Tom Brady(Image via Getty Images)
Listed for $34 million, the sprawling estate near Brookline Reservoir could surpass the reported $32.5 million sale of Tom Brady and Gisele Bündchen’s former home. Located at 55 Singletree Road, the hilltop estate covers 19,138 square feet on 2.06 acres. Built in 2015 by luxury homebuilder Thoughtforms, the residence combines generous living space with features designed for privacy and leisure. The property includes seven bedrooms, 16 bathrooms, five fireplaces, a swimming pool, a private tennis court and a fitness centre. Brookline assessed the property at $18,959,800 in 2025, according to records cited in local reporting. Its annual property tax bill reached $187,133, a substantial cost even for buyers shopping in the luxury market. Public records show that the parcel last sold in 1993 for just over $1 million. The current owner, an LLC linked to a partner at a Manhattan estate-planning firm, took out a $9.1 million mortgage in 2015.
A luxury mansion in Brookline, Massachusetts, is making a bold bid to claim the town’s most expensive home sale record. With seven bedrooms, a private tennis court and sweeping views of Boston, the property offers a glimpse into New England’s elite real estate market. However, its ambitious asking price comes as local home sales slow, leaving a big question: will a buyer pay enough to rewrite Brookline’s property history? A rooftop terrace also offers views of the Boston skyline, adding another attraction to the expansive home. The estate’s price stands out even in one of Massachusetts’ wealthiest communities. The land itself has a long history.
How Tom Brady’s former Brookline mansion set the benchmark
The couple bought a five-acre parcel at 112 Woodland Road from Pine Manor College for $4.5 million in 2013 before building a custom mansion designed by architect Richard Landry. The 12,112-square-foot home initially went on the market for $39.5 million in 2019. After price reductions and a brief withdrawal, it eventually sold for a reported $32.5 million in 2021. The new $34 million listing aims to exceed that figure, although the asking price does not guarantee a record-breaking sale. Data from MLS PIN cited by the Brookline Record showed that the town recorded 25 home sales in September, down 44% from 45 sales a year earlier. The median time properties spent on the market also doubled to 71 days. Stay updated with the latest Asian Games 2026 news , check the Asian Games medal tally and complete Asian Games schedule .
Tom Brady and Gisele Bündchen’s former Brookline estate remains a major reference point for the new listing. Join conversation Share your thoughts in the comments Be respectful · TOI community guidelines Brookline’s wider housing market could also complicate the seller’s ambitions. Still, exceptional estates often attract a different pool of buyers from ordinary homes. Whether this mansion can command its full asking price remains uncertain, but its listing has placed Brookline’s luxury property market back in the spotlight. Get the latest Sports News and Live updates. Download the TOI app.
The brokers have experience with high-value properties in the area, including the nearby estate of former Reebok founder Paul Fireman, which sold for $23 million in 2020. The Sarkis Team at Douglas Elliman Real Estate is handling the listing.