Nestled in the heart of North Rosedale, 296 Glen Road is a beautifully appointed 4-bedroom + office, 3-bathroom home that perfectly blends timeless charm with modern comfort. Situated on a 23.67 ft x 136 ft lot, just under 3,500 sq. ft. including lower level, this residence offers an inviting atmosphere on a quiet, family-friendly street just steps from Chorley Park. Inside, warmth and elegance define the space. The open-concept living and dining areas are bathed in natural light, featuring rich oak hardwood floors and a cozy wood-burning fireplace. The chef's kitchen is both stylish and functional, boasting heated travertine floors, stainless steel appliances, a Sub-Zero fridge, gas stove, and a custom breakfast nook with built-in window seating. French doors lead to a private backyard retreat, complete with an in-ground pool, sauna, and outdoor shower perfect for relaxing or entertaining.The second-floor primary suite offers a tranquil escape with a bay window, sitting area, walk-in closet, and fireplace. A second bedroom and a dedicated office space complete this level. The third floor is full of character, featuring two additional bedrooms and an enchanting hidden loft with exposed brick ideal for a playroom, reading nook, or extra storage accessed by both rooms. The finished lower level adds versatility, offering a spacious rec room/music room and ample storage. Located in the OLPH & Whitney school district and near Branksome Hall, this home is just a short stroll to scenic trails, the Brickworks, parks, and Summerhill Market. With a thoughtful layout, stunning outdoor space, and a prime location, 296 Glen Rd is a rare opportunity to own a home that truly has it all.