially right now during COVID, when people are like, ‘I don’t want to live in New York City and walk through the same door with 300 of my closest friends every day to get to my house.’ People are moving to Florida across the board in all the different price levels.

And a house at $29 million for someone in New York is cheap. They’re paying sometimes up to $8,000 a square foot for a piece of property where this is right at $1,300. And Florida’s open for business right now compared to a lot of places that are shut down because of COVID. We have no state income tax, which is obviously very attractive, and then it’s a place where you can be outside the majority of the year, which is also great during this kind of crisis.

But the bigger thing, I think, is people are now seeing that they can work remotely. People that are working on Wall Street don’t have to be on Wall Street anymore.

Then doing the same things we do for every house, like having amazing photography, great videos and getting the word out. This house was easy to get the word out on, because everyone and their brother wanted to write a story about it when we first launched.

Do you speak with Derek Jeter often about the listing?

I have a call with his team weekly and then he probably joins them early every three to four weeks to get a summary update. And when there’s a lot of activity, obviously, he joins them for sure, which we actually have had a lot of interest lately, from California, New York, Virginia, from actually valid people.

New York Yankees shortstop Derek Jeter speaks during the Baseball Hall of Fame press conference, Wednesday Jan. 22, 2020, in New York. (AP Photo/Bebeto Matthews)
New York Yankees shortstop Derek Jeter speaks during the Baseball Hall of Fame press conference, Wednesday Jan. 22, 2020, in New York. (AP Photo/Bebeto Matthews) [ BEBETO MATTHEWS | AP ]

I get probably three or four calls a week from people that obviously don’t have the means of purchasing this house, they just kind of want to get in and see what it looks like. So that’s been kind of fun filtering through the crazy leads to get to legitimate leads. But we’ve had about seven or eight showings with qualified people. There’s been shockingly a lot of interest within the last four weeks. So we have calls with Derek and his wife, Hannah, to give them updates on what’s going on.

How do you filter out the serious buyers from people who just want to come in and sight-see?

Thanks to the internet you can pretty much find out information about anybody these days, especially anyone that has the capacity of purchasing a $30 million house. So we do some initial research that way. We get a lot of calls from agents that are so excited someone called them on this house. Obviously, everyone is hopeful that they’re going to quote-unquote ‘win the lottery.’ So we actually have been assisting those agents and doing some background information research on their leads. And most of them are pretty disappointed when we find out some information about them.

We purchased a software that’s specific to Realtors that we can do some background research on people just using their phone number alone, to get information through public records for what kind of cars they own, what properties they own.

The outside of the home features fountains, a heated spa and a saltwater lap pool.
The outside of the home features fountains, a heated spa and a saltwater lap pool. [ Courtesy of Uneek Image ]

We’ve had people with like a 1987 Honda Civic that have been trying to get in and see the house. Granted, they might have the money to buy it, but probably not likely, especially when you can’t find any other information about them online.

Ultimately, people have to give us proof of funds that’s verifiable. A lot of people say, ‘I’m not really ready to give you my proof of funds yet.’ And those are the people that usually end up not being legitimate. Because if you’ve got the money, you’re used to a request like that and have someone that can easily provide the information to us.

When it comes to showings, how does that work with Tom Brady living in the house?

They have been very, very accommodating and helpful to us because they don’t want to be the reason the house doesn’t sell because we can’t get in to show it. So they’ve been super helpful for showing requests, getting everything show-ready, just like they would if it was their own house. They just sold several properties themselves so they know how hard it is to sell a high-end luxury property.

Tampa Bay Buccaneers quarterback Tom Brady (12) celebrates his fourth quarter touchdown at the Mercedes-Benz Superdome on Jan. 17, 2021 in New Orleans.
Tampa Bay Buccaneers quarterback Tom Brady (12) celebrates his fourth quarter touchdown at the Mercedes-Benz Superdome on Jan. 17, 2021 in New Orleans. [ DIRK SHADD | Times ]

We obviously have to give them advance notice, so we’re not just going to call and say, ‘Can I show it this afternoon?’ We give them advance notice. They haven’t actually turned down any showing requests.

I imagine that a big challenge with selling a home of this size and price tag could be that anybody who can afford it might opt to construct their own custom mansion instead. How are you dealing with that?

What we found is most people that are looking at this house, this is not their first house. This is one of several homes, and they may have gone through that lengthy design, build, permitting process before to build something like this — it takes about three years. Also, it’s kind of hard to find any land that’s this large to build on in South Tampa.

The design, permitting the build process is very lengthy and a lot of people with the wealth to purchase a home of this caliber want instant gratification.

Does a property’s association with famous athletes like Derek Jeter and Tom Brady inflate its value?

I don’t necessarily think it inflates the value but I think it inflates people’s awareness of the property. It definitely helps me with my job and getting the word out there, having a famous landlord and tenants associated with the house.

Related: 47,484 evictions were filed in Florida during 2020 pandemic months