Windermere House is a Muskoka landmark affectionately known as “The Lady of the Lake.” Its red-shingled roof and grand balcony overlook a sloping lawn that leads down to the crisp waters of Lake Rosseau.
The 56-room resort includes 6.62 acres of land, several food and beverage outlets, spa capabilities, an outdoor heated pool, a tennis court, 3,200 square feet of flexible function space, as well as Windermere cottage, a traditional four-bedroom cottage set back from the resort.
Windermere House has a long history in Muskoka. The resort’s founding stretches back to the 1860s when Thomas Aitken journeyed from his home in Scotland’s Shetland Islands to the pristine woods of Muskoka. Aitken intended to use his new plot of land for farming but crops struggled to take root in the shallow soil. So, he pivoted, opening his home to visiting sportsmen and fishing parties.
Steamboat service coupled with a new railway station in nearby Gravenhurst caused business to boom. By 1887, Aitken had renovated the resort, resembling its present-day appearance. At that time, the resort could accommodate 220 guests and a night’s stay cost $1.50.
Aitken died in 1919 at which point his family sold off a portion of the resort’s 200 acres to the newly formed Windermere Golf and Country Club. But resort operations stayed in the Aitken family until 1981 when it was acquired by George Ember of Toronto.
Ten years later, the resort served as the setting for the film The Long Kiss Goodnight, starring Geena Davis and Samuel L. Jackson. But during filming, the resort caught fire and burned to the ground, with some blaming the production’s lights. Only the stone veranda remained. Architect Joe Sibbald rebuilt the resort in its former image and Windermere House once again opened to guests in the summer of 1997.
The resort has changed hands several times since the Aitkens with Paul Jeffrey, founder of restaurant chains Kelsey’s and Montana’s, taking ownership in 2008 and operating the resort until his death in 2016. The resort was then passed on to a private investor.
Correction: An earlier version of this story incorrectly stated the property had been sold.
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