Rarely does a property offer this much space, flexibility and opportunity in such a sought-after setting. This remarkable in-town property features TWO beautiful homes on an incredible 110' x 310' lot, just steps from Island Lake Conservation Area. The main home is bright and inviting, with a spacious open-concept living area featuring a focal brick fireplace with barn board mantle and large windows overlooking the property. The updated kitchen offers a centre island, abundant storage and modern finishes, with a walkout to the expansive back deck and yard. Beautiful luxury vinyl plank flooring flows throughout. Upstairs are three bedrooms, including a generous primary suite with two closets and a 3-piece ensuite, plus a stunning 4-piece family bath with gorgeous tilework. The finished basement adds a fourth bedroom and large recreation room, perfect for movie and game nights. The second home offers exceptional versatility, with its own entrance, laundry and attached double garage. Designed for convenient main-floor living, it features a living room with gas fireplace and wood French doors to the backyard, a well-appointed kitchen with walk-in pantry, and two main-floor bedrooms. The primary suite features three closets and a semi-ensuite with linen storage and a relaxing jet tub. Above the garage, a spacious den/family room with gas fireplace, views of both front and rear yards, and generous storage provides even more living space. 3 electrical panels, 2 sump pumps and a Generac serving most of both homes provide added peace of mind. Plus, enjoy passive income through the solar panels. The property is truly exceptional with mature trees, gardens, storage sheds and endless character creating a private oasis rarely found in town. With Island Lake's beach and walking trails just steps away, plus great schools, the hospital and all of Orangeville's amenities nearby, this is an extraordinary opportunity to enjoy 2 homes, an exceptional property & an unbeatable location.