1086 Pennwood Road

An extraordinary opportunity awaits on the coveted shores of Upper Lake Muskoka, where legacy properties are held for generations, and the possibilities are as expansive as the view. Set on over 2 acres with 326 feet of pristine south-facing frontage, this rare offering features a gently sloping, child-friendly lot and a grandfathered setback that places the existing cottage just steps from the water. Perfect for a family looking to build memories in Muskoka, enjoy the property as it stands for a few idyllic summers while developing architectural plans for a custom retreat that takes full advantage of this exceptional footprint.The current 5-bedroom, 3-bath cottage offers nearly 2,800 sq ft of living space, complete with a Muskoka room, warm wood finishes, and incredible lake views. At the shoreline, a beautifully designed two-storey, 2 slip winterized boathouse provides private guest accommodations, a kitchenette, and an expansive sun deck framed in glass, the perfect perch for lingering into the golden hour. A hard-packed sandy beach and shallow entry make it ideal for young children, while deeper water off the dock is perfect for boating and swimming. Enjoy miles of adventure across the Big Three lakes.Whether you envision a refined family cottage or a showpiece of modern Muskoka design, this property combines immediate enjoyment with long-term potential, just minutes from Port Carling for dining, boutique shopping, and year-round convenience.