Located on a rare double dead-end street in prestigious Rosedale-Moore Park, this beautifully maintained family home offers over 4,000 square feet of warm, inviting living space backing onto a private fir-treed ravine setting. Loved by the same family for 35 years, it's the kind of home that effortlessly grows with a large family - offering room to gather, space to spread out, and quiet corners to retreat to. The main floor is designed for both everyday living and entertaining, with a gracious living room overlooking the front garden, a formal dining room with ravine views, and an oversized eat-in kitchen with extensive storage and a sun-filled breakfast area. Just beyond, the spacious family room feels like a cottage in the city, with floor-to-ceiling windows framing the trees, custom built-ins, a gas fireplace, and walkout access to an extra-wide deck perfect for family dinners, BBQs, and relaxed weekends outdoors. Upstairs, the second floor offers four generous bedrooms and three bathrooms, including a peaceful primary retreat tucked quietly at the back of the home with a large ensuite and walk-through closet. A second ensuite bedroom is ideal for guests, teens, or a nursery, while the additional bedrooms offer an ensuite office, storage, and exceptional flexibility for growing families. A private third-floor loft adds even more versatility with a fifth bedroom or office, den space, sauna, and balcony overlooking the ravine. The lower level includes a large recreation room, laundry, utility space, and abundant storage. There is easy parking for multiple cars, and convenient storage in garage. Set between 2 top-rated elementary schools (Whitney Jr PS, Our Lady of Perpetual Help), and surrounded by parks, trails, and nature, this quiet enclave offers a rare balance of tranquility and convenience just minutes from downtown via Mt. Pleasant Road. A truly special opportunity for families looking to put down roots in one of Toronto's most cherished neighbourhoods.