In Brookline, where sprawling estates rarely come to market and even fewer command eight-figure prices, one new listing is aiming straight for the top. Perched on a hilltop near the Brookline Reservoir, 55 Singletree Road has entered the market at $34 million, setting its sights on a record previously associated with one of New England’s most famous sporting couples.
If the seven-bedroom mansion achieves anything close to its asking price, it would eclipse the reported $32.5 million sale of Tom Brady and Gisele Bündchen’s former Brookline estate, making the property one of the most expensive residential sales the town has seen.
A mansion built on extraordinary scale
The numbers alone make 55 Singletree Road a formidable contender. According to the Boston Business Journal, the estate spans 19,138 square feet across 2.06 acres and includes seven bedrooms and 16 bathrooms, comprising 10 full and six partial baths.
The property also comes with five fireplaces, a swimming pool, a private tennis court, and a fitness centre. Its elevated position adds another layer to the offering, with listing details cited by Hoodline highlighting a private rooftop terrace with views towards the Boston skyline.
Rather than simply being a large suburban residence, the property has been conceived as a private compound with the amenities and proportions associated with a luxury retreat.
A carefully engineered custom build
The mansion dates to 2015, when Acton-based luxury home builder Thoughtforms undertook a substantial two-phase construction project. The company is known for custom residential projects across New England, and the Singletree Road estate reflects that emphasis on scale and bespoke construction.
The land has also experienced a dramatic rise in value over the decades. Public records cited by the Boston Business Journal show that the parcel last changed hands in 1993 for slightly more than $1 million. In 2015, the current owner, an LLC linked to a partner at a Manhattan estate-planning firm, took out a $9.1 million mortgage on the property.
Tax records cited in the reporting show the home was assessed at approximately $18.96 million in 2025, with an annual property tax bill of $187,133.
Taking aim at the Brady-Bündchen record
The property's ambitious asking price is closely tied to Brookline's luxury real estate history, particularly the former home of Brady and Bündchen.
The couple purchased their five-acre Woodland Road property from Pine Manor College for $4.5 million in 2013 before developing a 12,112-square-foot custom residence designed by architect Richard Landry. According to Realtor dot com reporting cited in the Business Journal's coverage, the estate was initially listed for $39.5 million in 2019. After price reductions and a period off the market, it eventually sold for a reported $32.5 million in 2021.
At $34 million, the Singletree Road property is therefore positioning itself to become Brookline's new residential benchmark.
A luxury listing in a slower market
Hoodline's reporting points to signs of cooling in Brookline's wider residential market, with September recording just 25 home sales compared with 45 during the same month a year earlier. Median days on market also rose to 71 days, double the previous year's figure.
But trophy homes often operate according to a different set of rules. Their scarcity, scale and highly specific buyer pool can make conventional market indicators less relevant.
The listing is being represented by The Sarkis Team at Douglas Elliman Real Estate, whose brokers have experience with Brookline's most expensive properties.
Whether 55 Singletree Road achieves its full $34 million asking price remains uncertain. But with its size, amenities and proximity to the town's previous record sale, the estate has already made its ambitions clear: it wants to become Brookline's newest symbol of ultra-luxury living.
Images Courtesy: Wikipedia, Instagram, and Town of Brookline