Forever views of coastal hills and Pacific ocean at the very end of a small country maintained road. Adjacent to hundreds of Open Space acreage. 1,600 + sq. ft. upper floor Great-Room with floor-to-ceiling windows. Large open kitchen / dining area and open living room with wet bar and guest bath. Upper level deck wraps around the entire exterior. Bedrooms are all downstairs each with access to the deck. Bonus room (great for crafts, possible den or bedroom) and laundry utility area. Downstairs is also aprox.1600 sq. ft.. House was being remodeled, but was not completed. Truly a fixer upper. Complete set of remodel plans included.
Discover a private architectural gem at 320 Grandview Drive, offering bold design, walls of glass, and sweeping views toward Stanford and the Bay. Nestled on a quiet, private road, the home feels worlds away yet close to everything. The open layout is filled with light and ready for a creative renovation. Inside, a spacious indoor pool and sauna could become a modern wellness retreat, and a large artist studio or workshop provides endless flexibility for work or play. This is a rare chance to transform a striking, light-filled home into a modern estate surrounded by privacy and nature. Within the Portola Valley Elementary School District, this private property offers rare architecture, space, and potential in one of Woodsides most desirable settings. Bring your vision the potential here is as big as the view.
Peaceful Woodside Retreat with Sweeping Bay Views Welcome to 168 Sunrise Drive, a serene retreat in the heart of Skywood Acres where you'll enjoy breathtaking panoramic views of the Bay, stretching from San Carlos to San Jose. Set on a spacious 53,577± sq. ft. lot, this home offers both privacy and connection to nature. A long driveway leads you to the inviting residence, surrounded by mature landscaping, lush foliage and the quiet beauty of Woodside's countryside. Inside, the home features 2 bedrooms, 2 baths, and a versatile bonus room perfect as an office, studio, or guest space. Vaulted ceilings and floor-to-ceiling windows fill the open living areas with sunlight, creating a warm, inviting space with stunning views from nearly every room. Step outside to a sunny deck and sparkling pool, the perfect place to relax, entertain, or take in the peaceful surroundings. Experience the best of Woodside living - privacy, natural beauty, and views that truly take your breath away. Just minutes from Menlo Park, Palo Alto, and top schools, it offers the rare blend of privacy, prestige and convenience.
Perched a top of Skyline Ridge, this gated custom estate offers spectacular views of the San Francisco South Bay, including Mt. Diablo, Stanford, and San Jose. Nestled on a private 5+ acre east-facing parcel near the 942-acre Wunderlich Park, the home features 5 bedrooms, 4.5 bathrooms, 4 large decks, and a 2-car garage. The gourmet kitchen with center island, dining room, and large pantry opens to the great room with vaulted ceiling, skylights, and 3 French doors. Upstairs showcases imported slate floors, a central family/activity room, a guest half bath, a library/office, and a spacious primary suite with a walk-in shower, a 2-person jetted spa, a private deck, double sinks, a bidet, and a walk-in closet. A nearby flexible room could serve as a bedroom, nursery, or den. The laundry area opens to a flat yard suitable for a future pool, tennis court, or stables. Downstairs includes 2 bedrooms, a large bath, a sitting room, and a fully self-contained ADU with private entry and a deck. In the coveted Portola Valley/Woodside School District, the estate feels private yet is minutes from Alice's Restaurant, Fogarty Winery, central Woodside, Stanford, and the Coast.
7.7 gated acres with Views, Pool, Tennis Court, & Guest house. Bordered by Thornewood Open Space Preserve, and with incredible San Francisco Bay and western hill views. Main home with dramatic formal rooms, walls of glass, and tile or hardwood floors. Sleek modern kitchen with oversized island seating. Main level primary suite with views and spa-like bath plus secondary suite. Lower-level recreation room, customized wine cellar room, plus two beds and bath. Partially enclosed hallway to the pool house with oversized bar, fireplace, 1.5 baths, and retractable glass doors fully opening to the pool. Detached guest house/ADU with full kitchen and bedroom suite plus separate fitness studio. Large circular pool, tennis court, stainless-steel outdoor kitchen, Pinot Noir vineyard, and vast level lawn. Portola Valley schools and direct access to miles of open-space trails.
Absolutely the BEST VIEW of the Bay. Wake up early and catch the stunning panoramic view of the sun rising from this 4 bed/3 Mid-Century Modern home in Woodside Hills. Sit back relax and enjoy expansive views of the San Francisco Bay. On a clear day looking a bit Northwest youll catch a glimpse of the Bay Bridge as well as Treasure Island. One of the iconic features of a Mid-Century Modern home is their floor to ceilings windows that provide one with scenic views as well as bringing in an abundance of natural light. As the day transitions from day to night your view will be filled with lights from the bay that can leave you breathless. This 2,430 sq. ft. home on a mostly flat one-acre lot provides an excellent opportunity for one to remodel or design/build the home of your dreams with spectacular priceless views in one the most desired locations on the Peninsula. It's just 35 miles from The City and only 26 miles from Silicon Valley. A short drive from downtown Woodside shops and restaurants. Fine dine at The Pub or enjoy a meal at Bucs of Woodside a fixture of Silicon Valley. Nature lovers can explore the nearby vast open spaces,parks and preserves which provide an abundance of hiking and biking trails. Don't miss your opportunity to make this your forever home. Virtually Staged
Privately positioned on approximately 1.85 acres with unobstructed views of Jasper Ridge Biological Preserve, this custom-built home offers a rare sense of serenity and seclusion just minutes from town. The setting is truly exceptional - vast, mostly level grounds bordered by open sky and native landscape. Designed for indoor/outdoor living, the home features an expansive flagstone terrace and covered front porch, along with a secluded rear terrace and spa - all surrounded by the natural beauty of Woodside and Portola Valley. A striking architectural presence is established with its signature shaped parapet, handcrafted detailing, and richly hued finishes inspired by classic Spanish Revival style. Inside, the warmth continues with red birch floors, wood-paneled cathedral ceilings, and hand-selected tilework from Walker Zanger. Every room captures the views, and the kitchen is appointed for serious cooking with premium appliances, a walk-in pantry with wine storage, and an open connection to the indoor/outdoor dining room. Moments from hiking and biking trails, top-rated schools, and local amenities, this is a home that lives like a country retreat yet remains just minutes from the heart of town and Highway 280.
Courtesy: Compass
650-529-1111
Renderings only. Providing over one-third acre of level double-wide land, this expansive parcel is an exceptional opportunity to build your dream home in the heart of Woodside. Pre-approved architectural plans, by Simpson Design Group, with ADU, pool and all landscaping, are available saving years of time in the building process. Offering gorgeous views of the Kite Hill Wildflower Preserve and just steps from its beautiful hiking trails, it is the rare combination of a tranquil country setting located just minutes from the town center. This property is also ideally situated with access to the acclaimed Woodside Elementary School (K8), making it a highly desirable address for those seeking a premier Peninsula lifestyle. Offering wonderful views and outstanding location, this lot presents the perfect canvas to create the home ready for permit issue, or to create your own dream home, in one of Silicon Valleys most sought-after communities. Plans to build a total of 4415 sq ft. Main house 3,475 sq ft. Garage 440 sq ft. ADU 500 sq ft.
SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to DREAM BIG with unmatched grandeur & privacy. An Italian Renaissance mansion engineered to commercial standards, but now awaiting your completion. Easy ingress/egress off Hwy 92 and Skyline presents this estate in sequestered privacy. A long driveway descends to the motor court & the Villa's monumental architectural scale. A 2-Story Lobby with Imperial Staircase is the powerful opening salvo. 4 levels of destinations inspire your finishing details: a Library off of the lobby, Two Enormous Primary Suites on the two main levels, 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 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. With SKY VILLA, you will take the lead as your own pioneer, a developer of a nearly complete architectural masterwork, ready to take flight in one of California's most prestigious communities.
Experience the ultimate retreat, where majestic redwoods, sweeping canyon vistas, and ocean views provide a stunning backdrop for everyday living. This 3,323 sq ft custom home features 5 bedrooms and 3.5 bathrooms. The main level boasts soaring ceilings, expansive windows, and skylights that flood the space with natural light, highlighting the breathtaking scenery. The open-concept design connects the spacious living area to the kitchen, featuring Brazilian soapstone countertops, rich wood flooring, and stainless steel appliances, perfect for entertaining or relaxing. An adjoining family room offers more space to unwind. Head downstairs to access the expansive deck, versatile bedrooms, and flexible spaces. Outdoor living takes center stage as you step onto the oversized deck, soak in the hot tub under a canopy of stars, or explore the meticulously terraced yard, offering space to garden, relax, or let your animals roam free. Ideally located, a short walk to miles of open space trails,10 minutes to Hwy 280 with easy access to SFO, Silicon Valley, and the Half Moon Bay coast, this home offers the perfect blend of serenity and convenience. Come experience the lifestyle you've been dreaming of, surrounded by nature, tranquility, and the welcoming community of Kings Mountain.
Discover total serenity at this exquisite and warm family home. The home has been very thoughtfully renovated to include all the comforts one could ever need. With an open floorplan kitchen and living room, and several floor to ceiling windows. Perfect for taking in the verdant green of the surrounding forest. The home is filled with abundant natural light, benefiting from the natural clearing the home was built on. Sweeping decks wrap around the back, facing the lush forest, offering ample space for hosting, gathering, and outdoor meals. A perfectly placed outdoor hot tub sits on the deck right next to the primary suite. The primary suite enjoys its own level of the home and access to the deck through sliding doors. Enjoy your morning coffee outside, taking in the sights and sounds of nature. A generously sized In-Law suite (ADU) provides flexible room for guests, room for activities, or rent it out. The property unfolds across a generous 2.5+ acre lot, providing an expansive canvas for outdoor enjoyment. Here, the true magic reveals itself: breathtaking panoramic views glimpsing the San Francisco Bay and the majestic surrounding forest. To be this surrounded by nature, while still being so unbelievably close to all the cities on the peninsula (15 min to 280), is truly special.
Private ~half-acre property is prime for redevelopment with an existing 3,365+/- sf house and ADU* with 5BDs and 5BAs, a carriage house with studio, paddock, two access gates and multiple outbuildings. This highly coveted location is within 0.5 mile of Woodside Village with Roberts Market, Bucks, the library, The Village Pub (Michelin starred), Village Hub and Village Bakery and Cafe, and near top rated schools, miles of hiking, biking and horseback riding trails and surrounding open space preserves. Nestled in the foothills of the Santa Cruz Mountains between the Pacific Ocean and SF Bay, Woodside is one of the wealthiest communities in Silicon Valley and the U.S. It is renowned for its natural beauty, redwood forests, equestrian culture, sprawling estates, high-profile residents and proximity to Stanford, venture capital firms and tech hubs like Palo Alto and Menlo Park. It is about 30 minutes from San Francisco and the coast, 1.5 hours from Napa Valley and located between two international airports and private jet centers. Affluent, private and understated, this scenic rural town of about 5,100 residents offers a low-key lifestyle and tranquil retreat within easy reach of thriving epicenters. *Some structures may have been built without permits; buyer to investigate.
Set on a 3.1-acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly-updated residence offers the perfect blend of refined luxury and modern comfort - just minutes from town. Flooded with natural light from expansive floor-to-ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public spaces in +/-5,555sf. The open-concept living room boasts 24-foot ceilings, massive curved windows, a striking fireplace, and flows seamlessly into the sun-filled dining room. The chef's kitchen opens to a huge family room with 10-foot ceilings, a dramatic fireplace, bar, and French doors opening to a patio-perfect for indoor/outdoor living. Designed for everyday comfort and entertainment, the home offers multiple terraces, temperature-controlled wine storage, and an expansive lower level replete with a gym, home theater, and full bath. Outdoor amenities include a pool with spa, tennis court, meandering paths that encircle the property, level lawns, and a vineyard. A detached 2BR/2BA, +/-1,135sf guest house is ideal for extended family or visitors. Access to the top-rated Woodside Elementary School completes this rare opportunity to experience a lifestyle of elegance, privacy, and convenience.
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 are 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 with its own private gate is a 2k sqft guest house boasting high ceilings, 2 beds & 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.
A rare offering on one of Central Woodsides most prestigious streets, just off Mountain Home Road, this extraordinary estate showcases architectural excellence, vineyard beauty, & a luminous natural setting. Spanning almost 4.4 acres with an optional adjacent 3-acre parcel also available, the grounds have been thoughtfully opened to invite abundant sunlight, enhancing both the ambiance and the usability of the land. Designed by Ugo Sap and built by Van Acker Construction, the main residence is defined by dramatic scale, elegant curved forms, and exceptional materials. An elevator connects the two levels, which include six en suite bedrooms including a show stopping primary suite with terrace and spa bath beneath a retractable skylight. The library has walnut paneling and custom wood cabinetry with custom inset lighting. Outdoor living is equally impressive, featuring a thriving Pinot Noir vineyard, olive orchard, and multiple destinations for entertaining. A spacious poolside guest house includes a bedroom, full kitchen, sauna, and bath, while a separate structure with bath and kitchenette is ideal for a fitness center or executive office. Plus a building which has temperature controlled wine storage. A truly world-class property with access to acclaimed Woodside School.
Step inside and step back in time to this to this stunning Henrik Bull-style home in Skywood Acres, where classic charm meets modern comfort. Nestled in a sunny tranquil setting, this architectural gem opens into a breathtaking great room with cathedral ceilings and walls of windows that frame sweeping treetop views. This seamless blend of indoor/outdoor living extends to an expansive deck offering a perfect retreat that harmonizes with nature. Reminiscent of a mountain ski lodge, this 2510 sqft private haven enjoys its own sunny microclimate and offers the ultimate escape, just 14 minutes to 280, 25 minutes to Stanford, minutes from Alices Restaurant, and private access to Wunderlick Park, Portola Valley schools. Main home features a primary bedroom that includes bathroom, dressing room and private office. Main level boasts a well-appointed kitchen, custom wood built-ins, opens to a grand living area. Downstairs 2 bedrooms and bath, 3 car garage with wine closet. Detached guest studio with sleeping loft. 1.5 acre lot includes a former sport court ready for new possibilities Make this getaway your private Shangri-La
Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The main floor features a gourmet kitchen with high-end appliances, sleek finishes, dining area, family room and dedicated home office offers the perfect space for remote work or creative pursuits. Upstairs, the bedrooms provide privacy and tranquility. A large, bright family room stands out as a favorite space, filled with natural light and a cozy, welcoming ambiance. Multiple large decks extend the living space outdoors, offering peaceful spots for relaxing, entertaining, or enjoying the majestic redwood surroundings. Additional features include a wine cellar and ample storage. Tucked just off the scenic Skyline Corridor with easy access to Hwy 92, 280/101, SFO, open space trails, restaurants, and award-winning Kings Mtn Elementary, this home offers a rare blend of privacy, convenience, and a strong sense of community fostered by friendly neighbors and the Kings Mtn Volunteer Art Fair.
Mountain Meadow - A Landmark Legacy-Extraordinary in provenance, scale, and preservation, this landmark estate spans nearly 25 acres, located on land protected by Peninsula Open Space Trust and surrounded by Golden Gate National Recreation Area parkland. Offering unmatched privacy yet just 20 minutes from San Francisco International Airport. Commissioned in 1927 as one of the debut residential work of renowned architect Gardner Dailey. Over a period of decades, the entire property has been thoughtfully restored with reverence for its heritage and a commitment to enduring quality. The main residence of almost 9,000 square feet has been brought forward for the next century with seismic retrofitting, state-of-the-art infrastructure, and artisan-level craftsmanship throughout. Continuing beyond the main residence is a 2 story guest/caretaker's house. The heritage grounds are a living piece of California history. Originally designed by the same landscape architect responsible for the adjacent Filoli estate, the gardens include a pool by Thomas Church. This is a once-in-a-lifetime opportunity to live within a rare expanse of natural beauty, wrapped in complete privacy, where historic architecture and legacy gardens have been renewed with clarity of purpose.
One of the most extraordinary properties on the SF Peninsula on almost 18 acres. The property has endless potential (including zoning for commercial use) and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. Woodside or PV schools. 17 minutes to Woodside town center.
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.
