Welcome to an exceptional ravine-facing residence in one of Pringle Creek's most desirable mature neighbourhoods. Set on an extraordinary 49.21 x 230 ft lot, this meticulously maintained home offers just under 3,000 sq ft of finished living space, timeless curb appeal, and a rare connection to nature in the heart of Whitby. Wake up to deer, rabbits, birds and abundant wildlife as you enjoy morning coffee in the four season solarium. Floor to ceiling windows frame 230 ft of ravine views, mature trees, and peaceful green space. A meditation garden, waterfall, hammock, patio, and multiple seating areas create private cottage living in the city, with endless potential for your dream outdoor retreat. A spacious two storey foyer opens to a bright, functional layout with hardwood flooring on the main floor and greenery visible from nearly every window. The formal living room is complemented by a separate family room with a rustic gas fireplace. The renovated kitchen offers quartz countertops, stainless steel appliances, abundant storage, a large island with seating, and an open flow to the dining room, eat in kitchen area, and solarium. Main floor laundry and a powder room complete the main. Upstairs, the generous primary bedroom includes a walk-in closet plus an adjoining room ideal as a dressing room, study, nursery, or additional closet. The renovated 5pc ensuite features a double vanity, jacuzzi tub, and glass enclosed tiled shower. Three additional bedrooms offer excellent family and guest space.The finished basement adds a large recreation room, games area, wet bar, gym, additional bedroom, and jacuzzi bathroom perfect for relaxing, fitness, movie nights, or working from home. Enjoy direct access to an extensive trail system, with nearby parks, green space, schools, shopping, recreation, and everyday conveniences. 74 Henderson Drive offers a fantastic ravine lot, space, setting, and family lifestyle that are increasingly difficult to find in established Whitby.