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Despite suffering from a touch of parking-lot-itis, little Lombard Street is a fascinating two-block walk. While starting at Jarvis Street leaves a little to be desired – with bookends of a drab brick hotel and a precast condo tower – things improve with the appearance of the Old Fire Hall, that 1886 gem by architect David Roberts Jr. that once vibrated with laughter from the comedy legends of Second City.

Next, a four-storey office building with bands of glazed white brick catches the eye on the south side, while, on the north, the handsome profile of the former 1907 city morgue by city architect Robert McCallum comes into view at No. 86. After that, check out the condo at No. 82 that looks like a hammerhead shark (look up!).

While the northeast and northwest corners of Lombard and Church contain parking lots, the southeast corner contains The Bentley, a brown-brick, 1926 parking garage that was converted to condominiums in 1981-82, and the southwest corner allows Peter Clewes's glassy 2006 spire to reach for the sky.

Crossing over and heading toward Victoria Street, we find what was formerly the Canadian government's Mackenzie Building, a massive, Modernist, 1960 Shore and Moffat composition that, when constructed, boasted the largest curtain wall in the country. Renovated and re-clad by Quadrangle Architects in 2000, it is now home to State Street Financial Centre. A welded-steel water feature by prominent Toronto sculptor Gerald Gladstone (1929-2005) was not preserved, however, which is a great loss. And speaking of preservation, this site was formerly home to architect Henry Langley's much beloved, four-storey, Second Empire, General Post Office (1871-73), demolished in 1958.

Since the demolition of Mr. Langley's GPO happened a decade before my birth, my attention has been focused, necessarily, on the two vacant heritage buildings across the street from State Street. Tattered but beautiful in red brick, 26 and 34 Lombard St. have been vacant for some time. Since my move to the area in early 2011, I've walked by the Richardsonian Romanesque Revival pair a hundred times, yet I always paused to marvel at their workmanship and wonder about their fate. Sometimes, I run my hand along the base of No. 34 and watch the red sandstone fall away like powder – the result of a century of salt nibbling at its porous feet.

Soon, however, Great Gulf, under the guidance of heritage firm E.R.A. Architects, will put a halt to that deterioration as part of a greater condominium development scheme called Yonge + Rich.

"We looked at a couple of different options for what to do," says Alan Vihant, Great Gulf senior vice-president of high-rise development, of the pair, "and we've gone back-and-forth, back-and-forth, between office [space] or really amazing loft apartments, and we've gone with loft apartments."

These will make wonderful homes, of course. Even better, the city has requested that Great Gulf preserve the semi-detached pair as "pavilions" on the site rather than allowing the more common approach of slicing off their faces, warehousing them, and then stitching them onto new glass towers like a death mask.

"These were very well built," says E.R.A. project architect Gillian Haley. "Much of the original fabric is there – it's astounding." Indeed, their architectural stasis has resulted in original wood window frames (some with dentils), a stamped-metal cornice, and amazing stonework and masonry details – massive arches, colonettes, turrets, carved fish, egg-and-dart moulding – that might have been painted over or, worse, covered with large signs or metal siding that would have hastened deterioration had there been a parade of short-term tenants. While E.R.A.'s research does point to rusted flashings, effluorescence and spalled brick (which indicates a moisture problem), missing mortar, iron oxide discolouration, and, further, it recommends complete replacement of those big red sandstone blocks (likely with red granite), the buildings are "in sound condition."

Thanks to E.R.A.'s report, I've also learned a little about their previous life. The more ornate building to the east, No. 34, was built first, in 1890, for printing company R.G. McLean. "They remain the prime occupant of this building until it is listed as vacant in 1972," the report states. In 1894, the west building was erected for Barclay, Clark & Company, engravers. Other printing-related businesses set up shop there as well. In 1905, "it appears that the Barclay Building is purchased by R.G. McLean and the two buildings joined." The architect(s) of these buildings, however, is unknown.

Moving west, a walk past the parking lot where a tidy row of Victorian row houses once sat (Great Gulf's new condo will refill this residential gap in Lombard's smile) brings us to the Comstock Building, another rhythmically arched, red brick, Romanesque Revival pile built in 1890 (now the Beer Academy). Attached and around the corner on Victoria Street is the banded, buff brick, former Strand Hotel (1908).

"This was quite a neat little stretch," says Ms. Haley. It still is, if you like the new mix of eras.

However, a walk along Lombard should not end here, but rather at the northwest corner of Victoria and Richmond streets. Despite being damaged by fire in 1981, one of the city's best Richardsonian buildings, Confederation Life (1890-92) by Knox, Elliot and Jarvis, stands sturdy and proud.

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