Tucked into the lush, rolling landscape of prestigious Hoggs Hollow, this rare and character rich 1927 bungalow seamlessly blends timeless charm with refined modern upgrades. Perched at the top of the valley just moments from Yonge Street minutes to Loblaws, Fine Coffee Shops, Restaurants and Quaint shopping. This residence offers the perfect balance of privacy, nature, and urban convenience - an exceptional alternative to condominium living. The thoughtfully renovated main level showcases a chef-inspired kitchen designed for both everyday living and elegant entertaining, featuring premium Miele built-in appliances, including a wall oven and coffee system, gas range, and an expansive centre island. A charming breakfast nook overlooks the rear yard & gardens, creating a serene setting for morning coffee. Step outside to your private patio retreat complete with a cabana-style shed ideal for intimate gatherings or quiet relaxation surrounded by mature greenery. The main level also features a spacious primary suite with a spa-like five-piece ensuite, including a freestanding soaking tub, glass enclosed shower, and dual sink vanity. A versatile den offers flexibility as a guest room, office, or secondary bedroom. The walk-up lower level adds valuable living space with a sunken recreation room highlighted by increased ceiling height and a gas fireplace with slate surround and wood mantle. Additional rooms with above-grade windows provide flexibility for home office, guests and if required In-Law/ Live Nanny Suite potential. A large three-piece bathroom and generous mechanical/storage room complete this level. Outdoors the engineered & reconstructed structurally sound double garage could provide extra bonus living and entertaining areas above. Perfectly positioned near premier lifestyle amenities including Rosedale Golf Club, the scenic trails of York Mills Valley Park, and top-tier Schools and Sunnybrook Health Sciences - one of Canada's Top Hospitals.