This savvy realtor couple waited for the perfect place to come on the market before they were pounded

The buyers: Jenny Simon, 38, and Shane Little, 33, both realtors

The story: Life and business partners Jenny and Shane moved in together in September 2020, after buying a two-bed condo in Leslieville. They loved walking around the neighborhood and even adopted a bulldog puppy named Dolly to accompany them on strollers. However, when the pandemic forced them to work from home, they realized that their unit was too small. Worse, the eight to 10 daily trips up and down the stairs to potty train their pooch chewed up a big chunk of their day. The first step was to rent a bigger place close by until the ideal property—a Riverdale townhouse with a backyard—came on the market. Then, with a budget of $1.5 million, they started their search.

Option 1: Grant Street, near Queen and Broadview

Listed at: $1,099,000
Sold for: $1,452,000

In August 2021, Jenny and Shane were renting a three-storey Victorian on Grant Street as they waited for a more permanent option to surface. They loved socializing among fellow dog owners on the block and being steps away from the bars and restaurants on Queen. When their next-door neighbors listed their house, Jenny, who is also a designer, immediately booked a tour. But the place came up short: the basement and third storey were unfinished, there was an extra kitchen they didn’t need, and the backyard was tiny. They kept looking.

Option 2: Cummings Street, near Dundas and De Grassi

Listed at: $1,099,000
Sold for: $1,405,000

A few weeks later, a semi-detached Riverdale became available. This one was closer to Dundas and checked a lot of Jenny and Shane’s boxes. But, despite it being just 300 meters from Grant Street, they found that Cummings lacked a certain spark. The street was less lively (many of its houses fronted alleys and adjacent streets), and they didn’t see a single dog walker when they visited. They weren’t getting the community vibe they were after, so they kept renting in the hope that a property on Grant Street would become available.

The buy: West Avenue, near Dundas and De Grassi

Listed at: $999,000
Sold for: $1,405,000

In December 2022, Jenny got a call from a fellow agent who was listing a three-bed, one-bath Edwardian on West Avenue, just a five-minute walk from where the couple was renting. Jenny and Shane loved the house for its high ceilings and big backyard, perfect for Dolly and their new puppy, Douglas. The next day, they put in an aggressive offer, which they based on comparable homes in the area. The sellers accepted a few hours later. “We were ecstatic to be owners again,” says Shane. “It took some time, but we’re finally home.”

Want to see your house hunt in Toronto Life? Drop us a line at [email protected].