Brookline Mansion Lists for Record $34 Million

The estate at 55 Singletree Road tests local market ceilings as Brookline home sales decline by 44 percent.

Updated on Oct. 22, 2026 in Residential

Brookline Mansion Lists for Record $34 Million

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

A 19,138-square-foot mansion in Brookline has hit the market for $34 million, potentially setting a new local sales record. The listing arrives during a cooling period for the town, which saw home sales drop 44 percent in September 2026 compared to the previous year.

Why it matters

The $34 million asking price represents a significant test of the luxury market amid a broader slowdown in local transaction volume. For homeowners, the sale serves as a high-end benchmark for property values as the median time on the market has stretched to 71 days.

The property at 55 Singletree Road sits on 2.06 acres and carries an annual property tax bill of $187,133 based on a 2025 assessment of $18,959,800. The current asking price of $34 million exceeds the $32.5 million sale price of Tom Brady's former Brookline estate.

The players

Thoughtforms

A luxury homebuilder known for high-end residential projects.

The Sarkis Team at Douglas Elliman Real Estate

The real estate group handling the listing for 55 Singletree Road.

Tom Brady

The former NFL quarterback whose previous Brookline estate holds the local sales benchmark.

The details

Built in 2015 by luxury homebuilder Thoughtforms, the estate offers 19,138 square feet of living space. The residence was financed in part by a $9.1 million mortgage taken out the same year construction concluded. Currently, The Sarkis Team at Douglas Elliman Real Estate is managing the listing, which competes in a market where buyers are currently taking a median of 71 days to close on residential properties.

1993: The parcel last sold for over $1 million.
2015: The residence was completed and a $9.1 million mortgage was secured.
2021: Tom Brady's former estate sold for $32.5 million.
September 2026: Brookline recorded only 25 total home sales.

The Home Front

This luxury listing arrives during a significant period of residential market contraction characterized by a 44 percent year-over-year decline in local sales volume. It sits in direct contrast to the long-standing price ceiling set by the 2021 sale of the former Brady estate at 112 Woodland Road.

Homeowners should track how this high-end listing compares to the recent 2025 town tax assessment of $18,959,800 for the property. If you are considering a sale, observe the 71-day median time on market to better align your expectations with current local buyer interest.

The takeaway

This $34 million listing serves as a major indicator of potential price resilience at the very top of the Brookline market. Keep an eye on local sales reports to see if this property sets a new ceiling or if longer market times persist for high-end homes.