(photo: 2054 Lakeshore Road East, Regan Irish & Associates)

 

A nearly 20,000-square-foot lakefront luxury home with all the trimmings may be what dreams are made of – but a $39-million listing won’t sell itself.

Matthew Regan and Alex Irish hold the listing for Ontario’s highest-priced home currently listed on Realtor.ca. 

2054 Lakeshore Road East, a 1.6-acre estate in an affluent southeast Oakville neighbourhood, had been on the market for one week as of Monday. 

While the home itself may be pristine – with its seven bedrooms, “Bellagio”-inspired fountain and waterfall, infinity pool, and manicured grounds – getting it sold will require Regan and Irish to get their hands dirty. 

 

Tapping the right circles

 

Regan said the seller came to Regan Irish & Associates, which is under the banner of Re/Max Escarpment Realty Inc., seeking representation with both domestic and international reach.

“You have to cast a pretty wide net,” he said, noting the monumental pricetag. 

Most listings follow a passive formula: put the property on MLS and wait for the right buyer to appear. 

“Where that falls short on a property like this is that it’s a very specific buyer. There are not many of them out there,” said Regan.

For a high-end home, the strategy flips. Instead of waiting, Regan and Irish have taken a hands-on approach, built on 60 years of combined experience.

“You’re really relying on a network,” Regan said. “If I call up an agent in Victoria or Vancouver, the chances are they know who we are because of the type of real estate we sell—and I know them.” This credibility opens doors to one-on-one conversations with agents who have access to affluent buyers in markets from Vancouver to Chicago to Los Angeles.

That outreach matters. A current prospect from Los Angeles, whose wife is Canadian, is seriously considering the property, said Regan.

With the Canadian dollar low against the U.S. dollar, the home becomes an even more attractive asset for American buyers, he said.

 

Not your typical open house

 

Rather than a public open house, the team hosted a unique, invitation-only agent event. Phones were not allowed inside the property, ensuring privacy for both the home and its owners. The gathering was professionally catered, creating a refined, memorable atmosphere.

What made it stand out even more was the scheduling. Showings were arranged by time slot, allowing the team to carefully manage foot traffic. This not only ensured the experience felt exclusive for guests, but also addressed security concerns that come with a property of this calibre.

 

The online element

 

Regan said search engine optimization plays a major role in attracting the right buyers online. “SEO is a big thing,” he said. The goal is to highlight the property’s most distinctive features in a way that makes it easy for potential buyers to find.

This home offers rare amenities that stand out in any search—an indoor golf simulator, an elevator to all five levels, an in-home movie theater, and a fully equipped gym accessible from the primary bedroom. 

By using targeted keywords tied to these amenities, the marketing ensures the listing appears in searches made by buyers specifically looking for such features. 

 

Quick close, or long game?

 

When it comes to selling a property at this level, timelines can be unpredictable. “There’s no one answer to that,” Regan said. This is the type of home a buyer of this affluence will view as a generational purchase—an opportunity that doesn’t come along very often, he said.

That can lead to a quick sale. Just one week on the market, the property already has two qualified buyers showing interest, including a second showing. For many in this price range, the home becomes part of a broader portfolio—“a crown jewel” as Regan calls it—which can prompt a faster decision.

But the flip side is that it could also take longer. The ideal buyer may not even be aware the property is for sale yet.

“Sometimes the perfect buyer doesn’t even know they want to buy something right now,” Regan said. It’s only when they come across the listing that they think, this looks interesting—let’s go see it.