At the foot of a winding village road on the shores of Lake Rosseau, discover the iconic Windermere House Resort. Atop a sloping lawn, hugged by a Victorian stone veranda and crowned by twin turrets, the resort, known as “the Lady of the Lake,” has been a Muskoka landmark since 1870. Now this heritage lakeside destination awaits a new chapter — 2508 Windermere Rd. is for sale.
Listed at $12 million, the property offers a 56-room resort, pub, numerous amenities and a four-bedroom cottage amid 6.62 acres of picturesque land that faces Lake Rosseau (a favourite spot among celebrities).
What started as a humble homestead for Thomas Aitken, a Scotsman who emigrated to Canada in the 1860s, soon became one of Muskoka’s first and most influential resorts.
A favoured site for hunters and fishermen, Aitken and his wife Mary recognized a business opportunity and began offering room and board.
A decade later, local steamboat services and a rail line to Gravenhurst opened the doors to Muskoka, making it a favourite holiday destination. To meet demand, the Aitken family became bonafide hoteliers and constructed the Windermere House Resort — a property that would remain a Lake Rosseau landmark for the next 150 years.
Sadly, in 1997, during the filming of A Long Kiss Goodnight starring Samuel L. Jackson, a fire destroyed most of the original building. However, the resort was soon rebuilt to match its former glory.
Tucked into the corner of the resort’s ground floor, the Windermere Pub is an original feature of the property. Its stone façade and convivial terrace with lake views makes it a favourite spot for an afternoon pint.
Further dining experiences can be found at the Rosseau Grill, an on-site restaurant, while the lobby bar is a lively spot for cocktail hours.
One of the advantages of owning a resort in Muskoka is the fabulous event-hosting opportunities. An idyllic spot for weddings, landmark celebrations and corporate gatherings, the Windermere House has long been a popular choice. It offers several large event rooms and ample outdoor space to get creative in.
Spa facilities and a slew of on-site leisure activities, including a tennis court and heated outdoor pool, are added pleasures. Nearby, the public marina and sandy beach offer hours of fun at the lake. The Windermere House is also mere moments from an 18-hole golf course and country club.
Several guest suites offer multiple bedrooms, a modern kitchen, and stylish living quarters with private balconies. There’s also a private four-bedroom cottage on the property for visitors who prefer a holiday home to themselves.
At dusk, Lake Rosseau glows.
The property also comes with a four-bedroom private cottage, named Windermere Cottage, which perhaps explains the price tag — you get a Muskoka cottage and a nifty investment opportunity all in one!
2508 Windermere Rd. is listed with Maggie Tomlinson of Chestnut Park Real Estate Ltd., Brokerage, Port Carling.
