LUXURY REDEFINED:
Dual Pools, Vineyard, and New Guest House Retreat
211 Winding Way, Woodside
307 OLIVE HILL LANE | WOODSIDE
At A Glance
- Exceptional estate home with new guesthouse, new second pool, and new landscaping, all of impeccable quality
- Approximately 3.08 acres with western hill views and Cabernet vineyard
- 6 bedrooms, office, and 5 baths in the main residence
- 2 bedrooms and 2 baths in the new guest house with full kitchen
- Approximately 10,000 total square feet (buyer to confirm)
- Hand-plastered walls and floors in German limestone or white oak
- Main-level primary bedroom suite and adjacent office, plus five lower-level bedrooms and three baths
- Fully renovated state-of-the-art theatre with 9.2.4 surround sound
- Temperature-controlled, customized wine cellar
- Detached fitness center and basketball half-court
- Two detached 2-car garages with EV charging
- Original oval pool and spa plus newly added large pool and spa, all saltwater
- 310-vine Cabernet vineyard, bountiful orchard, vegetable beds, and heritage olive trees
- Acclaimed Woodside Elementary School (K-8)
Offered at $34,995,000
One of Woodside’s premier estates, this property offers exceptional scale, quality, and lifestyle with a classically styled main home and a brand-new guest house built with authentic European detail. The main home is luxuriously appointed across two levels, with nearly every room opening to the outdoors. A state-of-the-art theatre and a temperature-controlled wine cellar are just two of many standout features. The newly completed guest house showcases roof tiles handmade in Provence and Genoise eaves, paired with modern seismic construction and smart home technology. Designed for entertaining, the guest house opens to a new saltwater pool and spa, of early 60 feet in length, and expansive limestone terrace with sound system, full outdoor kitchen, pizza oven, and easy catering access. A 310-vine Cabernet vineyard anchors the south-facing gardens, while heritage olive trees and oaks, a fragrant parterre rose garden, bountiful orchard, and raised vegetable beds enhance the estate’s agrarian beauty. The result is a property where timeless elegance and refined European living are masterfully expressed in an extraordinary private setting of more than 3 acres with western hill views.
