Tom Brady may have won six Super Bowls in 20 seasons with the New England Patriots, but he’s also established a winning record off the field—by moving around, buying and selling real estate from Montana to Los Angeles to New York. After all, it takes shrewd dealmaking to become one of the NFL’s highest-paid players of all time, with some $350 million in career earnings.
Having left the Patriots last season to play for the Tampa Bay Buccaneers, the 43-year-old Brady and his supermodel wife, Gisele Bündchen, finally left New England behind from a real estate perspective in December. The couple sold their 12,000-square-foot mansion in Brookline, Massachusetts, complete with a yoga studio and wine room, for a reported $32.5 million.
At the time, the Brady bunch were already renting Derek Jeter’s 30,000-square foot estate in Tampa, nicknamed “St. Jetersburg.” But even that mansion was just a placeholder. Late last year, Brady and Bündchen paid $17 million for a tear-down property on the “Billionaire’s Bunker,” Indian Creek Island, in Miami-Dade County, Florida. Their new neighbors include Jared Kushner and Ivanka Trump, along with the Emir of Qatar.
Win or lose on Super Bowl Sunday, Brady will retain a huge fortune, including multiple properties worth tens of millions of dollars. Below, a history of Brady’s record as a real estate player.
Young Tom: San Mateo, California
Brady’s parents bought a four-bedroom home in San Mateo in 1977 and have reportedly lived in it ever since. Their famous son’s old space is now a guest room. It turns out San Mateo was a good place to buy: that house is worth more than $2 million, according to Zillow estimates, likely an order of magnitude more than they purchased it for.
Purchased: 1977 (Price unknown)
Starter Penthouse: 310 Beacon Street, Boston
After years in New England, Brady and Bündchen aged out of this 5,300-square-foot triplex penthouse in Boston’s Back Bay in 2012, opting to relocate to a custom mansion in Brookline soon after. They left behind a gym, two roof decks and five fireplaces; as of 2014 the unit was reportedly on the market for $35,000 in rent per month.
Purchased: $6.2 million (2006, entire building) Sold: $9.2 million (2012)
Paging Dr. Dre: Brentwood, California
Brady and Bündchen sold this five-bedroom estate—featuring a moat filled with koi, an infinity pool and a home sauna—to hip hop mogul Dr. Dre in 2014. And because five fireplaces on Beacon Street evidently weren’t enough, there are seven to choose from in this home. At more than 18,000 square feet, this limestone mansion also features an underground spa, cabana, library and wooden dock.
Purchased: $11.75 million (2008) Sold: $40 million (2014)
Patriot Games: Brookline, Massachusetts
This custom home sits on the perimeter of The Country Club, an uber-exclusive hangout that reportedly wouldn’t let Brady join for years. (He eventually became a member in 2017.) Brady and Bündchen—who was once the world’s highest paid model—attempted to sell the property for $39.5 million, before eventually deflating the price by $7 million. Boasting five acres, a yoga studio and a cavernous motor court, there was plenty of room for two mega-earners in this home.
Purchased: $4.5 million (2013, for the land) Sold: $32.5 million (2020)
Winning the West: Yellowstone Club, Montana
Brady is reportedly a member of this exclusive resort near Big Sky, Montana. Other A-List residents include Jessica Biel and Justin Timberlake, and Bill and Melinda Gates. It costs a reported $300,000 to become a member, in addition to the price of buying property, which is also a requirement. That might set you back $25 million or more.
Sky High: One Madison Tower, New York
A private elevator leads into this high-rise apartment, which occupies an entire floor in New York’s Flatiron District. Amenities include floor-to-ceiling windows, three bedrooms and wraparound views of Manhattan. There’s a white marble island in the kitchen, perfect for cooking up a snack. Just remember: no mushrooms, iodized salt, peppers, eggplants, white sugar, or white flour.
Purchased: $11.7 million (2014) Sold: $13.95 million (2018)
Downtown Mobility: 70 Vestry Street, New York
Perched on the 12th floor of a Robert A.M. Stern-designed building in Tribeca, this condo has five bedrooms and totals 5,000 square feet. The couple reportedly sold the apartment earlier this year in favor of a smaller unit in the same building. Constructing a new mansion in Florida will inevitably occupy their time, so no need for all that space.
Purchased: $25.5 million (2016) Sold: $36.8 million (2021)
Billionaire Bunker: Indian Creek, Florida
Late last year, Brady and Bündchen spent $17 million for a home on one of the most exclusive enclaves in the world—Indian Creek in Miami. In addition to Jared and Ivanka, their new neighbors include billionaires Carl Icahn, Norman Braman, Jaime Gilinski Bacal and Edward Lampert, as well as singer Julio Iglesias. With a population last tallied at 86 people, privacy won’t be an issue here.