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The Winsor School’s $100 million question

Instead of selling its valuable land and relocating, the Winsor School is building, turning tennis courts into a parking lot and building a $75 million sports, arts, and classroom facility.jonathan wiggs/globe staff

The Winsor School is sitting on a winning lottery ticket, maybe worth $100 million. But it has no interest in cashing it in.

Leaders of the private school in Boston along Brookline Avenue at the corner of Longwood Avenue acknowledge they could rake in a lot of cash if they were to sell this spacious undeveloped property, a rare and prized asset in the heart of Boston’s booming Longwood Medical Area.

But, they say, they’re much happier tending to the green they’ve already got — all 4.4 acres of it.

The two treasured turf playing fields, prominent along Brookline Avenue, are a recreational retreat not only for the all-girls school’s physical education program and its soccer, field hockey, softball, and lacrosse teams, but also for athletes at neighboring colleges, which rent out the heavily booked terrain.


“Having two athletic fields in this location is precious to us,” said Rachel Stettler, head of the Winsor School, which enrolls some 430 students in grades 5 through 12. “It’s a rarity, and it’s so important to our program and our students, and we’ve been able to form wonderful partnerships with our academic neighbors.”

Over the past decade, hospitals, research centers, and other medical institutions around Longwood have built more than 1.6 million square feet of new development, worth more than $1 billion, according to data provided by the Boston Redevelopment Authority. The organizations have city approval for plans to add another 2.2 million square feet, worth another combined $2.6 billion.

Even the Winsor is growing. The school last year turned six abutting tennis courts into a parking lot and plans to spend significantly renovating and expanding its campus, including ongoing work to build a $75 million athletics, performing arts, and classroom facility right along the edge of one of the fields.


That field is temporarily out of commission so it can be used as a construction staging area. But once the project is done, the field will reopen.

Beyond that, the school envisions someday building a parking garage below the fields.

A lot of ideas, but cashing in is not one of them.

“Selling the land is not in the plan, at least not for this generation anyway,” said Stettler.

And the school’s ongoing makeover is proof it has no intention of relocating.

“It enables us, in a sense, to recommit to this site,” said Stettler. “We’ve been rooted in this neighborhood for so long and we’ve been very clear that we plan to remain rooted here.”

The area’s recent rapid expansion has caused already-high property values to skyrocket.

The Winsor fields are valued by city assessor’s at about $23 million.

Jonathan Wiggs/Globe Staff

But on the open market they could fetch much more than that, according to local real estate expert David I. Begelfer, who heads the Massachusetts chapter of the National Association for Industrial and Office Parks.

He estimated that an acre of property in that area of Boston could sell for around $20 million, meaning the Winsor school’s property is potentially worth $90 million.

The property is in a “prime location” and would sell for a “premium price,” said Begelfer.

Another reason it would be coveted? “The Longwood Medical Area is an extremely strong market. As far as open space, there’s virtually none.”

“Everyone there, the hospitals and research laboratories, they are all keeping there eyes out for opportunities,” Begelfer said. “If something like this were to come on the market, it wouldn't be there long.”


Stettler said she has never been directly approached with an offer but has heard indirectly from time to time about outside interest.

“We’ve definitely understood that it’s a very valuable piece of property,” she said.

The Winsor school launched a special “Playground Endowment Fund” campaign, raising $90,000 to buy the fields in 1924 from the Longwood Cricket Club, a tennis group now located in Chestnut Hill.

School trustees at the time described the purchase as “imperative . . . for maintaining the pre-eminence of the school.”

Today’s school leaders continue to hold the fields in high regard.

The grounds, which are lit at night, are typically in use during the spring and fall from 6 a.m. until 11 p.m. on weekdays and from 7 a.m. until 6 p.m. on weekends. The fields also get regular summertime use, including by youth sports camps and community organizations.

A conversion from real grass to artificial turf in 2008 keeps the fields, which are plowed during winter, green year round. The fields host gym classes as well as games and practices for Winsor teams and for sports programs run by Simmons, Wheelock, and Emmanuel colleges, and Northeastern University.

Roy Schifilliti, Wheelock’s vice president for administration, institutional effectiveness, and innovation, and who previously worked at Simmons, called the fields a “tremendous amenity.”

“To be able to have those high-quality fields next door really enhances the college experience we can provide to our students,” he said. “I like the idea that there’s this oasis in the middle of this really densely developed area.”


He was happy to hear the private school has no intention of selling.

Matt Rocheleau can be reached at matthew.rocheleau@globe.com. Follow him on Twitter @mrochele.