104 Hedge Road, Georgina

Winter Wind Cottage sits on an extra-wide waterfront lot on Hedge Road, one of Jacksons Point's most sought-after streets. Private and green, the property offers flat, usable table land that opens the door to sitting areas, family gatherings, and room for kids to play. A newly built stairway winds down through the hedges to two tiers of dockside deck at the water's edge, where the rock shelf gives way to sand - the kind of entry that makes a lake worth owning. Inside, the cottage unfolds around that same water. The kitchen, lit by a skylight beneath a cathedral ceiling, opens directly into a dining room walled in glass toward Lake Simcoe, with the great room set right alongside - beamed ceilings, a floor-to-ceiling fireplace, and windows that turn the lake into a permanent backdrop. Four bedrooms and three bathrooms give the layout real breathing room, and because the cottage runs wide rather than deep, that water view follows you through nearly every room. Live in it while you plan what comes next, or start reimagining now - this lot supports either path, and gives you the luxury of time to decide. This is Jacksons Point, a village that has held onto its identity as Toronto's original cottage country: a short walk to the Briars, an easy stroll for ice cream in the village, and a community with roots that go back generations. Lake Simcoe anchors it all - a four-season lake for boating and swimming through summer, skating and ice fishing once it freezes. Winter Wind Cottage is a chance to own a piece of it.