Alfredo Romano is the first to admit a soul-crushing process that careens dangerously close to failure and burns years off your life can sometimes have a happy ending. At least that’s his conclusion after overcoming one obstacle after another, in a journey at times resembling the Labours of Hercules, to build a new community in Toronto’s old Junction Triangle.

“I’m the first to admit we achieved a better result from all the years of hard negotiating,” says Mr. Romano, president of Castlepoint Numa, a Toronto real estate developer which also has large holdings on the city’s waterfront.

When it’s complete, Castlepoint’s eight-acre site, called Lower JCT, is expected to be a vibrant, mixed-use community with 1.1 million square feet of office, retail, residential and cultural space. There will be a total of seven buildings, 32 townhomes, parks, affordable housing, a daycare and bike paths – all contained on a parcel of former industrial land sandwiched between GO train tracks and within walking distance of two subway stations and streetcar lines in the west-end Bloor Street-Dundas Street corridor.

Lower JCT is a joint venture between Castlepoint and Toronto-based private equity firm Greybrook Realty Partners, which has placed more than $1-billion of investments over the past several years, mainly in Toronto and Miami. Equitable Bank is providing construction financing for the first two phases of Lower JCT.

The Lower JCT project is located west of Toronto's core in the Bloor Street-Dundas Street corridor. (Erik Heinrich/The Globe and Mail)

The Tower Automotive Building, a 10-storey heritage structure erected in 1919, will remain the neighbourhood’s signature motif and tallest building. It will be anchored by the Museum of Contemporary Art Toronto Canada (MOCA), which is relocating here at the end of the year into the first five floors (50,000 square feet) from a much smaller space on Queen Street West.

Mr. Romano envisages that a large number of his commercial tenants will be companies in the arts and digital media, drawn by the pull of MOCA. “I would like to say this was all inspired by a grand design, but that wasn’t the case,” says Mr. Romano, whose own career in real estate can be summed up with exactly the same words.

After finishing his master degree in history and theology at Harvard, Mr. Romano was accepted at McMaster University in Hamilton to complete a multidisciplinary PhD in 1985. He never started because he had a life-changing epiphany while filing his tax return. He counted five T4 slips from as many teaching institutions, with no full-time position as a professor in sight. So at 31, Mr. Romano took a job on Bay Street and soon started Castlepoint with his cousin, Mario Romano.

By 2008, Castlepoint was a successful developer but on the losing end of a bid to construct film studios in the Port Lands on Toronto’s eastern waterfront. It rebounded by buying the Junction property in the west end with plans to build rival studios. However, the Port Lands were soon in financial distress, so Castlepoint partnered with Paul Bronfman (whose Montreal family is famous for creating the Seagram liquor brand) and ROI Capital to buy out the owners. Today Pinewood Toronto Studios is a Hollywood-calibre facility with 10 sound stages and special effects capabilities.

The Tower Automotive Building, a 10-storey heritage structure erected in 1919, has been renamed Auto BLDG and will remain the signature motif of the site. (Erik Heinrich/The Globe and Mail)

With the Port Lands once again in play, Castlepoint had to find an alternate plan for its South Junction ambitions, and in 2011 submitted a blueprint to the City of Toronto. Nestlé Canada immediately objected to residential housing being built close to its chocolate factory on nearby Sterling Road. The city’s planning staff agreed and Castlepoint’s proposal was quashed almost as quickly as it had been unveiled. “We were in a pitched battle with Nestlé over the future direction of the area,” Mr. Romano remembers. “It got nasty.”

Resident groups supported the idea of revitalizing a desolate brownfield site that had been home to an Alcan aluminum factory for about 80 years, but certain conditions had to be met. At least a dozen meetings with stakeholders followed. Finally Castlepoint took its plan for the South Junction to the Ontario Municipal Board (OMB), which has the power to overrule municipalities in development matters.

All the stakeholders, including Nestlé, sat down at the same table and hashed out their differences. The key sticking points centred around the Tower Automotive Building. The city insisted no structure on the site exceed its height, and Nestlé wanted it rezoned to commercial from residential. Castlepoint conceded both points.

“The Automotive Building is an iconic structure and we’ve restored it to the highest standards,” says Mr. Romano. “With so much character it’s important that it maintain its prominence. That’s the smart approach.”