Inside Tom Brady’s Multimillion-Dollar Property Portfolio

Before he was collecting Super Bowl rings in Tampa, Brady was conquering Boston’s high-end housing market. He kicked off his reign in 2004, dropping $4.1 million on a sprawling condo in Back Bay’s iconic Burrage Mansion—a French château-style marvel studded with gargoyles and cherubs. The 3,412-square-foot spread featured twin fireplaces, a chef’s kitchen, and prime views of Commonwealth Avenue. Four years later, Brady cashed out for $5.3 million.

By 2006, he was ready to level up to Beacon Street, dropping $6.2 million on a 5,311-square-foot penthouse triplex complete with a library, media room, and a private roof deck overlooking the Charles River. Shortly after tying the knot with Bündchen, he put it on the market, eventually scoring $9.27 million in 2012.

Seeking suburban breathing room, the power couple eventually headed to Brookline. In 2014, they snagged five acres for $4.5 million and tapped celebrity architect Richard Landry to build a custom mega-compound. The result? A 12,112-square-foot main house—plus a 2,400-square-foot barn/guesthouse—outfitted with a yoga studio, wine cellar, playroom, and gym. After initially listing the estate for a cool $39.5 million in 2019, they ultimately finalized a $32.5 million sale in January 2021 as Brady packed his bags for Tampa.

Brady and Bündchen’s West Coast debuts were anything but subtle. After a brief rental stint in Brentwood, they bought raw land and enlisted Richard Landry and interior designer Joan Behnke to build a custom 18,298-square-foot eco-mansion. The estate featured solar arrays, reclaimed materials, an actual moat with a bridge, and a swimming pool designed to look like a natural lake. The project ran roughly $11.75 million—and just weeks after finishing it in 2014, they flipped the property to Dr. Dre for $40 million.

Brady wasn’t done with L.A., though. Post-divorce, he returned to buy a new home for $8.2 million in 2019. He then demolished the original structure only to build a sleek 14,000-square-foot sanctuary completed around 2024. The custom compound showcases floor-to-ceiling glass, a glass atrium, an artificial-turf terrace, and a resort-style pool setup.

The couple’s Manhattan chapter began in 2013 on the 48th floor of One Madison, where they dropped $11.7 million for a 3,310-square-foot perch with skyline views and Peter Marino-designed interiors. Five years later, they traded up to Tribeca, shelling out $25.5 million for a spread at 70 Vestry Street, the Robert A.M. Stern-designed limestone tower along the Hudson. The 14-story building has attracted the likes of actor Jennifer Lawrence and F1 champion Lewis Hamilton, who bought its $40.7 million penthouse in 2016.

When Tampa came calling in late 2020, Brady and Bündchen offloaded their main residence for $36.8 million. They didn’t cut ties with the building completely, though. That same month, Brady picked up a smaller $3.5 million unit, turning it into a decidedly luxe Manhattan pied-à-terre. Following the couple’s 2022 divorce, Brady held onto the pad, property records show.

When the power couple wanted to trade coastal sun for snow-capped solitude, they headed to the ultra-exclusive Yellowstone Club in Big Sky, Montana. The private, members-only ski and golf enclave has long been a refuge for the tech world’s biggest names. Bill Gates acquired a home there in 2009, while former Google CEO Eric Schmidt and Meta founder Mark Zuckerberg have also been linked to the club. Membership reportedly requires an initiation fee of roughly $450,000, the purchase of a multimillion-dollar home, and annual dues topping $50,000. Bündchen has reportedly retained access to the couple’s Montana getaway post-split.

Down in Santa Teresa, Costa Rica, the couple reportedly created a secluded tropical sanctuary hidden in the jungle overlooking the Pacific. Highlighted in a Vogue feature, the compound features open-air pavilions, infinity pools, and direct beach access. Bündchen allegedly claimed the estate in their asset division and continues to use it.

When Brady went to the Buccaneers in 2020, he didn’t jump straight into buying. Instead, he rented Derek Jeter’s massive 22,000-square-foot waterfront mansion on Davis Islands—dubbed St. Jetersburg—complete with seven bedrooms, deep-water docks, and two boat lifts.

Later that year, he and Bündchen went all-in on Miami, dropping $17 million on a two-acre lot on Indian Creek Island, better known as Billionaire Bunker. They quickly leveled the existing home to make way for a sprawling custom waterfront compound designed by Scott Mitchell. Brady’s neighbors include an impressive collection of billionaires and celebrities, from Jeff Bezos and Zuckerberg to Ivanka Trump and Jared Kushner.

Following their October 2022 split, Brady kept the plot, reworked the architectural plans, transferred the property into a new trust, and secured a $35 million construction loan to push the project across the finish line. The result is a fully realized 25,000-square-foot bachelor fortress wrapped in pale stone and glass, with a double-height living area, detached guesthouse and wellness pavilion, manicured lawns running down to Biscayne Bay, and a massive dock holding his $6.5 million Wajer speedboat alongside a pair of WaveRunners.

While reports surfaced that Brady quietly tested the waters by shopping the estate off-market for a staggering $150 million, recent property filings indicate he formally declared the Indian Creek compound as his Florida homestead and permanent residence.