The Chase: This couple raced to find a west-end starter home before the birth of their first child

The buyers: Alexandar, 33, an underwriter at an insurance company, and his wife, Sarah, also 33, a private client coordinator at an asset management firm, with their dogs, Draper and Chester.

The story: Last year, Alexandar and Sarah were paying $1,600 a month for a one-bedroom rental at Avenue and Wilson. They wanted to start a family and had been saving for a larger place—ideally a detached house with two bedrooms, a parking spot and a yard for their dogs. They set their sights on the west end north of St. Clair, which was equidistant from Alexandar’s family in Parkdale and Sarah’s family in North York. Then, in February, they got good news: Sarah was pregnant. With a budget of $800,000, they began their search.

Option 1: Silverthorn Avenue near Caledonia and Rogers Road

Listed at: $749,900 Sold for: $870,000

In March, Alexandar and Sarah looked at this renovated two-bedroom, two-bathroom bungalow on Silverthorn Avenue in Weston–Pelham Park. The bedrooms were tiny, and the stairs to the basement were awkwardly positioned in the middle of the house. Still, the interior had been upgraded, the place had a one-car garage and its location was in their target zone. They bid $50,000 over asking, right at their $800,000 budget ceiling, but lost out to a higher bidder. Alexandar and Sarah continued looking.

Option 2: Silverthorn Avenue near Caledonia and Eglinton

Listed at: $798,900 Sold for: $860,000

Two months later, the couple found a listing farther north on Silverthorn, in Keelesdale–Eglinton West. Another two-bedroom, two-bathroom bungalow, the place came with an open-concept layout and a finished basement that could be converted into a rec room or a third bedroom. There was no parking on-site but plenty of street parking and lots of nearby green spaces for the pooches. They were worried about losing another bidding war, so they dug into additional savings to make an offer of $805,000—but they were outbid once again, this time by $55,000.

The Buy: Silverthorn Avenue near Caledonia and St. Clair

Listed at: $779,900 Sold for: $800,000

Alexandar and Sarah came upon this property in June, also on Silverthorn. It wasn’t detached, but it had three bedrooms and two bathrooms and was fully renovated with a finished basement. It also had a two-car driveway and was steps from SADRA Park: perfect for the doggos. Plus, it had a porch. Factoring in the slow market, the couple made a bid of $800,000. It paid off. They moved in at the end of the summer and welcomed their daughter, in November. “We plan on staying here for some time,” says Alexandar. “There are so many young families—it’s incredible.”