Never before on the market, this landmark property was built in 1941 for James Flood and his family, one of the most prominent families in Northern California's history. The rare and unrivaled setting encompasses approximately 91.94 acres of glorious land with rolling oak-studded hills, open meadows, and endless views - yet all less than 2 miles from the center of the town of Woodside. The main residence is a grand, yet understated architectural achievement in the classic Colonial style with well-maintained interiors that reflect the beauty of the era's fine craftsmanship - richly stained hardwood floors, extensive millwork, crystal lighting, and many French doors that open to the amazing setting. Surrounded by absolute privacy, the ~9000 sq.ft. residence is enveloped with formal grounds by renowned landscape architect Thomas Church, including his signature pool, plus a tennis court. Miles of ranch roads and riding trails traverse the property winding past a lake, reservoir, a vineyard, and West Union Creek - and bordered on one side by Huddart Park for added seclusion. Offering one of the largest private parcels on the Peninsula, this truly is a once-in-a lifetime opportunity to own a landmark estate for yet another generation to come.