One of North Rosedale’s most admired and coveted estate residences, originally built in 1921, has undergone a complete transformation and expansion under the meticulous care of Karen Kayne Design, creating an exquisite transitional home tailored for modern family living. Directly facing the lawns and lush mature trees of Chorley Park, this magnificent residence sits on an extraordinary 62 by 235-foot lot spanning a full one-third of an acre. A large covered front verandah offers a peaceful vantage point to enjoy the surrounding green landscape. Inside, approximately 5,825 square feet of total living space (across all levels) gracefully combines classic architecture with a warm atmosphere of understated refinement. Each light-filled room thoughtfully flows into the next, establishing a natural sense of harmony, serenity and enduring comfort. The layout is simply extraordinary! Top-tier finishes abound. The chef’s kitchen has a La Cornue range at its centre, along with two Sub Zero fridges and two Miele dishwashers. Formal and casual dining can be enjoyed both indoors and out. The ultra-private and exceptionally deep garden serves as a remarkable outdoor oasis, carefully crafted for both quiet relaxation and formal entertaining. Square-cut Hampton limestone terraces and stone patios frame a heated inground concrete pool, complete with an integrated hot tub and two dedicated change rooms. An intimate covered dining terrace overlooks the pool, with extraordinary privacy thanks to magnificent, mature trees, hedges and plantings. Stellar construction standards are evident throughout, highlighted by exceptional custom built-ins, windows and doors. Winters are managed easily with two fireplaces, in-floor heating in every room and an attached heated garage for two tandem cars, paired with a heated concrete driveway accommodating four additional vehicles. Positioned perfectly in North Rosedale, this setting offers unmatched convenience and access to the neighbourhood’s finest educational and recreational amenities. Coveted public and Catholic schools are within easy walking distance, as is leading K-12 Branksome Hall school for girls. Other renowned private schools are just a short drive away. Daily errands and gourmet provisions are a short walk away to Summerhill Market. With the prominent position directly facing Chorley Park, you can step onto the Beltline to jog or walk the dog through scenic nature trails, taking you straight down to the vibrant Saturday farmers’ market at Evergreen Brick Works. Intentionally designed and elevated in every detail, this masterwork estate property quietly shapes daily living through enduring beauty and a unique location. 266 Douglas Drive creates memories to inspire!