This extraordinary Woodside estate spans 6.4 level acres w/sun-swept vineyards & western hill views. The compound comprises multiple architecturally significant buildings, including the main residence, guest house, a multi-room wellness studio w/wine cellar & 6-car garages plus a working lab w/anti-static flooring. Designed for exceptional privacy & self-sufficiency, the property features a 35kW photovoltaic solar system, a 125kW whole-house backup generator, & a 1,600 amp electrical service. A comprehensive, enterprise-grade infrastructure includes a network w/fiber connectivity linking each building to the main racks, supported by a firewall, 26 ethernet switches, & 15 Wi-Fi access points. A whole-house audio system powered by advanced network amplifiers & Lutron-app controlled light further elevate the living experience. The grounds are equally compelling, with a well for irrigation, a clay tennis court, lighted sport court, & approximately 2 acres of Pinot Noir grafted aged vines. A whimsical designed 3-tree playhouse & fort adds a rare & enchanting element to the landscape. The result is a true sanctuary--where architectural beauty , advanced infrastructure and natural surroundings converge in one of Silicon Valley's most exceptional settings.
Luxury retreat offers a serene escape on 9+ acres, secured by an electronic gate. Under 2 miles and just minutes to Alices restarant. Stunning style on one level, the home features dramatic light-filled interiors with an open-concept design, SOARING CEILINGS, and abundant sliding glass doors and skylights. Bamboo floors, vertical grain cabinetry, and polished concrete counters. The main rooms revolve around a central patio with a stunning heritage oak tree, while an expansive rear deck with a large spa beneath the redwoods and a sunswept front yard for gardening enhance the outdoor experience. Three privately located bedrooms, each with its own bath, ensure comfort and flexibility. An equally well-appointed ADU above the garage includes a kitchen, bath, and laundry. Total privacy directly adjacent to MidPen open space. Flat useable grounds with large vegetable garden, ample of paved parking, large ground level deck and heritage oak entertainment area for large parties. Open sunny side toward views and beauty of Redwood forest on the oposite side of the house with heated spa under the redwoods. Main house 2870 sq.ft, plus ADU 550 sq.ft., plus attached garage 525 sq.ft for total of 3945 sq.ft.
One of Woodside's premier estates, encompassing nearly 10,000 square feet across all structures, this property offers exceptional scale, quality, and lifestyle, highlighted by a classically styled main residence and a brand-new guest house crafted 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 pairs handmade roof tiles and Genoise eaves inspired by the South of France with state-of-the-art smart home technology. Designed for entertaining, the guest house opens to a new saltwater pool and spa and expansive limestone terrace with a full outdoor kitchen 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 estates 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. Main Residence 6,485 Guest House 1,505 Garage One 560 Garage Two 520 Gym 560
Striking contemporary architecture and San Francisco Bay views define this custom home built with sustainable features that include solar power, radiant floor heating, dual-zone climate control, and a thoughtfully designed sunroom that supports passive ventilation for year-round comfort. Distinctive materials include exposed Alaskan cedar beams, clear vertical grain cedar ceilings, Brazilian oak wall paneling, and floors of limestone and bamboo, complemented by Poggenpohl cabinetry and commercial-grade windows. Arranged over multiple levels with 4 spacious bedrooms, the home follows the natural contours of the site and has expansive glass, clerestory windows, and carefully framed outlooks to beautiful vistas all around. The level rear grounds with vast lawn, limestone terrace, and fire pit provide inviting spaces for outdoor living and entertaining. Built for design and performance, this is a truly distinctive home in a premier setting.
Nestled in a highly sought-after Woodside neighborhood, this single-family home offers the rare combination of privacy, space, & future potential. Situated on an expansive ~0.340.37 acre lot (15,000+ sq. ft.), the property provides generous outdoor space ideal for entertaining, expansion, or the opportunity to build your custom dream home. The residence features a remodeled kitchen & an upgraded 150-amp electrical panel (completed in 2011), offering a solid foundation for comfortable living or further enhancements. Located in a low-density, established community, this home enjoys a serene, mature setting with exceptional privacy. Zoned for top-rated Woodside Elem., & Woodside High, its an excellent choice for those seeking both tranquility and access to quality education. Convenience meets location with just a 1015 minute drive to Downtown Redwood City, where youll find an array of dining, shopping, & everyday amenities. Commuters will appreciate the close proximity to Redwood City Caltrain Station and easy access to Highway 101 & I-280 via Woodside Road. A unique opportunity to own in one of Woodsides most desirable areas with endless potential.
Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning just over 3.4 acres, this expansive property showcases rare Bay views. There is an existing planning study for guidance in future opportunities. Positioned at the end of a private lane, the setting reflects the essence of Woodside country living, with lush perimeter trees and vast open land that offer a serene and private natural environment. The gated property includes an existing one-level home, a pool, and an original tennis court. Just one mile from Woodside Town Center and acclaimed Woodside Elementary School, and only minutes to Stanford University, Sand Hill Road venture capital firms, and the heart of Silicon Valley, this location offers both seclusion and convenience.
Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc countertops. Every bedroom and main living area opens to wraparound decks with sweeping views. Dedicated office for remote work, and a large 2-car garage. Level yard for entertaining, with room for pickle ball court, plus a sunny pool area. Direct walking distance access to scenic hiking on Mid-Pen Open Space trails. Convenient door-to-door bus to top-rated Portola Valley schools.
Discover this exceptional opportunity to own a generational estate spanning 7 acres across 3 separate parcels, each with its own APN. Through a private gate & down a long winding driveway, you're greeted by a circular motor court with incredible views of the Santa Cruz Mountains. The main residence offers 4,340 sqft featuring 6 beds & 5.5 baths, with exceptional upgrades throughout. On the east side of the property there is a large building pad; once the site of a horse stable, recently prepared for development. This pad is situated on the border of 2 of the 3 parcels & includes direct access from Moore Rd via a natural pathway. Nestled on the western edge of the property through via separate entrance is a 2k sqft guest house boasting high ceilings, 2 bed-1 bath, all opening out to an infinity-edge pool surrounded by lush landscaping. Winding pathways connect this serene retreat to the rest of the estate. This is a truly versatile offering with significant future upside through lot line adjustments, possible subdivision, or exploring SB9 opportunities. A unique & rare chance to create a lasting legacy in one of the most coveted zip codes in the country. Designated under the Las Lomitas school district with proximity to private institutions such as Sacred Heart & Woodside Priory.
*NOW REDUCED FOR SALE ON OFFER DATE THURSDAY JULY 9, 12 NOON* SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase 4 levels of destinations inspire your finishing details Library off the lobby Two Enormous Primary Suites (one main level, one upstairs) Multiple Offices Immense walk-in closets Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest Flat rear grounds inspire a future pool & ADU Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.


Woodside is located in California. Woodside, California has a population of 5,316. Woodside is more family-centric than the surrounding county with 40.87% of the households containing married families with children. The county average for households married with children is 35.93%.
The median household income in Woodside, California is $250,001. The median household income for the surrounding county is $136,837 compared to the national median of $69,021. The median age of people living in Woodside is 45.6 years.
The average high temperature in July is 80.9 degrees, with an average low temperature in January of 39.4 degrees. The average rainfall is approximately 37 inches per year, with 0.9 inches of snow per year.