Brookline Mansion Lists for Record $34 Million

A massive 19,138-square-foot estate in Brookline has officially hit the market with a record-breaking asking price.

Updated on Oct. 22, 2026 in Residential

Bold vector editorial illustration of a grand luxury mansion, representing high-end real estate in the Brookline market. — A 19,138-square-foot Brookline estate has listed for $34 million, potentially setting a new local record for residential property sales. AI Illustration. Upload story photo >

Live Poll

In the current market, would you consider now a good time to purchase a luxury home?

The property located at 55 Singletree Road is listed for $34 million, potentially setting a new benchmark for residential sales in the city. The mansion spans 19,138 square feet across 2.06 acres.

Why it matters

The listing challenges the local record set by the 2021 sale of Tom Brady's former home, which fetched $32.5 million. This high-profile offering arrives as Brookline navigates a cooling real estate market.

The property was assessed by Brookline at $18,959,800 in 2025 and carries an annual tax bill of $187,133. It features 19,138 square feet of space on a 2.06-acre parcel.

The players

The Sarkis Team

This is a real estate group at Douglas Elliman Real Estate responsible for managing the listing of the property.

Thoughtforms

This entity is a luxury homebuilder that constructed the residence at 55 Singletree Road in 2015.

Tom Brady

He is a former professional athlete whose former Brookline estate previously set the city's residential sales record.

The details

Built in 2015 by luxury homebuilder Thoughtforms, the estate is being represented by The Sarkis Team at Douglas Elliman Real Estate. The parcel was purchased for over $1 million in 1993, with the current owner securing a $9.1 million mortgage in 2015.

1993: The parcel last sold for over $1 million.
2013: Tom Brady bought a five-acre parcel.
2015: The residence was built and a mortgage was taken out.
2021: Tom Brady's former home sold for $32.5 million.
September 2026: Brookline recorded 25 home sales.

Culture Shift

The property hits the market as Brookline home sales recorded in September 2026 fell by 44 percent compared to the previous year. This shift highlights a cooling luxury sector where the median time on the market has reached 71 days.

Potential buyers should note that the property is assessed at nearly $19 million, which directly influences the significant annual tax burden of $187,133. Given that the broader market is seeing a 44 percent decline in sales, interested parties may encounter less competition than in previous years.

The takeaway

This listing tests the upper limits of local property values during a period of reduced transactional activity. Investors and buyers should observe whether this high-end asset successfully finds a buyer in a market currently averaging 71 days on the market.