Remarkable Vineyard Estate Compound

211 Winding Way, Woodside

At A Glance

  • Vineyard estate compound on approximately 6.4 acres
  • Over 2 acres of productive Pinot Noir and Cabernet vines
  • Main residence with 3 bedrooms, office, and 3.5 baths
  • Guest house with 2 bedrooms and 2 baths
  • Studio building with bath with shower, steam room, sauna, and 2 recreation/living rooms, one with wine cellar
  • Two 3-car garages, one with attached gym and each with EV charging
  • Upgraded Venetian plaster walls in many rooms

  • Approximately 11,705 total square feet
    – Main residence: 5,995 sq ft
    – Guest house: 1,499 sq ft
    – Studio: 1,492 sq ft
    – Pool cabaƱa: 238 sq ft
    – Garages: 2,481 sq ft
  • Clay tennis court, sport court, saltwater pool, spa, barbecue kitchen, fireplace, 3 outdoor showers, and elaborate tree fort and playhouses
  • 35kWp photovoltaic system
  • Whole-house backup generator
  • High-end security and surveillance
  • Acclaimed Portola Valley schools

Price upon request

This extraordinary estate spans 6.4 level acres with sun-swept vineyards and western hill views. The compound comprises multiple architecturally significant buildings, including the main home, a guest house, a multiroom wellness studio, and garages for six cars, plus an attached fitness center. Designed for exceptional privacy and self-sufficiency, the property is solar powered with a backup generator and comprehensive security and surveillance systems. Every space is exquisitely appointed with an organic ambiance complemented by Venetian plaster walls and refined finishes throughout. Resort-caliber amenities enhance the grounds, including a saltwater pool and spa, clay tennis court, sport court, elaborate connected tree forts and playhouses, and more than 2 acres of Pinot Noir and Cabernet vines. The result is a rare sanctuary where architectural beauty, natural surroundings, and sophisticated living come together in one remarkable Silicon Valley setting.