A condo developer eyeing a heritage site that harkens back to the days when Yorkville was a haven for hippies and a magnet for famous folkies hit a road block at city hall Wednesday.

Empire Communities had applied for a demolition permit that would have allowed it to bulldoze the site of the Purple Onion, a folk club that in its bohemian heyday back in the 1960s hosted the likes of Buffy Sainte-Marie, Gordon Lightfoot and Carly Simon.

But on Wednesday the heritage preservation board voted to recommend that council deny that permit.

Coun. Kristyn Wong-Tam (Ward 27 Toronto Centre-Rosedale) says she and her constituents were "taken by surprise" when a developer filed an application for a demolition permit at 33-45 Avenue Rd. (CBC)

Empire is currently at odds with the city over its plan to build a 33-story condo tower on the site, at the northeast corner of Avenue Road and Yorkville Avenue. The city says the building is taller than local zoning allows. The dispute is to be heard by the Ontario Municipal Board (OMB) next month.

But local Coun. Kristyn Wong-Tam, who also sits on the preservation board, said at Wednesday's meeting that the developer's application for a demolition permit Nov. 2 "has taken us by surprise."

A plaque commemorating the Purple Onion, an iconic folk music venue at 35 Avenue Rd. in 1960s Yorkville was unveiled earlier this year. (CBC)

​According to drawings submitted to the city last year, parts of the Victorian buildings that housed the Purple Onion and another iconic 1960s meeting place, York Square, would be retained in the new development.

"To see the demolition application move forward was, number one, alarming, and number two, it also signifies bad faith to the process," Wong-Tam said.

City council will rule on the demolition permit at its Jan. 31 meeting. If the permit is denied, Empire can appeal the decision to the OMB.

On Tuesday, Mary MacDonald, manager of heritage preservation for the city, said she opposed the demolition application

"There couldn't be anything more alarming," she said.

"What we need to do is preserve the heritage structures," Wong-Tam told CBC Toronto last week. "It's part of our history in this city and in this case the village of Yorkville doesn't need a new glass tower, especially at the detriment of losing this very valuable heritage asset."

An artist's rendering of the proposed re-development, supplied in 2015 to the city by developer Empire Communities. But city planners say it's not clear whether the houses would be retained. (Zeidler/Richmond/Torrance architects)

According to the heritage designation, the row of Victorian buildings between 33 and 45 Avenue Rd. are also notable because they feature a 1969 renovation by award-winning Toronto architect Jack Diamond, who added to the Victorian facades a red- brick skin, with large circular windows.

The area was designated a heritage site two years ago.

Mike McKenna, a guitar player with Luke and the Apostles who played at the Purple Onion and other Yorkville coffee-houses in the 1960s, said Friday tearing down the cluster of buildings "would be a horrible thing to do. If anything they should be doing more to promote what actually went down in those years.

Mike McKenna, who played at the Purple Onion with his band Luke and the Apostles in the 1960s, visited York Square last Friday, Dec. 2. (CBC)

"Artists, poets. I mean, so much came out of this area and it seems to be that not too many people remember all the stuff that came out, but it was a huge part. The energy is here even still."

Last year's drawings from Empire show a majestic, 30-story glass condo tower, atop a three-story pedestal of retail and public spaces. The pedestal also includes parts of the Victorian structures, and a revamped York Square.

But MacDonald said reducing the structures to their facades is not in keeping with the city's heritage conservation policy.

"I just don't know what they're thinking," Macdonald said. "But it does seem to me that you're moving to an OMB hearing, to concurrently apply to tear down every building, your commitment to conservation has to be called into question.

Architect Jack Diamond, whose red-brick refacing of the structures on Avenue Road at Yorkville Avenue in 1969 contributed to the buildings' heritage designation, walks in York Square on Monday, Dec. 4. (CBC)

"The wholesale erasure goes against every planning policy we have."

One person who is not against demolition is architect Diamond, 84. He said he wouldn't mind if his red brick construction was torn down, as long as a new building is supported with proper infrastructure and connects pedestrians to the streetscape.

"All the things it did were really important things to do," he told CBC Toronto Thursday. "But it wasn't spectacular, architecturally.

"Cities change."

CBC Toronto has tried repeatedly to contact Empire Communities and its lawyer. Those calls and emails have not yet been returned.