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Former Maple Leafs boss Brendan Shanahan's mansion on sale for mega-millions

This is an unmatched opportunity. A rare chance to own a landmark Rosedale property ... Truly for the most discerning buyer."

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If you’ve got around $14 million to spare, a sprawling historical mansion that former Toronto Maple Leafs boss Brendan Shanahan lived in during his time in Toronto can be yours.

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His Rosedale estate just went on the market, listed at $13.95 million.

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“Set on an extraordinary 80 x 229-foot lot — spanning over one-third of an acre — this meticulously restored home offers over 11,500 square feet of living space across four levels,” boasts the listing description.

The estate was purchased about two years after the Hockey Hall of Famer and Mimico native’s 2014 hiring as president of the Maple Leafs.

Shanahan was fired in May after the Leafs won only two playoff series during his tenure.

The property was sold for $9.15 million in December 2016 by former Bank of Montreal executive Frank Techar.

It was originally built in 1898 for a relative of pork baron William Henry Davies (the man who inspired Toronto to be known as Hogtown) and was designed by renowned architect Frederik H. Herbert. It was later restored by architect William Mockler, and another recent previous owner was entrepreneur and author Bruno Gideon.

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Years ago, it reportedly was owned by Franklin Jackes, a politician and member of Toronto’s first city council.

“This elegant residence showcases original architectural flourishes, including hand-carved moldings, eight fireplaces, and a dramatic entrance foyer. Soaring ceilings and intricate details throughout preserve the home’s 1890 heritage, while incorporating every modern luxury,” the listing says.

“The home features a huge gourmet kitchen, three outstanding family living areas, spa-inspired bathrooms, and an expansive four-room primary suite. A four-floor elevator ensures effortless access to every level. The backyard is a private urban oasis framed by manicured gardens and offering a magnificent pool and spa, along with multiple terraced patios for entertaining,” it says.

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The kitchen from the listing for 20 Elm in Rosedale. CHESTNUT PARK REAL ESTATE/REALTOR.CA

“A gated driveway leads to a detached three-car garage, with parking for up to nine vehicles … This is an unmatched opportunity. A rare chance to own a landmark Rosedale property perfect for grand entertaining and refined daily living. Truly for the most discerning buyer.”

The regal property has six bedrooms and nine bathrooms.

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Maple Leafs Sports and Entertainment president and CEO Keith Pelley fired Shanahan after the team’s collapse in the second round of the playoffs at the hands of the Florida Panthers.

At the time, Pelley said:

“Brendan put this franchise in better position in so many ways, but it’s about results and winning.

“Change is hard. We made progress under Brad (Treliving, Shanahan’s hire to replace Kyle Dubas following a power struggle) and I think we’d all agree (head coach Craig Berube) changed the culture. Now we’ll make another step. Further change will be needed to get us to the next level and (the firing) was the first step in that direction.”

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Leafs president Brendan Shanahan (left) and GM Brad Treliving
Then Toronto Maple Leafs president Brendan Shanahan (left) and general manager Brad Treliving watch their team’s optional skate at the Ford Performance Centre in Toronto on May 13, 2025. Photo by Ernest Doroszuk /Toronto Sun

Shanahan said in his own statement:

“I want to thank the board for the tremendous support they have shown me over my tenure. Toronto is where I was born and raised, where my family still lives, and being a part of this historic franchise will always be one of the greatest honours of my life.

“I want to thank the entire Leafs’ staff for their commitment and hard work over the years — they are second to none in the NHL.”

He also singled out alumni who served as ambassadors, and the vast support of Leafs Nation.

It’s unclear where Shanahan will be headed next after a potential role with the New York Islanders didn’t pan out.

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The pool and backyard from the listing for 20 Elm in Rosedale. CHESTNUT PARK REAL ESTATE/REALTOR.CA
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