The 55 Singletree Road estate has entered the Brookline market at a $34 million asking price, a figure calculated to eclipse the town’s previous benchmark. This hilltop property seeks to surpass the $32.5 million sale of the former Tom Brady and Gisele Bündchen residence, establishing a new ceiling for ultra-luxury real estate in the area.
Built in 2015 by Acton-based luxury builder Thoughtforms, the home spans 19,138 square feet across 2.06 acres. It features seven bedrooms, 16 bathrooms, a private tennis court, and a rooftop terrace overlooking the Boston skyline. Public records show the parcel last changed hands in 1993 for just over $1 million, a stark contrast to its current valuation.
The current owner, an LLC linked to a Manhattan estate-planning partner, took out a $9.1 million mortgage on the property in 2015. Tax records indicate a 2025 assessment of approximately $18.96 million, with an annual property tax bill of $187,133. The listing is represented by The Sarkis Team at Douglas Elliman Real Estate.
This aggressive pricing arrives despite signs of cooling in the broader local market. September recorded just 25 home sales compared to 45 the previous year, and median days on market doubled to 71. However, trophy homes often operate in a separate economic tier where scarcity drives demand.
Whether the estate sells for its full asking price remains to be seen. The previous record-setter, the Woodland Road property, was initially listed at $39.5 million in 2019 before settling at $32.5 million in 2021. The market will decide if 55 Singletree Road maintains its premium valuation or follows a similar trajectory of price adjustment.