Photo courtesy of Beth Dickerson, Gibson Sotheby’s International Realty

For the sports commentators busy bloviating over Tom Brady’s decision to sell his Brookline manse, I have a very simple message: You’re barking up the wrong goal post.

I covered the business of sports for several years in Boston, but I don’t have any secret sources in the so-called “Brady camp” or in the Kraft organization.

That said, I have also written about real estate long enough to know that the decision by Brady and his wife Gisele Bündchen to sell their $39.5 million palace in Brookline probably has everything to do with concerns over the future of their not exactly insignificant investment in the local real estate market and little if anything to do with Tom Terrific’s future with the Patriots.

Brady and Bündchen – or Tom and Gisele, if I might – have some solid real estate reasons for wanting to bail on the 14,000 square foot home they built just a few short years ago.

Tommy Knows When to Sell

For starters, Brookline has been hunting for land on which to build a new school, and one site the town considered was the nearby campus of struggling Pine Manor College. The celebrity couple bought a chunk of the same property a few years back to build their house.

Luxury mansions and big, noisy public schools don’t make for particularly great neighbors, at least from the perspective of a multimillion-dollar mansion-owning sports celebrity.

Brookline is now focusing on other sites for its new school but hitting the market now might not be such a bad idea for the GOAT, especially if the town’s roulette wheel of a school site selection process winds up landing again on Pine Manor.

Neighborhood changes aside, the greatest quarterback in NFL history has also established a reputation over the years as a fairly savvy player off the field when it comes to the buying and selling of luxury real estate.

Tommy knows when to hold his cards and when to fold them, or, in real estate terms, when to buy and when to sell.

“You are spot on with Tom’s thinking,” said Michael Carucci, executive vice president of Gibson Sotheby’s International Realty. “He knows it’s going to take some time to sell such an expensive home and wants to get in front of the market. This has nothing to do with the Patriots.”

A Track Record of Success

While Brady has not always struck real estate gold on every deal, he’s had a very high success rate, reaping millions buying and selling luxury condos and homes in the Back Bay, Manhattan, and Southern California.

And for all the sports nuts out there worried Brady is about to skip town, the Pats’ six-time Super Bowl winner has bought and sold many homes and condos over his two-decade-long NFL career, with little if any correlation to what has been happening in his professional life.

He made a cool $1.1 million on the sale of his $5.2 million Burrage House condo on Commonwealth Avenue in February 2008.

The sale’s timing was impeccable – several months before the real estate market imploded under the onslaught of the Great Recession.

Brady netted another $3 million from the sale of a $17 million condo in the Time Warner building in 2011.

All the sports writers and gossip columnists went nuts again when Tom and Giselle built a $33 million mega mansion out in Southern California in 2012, with all sorts of speculation about Brady eyeing a return to his Golden State roots.

So much for that. The pair turned around and sold the whole thing for $40 million to Dr. Dre in the summer of 2014 before landing right back in the Boston area.

Scott Van Voorhis

They proceeded to shell out a tidy $4.5 million to snap up a 5-acre chunk of Pine Manor’s bucolic college campus in Brookline, where they built a five-bedroom, 14,000-square-foot estate with a swimming pool, library, yoga studio wine cellar and other spectacular amenities.

Again, Brady’s real estate timing was right on the money. Since 2014, Greater Boston real estate prices have gone through the roof, with toney towns and suburbs like Brookline leading the way.

What Does Brady See Coming?

Given his prolific activity in the real estate market, trying to divine Brady’s professional plans from his latest mansion move is a fool’s errand.

But that doesn’t mean we can’t learn anything from it. To the contrary, it may speak volumes about where Brady sees the real estate market right now, especially when it comes to whether prices, especially on the luxury end, may be peaking.

As a quarterback, Brady is legendary for his precision passes on the gridiron, often appearing to be several steps ahead of even the best defense the Patriots’ opponents can throw at him.

As he puts his $39.5 million mansion on the market – Beth Dickerson of Gibson Sotheby’s International Realty in Back Bay is the listing agent – one wonders what Brady sees coming down the pike.

Scott Van Voorhis is Banker & Tradesman’s columnist; opinions expressed are his own. He may be reached at sbvanvoorhis@hotmail.com. 

Brady’s Mansion Listing Shows Boston Market Could Be Peaking

by Scott Van Voorhis time to read: 3 min
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