Features

307 Olive Hill Lane, Woodside

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.

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

DETAILS OF THE MAIN HOME

Entrance
Custom gates open to a long paver stone driveway at the end of the street culminating in a circular motor court; a flagstone path leads to a fountain courtyard at the front entrance

Foyer

Floors in limestone imported from Germany and hand-plastered walls continue into the main living areas and hallway

Family Room

Grand scale room with exposed beam cathedral ceiling and gas-log fireplace with intricately carved antique mantelpiece and scrolled iron doors; French doors plus wall of stacking glass doors to a covered terrace with western hill views

Living Room & Dining Room

Three sets of double French doors on each side of the room to balconies or the main terrace; gas-log fireplace with elaborately carved limestone mantelpiece

Kitchen

Custom pear wood cabinetry and granite slab counters plus island with brushed granite waterfall wrap and counter seating; casual dining area, customized walk-in pantry, and desk alcove with thick art glass counters

Appliances

Thermador 6-burner gas cooktop; two Dacor ovens; GE microwave; two Thermador dishwashers; Sub-Zero refrigerator; Sub-Zero wine cooler

Bath

Porcelain pedestal sink, automated commode, shower, and French door to the spa terrace and pool

Office & Staircase Library

Open main staircase lined floor to ceiling with library shelves opposite the office with wall of custom cabinetry and integrated gas-log fireplace; French doors open to a private balcony

Main-Level Primary Suite

Double-door entrance, cathedral ceiling, French doors to a private balcony, and gas-log fireplace surrounded by cabinetry; two fully customized walk-in closets; en suite limestone bath with dual-sink vanity, deep tub, steam shower, private automated commode, balcony, and heated floors

Lower-Level Bedrooms and Baths

Five bedrooms and three bathrooms, including: two with direct access to a shared remodeled bath with dual-sink vanity and tub with overhead shower; two with direct access to a shared bath with shower and private automated commode; one with en suite dual-entry bath with shower; each bedroom has a French door to the grounds

Theater

State-of-the-art remodel with 9.2.4 surround sound, retractable cinema screen, upholstered walls, projector, gas-log fireplace, and three sets of French doors to balconies

Wine Cellar

Fully customized racking, stone walls, and temperature control

Other Interior Features

Lower-level laundry room with sink, Electrolux washer/dryer, Sub-Zero refrigerator, and KitchenAid dishwasher
Central vacuum; security and surveillance; air conditioning; smart home controls; automatic irrigation
Comcast IGB service with Starlink backup service

DETAILS OF THE GUEST HOUSE

Entrance
Private front entrance with fountain and multiple French doors plus matching French doors from the pool terrace; classic window shutters, handmade reclaimed roof tiles, and Genoise eaves detail in clay barrel tiles

Great Room
Tremendous living/entertaining space with limestone floors that extend throughout, multiple French doors with Cremone hardware, and gas-log fireplace

Kitchen & Appliances
Paint-grade mahogany cabinets, including island with counter seating, with marble counters and hand-painted tile backsplashes; appliances include a La Cornue gas range (wired for electric), pot filler, Cove dishwasher, Sub-Zero refrigerator, Sub-Zero wine cooler

Bedrooms and Baths
Bedroom with French doors to the pool; bath with shower and automated commode; second bedroom or office with French doors to the pool and en suite bath with shower, automated commode, and outside entrance

Other Features
Heated floors plus forced-air heat and air conditioning; Asko washer and dryer; Crestron home automation; built-in ribbon speakers and subwoofers; full sound system outside; outdoor shower and foot bath; retractable screens on all doors and operable outside shutters

THE GROUNDS & FITNESS STUDIO

Fitness center tucked into the hillside with outdoor entrance via multiple French doors; entire wall of fully mirrored storage cabinetry and white oak floors
Original oval pool and main terrace with sunken spa, both with saltwater
New infinity edge saltwater pool and separate spa, of nearly 60 feet in length, adjacent to the guest house; expansive terrace with gas fire pit, imported fountain, solid limestone columns with metal arbor and heaters, and nearby changing room plumbed for a shower
Full outdoor kitchen with gas cooktop, pizza oven, icemaker, dishwasher, refrigerator, refrigerator and freezer drawers, warming drawer, and barbecue
Fragrant parterre rose garden with fountain, heritage oak trees, and secret gardens
Bountiful orchard with apples, cherries, apricots, blueberries, avocado, citrus, plus 120+ year old olive trees
Terraced gardens with raised vegetable beds
Basketball half-court
South-facing 310-vine Cabernet vineyard
Vast level lawn areas
Two detached, partially enclosed, 2-car garages with built-in storage and one with Tesla charger
Low voltage landscape lighting
Electric entrance gate with intercom
Second gated service entrance