The 1800s were not quite finished when a fine home went up on Wentworth Street South.

With its domed turret, slate roof and elaborate brickwork, the house would surely always make its owners proud.

So what happened? For many years, 89 Wentworth South has sat empty. The original wrought iron fence is still out front, but the windows are boarded, the doors are locked, the pride is gone.

And right next door, there is a once-handsome three-storey apartment building with inviting balconies and a name in stone on top - Tudor Hall. It too sits empty.

It looks as though the grand home at No. 89 was built in 1897 for a man of business named Edward McCoy. The architect was likely the well-regarded Alfred W. Peene, who happened to live just down the street.

By 1904, the house belonged to Elizabeth Duggan. Her father was George Elias Tuckett, the tobacco baron whose family compound at King and Queen is what we know today as the Scottish Rite.

Duggan was widowed after her husband, a prominent lawyer, died following complications after a sign fell on him in Chicago. But Duggan and her children were fine in the big house on Wentworth, because her father's will stated she would get an annual allowance of about $160,000 in today's money.

If we were to stop by there in the mid-1920s, we'd find that No. 89 was home to the monied class no more. It had become Manor Apartments, divided into five units. The tenants: E.A. Cooper, shoe salesman; D.B. Papple, "traveller" for Canadian Mausoleums; Leslie Cutler, worker at Westinghouse; Isabelle Graham, teacher; B.H. Milledge, toolmaker at Dominion Glass.

And next door, on the substantial grounds south of the old mansion, up went that pleasant structure called Tudor Hall.

If we stopped by the street 50 years ago, we would have found two new apartment blocks just north of stately No. 89. Squat, square places, short on curb appeal.

Today all four buildings - Nos. 71, 75, 89 & 91 - are owned by Andy Cutrona, president of a Toronto-based outfit called the MacDane Group, a name made from the initials of his wife and children. He is 65, and his website shows a portfolio that stretches all over Ontario, plus Nova Scotia, some 50 buildings.

"We buy inferior product," he says.

The objective is to make them better - and profitable.

Some people on the street say historic No. 89 has been empty at least 20 years, but Cutrona believes it's no more than 15. He says he got the four properties cheap, with "virtually no down payment."

A good deal would have been "$35 a door," he says, or $35,000 a unit.

He got these at $25,000 a unit.

One problem. It turned out Nos. 89 and 91 were in bad shape, and the city told Cutrona to make repairs or shut them down. He chose the latter: "I've probably lost a million bucks on those buildings."

Both have sat empty, he says, "because we had properties with greater opportunity that required less capital."

And he didn't see values here rising. "I said, 'Is Hamilton ever going to turn around?'"

Now that's happening. So he has $3 million in funds earmarked to begin an overhaul of the two empty buildings next spring.

Both 89 and 91 are on the city's Inventory of Buildings of Architectural and/or Historical Interest, but that offers no protection from demolition.

Loading... Loading... Loading... Loading... Loading... Loading...

Cutrona wasn't interested in knocking them down, but has he ever considered selling the pair?

"We never flip properties," he says. "The reason is that we fall in love with them."

Leaving these two buildings empty so long is a curious way to show love. We will see if next spring brings salvation at last.