These Are the Most Expensive Homes in Brookline

150 Woodland Road / Photo by Daniel Milstein Photography

There’s no shortage of extravagant manors in the leafy green hills of Brookline. In fact, Boston’s verdant suburb is home to the single-most expensive house for sale in Massachusetts. So it’s only fitting, then, that we get a peek at the homes in second place.

In a new report, real estate analytics firm NeighborhoodX identified the most expensive homes for sale in Brookline. Their asking prices start at a paltry $3.97 million and go all the way up to $90 million, and they range from contemporary castles to traditional Colonial-style houses.

The list of 11 homes is topped by 150 Woodland Road, the sprawling estate of Reebok founder Paul Fireman. At $90 million, it asks about seven times the price of the second-most expensive home in Brookline. The 26,000-square-foot mansion has eight bedrooms, seven full bathrooms, five partial bathrooms, and a four-car garage. It’s followed by an architecturally interesting abode on Leicester Street. With a five-car garage and 20-person dining room, the place seems like a steal at $12.8 million compared to 150 Woodland Road.

166 Fisher Avenue / Photo courtesy of Gibson Sotheby’s International Realty

Out of Brookline’s priciest pads, the most affordable on the list is a single-family on Warren Street. The six-bedroom residence near Brookline Reservoir asks $3,975,000 and stretches to 6,325 square feet.

“Part of the driver of the high prices is the sheer size of the properties,” says NeighborhoodX cofounder Constantine Valhouli. “But they are not all as expensive on a per-square-foot basis.”

Excluding the $90 million outlier, the homes in the report range from $450 to $1,377 per square foot. Valhouli adds these prices are comparable to those in Dorchester—at $449 per square foot—and Back Bay, which averages at $1,410 per square foot.

Other costly highlights include a Mediterranean villa and a home that was once part of the Greenough family compound.

See the complete list of Brookline’s most expensive homes below.