Despite a steadily growing skyline of glittering condominiums, some of Toronto's oldest streets sit as testimony to its earlier glory, a graveyard of once-luxury buildings now in disrepair.

With more than 7,000 heritage properties in Toronto already, the city is facing a growing list of buildings with the merit and character to be designated heritage sites but lack the funds to be actively maintained.

"The City of Toronto won't have the resources to individually investigate every single property to see if it's actually properly updated and maintained," Coun. Kristyn Wong-Tam said.

Boarded up and unused

Ever wonder how Toronto's Liberty Village got its name? Now a network of condominiums, the neighbourhood was once home to a men's prison and the street where newly released inmates took their first steps as free men was known as Liberty Street.

But like many of Toronto's earliest buildings, the old Toronto Prison Chapel building, first built in 1873, sits boarded up and unused. And there are many more like it.

Wong-Tam said the city has created incentives for people who own heritage properties to maintain them with tax rebates or other financial compensation.  

The city is also exploring new ways of allocating heritage designations and could potentially give the title to entire neighbourhoods rather than individual homes, called heritage conservation districts.

But while most heritage property owners take care of their buildings, it's clear that many do not — even with the threat of being fined.

And the consequences are hard to miss.

Less than two weeks ago, a massive fire tore through a heritage home on Jarvis Street, a thoroughfare once known as Millionaire's Row.

You'd never know it was once home to one of Toronto's first chief medical officers in the early 1900s.

New life as commercial sites

Another Jarvis Street house built in 1875 and formerly known as "The Grey Lady" almost faced the same fate when an electrical fire broke out there on Thursday.

Fortunately, fire trucks were able to knock down the flames within an hour and the building wasn't damaged.

In that case, the building was being repaired as part of a redevelopment project by HIV/AIDS hospital Casey House that would see the historic home turned into a hospice.

Other historic buildings are being reborn as commercial sites, including one house once owned by the Gooderham family. It's now a restaurant. Another on Bathurst Street is being taken apart and restored to become a Loblaws store and condominiums.

But some aren't happy about the buildings' reincarnations.

"For some of the historical purists of course we say, 'No, every old building in Toronto has to become a museum,'" said Richard Fiennes-Clinton of Muddy York Tours. "Unfortunately that's just not a reality."