The Waldorf Astoria Lofts are well-named, as they were carved from the old Waldorf-Astoria hotel on Charles Street East. Built in the late 1950s, they may have had a short life as apartment buildings before being converted to lofts in 1989. As with many other hotels that were converted to residential use, they are not the usual brick-and-beam factory charmers. But they have their own New York City style and a location that cannot be beat.

The Waldorf Astoria Lofts at 80 and 88 Charles Street East

I cannot find any photos of their original appearance, but the conversion process gave them a certain charm. Somehow, the new facades gave them a brownstone feel, which blends in nicely with the buildings along Charles and helps provide counter-point to all of the new glass and steel being erected around them. And being only a few steps to Yonge and Bloor, subways, shopping, and Yorkville – these buildings represent excellent value for their location and size. Especially compared to the newer condos.

Inside a renovated unit at the Waldorf Astoria Lofts

When you hear Waldorf-Astoria you think of Victorian grandeur, and these lofts look like they’ve been there for 100 years. But there were only built back in the 1950s. The lots they occupy do go way back, as you can see houses on them in the 1890 Goad’s Insurance Map. Unfortunately they are not labeled, so I don’t know how lived there or how the buildings and their uses evolved.

Inside a renovated unit at the Waldorf Astoria Lofts

The buildings have always been paired, though separate. They were always connected via their underground garage, though. And even now they share a condo corporation. How a hotel came to be built like this, in two separate buildings, is a mystery. I had trouble tracking down anything that would prove the provenance of the buildings, until I came across Bob Dylan’s 1964 visit to Toronto.

Bob Dylan’s lyrics to Chimes of Freedom, written in 1964 on Waldorf-Astoria hotel stationary

A then-23-year-old Bob Dylan came to Canada to perform some of his new (now classic) songs. He was to perform the songs on the Ed Sullivan Show. Sullivan, said Dylan, approved of the songs but executives of the Columbia Broadcasting System vetoed the performance. So he came to Canada for the freedom to sing his songs. The show he appeared on, Quest, was a regular series that featured various artists and ran on the CBC from 1961 to 1964. In my ever-continuing quest to connect the historic dots of Toronto through lofts, this show would have been filmed at the CBC building at 90 Sumach, now the Lofts of 90 Sumach. Cool, eh?

The hallways of the Waldorf Astoria Lofts, which probably don’t look much different now than they did when Dylan stayed here

And… Dylan stayed at the Waldorf-Astoria hotel on Charles Street. We know this, because he wrote “Chimes Of Freedom” while he was here. And the hotel stationary he wrote the song on survives. What sort of place it was then, I don’t know, there just isn’t any real record of the place outside of this episode.

Walkway between the two buildings of the Waldorf Astoria Lofts

The buildings next come to notice in 1980 when the pioneering gay bar Boots moved into the basement. That was not to last, though, as noise complaints drove them out in 1981 to a new location on Sherbourne. Discussions of the early rainbow scene in Toronto that mention Boots have noted that it was in the basement of a hotel – a hotel that was a dump, at that.

1956 aerial photo shows 80 Charles Street East completed, but number 88 not yet built

But then I found a rather extensive demographic study of the Church / Wellesley neighbourhood notes that claims they were built as apartments. My only concern there, though, is that their dates are not quite correct. They name “The Waldorf Apartments” at 80 Charles East as being built between 1954 and 1957, and The Astoria as coming no earlier than 1958 and possibly even in the 1960s. But a quick analysis of city aerial photos shows that 80 Charles was built by 1956 and 88 Charles was completed the following year.

The 1957 aerial photo now shows 88 Charles completed

I have a sneaky suspicion that they were converted from hotels to apartments at some point in the 1980s, before conversion to condo. Or, the other possibility is that they were more of a New York-style hotel, where people lived there on a more permanent basis, as opposed to a place to stay for out-of-town visitors. The lack of laundry in the units is interesting, but that was not uncommon in both hotels and apartments.

Inside one of the Waldorf Astoria Lofts on Charles Street East

Regardless, it is an interesting little tidbit of Toronto history. Before Trump and Shangri-La dropped their huge edifices of glass and steel and money on Toronto, there were interesting little hotels on side streets where rock royalty came to stay.

Rooftop terrace of the Waldorf Astoria Lofts with amazing downtown views

80 Charles Street has 57 units across 8 floors, 88 Charles is slightly larger with 77 units over 9 floors. The types of lofts include bachelor units, one bedroom, one bedroom plus a den, as well as two bedrooms with two full bathrooms. The sizes range from around 450 square feet to just over one 1,200 square feet. Penthouse units at 88 Charles have 2 levels.

Make the Waldorf Astoria Lofts yours today!

Amenities are sparse, with just a fitness facility rooftop deck. Condo fees are not low, but they do include all utilities, which sure is nice. Parking is underground, and the spots are owned. Many of the units still look like apartments, with parquet floors, dated kitchens and electric heating. The real giveaway as to the history of the units is the lack of ensuite laundry. Unless your unit has been upgraded with private laundry, you will be visiting the common laundry room to wash yer duds.

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Contact Laurin Jeffrey for more information – 416-388-1960

Laurin Jeffrey is a Toronto real estate agent with Century 21 Regal Realty.
He did not write every article, some are reproduced here for people who
are interested in Toronto real estate. He does not work for any builders.
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