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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

$4,850,000

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.

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 LN, Woodside

Listed by Judy Citron, 650-400-8424 from Compass
(If provided) CoList: Talia Citron from Compass

$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

$3,350,000

Set on approximately one-third acre in a serene Woodside setting, 232 Highland Terrace offers privacy, distinctive architecture, and exceptional indoor/outdoor living. Mature trees frame beautifully landscaped grounds with roses and fruit trees, while expansive patios and decks capture western hill views. The updated residence is rich in character, with wide-plank hardwood floors, a soaring paneled and skylit cathedral ceiling, hand-painted tilework, a distinctive pressed-metal ceiling, and French and Dutch doors opening outdoors. Just off the foyer is an office or playroom with multiple windows and mini-split ceiling HVAC. The primary suite features a steam shower and private deck with recessed spa. An authentic-style Japanese tea house, secluded koi pond, outdoor shower, and detached studio with bath provide flexible spaces for guests, work, wellness, or creative pursuits. Plans for an expansion of the main residence have been submitted to the Town of Woodside and remain active through approximately February 2027, offering the opportunity to further enhance the property. Just minutes from Woodside Town Center and acclaimed Woodside Elementary School, this distinctive property combines privacy, character, flexibility, and convenience.

4 Beds ⋅ 3 Baths ⋅ ML82060102 MLS

Set on approximately one-third acre in a serene Woodside setting, 232 Highland Terrace offers privacy, distinctive architecture, and exceptional indoor/outdoor living. Mature trees frame beautifully landscaped grounds with roses and fruit trees, while expansive patios and decks capture western hill views. The updated residence is rich in character, with wide-plank hardwood floors, a soaring paneled and skylit cathedral ceiling, hand-painted tilework, a distinctive pressed-metal ceiling, and French and Dutch doors opening outdoors. Just off the foyer is an office or playroom with multiple windows and mini-split ceiling HVAC. The primary suite features a steam shower and private deck with recessed spa. An authentic-style Japanese tea house, secluded koi pond, outdoor shower, and detached studio with bath provide flexible spaces for guests, work, wellness, or creative pursuits. Plans for an expansion of the main residence have been submitted to the Town of Woodside and remain active through approximately February 2027, offering the opportunity to further enhance the property. Just minutes from Woodside Town Center and acclaimed Woodside Elementary School, this distinctive property combines privacy, character, flexibility, and convenience.

232 Highland TER, Woodside

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

Sold listing courtesy of Helen Miller from APR

$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

$4,625,000

Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

4 Beds ⋅ 4 Baths ⋅ ML82051662 MLS

Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

144 Alta Mesa RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Joan Cattermole from APR

$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

$4,500,000

Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a quiet part of the sought-after Woodside Glens neighborhood, features a host of thoughtful upgrades by long time owners. They created a floor plan which showcases views from nearly every room and which, with its ipe hardwood spacious rear decks, presents a host of seamlessly flowing indoor/outdoor entertainment options. All new appliances were added in the chefs kitchen, the hardwood floors were recently refinished, new dual paned windows installed, high end finishes and touches were made throughout and the outside grounds sport attractive low maintenance, water-conserving plantings. Designed around light and nature, the home currently has three bedrooms on the main level and a lower level with an expansive family room and adjacent primary suite, all of which provide a range of configuration alternatives for home office, workout or entertainment setups. Come see this amazing home!

4 Beds ⋅ 4 Baths ⋅ ML82041987 MLS

Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a quiet part of the sought-after Woodside Glens neighborhood, features a host of thoughtful upgrades by long time owners. They created a floor plan which showcases views from nearly every room and which, with its ipe hardwood spacious rear decks, presents a host of seamlessly flowing indoor/outdoor entertainment options. All new appliances were added in the chefs kitchen, the hardwood floors were recently refinished, new dual paned windows installed, high end finishes and touches were made throughout and the outside grounds sport attractive low maintenance, water-conserving plantings. Designed around light and nature, the home currently has three bedrooms on the main level and a lower level with an expansive family room and adjacent primary suite, all of which provide a range of configuration alternatives for home office, workout or entertainment setups. Come see this amazing home!

175 Alta Mesa RD, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Lucy Goldenshteyn from RDFIN

$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

$2,925,000

Discover a blend of charm and modern living in this beautifully updated Woodside home, nestled beneath a canopy of majestic oak trees. Originally built as a summer cottage in 1927, this 3-bedroom, 2-bathroom residence has been thoughtfully expanded and renovated while preserving its vintage character. The heart of the home features a recently remodeled kitchen designed for both everyday living and entertaining. Natural light pours through skylights and a large sliding door that opens to a private patio, seamlessly connecting indoor and outdoor spaces. The dining room showcases a wall of windows framing views of the lush yard and filtered sunlight through the surrounding oaks. A private primary retreat, completed in 2017 with foundation and seismic retrofitting, offers a peaceful sanctuary with luxurious appointments and imported stone floors. A standout feature is the fully equipped guest house with its own kitchen and full bathroom, perfect for extended family, guests, a home office, or rental income potential. Located in the desirable Woodside Glens neighborhood, this home offers exceptional proximity to downtown Woodside and Woodside Elementary School. Roberts Market, charming cafés, and local favorites are just a short stroll away.

3 Beds ⋅ 2 Baths ⋅ ML82032025 MLS

Discover a blend of charm and modern living in this beautifully updated Woodside home, nestled beneath a canopy of majestic oak trees. Originally built as a summer cottage in 1927, this 3-bedroom, 2-bathroom residence has been thoughtfully expanded and renovated while preserving its vintage character. The heart of the home features a recently remodeled kitchen designed for both everyday living and entertaining. Natural light pours through skylights and a large sliding door that opens to a private patio, seamlessly connecting indoor and outdoor spaces. The dining room showcases a wall of windows framing views of the lush yard and filtered sunlight through the surrounding oaks. A private primary retreat, completed in 2017 with foundation and seismic retrofitting, offers a peaceful sanctuary with luxurious appointments and imported stone floors. A standout feature is the fully equipped guest house with its own kitchen and full bathroom, perfect for extended family, guests, a home office, or rental income potential. Located in the desirable Woodside Glens neighborhood, this home offers exceptional proximity to downtown Woodside and Woodside Elementary School. Roberts Market, charming cafés, and local favorites are just a short stroll away.

240 Glenwood AVE, Woodside

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

Sold listing courtesy of John Shroyer from TODAY

$2,718,000

Set on a rare 3-parcel, 0.43-acre lot, this one-of-a-kind Woodside property blends timeless character with modern updates in one of the areas most coveted neighborhoods. Surrounded by mature oaks and breathtaking foothill views, it offers the perfect balance of privacy, nature, and conveniencejust minutes from scenic trails, open space preserves, major freeways, and vibrant downtown Woodside. Originally built in the 1920s, the home exudes classic charm while showcasing thoughtful renovations, including a beautifully updated kitchen, fresh interior paint, and a versatile lower-level guest or bonus suite. Vaulted wood-beamed ceilings add warmth and character to the main living areas, complemented by a formal dining room and multiple flex-use rooms that can serve as offices, guest quarters, or creative spaces. On the first floor, you'll find a full bathroom, bonus living or guest area, plus a bonus room ideal for storage, a home workshop, or future expansion. With over 2,400 sq. ft. of living space, this flexible layout offers endless potential for customization and growth. Offering an exceptional opportunity, this property is perfect for builders, investors, or those dreaming of creating their own Woodside retreat.

3 Beds ⋅ 2 Baths ⋅ ML82026774 MLS

Set on a rare 3-parcel, 0.43-acre lot, this one-of-a-kind Woodside property blends timeless character with modern updates in one of the areas most coveted neighborhoods. Surrounded by mature oaks and breathtaking foothill views, it offers the perfect balance of privacy, nature, and conveniencejust minutes from scenic trails, open space preserves, major freeways, and vibrant downtown Woodside. Originally built in the 1920s, the home exudes classic charm while showcasing thoughtful renovations, including a beautifully updated kitchen, fresh interior paint, and a versatile lower-level guest or bonus suite. Vaulted wood-beamed ceilings add warmth and character to the main living areas, complemented by a formal dining room and multiple flex-use rooms that can serve as offices, guest quarters, or creative spaces. On the first floor, you'll find a full bathroom, bonus living or guest area, plus a bonus room ideal for storage, a home workshop, or future expansion. With over 2,400 sq. ft. of living space, this flexible layout offers endless potential for customization and growth. Offering an exceptional opportunity, this property is perfect for builders, investors, or those dreaming of creating their own Woodside retreat.

112 Highland TER, Woodside

Listed by Sammi Moser-Wingo, 408-857-2026 from The Agency
(If provided) CoList: Donald Moser from The Agency

Sold listing courtesy of Lilly Tamayo from NTERO

$3,800,000

A Six-Bedroom Modern Masterpiece in Woodside Glens. Discover a stunning 2024 reimagined home where modern design meets family functionality just one mile from Woodside Town Center. This 6-bedroom, 3-bath smart home offers 3,087 sq. ft. of beautifully expanded and remodeled living space on a ~7,000 sq. ft. flat lot. The dramatic entry with custom iron and glass doors opens to airy, vaulted living spaces and a great room with a sleek all-white kitchen featuring quartz counters and Bosch appliances. The flexible layout includes a lower-level wing with two bedrooms, an office, laundry, and a rec room opening to the terrace ideal for guests, work, or play. Upstairs, the private primary suite offers skylit ceilings, a spa-like bath, and a balcony with western hill views. Smart-home systems, whole-home audio, three-zone heat pump climate control, and full fire sprinklers ensure comfort and peace of mind. Outdoor living shines with an expansive terrace, full outdoor kitchen, and RV hookups. Located in the acclaimed Woodside Elementary School District.

6 Beds ⋅ 3 Baths ⋅ ML82022347 MLS

A Six-Bedroom Modern Masterpiece in Woodside Glens. Discover a stunning 2024 reimagined home where modern design meets family functionality just one mile from Woodside Town Center. This 6-bedroom, 3-bath smart home offers 3,087 sq. ft. of beautifully expanded and remodeled living space on a ~7,000 sq. ft. flat lot. The dramatic entry with custom iron and glass doors opens to airy, vaulted living spaces and a great room with a sleek all-white kitchen featuring quartz counters and Bosch appliances. The flexible layout includes a lower-level wing with two bedrooms, an office, laundry, and a rec room opening to the terrace ideal for guests, work, or play. Upstairs, the private primary suite offers skylit ceilings, a spa-like bath, and a balcony with western hill views. Smart-home systems, whole-home audio, three-zone heat pump climate control, and full fire sprinklers ensure comfort and peace of mind. Outdoor living shines with an expansive terrace, full outdoor kitchen, and RV hookups. Located in the acclaimed Woodside Elementary School District.

118 Hillside DR, Woodside

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

Sold listing courtesy of Michael R. Perrelli from CBR

$2,750,000

APPROVED PLANS AND PERMITS PULLED. 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. Over 4,415 total square feet with 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. Listing photos of the home are renderings only, there is not currently a home on this lot. Potential for approximately 4,415 total sq ft || main house : 3 bd, 2.5 ba, 3,475 sq ft | adu 500 sf | 440 sq ft 2 car garage. 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.

ML82020559 MLS

APPROVED PLANS AND PERMITS PULLED. 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. Over 4,415 total square feet with 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. Listing photos of the home are renderings only, there is not currently a home on this lot. Potential for approximately 4,415 total sq ft || main house : 3 bd, 2.5 ba, 3,475 sq ft | adu 500 sf | 440 sq ft 2 car garage. 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.

152 Alta Mesa RD, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Glenn Sennett from CBR

$3,500,000

Custom built in 1992 on one of the largest parcels in the area. Over 14,000 sq. foot lot. On the market for the first time! Sweeping western hill views, close-in convenience, plus pool and spa. A dramatic great room with soaring two-story ceiling, arched clerestory windows, and skylights highlights the open floor plan that connects living, dining, and kitchen areas to a spacious view deck. 4 bedrooms and an office are arranged across 3 levels, including a main-level primary bedroom with adjoining bath and bedroom ideal for office or nursery. The upper level has a office and skylit loft lounge, while the lower level has two bedrooms, a full bath, and recreation room with refreshment bar opening to the pool deck. Outdoor amenities include a large above-ground pool surrounded with vast decking for entertaining space plus a separate spa. All just minutes to Town Center, hiking trails, and acclaimed Woodside School. Room to add an ADU.

4 Beds ⋅ 3 Baths ⋅ ML82020106 MLS

Custom built in 1992 on one of the largest parcels in the area. Over 14,000 sq. foot lot. On the market for the first time! Sweeping western hill views, close-in convenience, plus pool and spa. A dramatic great room with soaring two-story ceiling, arched clerestory windows, and skylights highlights the open floor plan that connects living, dining, and kitchen areas to a spacious view deck. 4 bedrooms and an office are arranged across 3 levels, including a main-level primary bedroom with adjoining bath and bedroom ideal for office or nursery. The upper level has a office and skylit loft lounge, while the lower level has two bedrooms, a full bath, and recreation room with refreshment bar opening to the pool deck. Outdoor amenities include a large above-ground pool surrounded with vast decking for entertaining space plus a separate spa. All just minutes to Town Center, hiking trails, and acclaimed Woodside School. Room to add an ADU.

129 Hillside DR, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Cliff Whearley from WRLY

$3,800,000

Great cul-de-sac location, this sunny, designer-updated home is as charming as it is comfortable. Just minutes from downtown Woodside and top-rated K-8 Woodside School, this location in the Glens is coveted. Step inside to discover the main level, featuring three bedrooms, including two with en-suite baths. The primary suite is a peaceful sanctuary with a generous footprint, sitting area, and direct access to the deck. A third full bath accommodates guests and the third bedroom. The heart of the home is open-concept, with a family room that flows seamlessly into an updated kitchen. Flow into the formal dining room and the inviting living room, where picture windows, custom built-ins, and one of two elegant stone fireplaces create a welcoming atmosphere. Step outside onto the expansive deck for effortless indoor-outdoor living and entertaining. Downstairs, discover a flexible fourth bedroom that can also serve as a home office or bonus room. With exposed beam ceilings, French doors leading to a private patio and fire pit, this may become your favorite space. A separate laundry room and two-car garage add functionality. The landscaped, tiered, and fenced backyard is perfect for entertaining, playing, or enjoying the serene natural surroundings.

4 Beds ⋅ 3 Baths ⋅ ML82019068 MLS

Great cul-de-sac location, this sunny, designer-updated home is as charming as it is comfortable. Just minutes from downtown Woodside and top-rated K-8 Woodside School, this location in the Glens is coveted. Step inside to discover the main level, featuring three bedrooms, including two with en-suite baths. The primary suite is a peaceful sanctuary with a generous footprint, sitting area, and direct access to the deck. A third full bath accommodates guests and the third bedroom. The heart of the home is open-concept, with a family room that flows seamlessly into an updated kitchen. Flow into the formal dining room and the inviting living room, where picture windows, custom built-ins, and one of two elegant stone fireplaces create a welcoming atmosphere. Step outside onto the expansive deck for effortless indoor-outdoor living and entertaining. Downstairs, discover a flexible fourth bedroom that can also serve as a home office or bonus room. With exposed beam ceilings, French doors leading to a private patio and fire pit, this may become your favorite space. A separate laundry room and two-car garage add functionality. The landscaped, tiered, and fenced backyard is perfect for entertaining, playing, or enjoying the serene natural surroundings.

115 Toyon CT, Woodside

Listed by Kimberly Hansen, 415-806-8230 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Ginna Lazar from LHG

$2,450,000

Welcome to this stunning 3-bedroom, 2-bathroom home located in the beautiful Woodside Glens! The Living Room, which features expansive windows and a large skylight brings the beautiful surroundings indoors, is a true standout in this very comfortable and stylish home. Far from the average Silicon Valley Ranch Style home, this home envelopes you in natural surroundings while just being minutes away from the many conveniences and attractions of the area. Many recent upgrades such as a 5.6KW Solar PV System, High Efficiency Heat Pump systems for both Hot Water and comfortable Heating & Cooling, Renovated Kitchen and Bathrooms, Dual Pane Windows, thoughtful lighting and durable flooring create a move-in ready home that you will be both excited and proud to call yours. Large common areas, privacy, and ensuite bedrooms on both floors create a very flexible and useful floorplan. The grounds are inviting with a small greenhouse, a seasonal creek and blossoms abounding - Very special indeed! A spacious utility room, a two car garage featuring TWO Level 2 EV car chargers, plus a carport round out the features. Near Stanford University, the superb Roberts Market, as well as major Silicon Valley employers and excellent recreational opportunities for hiking, cycling or equestrians.

3 Beds ⋅ 2 Baths ⋅ ML81996224 MLS

Welcome to this stunning 3-bedroom, 2-bathroom home located in the beautiful Woodside Glens! The Living Room, which features expansive windows and a large skylight brings the beautiful surroundings indoors, is a true standout in this very comfortable and stylish home. Far from the average Silicon Valley Ranch Style home, this home envelopes you in natural surroundings while just being minutes away from the many conveniences and attractions of the area. Many recent upgrades such as a 5.6KW Solar PV System, High Efficiency Heat Pump systems for both Hot Water and comfortable Heating & Cooling, Renovated Kitchen and Bathrooms, Dual Pane Windows, thoughtful lighting and durable flooring create a move-in ready home that you will be both excited and proud to call yours. Large common areas, privacy, and ensuite bedrooms on both floors create a very flexible and useful floorplan. The grounds are inviting with a small greenhouse, a seasonal creek and blossoms abounding - Very special indeed! A spacious utility room, a two car garage featuring TWO Level 2 EV car chargers, plus a carport round out the features. Near Stanford University, the superb Roberts Market, as well as major Silicon Valley employers and excellent recreational opportunities for hiking, cycling or equestrians.

150 Otis AVE, Woodside

Listed by Dave Keefe Team, 650-887-3721 from Action Properties Inc
(If provided) CoList: from

Sold listing courtesy of Daniel Assadi from COMPS

$2,450,000

Price reduced! Come see this wonderfully updated 4 BR/2 BA charming home in Central Woodside located in a private setting within walking distance to Town Center shops, restaurants and acclaimed Woodside School (pre-K to 8th). The home is situated on a quiet cul-de-sac in the Woodside Glens neighborhood which now features new safe walking paths throughout and is steps away from the extensive open space trail system leading to nearby Kite Hill; Entry level floor plan is designed for entertaining and includes an upgraded kitchen with new Bosch appliances and custom cabinetry, adjacent living & dining rooms, gas-burning fireplace; 2 upper bedrooms double as family room or office; Dutch door leading to 1,090 sf of sunny rear decks; The additional level features recently upgraded primary suite with sliding door to the lower deck and stairway to the fully fenced rear yard with recently installed turf and nearby seasonal creek; a fourth bedroom and laundry room are also on the lower level; the current owner made full upgrades to the kitchen and primary suite and they added a new HVAC system, a new water heater, hardwood flooring throughout lower level, and completed a major foundation upgrade, along with an extensive driveway improvement to provide parking for four cars

4 Beds ⋅ 2 Baths ⋅ ML81995189 MLS

Price reduced! Come see this wonderfully updated 4 BR/2 BA charming home in Central Woodside located in a private setting within walking distance to Town Center shops, restaurants and acclaimed Woodside School (pre-K to 8th). The home is situated on a quiet cul-de-sac in the Woodside Glens neighborhood which now features new safe walking paths throughout and is steps away from the extensive open space trail system leading to nearby Kite Hill; Entry level floor plan is designed for entertaining and includes an upgraded kitchen with new Bosch appliances and custom cabinetry, adjacent living & dining rooms, gas-burning fireplace; 2 upper bedrooms double as family room or office; Dutch door leading to 1,090 sf of sunny rear decks; The additional level features recently upgraded primary suite with sliding door to the lower deck and stairway to the fully fenced rear yard with recently installed turf and nearby seasonal creek; a fourth bedroom and laundry room are also on the lower level; the current owner made full upgrades to the kitchen and primary suite and they added a new HVAC system, a new water heater, hardwood flooring throughout lower level, and completed a major foundation upgrade, along with an extensive driveway improvement to provide parking for four cars

136 Otis AVE, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Debbie Burness from SHGM18

$3,850,000

Updated and renovated, this home is ideally located opposite the picturesque Kite Hill permanent open space. Introducing the home is a spacious great room that encompasses a living room, with modern stone gas fireplace, and a step-down seating area with an impressive wall-to-wall window view of the rock and cactus garden. Adjacent to this is a formal dining room and newly remodeled kitchen with quartz counters and all new stainless steel appliances. There are 4 bedrooms and 2 baths plus a detached bonus room ideal for today's remote office, or for a game room or fitness center. Outside, are sun-drenched spaces, a stunning rock and cactus garden complete with pathways and a seating area, plus a private rear garden with large deck for entertaining around the sparkling pool. Adding the finishing touch is this homes access to the highly regarded Woodside School (K-8) and proximity to the Woodside Village.

4 Beds ⋅ 2 Baths ⋅ ML81992626 MLS

Updated and renovated, this home is ideally located opposite the picturesque Kite Hill permanent open space. Introducing the home is a spacious great room that encompasses a living room, with modern stone gas fireplace, and a step-down seating area with an impressive wall-to-wall window view of the rock and cactus garden. Adjacent to this is a formal dining room and newly remodeled kitchen with quartz counters and all new stainless steel appliances. There are 4 bedrooms and 2 baths plus a detached bonus room ideal for today's remote office, or for a game room or fitness center. Outside, are sun-drenched spaces, a stunning rock and cactus garden complete with pathways and a seating area, plus a private rear garden with large deck for entertaining around the sparkling pool. Adding the finishing touch is this homes access to the highly regarded Woodside School (K-8) and proximity to the Woodside Village.

160 Alta Mesa RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Afsoon Shahrdar from TODAY

$2,900,000

New Price! Here is your chance to build your dream home in Central Woodside in a premier location, only a walk away from Woodside Town Center shops, restaurants and the acclaimed Woodside School (pre-K to 8th). Dream home concept renderings presented by Steve Simpson of SDG Architecture. This exceptional approximately 20,125 sq ft (.5 acre) flat vacant lot is in a sought-after location on a quiet cul-de-sac close to the entrance to the Woodside Glens neighborhood. Utility connections are in place and buyers can consult with the Town of Woodside Planning Department to confirm the allowable specifications for a new home and any accessory dwelling units. Seller is offering concessions.

ML81977285 MLS

New Price! Here is your chance to build your dream home in Central Woodside in a premier location, only a walk away from Woodside Town Center shops, restaurants and the acclaimed Woodside School (pre-K to 8th). Dream home concept renderings presented by Steve Simpson of SDG Architecture. This exceptional approximately 20,125 sq ft (.5 acre) flat vacant lot is in a sought-after location on a quiet cul-de-sac close to the entrance to the Woodside Glens neighborhood. Utility connections are in place and buyers can consult with the Town of Woodside Planning Department to confirm the allowable specifications for a new home and any accessory dwelling units. Seller is offering concessions.

128 Toyon CT, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Nathalie D.S.A from SGP

$5,000,000

This home has it all with close-in Woodside Glens convenience, entirely rebuilt luxury, and a glorious setting with over one-third acre of level grounds and Western hill views. Authentic Craftsman style is exemplified by peaked rooflines and a series of classic tapered columns that wrap around the inviting covered porch. Designed for seamless indoor/outdoor living, the setting is remarkable, featuring fully usable grounds for leisure, sports, and wellness in complete privacy. Rebuilt from the ground up in 2011, this two-story home exudes classic elegance with hardwood and travertine floors, refined millwork, and an expansive great room alongside a formal living room. Personal accommodations include 4 bedrooms, an office, plus 3.5 baths. On the main level, two bedrooms share a bath, while the primary and secondary suites are located upstairs. Bathrooms are beautifully appointed, each with fixed rain and hand-held sprays, and the primary suite includes the added luxury of heated floors. Additional highlights encompass owned solar panels, a rare attached 3-car garage, and potential for a pool and Accessory Dwelling Unit. The home's proximity to the town center and acclaimed Woodside School completes the picture.

4 Beds ⋅ 4 Baths ⋅ ML81973117 MLS

This home has it all with close-in Woodside Glens convenience, entirely rebuilt luxury, and a glorious setting with over one-third acre of level grounds and Western hill views. Authentic Craftsman style is exemplified by peaked rooflines and a series of classic tapered columns that wrap around the inviting covered porch. Designed for seamless indoor/outdoor living, the setting is remarkable, featuring fully usable grounds for leisure, sports, and wellness in complete privacy. Rebuilt from the ground up in 2011, this two-story home exudes classic elegance with hardwood and travertine floors, refined millwork, and an expansive great room alongside a formal living room. Personal accommodations include 4 bedrooms, an office, plus 3.5 baths. On the main level, two bedrooms share a bath, while the primary and secondary suites are located upstairs. Bathrooms are beautifully appointed, each with fixed rain and hand-held sprays, and the primary suite includes the added luxury of heated floors. Additional highlights encompass owned solar panels, a rare attached 3-car garage, and potential for a pool and Accessory Dwelling Unit. The home's proximity to the town center and acclaimed Woodside School completes the picture.

115 Highland TER, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Deborah Kehrberg from APR

$5,200,000

Rare new-build contemporary in Woodside! Designed by Steve Simpson/SDG Architecture and built by Milne Design and Build, both know for attention to detail, this spectacular dream home provides your own private sanctuary. Its total livable area of 3,875 sf, is comprised of a two story 4 BR / 4.5 BA Main Home (approx 3,175 sf) with an artful blend of wood finishes, large windows and dark steel beams. Its main level open floor plan has a large chefs kitchen connected to a light-filled living room and dining area and also features a separate office which can double as the fourth bedroom. A lower level boasts three additional bedrooms, including a large primary suite, walk-in closet, soaking tub, shower and dual sinks and a spacious laundry room. The main home also has a coveted attached two-car garage (approx 465 sf) along with several additional off street parking areas. An adjacent detached two level 1 BR/1BA Guest House (approx 700 sf) has a full kitchen and guest suite, lower bedroom and covered exercise patio, providing perfect optionality for a remote office, hosting visitors or indoor/outdoor exercising. The property is situated on a less traveled one way street within walking distance to Town Center shops, restaurants and the acclaimed Woodside School (pre-K to 8th)

5 Beds ⋅ 6 Baths ⋅ ML81966423 MLS

Rare new-build contemporary in Woodside! Designed by Steve Simpson/SDG Architecture and built by Milne Design and Build, both know for attention to detail, this spectacular dream home provides your own private sanctuary. Its total livable area of 3,875 sf, is comprised of a two story 4 BR / 4.5 BA Main Home (approx 3,175 sf) with an artful blend of wood finishes, large windows and dark steel beams. Its main level open floor plan has a large chefs kitchen connected to a light-filled living room and dining area and also features a separate office which can double as the fourth bedroom. A lower level boasts three additional bedrooms, including a large primary suite, walk-in closet, soaking tub, shower and dual sinks and a spacious laundry room. The main home also has a coveted attached two-car garage (approx 465 sf) along with several additional off street parking areas. An adjacent detached two level 1 BR/1BA Guest House (approx 700 sf) has a full kitchen and guest suite, lower bedroom and covered exercise patio, providing perfect optionality for a remote office, hosting visitors or indoor/outdoor exercising. The property is situated on a less traveled one way street within walking distance to Town Center shops, restaurants and the acclaimed Woodside School (pre-K to 8th)

327 Hillside DR, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Helen Miller from APR

$2,900,000

Great opportunity for a new home on a level lot with views of Kite Hill in Woodside. Over one-third acre of level land looking out to Kite Hill Wildflower Preserve. . Close-in location walk to the town center and acclaimed Woodside Elementary (K-8) School.

ML81942201 MLS

Great opportunity for a new home on a level lot with views of Kite Hill in Woodside. Over one-third acre of level land looking out to Kite Hill Wildflower Preserve. . Close-in location walk to the town center and acclaimed Woodside Elementary (K-8) School.

152 Alta Mesa RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Scott Dancer from APR

$2,000,000

Your own piece of paradise awaits you. Close to the Woodside Village and highly acclaimed Woodside Elementary School K-8. Nestled among oak trees, this Woodside Glens home is tucked away on nearly half an acre overlooking a seasonal creek at the end of a quiet cul-de-sac with access to the Joan Olson Natural Preserve and trails. This move-in ready sunny home features abundant natural light and forest views from every room. The main level has three bedrooms and two bathrooms. The lower level includes rooms for an office, fitness/play space, and laundry. Highlights include hardwood floors, an updated kitchen with stainless steel appliances, dedicated off-street parking, and sunny spaces for flower/vegetable gardens. Enjoy the relaxed California indoor-outdoor lifestyle with a spacious deck off the main living area, with views of the property's seasonal creek and trail. This magical woodland retreat is conveniently located for commutes to SF and Silicon Valley, with 280 just minutes away.

3 Beds ⋅ 2 Baths ⋅ ML81937133 MLS

Your own piece of paradise awaits you. Close to the Woodside Village and highly acclaimed Woodside Elementary School K-8. Nestled among oak trees, this Woodside Glens home is tucked away on nearly half an acre overlooking a seasonal creek at the end of a quiet cul-de-sac with access to the Joan Olson Natural Preserve and trails. This move-in ready sunny home features abundant natural light and forest views from every room. The main level has three bedrooms and two bathrooms. The lower level includes rooms for an office, fitness/play space, and laundry. Highlights include hardwood floors, an updated kitchen with stainless steel appliances, dedicated off-street parking, and sunny spaces for flower/vegetable gardens. Enjoy the relaxed California indoor-outdoor lifestyle with a spacious deck off the main living area, with views of the property's seasonal creek and trail. This magical woodland retreat is conveniently located for commutes to SF and Silicon Valley, with 280 just minutes away.

160 Otis AVE, Woodside

Listed by Erika Demma, 650-888-6558 from Compass
(If provided) CoList: Deborah Kehrberg from Compass

Sold listing courtesy of Michael Warren from COMPS

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