A Landmark Residence In The Heart Of Lawrence Park South. Set on an exceptional 50' x 134' lot, 258 Cortleigh Boulevard is a rare offering that masterfully blends timeless architecture, uncompromising craftsmanship, and sophisticated contemporary luxury. Offering approximately 6500 sq. ft. of impeccably finished living space across three levels, this custom-built residence has been thoughtfully designed for exceptional family living and grand-scale entertaining. The spectacular main level features soaring ceilings and a dramatic family room that flows seamlessly into a chef-inspired gourmet kitchen appointed with premium appliances, a stunning marble island, and a fully equipped service kitchen. Every space has been curated with bespoke millwork and meticulous attention to detail. The luxurious primary retreat offers custom walk-in closets and a breathtaking spa-inspired ensuite, while the masterpiece provides generously proportioned bedrooms and an office, and versatile family spaces designed for modern living. The exceptional lower level rivals the finest private clubs, featuring a sophisticated recreation lounge, fitness centre, and private guest or nanny suite. Designed for seamless indoor/outdoor living, the beautifully landscaped backyard is a true private oasis with a resort-inspired concrete swimming pool. Luxury extends to every detail with a private elevator servicing all levels, garage car lift for two cars, radiant heated floors, Control4 smart home automation, premium mechanical systems, and uncompromising quality throughout. Ideally located in one of Toronto's most prestigious neighbourhoods, just moments from the city's finest public and private schools, parks, boutique shopping, dining, and transit, 258Cortleigh represents an extraordinary opportunity to acquire one of Lawrence Park South's finest custom residences, offering exceptional value, timeless design, and an unparalleled lifestyle.