Italianate grandeur and modern design are one at this world-class estate located in one of the country's most prestigious and sought-after communities. 27 Upper Road in Ross, California presents a rare chance to live life at the top of it all, with panoramic views of Mount Tamalpais, the verdant hills of Marin, and the San Pablo Bay. Located on grounds adorned with Ron Herman designed gardens and an Italian style pool with an Olympic-length swim lane, hanging gardens, fountain, spa, and surrounding verdant lawns, the approximately 10,228 square foot residence features five en suite bedrooms, a resort-like primary suite, and a private staff/in-law/au pair suite in the main residence. A separate guest cottage features a bedroom, bathroom, living area, kitchenette, and home gym.  Driving through the property's gates, and up to the grand motor court, you are graced by Cypress and Olive trees, beautifully complementing the house's terra cotta tiling and Tuscan arches. A dramatic triple-height foyer with wrought iron doors and inlaid marble floors commands attention, setting the tone of refined elegance and grandeur celebrated throughout the home. Gracious living and entertaining spaces include a formal living room with frescoed ceilings and limestone fireplace, a dining room with stone columns and coffered ceiling, a family room with limestone fireplace, beamed ceilings and French doors to a terrace with majestic views. Recently updated, the home’s timeless design is complemented by sleek interiors, contemporary finishes, and high design. Additional amenities include home theatre/music room, and a temperature-controlled wine cellar for approximately 30,000 bottles. Full Crestron automation and Lutron lighting throughout the home. AV and sound systems with 25+ zones. Over 20 security cameras, secure vault and safety mechanisms complete this world-class estate situated on 2.84± acres. Marin's famous hiking and biking trails are in walking distance, including picturesque Phoenix Lake. Add to that the nation's top award-winning schools, 27 Upper Road offers a once-in-a-lifetime opportunity for a fortunate family or the entertainer extraordinaire.