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136 Bardet Road, Woodside
$5,495,000
3 Beds ⋅ 3 Baths ⋅ ML82066217 MLS
Beautiful country chic style. Completely transformed inside and out, this beautifully reimagined home captures the essence of sophisticated country chic in a remarkably private and peaceful setting. Expanded & extensively renovated with all-new infrastructure, the one-story home showcases exceptional attention to detail, with French oak hardwood floors, custom millwork, and beautifully crafted doors and windows. A beamed and paneled cathedral ceiling lends architectural character to the spacious living room, while an inviting dining area, designer kitchen with Calacatta marble finishes, & separate family room provide comfortable spaces for everyday living & entertaining. Three bedrooms & three baths include two lovely suites, each opening to a private garden setting. The setting is equally enchanting, with exceptional privacy amid expansive, level grounds and lush landscaping that creates a secluded retreat. Two distinct garden areas, each with bluestone terraces and lawn, provide inviting spaces for relaxation & entertaining, all against a backdrop of western hill views. Despite the wonderful sense of seclusion, Woodside town center is less than one-half mile away, with its restaurants, shops, and small-town atmosphere, & the property is within the acclaimed Woodside Elementary.

136 Bardet Road, Woodside

1190 Bear Gulch Road, Woodside
$2,995,000
6 Beds ⋅ 7 Baths ⋅ ML82066176 MLS
A unique opportunity awaits to restore this significant contemporary estate on approximately 7.1 acres with dramatic San Francisco Bay & East Bay hill views from all three levels. Built in 1991 & spanning more than 7,000 square feet of living space, the home is distinguished by commanding architecture with soaring ceilings, expansive walls of glass, skylights, steel cable-strung railings, & glass-block details. Some rooms currently have no finished flooring, drywall has been removed in select areas, & some doors & windows are in need of repair presenting the opportunity to restore & reimagine the interiors while retaining the home's distinctive architectural framework. Numerous terraces & balconies take full advantage of the Bay views & surrounding wooded setting. Level tiered front grounds, deck, & playground provide additional outdoor space. Reached via private gated road, the parklike setting feels exceptionally secluded & adjoins 942-acre Wunderlich Park with miles of hiking & riding trails, yet Woodside Town Center is just 15 minutes away. Access to acclaimed Woodside Elementary School further enhances this exceptional opportunity to restore a substantial Woodside estate to its full potential.

1190 Bear Gulch Road, Woodside

no property photo
$4,195,000
6 Beds ⋅ 3 Baths ⋅ ML82066102 MLS
Set in Woodside Glens and the K-8 Woodside Elementary School District, about a mile from Town Center, this light-filled ~3,000 sq ft home has six bedrooms, three full baths, and a skylit office. A 2024 addition joined the 1920s home, giving you room for everyone, whether you need kids' bedrooms, home offices, guests, or a gym. Iron-and-glass front doors open to a cathedral entry and a living room with vaulted ceilings and exposed wood beams. The great room includes a white quartz kitchen with a peninsula and Bosch gas range, a sitting area, and glass-walled dining. The main level includes three bedrooms, a bath with a marble-topped vanity, and a closet ready for a second stacked washer/dryer. Upstairs, the skylit primary suite has a loft, walk-in closet, heated bath floors, curbless shower for two, and a balcony for sunsets over the hills. Downstairs, a bonus lounge with a beverage cooler, 65-inch TV, and in-wall audio opens through stacking glass doors to the terrace, alongside two bedrooms, the office, a full bath, and the main laundry room. Relax on the front porch, or entertain on the terrace by the heritage oak, with a pergola and outdoor kitchen. Includes smart lighting, audio, fire sprinklers, RV hookups, and a 50-amp outlet for EV in the garage.

118 Hillside Drive, Woodside

307 Olive Hill Lane, Woodside
$29,995,000
8 Beds ⋅ 7 Baths ⋅ ML82065658 MLS
This exceptional property spans more than 3 acres with sweeping western hill views and 9,880 square feet of total living space. The main home was completely rebuilt in 2000, and in 2025, an entirely new guest house and entertainment complex was added to the estate. The classically styled main residence features nearly every room opening to the views and includes a state-of-the-art theater and temperature-controlled wine cellar. The newly completed guest house showcases authentic European detail with roof tiles handmade in Provence and Genoise eaves, complemented with modern construction and smart home technology. A new saltwater pool and spa, nearly 60 feet in length, is surrounded by an expansive terrace with sound system, outdoor kitchen, pizza oven, and easy catering access. The south-facing grounds are equally impressive, with a 310-vine Cabernet vineyard, heritage olive trees and oaks, a parterre rose garden, bountiful orchard, and raised vegetable beds. Reflecting timeless European elegance and exceptional craftsmanship, the estate is remarkably private, with far-reaching views enhancing the entire setting and all midway between Silicon Valley and San Francisco.

307 Olive Hill Lane, Woodside

388 Albion Avenue, Woodside
$14,800,000
2 Beds ⋅ 2 Baths ⋅ ML82064344 MLS
One of the most premier locations in Central Woodside! Within walking distance to the Town Center shops & restaurants and highly acclaimed Woodside Elementary K-8. This exceptional property is nestled on just over 4 acres (175,977sf) offering a rare combination of privacy with lovely views of the western hills. A private oasis, consisting of 3 separate cottages, offers a unique opportunity for a builder or developer to generate rental income while plans are designed and construction is underway. Located in one of the worlds most exclusive zip codes, nearby Venture Capital hub Sandhill Road, Stanford University & Silicon Valley. Set amid the natural beauty of Woodside, enjoy all of the renowned hiking, biking and horseback trails that make Woodside such a special place. Easy access to major commuter routes 280, 92 and 101 This is a rare opportunity to create a private estate!

388 Albion Avenue, Woodside

775 W California Way, Woodside
$4,850,000
4 Beds ⋅ 3 Baths ⋅ ML82063093 MLS
775 West California Way is calling you home! Located in the highly regarded Woodside School District and ideally situated near Woodside Town Center, this meticulously maintained retreat has been loved by the same family for more than 50 years. Set on nearly an acre, this approx. 3,060 sq ft oasis offers 4 bedrooms, 2.5 baths, oversized garage space, abundant storage and an expansive lower-level bonus room with separate entrance. Natural light and gleaming hardwood floors fill the formal living room, dining room and family room. Create memorable meals with a Wolf cooktop, host holiday gatherings, or spend summer days around the beautiful pool. Enjoy the charm of Woodside with local favorites including Roberts Market, Roberts Hardware, Bucks Restaurant, The Village Bakery and The Village Pub nearby. Private yet convenient to San Francisco and Silicon Valley, this is more than a house - it's a place to make memories and call home!

775 W California Way, Woodside

25 Corto Lane, Woodside
$4,850,000
3 Beds ⋅ 3 Baths ⋅ ML82062831 MLS
Rarely available flat lot and ideally located close to Woodside Town Center, this inviting single-level ranch-style home combines timeless appeal with exceptional flexibility and private outdoor living. A welcoming front porch and newly refreshed interiors. The spacious living and dining room combination is anchored by a gas fireplace, creating an inviting setting for both everyday living and entertaining. The bright kitchen features white-painted cabinetry, granite countertops, a tumbled stone backsplash, and stainless-steel appliances, including dual ovens and a Bosch refrigerator. A skylight brings in abundant natural light, while a walk-in pantry provides excellent storage. The adjoining breakfast area opens directly to the rear grounds, where the stone patio, low stone detailed seating walls, and expansive level lawn create a private, sun-filled setting for outdoor enjoyment. Three bedrooms are located together, including the primary suite with views of the backyard, while two additional rooms and half bath in a separate wing offer tremendous versatility for a dedicated office, gym, recreation room, or other lifestyle needs. Just minutes from Roberts Market, Woodside Town Center, and Highway 280, the home also enjoys access to acclaimed Woodside Elementary School.

25 Corto Lane, Woodside

63 Ridge Court, Woodside
$3,489,000
4 Beds ⋅ 3 Baths ⋅ ML82062642 MLS
Beautifully updated interiors & striking architectural character define this exceptional home in the Glens newly built in 2007. Tucked away at the end of a peaceful cul-de-sac just one mile from the Woodside town shopping & acclaimed restaurants as well as the highly rated TK-8 Woodside Elementary school. Framed by custom Corten-style fencing, terraced gardens, & underground utilities rarely found in this neighborhood, the property presents an added sense of privacy & refinement. Freshly painted interiors & hardwood floors introduce warm, inviting spaces filled with natural light. Original architectural details are 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. Flexible floor plan, spacious primary suite with fireplace, customized walk-in closet, & newly finished bath. There is also expansion & ADU potential (subject to Town approval & applicable development standards). Fully fenced front & rear yard offer expansive areas for entertaining & relaxation with a level rear lawn, expansive deck, paver stone terrace, & large spa, all in a tranquil park-like setting.

63 Ridge Court, Woodside

411 Glenwood Avenue, Woodside
$3,389,000
3 Beds ⋅ 2 Baths ⋅ ML82059026 MLS
There is a particular quiet at 411 Glenwood Avenue. Stand on the main level and look through walls of glass. The first thing you notice is the treetops. The second is what you do not see: neighbors. The Oak canopy and the open expanse of the Joan Olson Preserve fill the windows instead. Friends who visit call it the Treehouse. Built in 1959, the home keeps its mid-century bones: mahogany paneling, a brick fireplace, and warm cork and hardwood floors. The kitchen opens to the great room, with stone counters and a gas cooktop. Walls of glass open onto a broad deck for slow dinners, the preserve as backdrop. Upstairs, the bedrooms share that same treetop view. Downstairs adds real flexibility: an open room with a slider to a flat, green yard, suited to an office or playroom, an en suite bedroom with its own patio, plus laundry and storage. Cross the street and you are on a trailhead into the preserve, a shortcut into downtown Woodside on foot, coffee in hand, oaks the whole way. Downtown, with the Village Bakery, Buck's, and Highway 280, is minutes out. The home sits within the highly rated Woodside Elementary School District, TK - 8. 411 Glenwood does not ask you to choose between nature and convenience. It offers both, as the best Woodside properties do.

411 Glenwood Avenue, Woodside

103 Toyon Court, Woodside
$4,950,000
4 Beds ⋅ 4 Baths ⋅ ML82046648 MLS
More than one-third acre creates an exceptional setting for this spacious home with 4 bedrooms, 3.5 baths, and multiple living areas designed for today. There are formal living and dining rooms, a designer kitchen with Carrara marble finishes and wine bar, a welcoming family room, a lower-level recreation and media room, and a private bedroom with its own entrance and adjacent bath that is ideal for guests or office use. The primary suite is privately located and features a steam shower and jetted tub. Outdoor living is equally inviting with an arbor-covered deck, newly planted lawns, terraced gardens, play area, and raised vegetable beds. Located on a cul-de-sac street less than one mile from the Woodside town center and served by renowned Woodside Elementary School (TK-8). Additional highlights include abundant storage, optional RV parking with hookups, and refreshed landscaping throughout.

103 Toyon Court, Woodside

235 Hillside Drive, Woodside
$2,150,000
3 Beds ⋅ 2 Baths ⋅ ML82032924 MLS
BEST VALUE IN WOODSIDE!! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. The nearly 0.5 acre lot features abundant, 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.

235 Hillside Drive, Woodside

309 Olive Hill Lane, Woodside
$11,000,000
2 Beds ⋅ 4 Baths ⋅ ML82039836 MLS
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.

309 Olive Hill Lane, Woodside

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All measurements and all calculations of area (i.e., Sq Ft and Acreage) are approximate. Broker has represented to MetroList that Broker has a valid listing signed by seller authorizing placement in the MLS. Above information is provided by Seller and/or other sources and has not been verified by Broker. Copyright 2026 MetroList Services, Inc. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of MetroList® MLS. All information has been provided by seller/other sources and has not been verified by broker. All interested persons should independently verify the accuracy of all information. Last updated .

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