The buyers: Jake Sheehan (right), a 24-year-old insurance and investment advisor, and Pat Quinn (left), who’s 25 and a manager of a BMW dealership. They’ve been best friends since their days at St. Michael’s College School.
The story: Sheehan was still living with his parents at Yonge and Lawrence, and Quinn was tired of renting. Over beers one night, they resolved to become the first homeowners in their social circle. Together, they could avoid the entry-level 400-square-foot condo and afford something sizable in a prime neighbourhood.
The price range: $450,000–$550,000.
The criteria: Both are big skiers, surfers and cyclists, so they needed basement storage space for their gear. They also wanted two parking spots, bedrooms on separate floors (for privacy), an open-concept common area for entertaining and a home office for Sheehan. Leslieville was their first choice: they’d be close to their Lake Ontario surfing spots and the nightlife on Queen.
The agent: Mary-Anne Talbot, RE/MAX Hallmark.
The search: Twenty-five places over three months.

Option 1: Booth Avenue (near Eastern and Logan), listed at $474,900, sold for $450,000 “It had it all on paper,” Sheehan says of the two-storey, three-bedroom semi. French doors on the first floor opened onto the backyard, and the basement was in good condition. But they weren’t keen on having all three bedrooms on the second floor.

Option 2: Heward Avenue (near Eastern and Pape), listed at $599,000, sold for $543,000 This semi had ample parking, a large backyard and an open-concept living area, but three of the four bedrooms shared a level. The fourth, a loft space with slanted ceilings, was a problem for Sheehan, who is six‑foot-two. And the third bedroom, to be used as an office, was too small.

Option 3: Ashdale Avenue (near Dundas and Coxwell), listed at $519,900, now off the market The features of this detached house charmed them: hardwood floors, a kitchen island and lots of light. “It was what the agents call ‘cozy,’” Sheehan says. “But the bedrooms were way too small for us.”

The buy: Leslie Street (at Queen), listed at $549,000, sold for $523,500 It was love at first showing: plenty of party space, parking, a full basement, a bedroom and an office on the second floor for Sheehan, and a large third-floor bedroom with an ensuite bathroom for Quinn. Plus, surfing at Ashbridges Bay is only a two-minute drive away. It had been on the market for 30 days, so they figured they could go low. Way low. “We came in at $450,000,” Sheehan says, “and I think the sellers were borderline insulted. It was a nerve-wracking negotiation, but our agent did a good job of keeping us at the table.”