The Chase: A Dubai couple look for an income property on the other side of the globe

The buyers: Maha Zeibak, a 37-year-old fashion retail consultant, and her husband, Osman Aboubakr, a 42-year-old lawyer who moonlights as an actor.

The story: Osman and Maha met in Dubai in 2014. He’d moved there for work, and she’d fallen in love with the city during a visit. Shortly after they started dating, they realized they’d grown up in the same apartment building in North York. With fate on their side, they got hitched in 2015 and began looking for an investment property they could rent out and possibly move into. They checked out places in Dubai, London and Florence, but eventually set their sights on Toronto, where they have family and the housing market is more stable. Maha enlisted her friend, real estate agent Elias Kibalian, to help them search for a house—preferably an older one, with character, and close to downtown. They set a budget of $1.2 million and flew to Toronto three times in 2016 for viewings.

Option 1

Wolseley Street (near Queen and Bathurst). Listed at $989,000, sold for $950,000.
This Victorian three-bedroom townhouse near Trinity Bellwoods came complete with a fireplace in the living room, original wooden trim and a finished basement. It seemed like a perfect rental property, and Maha and Osman liked the location, near Queen West. But, on further consideration, they decided they wanted a less established neighbourhood—ideally someplace where their investment would have more potential for growth. They opted not to bid, and began searching for properties in more up-and-coming areas.
 

Option 2

Elm Grove Avenue (near Queen and Dufferin). Listed at $1,069,000, sold for $1,065,000.
This property, a three-bedroom townhouse on a quiet street near the Parkdale strip, came with all sorts of attractive bells and whistles: there was a walk-in closet in the master bedroom, a private backyard perfect for barbecuing or entertaining guests, and dark maple hardwood floors throughout. But Maha and Osman had been hoping to find an older home, with a bit of antique charm. This place, built in 2011, was too modern for their taste. Figuring they could do better if they kept searching, they decided to move along without making an offer.
 

The buy

Seaton Street (near Dundas and Sherbourne). Listed and sold for $1,375,000.
During their third trip to Toronto, their agent led them to this four-bedroom semi, built in 1876 and located a short walk from the shops and restaurants of Cabbagetown. They adored the bay-and-gable red-brick exterior, the backyard pond and the formal dining room. They put in an offer at asking, and, miraculously, the sellers accepted. Maha and Osman quickly found tenants. Although they don’t have plans to move, they often fantasize about living in their home on the other side of the globe.

The Hunt

City

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Ada, a 29-year-old costume designer, found herself at a Hamilton house party hosted by a family she’d never met. The night only got weirder from there