Classic Craftsman architecture & beautifully updated interiors define this exceptional home in the Glens, tucked away at the end of a peaceful cul-de-sac just one mile from the Woodside town center. Framed by custom Corten-style fencing, terraced gardens, & underground utilities rarely found in this neighborhood, the property offers a distinctive presence with an added sense of privacy & refinement. Freshly painted interiors & hardwood floors introduce warm, inviting spaces filled with natural light. Traditional Craftsman character is complemented by contemporary finishes, custom cabinetry, granite surfaces, expansive windows, & sliding glass doors opening to the outdoor living areas. Cathedral ceilings enhance the open-concept design, creating wonderful scale for everyday living & entertaining. The flexible floor plan includes 3 bedrooms, a dedicated office, & 2.5 baths, including a spacious primary suite with fireplace, customized walk-in closet, & newly finished bath. Fully fenced front & rear yards offer expansive areas for entertaining & relaxation with level lawn, expansive deck, paver stone terrace, & large spa, all in a tranquil park-like setting. Access to the excellent Woodside Elementary School (TK-8) further enhances the appeal of this special offering.
Classic architecture & beautifully curated grounds define this inviting Woodside home set on more than one-third acre moments from the town center. Stone-clad exteriors, newly planted lawns, & a picture-perfect approach introduce interiors that are warm, welcoming, & thoughtfully designed for everyday living. Natural light fills the home through expansive windows, hardwood floors, detailed millwork, & a floor plan that offers both openness & comfortable separation of spaces. Main living areas transition easily from formal rooms to casual gathering spaces, welcoming family room & well-appointed kitchen designed for both function & connection. Lower-level recreation/media room adds flexibility for entertainment or office use. Privately located primary suite with jetted tub & steam shower, bedroom with its own outside entrance & adjacent bath ideal for guest quarters. Outdoor living is a central focus, with a large arbor-covered deck extending from the home & terraced grounds below featuring a play area & garden spaces, all enhanced by refreshed landscaping. Located on a cul-de-sac street in the Woodside Glens neighborhood, with acclaimed Woodside School & offers a combination of traditional appeal, updated comfort, & an exceptionally convenient setting with a true sense of retreat.
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.
Designer Transformation on 1.5 Private Acres Steps to Town A remarkable whole-home transformation has elevated this property into a showcase of design, quality, and livability. Spanning approximately 1.5 acres just minutes from the town center, the setting unfolds with park-like grounds that capture the essence of Woodside country living. Inside, a beautifully orchestrated floor plan offers predominantly single-level living with subtle elevation changes that define spaces while maintaining an open, flowing arrangement ideal for both everyday living and entertaining. Every detail reflects a designers eye, with cohesive finishes and thoughtfully selected materials creating a sophisticated yet welcoming atmosphere throughout. A well-appointed 2-bedroom, 1-bath guest house with full kitchen and laundry adds exceptional flexibility for extended family, guests, or even office use. Outdoor amenities are equally compelling, highlighted by a sparkling pool, vast lawn areas, and a bountiful orchard alongside a charming chicken coop that enhances the property's country appeal. All of this plus access to acclaimed Woodside Elementary School, offering a rare combination of privacy, scale, and convenience.
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 Acre with Sweeping Bay Views in Woodside Hills. Sweeping San Francisco Bay views take center stage at this exceptional Woodside Hills property with fresh updates throughout. Spanning one acre, the elevated corner lot is positioned to capture the expansive views while also providing generous level areas for outdoor living. Enhancing the setting is the gentle sound of a meandering creek and strolling paths that create a distinctly parklike ambiance. Fresh interior updates include new paint, refinished hardwood floors, and new carpet, all complementing the living rooms signature vaulted ceiling, handcrafted with layered redwood cedar rising to a dramatic center peak. Multiple fireplaces add warmth and character, while glass doors open to several outdoor spaces oriented to enjoy the Bay views. The formal living room and dining room each have Bay views, plus there is a large open kitchen and family room for everyday gatherings. Four bedrooms, an office, and 3.5 baths are well arranged, featuring a main-level primary suite and a second suite comprising the entire lower-level with outside access and flexibility for future ADU conversion. An attached two-car garage and abundant off-street parking complete this inviting retreat with close-in convenience.
New Price! Set at the end of a private, gated country lane on approximately 1.11 fully usable acres, this elegant estate with French country architecture offers an exceptional blend of refined living and natural beauty, with sweeping views of the Western Hills and stunning sunsets. The main residence features 4 BR and 5.5 BA and a dedicated office/library with inspiring views. A recently updated chefs kitchen with a sunny breakfast area, main-level primary suite with connecting recreation room, patterned oak hardwood floors, and dual-paned windows throughout create a warm yet sophisticated ambiance. Designed for indoor/outdoor entertaining with expansive terraces and beautifully landscaped gardens this is a one of a kind home. A detached 1 BR 1 BA guest house has a full kitchen, wood-burning fireplace, and high ceilings, perfect for guests, extended family, or independent work space. An additional 520 square feet of garage space and 795 square feet of basement storage provide functionality alongside luxury. Ideally located within walking distance to Woodside Town Centers shops and restaurants, and close to Woodside School (Pre-K8th), Interstate 280, Sand Hill Road, and Stanford University, this home exemplifies the best of serene, convenient, and elegant Woodside living
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
Tucked away on a private, gated cul-de-sac, 200 Todo El Mundo in Woodside offers the perfect balance of privacy, convenience, and natural beauty. Situated on approximately 1.5 acres of flat, usable land bordered by a seasonal creek, the property features expansive front and back irrigated lawns and a peaceful, park-like setting. The European-influenced traditional 4,885-square-foot main residence is designed for effortless indoor-outdoor entertaining, with several rooms opening through French doors to two sunny decks. A dramatic living room with soaring two-story ceilings and fireplace anchors the home, complemented by a spacious family room with its own fireplace and wet bar, a cozy kitchen and a private dining room ideal for intimate gatherings. The thoughtful five-bedroom, three-and-a-half-bath layout includes a serene upper-level Primary Suite with a full bath, sauna, fireplace and walk-in closet, two additional upstairs bedrooms and two main-level bedrooms with a full bath and tub. With its proximity to Woodside Town Center, Woodside Plaza shopping, Sand Hill Road, Stanford University, and nearby freeway access to major Silicon Valley destinations, this exceptional property offers a rare opportunity to enjoy the Woodside lifestylequiet, connected, and surrounded by nature
A rare, fully realized legacy compound offering the soul of a European retreat in the heart of Woodside. Hidden within 3.2 acres of curated gardens and ancient oaks, this meticulously renovated sanctuary blends old-world artistry, hand-painted murals, artisan tile, and beamed ceilings with the peace of mind of enterprise-grade infrastructure. The grounds are a private resort masterpiece designed for serene living, anchored by a rare clay tennis court, a waterfall grotto, a pool and spa, a pitch-and-putt green, and a bocce court. The main residence features four refined suites, a professional grade kitchen, a magnificent wine cellar, and a private executive office. Multi-generational living is perfected with a 2-bedroom family cottage, a 1-bedroom guest house, and a detached fitness center with sauna and Tonal strength training equipment. Beyond the charm, the estate offers total autonomy with redundant internet access, a backup generator, and advanced surveillance. This is the ultimate turnkey acquisition: an impossible-to-replicate blend of character and modern high-performance living, perfectly positioned minutes away from Silicon Valleys entrepreneurial eco-systems most iconic hubs.
Set upon an extraordinary 3.25-acre setting, this charming one-story home offers a rare sense of seclusion and natural beauty, further enhanced by its adjacency to a protected 6-acre parcel that ensures enduring privacy. The grounds are a true sanctuary, featuring a 40-year-old native garden that blooms nearly year-round, and a spacious rear deck overlooks this serene landscape, creating a seamless connection between indoor comfort and outdoor living. The property is graced with mature fruit trees, including pear, cherry and peach trees that add both charm and seasonal delight. Inside, the living room is a striking centerpiece, featuring a grand stone fireplace with a wood stove insert, complemented by soaring redwood-beam ceilings that add warmth and character to the space. A generously sized family room offers flexibility for relaxation, entertaining, or extended living. Modern convenience meets country tranquility with reliable high-speed internet, making this an ideal retreat without compromise. Surrounded by scenic, horse- and dog-friendly trails and supported by a welcoming, close-knit neighborhood, this is a setting that offers both peaceful escape and a genuine sense of community and exceptional opportunity to experience refined rural living at its finest.
One-of-a-kind mountain retreat on a sun-drenched, fenced 1/3-acre lot surrounded by majestic redwoods. This charming 1930s log cabin has been thoughtfully expanded with a quality newer master suite addition. Features include vaulted ceilings, radiant heated hardwood and tile floors, dual-pane windows, and an open kitchen with granite counters and a designer six-burner gas range. Enjoy serene views and all-day sunlight from the expansive south-facing deck. The detached garage includes an EV charger, attic storage, and parking for multiple vehicles. Landscaped with drought-tolerant native plants. Located within walking distance to Alices Restaurant, Skywood Trading Post, and miles of scenic hiking and biking trails. Easy access to Skyline Blvd and Hwy 84 for a smooth commute to Silicon Valley or the coast. Classic charm meets modern comfort in a peaceful, tight-knit communityperfect as a full-time residence or weekend getaway.
Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.
Set on 2.6+ wooded acres in the hills, this warm & beautifully renovated home offers something genuinely rare on the Peninsula: complete privacy amid towering redwood trees, a profound sense of forest immersion, and less than 15 minutes to Sand Hill & 280. The updated & open floor plan kitchen flows into generous dining and living spaces, all oriented towards sweeping forest views. Natural light fills the space, and wraparound decks extend living outdoors, with a hot tub just off the primary suite. A flexible two bedroom wing can accommodate children, teens, guest rooms, or office and studio space. An independent 1-bdrm ADU with its own kitchen / bath is ideal for rental income, an au pair, or an aging parent. The kitchen, secondary bathrooms, finishes, HVAC, roof, and water heater - have all been recently renovated, and pre-sale inspections were completed with virtually all items addressed. Hiking, cycling & equestrian trails connect directly to the property, and the land is zoned for horses. Stanford's campus is a short, predictable 25 min commute away. Zoned for Portola Valley El / Mid schools and Woodside HS, with several excellent private schools nearby. Soaring redwoods, architectural warmth & effortless access to the heart of Silicon Valley - come see it for yourself.
MOTIVATED SELLER! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. Spanning approximately 2,200 sq. ft. on a nearly 0.5 acre lot, this home features verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows which bring the natural beauty of the Glens inside. The floor plan includes a vintage kitchen, a dining area overlooking the oaks, and two bedrooms -- one featuring its own fireplace. � Central air-conditioning provides year-round comfort. Upstairs is a versatile loft with a storage area. The lower level features a large bedroom with� a bathroom and shower, an oversize 2-car garage, plus driveway space for 2 additional vehicles. With the large lot, an ADU is possible (buyer to confirm with the town). Located in the district for top-rated Woodside Elementary (K-8) and Woodside High, this home is moments from Woodside Village and offers a convenient commute to the entire Bay Area via Hwy 280. Experience the quintessential Woodside lifestyle in this timeless woodland sanctuary.
Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers a rare blend of privacy, scale, and resort inspired living. Thoughtfully designed to balance formal and casual living, the home features a gracious entry introducing light filled interiors with high ceilings, refined millwork, and an elegant flow throughout. The living and dining rooms offer defined spaces for entertaining, while the well appointed kitchen with custom cabinetry, stone countertops, and a central island anchors the homes gathering spaces and opens to the adjacent family room. The family room connects seamlessly to the outdoors, extending daily living into the surrounding landscape. The primary suite is a private retreat with generous proportions, a view deck, and a spa like bath. Three additional bedrooms provide flexibility for guests, office, or extended living. Designed for everyday living and entertaining, the grounds offer expansive patios, a pool, and a covered lounge area. Multiple vantage points capture natural beauty and Bay views, creating a sense of tranquility throughout. Now thoughtfully repositioned for todays market, offering a timely opportunity to secure a premier Woodside residence with convenient access to Peninsula amenities.
This Custom built home is perched high on the Skyline ridge (approx. 2000' elevation) with the Pacific Ocean on one side the SF Bay on the other. Located in the exclusive Woodside neighborhood of Kings Mountain, this modern retreat was built with natural filtered light through the Redwoods in mind surrounded by about an acre of wooded privacy. Think open floor plan flow, soaring ceilings, and a wall of glass framing endless redwood canopies. Gourmet kitchen opens to a family gathering area with wood burning stone fireplace. Spa-like baths with a steam shower in the master bathroom, large deck in back for your entertainment needs, a private heated lap pool below, and a separate entrance to an attached ADU/art studio/private office with it's own kitchen and bathroom - it's all here, your own mountain retreat wrapped on a rare level lot where hi-tech meets tranquility and serenity. Woodside's hidden gem where you can become part of a true community - minutes from a top rated elementary school, very active and vibrant community. Only 10-15mins drive to either San Mateo or Half Moon Bay, 20 min to SFO, 25 min to Stanford and 30-40mins to SF - yet worlds away from the chaos. Perfect for remote execs/workers, nature lovers, hikers/bikers, or anyone craving Elevation - literally!
Hidden gem on nearly half an acre behind a private gated entry with professionally landscaped grounds, mature orchard trees, & year-round blooms. The exceptional single-level 3 bedroom, 3 bath 1,842 sqft main residence was completely renovated in 2017 & features an open, light-filled floor plan with skylights & French Oak floors throughout. The entry opens to a spacious living room with custom built-ins & designer lighting, flowing seamlessly into the chef's kitchen with a large center island, Thermador appliances, & dining area. Multiple glass doors open to a stunning 400+/-sq ft lanai, creating effortless indoor/outdoor living. The primary suite retreat with spa-like bath featuring Italian porcelain tile, mosaic marble floors, chandelier, & custom closet. Outdoor living spaces include multiple seating areas, an outdoor kitchen, & gas fire pit, ideal for entertaining year-round. A detached garage offers approx. 687 sqft of flexible space for guest suite or home office, plus an additional 600+/- sqft basement. Additional features include a private well & potential to add an ADU or expand further. Ideally located moments from Village shops & restaurants, hiking & biking trails, Edgewood Park, Stanford University, major tech campuses, & Interstate 280. Excellent Woodside schools.
This custom-built home in Woodside Glens features a Southern exposure with stunning 180-degree views. Enjoy a view from almost every room, sunrise from the living room and kitchen is remarkable. With the .58 acre lot and numerous trees you have privacy and forest like serenity. Three bedrooms and three full baths compliment the large kitchen. Two freestanding gas heaters provide rustic elegant heat, perfect for that cozy seating area. There is also central heat for the rest of the house. The unfinished basement could be the perfect man cave and or wine cellar, you have options. The pool area needs TLC but has tremendous potential. Bring your builder, designer and your vision to create your own Woodside experience!
Tranquil Woodside Retreat Nestled within one of Woodside's most sought-after enclaves, this enchanting single-family residence offers a rare blend of privacy, natural beauty, and timeless appeal. Set on expansive, level to gently sloping grounds, the property is ideal for equestrian use, featuring serene open spaces framed by mature trees and lush, thoughtfully designed landscaping. Bathed in dappled sunlight, the home exudes warmth and charm throughout. The well-appointed floor plan includes 4 bedrooms and 2.5 bathrooms, with inviting living spaces that seamlessly connect to the outdoors perfect for both relaxed everyday living and elegant entertaining. Step outside to your own private oasis, complete with a pool, lush lawns, barn and meandering brick walkways. Whether enjoying quiet mornings or hosting gatherings, the setting offers unmatched serenity and beauty. Located within the boundaries of the highly acclaimed Woodside Elementary School, this exceptional property combines rural tranquility with convenient access to nearby amenities. A rare opportunity to experience the quintessential Woodside lifestyle.
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 by Pacific Peninsula Architects 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.
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.
Set on quiet Native Sons Road, this approximately 3.63-acre property offers privacy, natural beauty, and an opportunity to restore or reimagine a home in one of the Peninsulas most beloved mountain communities. A charming cottage surrounded by mature trees and near El Corte de Madera Open Space Preserve, the setting feels peaceful and inspiring. The existing residence is ready for a new vision, whether as a creative retreat, writer's paradise, weekend escape, or future custom home. With vintage character and a truly special setting, this property invites its next owner to reimagine and create a personal sanctuary in the heart of Woodside's beloved Kings Mountain.
Sweeping, unobstructed San Francisco Bay views define this contemporary estate set on more than an acre in Woodside Hills, with dramatic scenery enjoyed from nearly every room. Walls of glass, soaring ceilings, and refined finishes including marble, granite, and travertine floors create a striking yet warm aesthetic throughout approximately 4,800 square feet across two levels. The expansive kitchen and family room anchor the main level, complemented by gracious formal living and dining spaces that provide multiple areas for entertaining. The upper level offers additional gathering space including a media room, along with four bedroom suites highlighted by a luxurious primary retreat with a spa-inspired bath. Outside, the grounds feature a pool and pergola-covered terrace, all oriented toward the views. Climate control ensures year-round comfort, while a gated setting offers privacy close to parks, nature preserves, and convenient commute options.
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.

Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information has not been verified, is not guaranteed, and is subject to change. Copyright 2026 Bay Area Real Estate Information Services, Inc. All rights reserved. Copyright 2026 Bay Area Real Estate Information Services, Inc. All rights reserved. |
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.