16420 South Kennedy Road, Los Gatos

A Rare Los Gatos Masterpiece – The Legacy Estate on South Kennedy

Perched atop a private 1.5-acre knoll in one of Los Gatos’ most coveted neighborhoods, this extraordinary Craftsman Farmhouse is a once-in-a-lifetime opportunity. Originally built in 1916 by visionary developer Mr. Phillips, this home was designed with the finest materials to withstand time—preserving its architectural elegance while embracing modern luxury.

Thoughtfully expanded and masterfully reimagined in 2002, this 6,087± sq. ft. estate offers 6 bedrooms, 5 full baths, 2 half baths, and a dedicated office, providing ample space for living, working, and entertaining. Designed to capture the stunning views from every room, the home is surrounded by towering oaks and lush, park-like grounds, offering both privacy and serenity.

Inside, warm oak flooring, custom millwork, and soaring ceilings create a grand yet inviting atmosphere. The expansive gathering spaces include a formal living and dining room, reading/game room, family room, a second-floor den, and a chef’s kitchen that seamlessly opens to outdoor entertaining areas.

The outdoor spaces are equally breathtaking, featuring wraparound porches, private balconies, an entertainer’s patio with a full outdoor kitchen and fire pit, and a sweeping lawn large enough for a soccer field. This gated estate is a true retreat, yet remains just minutes from top-rated Los Gatos schools: Van Meter Elementary, Fisher Middle, and Los Gatos High (buyer to verify), scenic hiking and biking trails, vibrant downtown shopping, and fine dining.

This is more than a home—it’s a legacy. A rare, historic gem that blends timeless craftsmanship with modern luxury in an unparalleled setting.