An exceptional piece of North Shore history, “Lily Pond Hollow” is nestled in the heart of prestigious Brookville, offering an extraordinary combination of expansive living space, complete privacy, breathtaking scenic views, and convenience to New York City. This distinguished gentleman's farmhouse has been seamlessly and thoughtfully expanded for modern living, featuring a great room, grand primary suite, and three-car garage, while preserving its timeless character and historic charm. Set on over two bucolic acres, this remarkable estate features arboretum-like grounds with rolling lawns, formal gardens, mature specimen trees, and original stone garden walls. Named for its serene views overlooking a picturesque freshwater lily pond, the property offers a setting of natural beauty and tranquility. The residence boasts generous square footage and expansive, light-filled interiors, striking the perfect balance between grand entertaining spaces and intimate everyday comfort. A banquet-sized dining room, inviting sitting room, charming breakfast room, and sun-drenched great room lined with French doors showcase panoramic views of the picturesque grounds and pond throughout the seasons. Upstairs, four generously proportioned bedrooms with fireplaces offer warmth and character, with the potential for a fifth guest bedroom. The primary suite occupies its own private wing, featuring high ceilings, elegant crown molding, a fireplace, custom built-ins, and a spacious sitting area highlighted by a large Palladian window. The expansive primary bathroom includes a separate soaking tub room with its own fireplace, creating a peaceful retreat. Location is among the estate's most desirable assets. Situated within the nationally recognized Jericho Union Free School District, the property offers the perfect combination of North Shore living and exceptional accessibility. Enjoy immediate proximity to major highways, convenient access to nearby train stations, and an easy commute to Manhattan, approximately 25 miles away, with direct train service available in as little as 43 minutes.