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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.

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 DR, Woodside

Listed by Michael Warren, 650-315-0224 from Compass
(If provided) CoList: from

$3,489,000

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.

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 CT, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

$3,389,000

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.

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 AVE, Woodside

Listed by Chris Iverson, 650-450-0450 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$4,950,000

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.

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 CT, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

$2,150,000

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.

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 DR, Woodside

Listed by Steve Rumberg, 408-981-2383 from Keller Williams Realty-Silicon Valley
(If provided) CoList: from

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