Chestnut Hill Developments started building infill low-rise homes in Toronto 44 years ago, a year before a housing market crash. It survived that downturn, and is continuing to forge ahead today despite new challenges in the condo sector.

Chestnut Hill has evolved and grown over the decades to become one of the more active highrise condominium developers in the Greater Toronto Area.

“Our first highrise condo was in Pickering, which was called San Francisco by the Bay, which had three towers,” president and chief operating officer Ralph Del Duca told RENX.

The Toronto-based company has been involved with low-, mid- and highrise residential projects in Pickering, as well as Newmarket and Whitby, either on its own or in partnerships. Its primary focus is marketing, selling and then developing highrise condos.

“We saw there was a need for housing before the government realized there's a need for housing,” said Del Duca, a 43-year employee of the company. “Affordable housing means giving people a piece of property they can live in - not 220 square feet that sells for $399,000 so they can afford to buy it, but they’re living in a closet.”

Developments on Toronto’s Viewmount Avenue

Two of Chestnut Hill’s current priorities are developing assemblies of former single-family residences from 250-258 and 262-274 Viewmount Ave. in Toronto’s Glencairn and Marlee area. The company has already had success nearby with The Dylan, a 10-storey, 220-unit condo at 831 Glencairn that sold out and is now being occupied.

Chestnut Hill is proposing a Kirkor Architects and Planners-designed 40-storey, 477-unit condo at 250-258 Viewmount, next to the Glencairn subway station; and a Kirkor-designed 38-storey, 455-unit condo rising from a five-storey podium at 262-274 Viewmount.

Both are awaiting municipal approvals and Del Duca estimates they’ll be occupied in the early 2030s.

Sales also launched in the fall for The Wilde, a Kirkor-designed 30-storey, 362-unit condo with a tiered podium at 805 Glencairn. Del Duca said sales are going “extremely well” and construction should start in early 2026, with occupancy scheduled for 2029.

“We don't buy land to flip and assign and just make money,” Del Duca explained. “Our program is always to take it to the highest and best use, and to take it right through the process.”

Chestnut Hill has also purchased a small commercial plaza on Marlee where it plans to construct two more condos with between 800 and 900 units. It hasn’t yet made its submission to the City of Toronto for that project.

Densifying an under-utilized area

“We saw that this was an under-utilized area for both the subway and for people,” Del Duca said of the Glencairn and Marlee node. “It's sort of the new midtown. It's not Yonge and Eglinton, but it's on the subway that will take you downtown or to York University.”  

The children of long-time residents are now also looking to live there, and others who used to live in the area are interested in moving back, according to Del Duca. He called it a safe and centrally located neighbourhood with wide appeal.

“To the west of there, you have the new designer district on Caledonia. You have restaurants up and down Bathurst. You have restaurants on Dufferin Street. You have access to the LRT at Eglinton, if it ever opens, and you've got all the shops on Eglinton.

"There are a lot of things that make it pedestrian friendly and also transportation friendly.”

Other Chestnut Hill developments

The first two towers at Pickering’s Universal City master-planned community have been completed and occupied. The 30-storey, 359-unit third tower sold out and is being occupied.

The sold-out, 27-storey, 320-unit Universal City East is up to the 23rd floor of construction. Below-ground construction is under way at the fifth condo — the 37-storey, 482-unit The Grand — as sales continue.

Universal City, in the Bayly Street and Sandy Beach Road area, was originally envisioned as a five-tower development but has since expanded to seven towers. It also features commercial space at grade, a 3.5-acre piazza and a playground area.

“We hope to put in restaurants so people can just go outside and eat in their space, as well as dental offices, medical offices and all the necessary commercial space that people who live there need,” Del Duca said.

Chestnut Hill is working with the City of Vaughan toward receiving approval for building 7080 Yonge, a Kirkor-designed 44-storey, 638-unit condo with commercial space at grade. The plan is to take it to market in late 2026.

Planning for the future

Chestnut Hill uses its own capital along with financing from major banks to fund its developments and doesn’t look to outside investors or alternative lenders.

“It's our money so that's why we look at everything as though we own it, before we sell it to somebody else,” Del Duca said.

Chestnut Hill continues to look for high- and lowrise development sites and hasn’t been scared off by the severe slump in the condo market.

“We've always believed that when everybody's running the other way, you run your way and you get to where you want to go,” Del Duca said, “and it's worked for us. 

“We're not a high-leveraged company so we're very cautious in the way we do business. We build what we sell and we deliver what we build. That's important for us.”

Del Duca said Chestnut Hill may consider developing purpose-built rental apartments in the future, but for now it’s only building condos.

“We don't plan to cancel projects and we never did,” Del Duca said. “If we have to, we'll keep the units ourselves and rent them out. 

“But we make sure that people get what they chose us for. They believed in us and we believe in them, and we want to keep that relationship going.”