A hilltop mansion next to the Brookline Reservoir has just hit the market for $34 million, and its backers want it to do something no other home in town has managed: outsell Tom Brady's old place. The seven-bedroom estate at 55 Singletree Road spans 19,138 square feet, and if it fetches anywhere close to its asking price, it would surpass the reported $32.5 million sale of Brady and Gisele Bündchen's former Brookline estate.
The Boston Business Journal covered the listing, detailing the scale of the property: a 2.06-acre lot with 16 bathrooms (10 full and six partial), five fireplaces, a swimming pool, a private tennis court and a fitness center. The site also notes the home sits on an elevated hilltop, a layout that, according to a listing described by Zillow, includes a private rooftop terrace with views of the Boston skyline.
A Two-Phase Build From a Regional Luxury Builder
The mansion was constructed in 2015 through an extensive two-phase building project, the Boston Business Journal reports, carried out by Acton-based luxury custom home builder Thoughtforms, a firm that specializes in high-end New England residential construction. The underlying land tells its own story of appreciation: public records cited in the same report show the parcel last sold in 1993 for just over $1 million, and its current owner — an LLC tied to a partner at a Manhattan estate-planning firm — took out a $9.1 million mortgage on the property in 2015.
Tax records compiled by real estate brokerages and cited by Coldwell Banker show the town assessed the home at $18,959,800 in 2025, generating an annual property tax bill of $187,133. Brookline's residential tax rate of $10.24 per $1,000 is for FY2026, not the rate that produced that FY2025 bill.
Chasing the Ghost of Brady's Old Address
The $34 million price tag is a direct challenge to a record set by one of New England's most famous former residents. Brady and Bündchen originally bought their 5-acre lot at 112 Woodland Road from Pine Manor College for $4.5 million in 2013, then built a 12,112-square-foot custom mansion designed by Richard Landry, according to Realtor.com. They listed it for $39.5 million in 2019 before a buyer surfaced at the end of 2020; the reported $32.5 million sale was in 2021 — a saga that involved multiple price cuts and a brief withdrawal from the market.
The 55 Singletree Road listing is being handled by The Sarkis Team at Douglas Elliman Real Estate, whose lead brokers previously worked the seller side of Reebok founder Paul Fireman's nearby 27,000-square-foot estate, which sold for $23 million in 2020 after years on the market, per the same Realtor.com account. That history suggests the brokerage is accustomed to the slow, negotiated pace that tends to define Brookline's rarest sales.
A Cooling Market, But Trophy Homes Play by Different Rules
The listing arrives as Brookline's broader housing market shows clear signs of a slowdown. Market data compiled from MLS PIN by the Bushari Team at Compass and reported by the Brookline Record shows the town recorded just 25 home sales in September, a 44% decline from 45 sales the same month a year earlier, while median days on market doubled year-over-year to 71 days.
Yet trophy properties in the eight-figure range occupy a different price tier. A restored Brookline property has sold for $12 million.
A State Law Allows Accessory Dwelling Units
Massachusetts law allows single-family residential properties to add an accessory dwelling unit by right, with a size cap of up to 900 square feet.
Brady's former Woodland Road home was in Brookline. Whether 55 Singletree Road actually lands its full $34 million ask, or instead follows the familiar Brookline pattern of price cuts and private negotiation that defined the Brady sale, remains to be seen.
