Welcome to 4481 Deanwood Drive, an exceptional residence set along one of Woodland Hills South's most coveted streets in the prestigious Vista de Oro tract. Offered for the first time by the original owner, this remarkable property has been recently renovated from top to bottom, showcasing high-end finishes, refined upgrades, and an unwavering commitment to quality. The main residence offers four bedrooms and three-and-a-half bathrooms, including two luxurious primary suites, providing exceptional flexibility and privacy for family and guests, along with the convenience of laundry facilities both upstairs and downstairs. A beautifully crafted 472-square-foot container-built guest house/ADU features its own viewing deck and fully self-sufficient living area, making it ideal as an in-law suite, private office, recording studio, gym, or creative retreat, while also offering significant rental-income potential. A long private driveway leads to the residence and attached three-car garage, while fresh interior and exterior paint, new ceiling fans, and designer light fixtures further enhance the home. The primary suite occupies its own private wing with a substantial walk-in closet, oversized beautifully appointed bathroom, and sweeping panoramic San Fernando Valley views. Step outside to an extraordinary private sanctuary with lush landscaping, romantic sitting areas, a gorgeous courtyard fountain, and breathtaking views from virtually every area of the property, including spectacular daily sunsets that transform the sky into unforgettable cotton-candy hues. Residents also enjoy spectacular community amenities, including a beautiful tennis court, inviting pool, and recreation room, creating a resort-like extension of the home. With commanding views, sophisticated renovations, flexible guest accommodations, significant rental-income potential, lavish grounds, and exceptional privacy, 4481 Deanwood Drive presents a rare opportunity for elevated living in one of Woodland Hills South's most exclusive enclaves.