About 15681 Kennedy Road
Property Information
Experience the epitome of luxury living at Villa di Fiori, an award-winning architectural masterpiece nestled in the breathtaking vistas of Los Gatos, Silicon Valley. This extraordinary multi-generational smart home, recently remodeled in 2025, spans approximately 12,405 sq ft across 3.56 acres of meticulously designed private space. Featuring two exquisite dwellings, a brand new Tesla roof, and an infinity-edge PebbleTec pool with a Jacuzzi, this estate offers 8 sumptuous suites, 10.5 baths, and an array of entertainment options including an expansive theater lounge, game room, executive office, gym, wine cellar, and music room. With state-of-the-art smart home technology, 24-hour surveillance, and stunning panoramic sunset views, Villa di Fiori is not just a home; it’s a sanctuary of elegance and innovation, perfect for hosting grand gatherings or enjoying serene moments in your own private oasis.
15681 Kennedy Rd is characterized by a distinctive fusion of European artistry, modern amenities, and cutting edge innovation. High definition surround sound and artistic design were prioritized in creating the ambiance for this former San Jose Symphony Showcase Mansion, which can effortlessly host over 125 guests. Enjoy the soothing sound of cascading water and the fragrance of fresh roses as you stroll through the courtyard, inviting you to unwind & rejuvenate in the Lap of Luxury. Italian-inspired architectural features, verandas & fountains embellished with roses, Italian cypress, a verdant olive grove, and intricately sculpted gardens.
Minutes from vibrant DT Los Gatos. Join in for a variety of exciting festivities that bring the town to life, celebrating everything from art and music, to food and wine, to the winter holidays. Stroll the tree-lined historic downtown, surrounded by unique boutiques, delightful Michelin-rated dining options, renowned wine tasting rooms and breweries, all housed within charming buildings that reflect the town's storied past. Los Gatos is a paradise for those who love the outdoors offering endless opportunities for running, hiking, biking or simply enjoying the fresh air. Experience the warmth of Los Gatos. Welcome home.
Offered at: $12,888,888
2 gated entries | 2 dwellings | 2 solar systems | 360 degree Panoramic Sunset Views | 8 suites | 10.5 baths | 4 fireplaces | 2 balconies | 2 California doors |3 staircases | 2 bars | entertainer’s kitchen | dirty kitchen | guest house kitchen |outdoor kitchen | 3 laundries | 3 tankless water heaters | whole-house filtration | fire-pit courtyard
Contact Shiela-Marie Ventura for any and all inquires at (408) 218-1405, sm@kwluxuryofficial.com for more information or to schedule a private tour.
Disclosures & inspections can be downloaded here: https://app.disclosures.io/link/15681-Kennedy-Road-5gnyz4we
3-D Property Tour
15681 Kennedy Rd 3-D Property Tour
Dollhouse click through of every room, including Guest House, Courtyards and Rear Grounds
meet the listing team
Shiela-Marie Ventura CLHMS | Million Dollar Guild™ Elite | KW Luxury Official - Silicon Valley
Specializing in the luxury communities of Silicon Valley, Mrs. Ventura is a master of luxury real estate. By thoughtfully
personalizing every detail to exceed your requirements, she's elevated luxury real estate, transforming it into an exceptional experience.
Serving your friends, family, and acquaintances for the past 17 years. Mrs. Ventura is motivated by the satisfaction you get when she delivers and she strives to create experiences as effortless as they are memorable. What’s more, she leads with heart, a value core to the Keller Williams Luxury credo.
Co-Listed with Adam Dallas | Coldwell Banker Realty - Los Gatos
Adam is born and raised in the town of Los Gatos.
Our team of experienced real estate professionals has a wealth of knowledge about the local market.
Together, we can help you get the answers you need to make your dream a reality.
About the town
City of Los Gatos
Bikes, Parks & Trails Map
City of Los Gatos
With 330 sunny days a year and a rich network of parks and trails, it’s a haven for outdoor lovers. Year-round events celebrate art, food, wine, music, and the holidays — offering something for everyone.
Los Gatos Events
Bikes, Parks & Trails Map
City of Los Gatos
Music in the Park - Sundays 5-7pm
Farmer’s Market - Sundays 9-1pm
Jazz on the Plazz - Wednesdays 6:30 - 8:30pm
Los Gatos Art & Wine Festival - September 20 & 21
Halloween Pawlooza - October 31
Los Gatos in Lights - December 7th
Symphony in the Park - July 4th
Bikes, Parks & Trails Map
Bikes, Parks & Trails Map
Bikes, Parks & Trails Map
Nestled against the Santa Cruz Mountains, Los Gatos is more than a vibrant, picturesque historic town. Los Gatos is also an incredible paradise for outdoor adventures.Year round, residents and visitors. Whether you’re seeking a stroll along the creek, a relaxing paddle on a reservoir, a hike to a hilltop vista, or an invigorating bike rid
Nestled against the Santa Cruz Mountains, Los Gatos is more than a vibrant, picturesque historic town. Los Gatos is also an incredible paradise for outdoor adventures.Year round, residents and visitors. Whether you’re seeking a stroll along the creek, a relaxing paddle on a reservoir, a hike to a hilltop vista, or an invigorating bike ride that seems to stretch out endlessly before you, Los Gatos offers something for everyone.
