A party-loving couple get serious about real estate and reap the rewards

Daryl Oliver, a 46-year-old Air Canada flight attendant, and his husband, Andrew Parr, the 55-year-old CEO of the College of Naturopaths of Ontario, met in a bar on Church Street in 1992. Before long, they were building a management consultancy together and taking lavish vacations in Cancún and Mykonos, a perk of Daryl’s job. All the hard work (and equally hard partying) left them with little time or inclination to invest in real estate.

In 2001, they were happily renting a condo in a building in Etobicoke when they saw a two-bedroom on the 15th floor listed for sale. They pounced. They loved the place—until special assessments to fix a leaky sewage system landed in their mailbox. The experience soured them on condos, but they couldn’t afford a house.

Andrew took a higher-paying job, and they began aggressively paying down their mortgage. By 2010, they were ready to move, but prices were climbing faster than they could save. Their real estate agent suggested a townhouse in Parkdale. Initially, Daryl and Andrew recoiled at the idea of another condo (this one steps from a Hells Angels hangout), but the neighbourhood was rapidly improving, and the unit looked and felt like a house.

They bought the place and, five years later, decided to cash in. With the proceeds, they purchased land near Haliburton, where they’re building a chalet that will one day be their retirement home.

The first buy

Lake Shore Boulevard West (near Park Lawn)
Purchased for $333,000 in 2001 Sold for $439,000 in 2011

Daryl and Andrew loved this two-bedroom unit’s 1,200-square-foot floor plan and Lake Ontario views—but not the building’s leaky sewage system.

The second buy

Elm Grove (near Queen and Dufferin)
Purchased for $798,000 in 2011 Sold for $1,162,000 in 2016

They were leery of the Hells Angels clubhouse down the street but ended up buying this townhouse for $10,000 under asking. The bikers’ parties were noisy but mercifully brief.

The third buy

Salerno Lake (near Haliburton)
Land purchased for $230,000 in 2015

With $486,000 in cash and a $450,000 mortgage, they were able to build a chalet in cottage country. There’s a master suite on the main floor for when they’re too old to climb stairs.

The bottom line

A decade of financial focus and price appreciation helped Daryl and Andrew save almost $500,000 for a home that could see them through the rest of their lives.