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$2,995,000

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 Terrace, Woodside

$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 Avenue, Woodside

$3,575,000

Move in today, expand tomorrow. Nearly one-half acre of level land less than one-half mile from the Woodside town center. Fresh paint, refinished hardwood floors, and numerous updates make the home ready to enjoy, while the expansive property presents exceptional opportunities for future expansion or building new. The home has 3 bedrooms, 2 baths, an updated kitchen, living room with fireplace, attached 2-car garage, energy-efficient heat pump for heating and cooling, updated electrical service, and EV charging. Just down the street from renowned Woodside Elementary School (TK-8).

3 Beds ⋅ 2 Baths ⋅ ML82050810 MLS

Move in today, expand tomorrow. Nearly one-half acre of level land less than one-half mile from the Woodside town center. Fresh paint, refinished hardwood floors, and numerous updates make the home ready to enjoy, while the expansive property presents exceptional opportunities for future expansion or building new. The home has 3 bedrooms, 2 baths, an updated kitchen, living room with fireplace, attached 2-car garage, energy-efficient heat pump for heating and cooling, updated electrical service, and EV charging. Just down the street from renowned Woodside Elementary School (TK-8).

3270 Woodside Road, Woodside

$5,495,000

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 Court, Woodside

$34,995,000

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.

8 Beds ⋅ 7 Baths ⋅ ML82038776 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

$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 Drive, Woodside

$11,000,000

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.

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

$599,000

Build your dream home on this exceptional 1.2+ acre lot in the prestigious town of Woodside. Surrounded by open space and scenic parks, the property offers direct access to miles of trails perfect for hiking, biking, and horseback riding embracing the true Woodside lifestyle. Ideally located near Interstate 280, youll enjoy convenient access north to San Francisco and south to Silicon Valley, all while returning home to a peaceful, private setting. Just minutes from Woodside Town Center, Roberts Market, and award-winning Woodside Elementary School, this is a rare opportunity to create a custom estate in one of the Peninsulas most sought-after communities.

ML82036894 MLS

Build your dream home on this exceptional 1.2+ acre lot in the prestigious town of Woodside. Surrounded by open space and scenic parks, the property offers direct access to miles of trails perfect for hiking, biking, and horseback riding embracing the true Woodside lifestyle. Ideally located near Interstate 280, youll enjoy convenient access north to San Francisco and south to Silicon Valley, all while returning home to a peaceful, private setting. Just minutes from Woodside Town Center, Roberts Market, and award-winning Woodside Elementary School, this is a rare opportunity to create a custom estate in one of the Peninsulas most sought-after communities.

559 Patrol Road, Woodside

$3,088,000

SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase | 4 levels of destinations inspire your finishing details | Library off the lobby | Two Enormous Primary Suites (one main level, one upstairs) | Multiple Offices | Immense walk-in closets | Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest | Flat rear grounds inspire a future pool & ADU | Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage | Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.

4 Beds ⋅ 8 Baths ⋅ ML82017325 MLS

SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase | 4 levels of destinations inspire your finishing details | Library off the lobby | Two Enormous Primary Suites (one main level, one upstairs) | Multiple Offices | Immense walk-in closets | Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest | Flat rear grounds inspire a future pool & ADU | Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage | Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.

1 Reids Roost Road, Woodside

$1,575,000

Architectural design takes advantage of expansive views of the western hills from most rooms. The front garden area of the property was carefully designed to create an expansive flat area for entertaining and gardening. Abundant parking onsite which includes a 2 car garage, a 3 car uncovered off street parking area, plus 2 parking spaces along the street. In addition to the main house is a self-contained ADU which can serve for extended family or as a rental unit. A rare opportunity on a large scenic lot presents a great opportunity to create a brand-new beautiful home in central Woodside with a private setting. Close to the heart of Silicon Valley and just minutes to Stanford shopping and medical center. Award winning Woodside Schools are a short walk from the site as well as restaurants and shopping in the Village of Woodside. 3615 total sq. ft. consisting of 3,175 livable & 440 garage. All public utilities available.

ML81968553 MLS

Architectural design takes advantage of expansive views of the western hills from most rooms. The front garden area of the property was carefully designed to create an expansive flat area for entertaining and gardening. Abundant parking onsite which includes a 2 car garage, a 3 car uncovered off street parking area, plus 2 parking spaces along the street. In addition to the main house is a self-contained ADU which can serve for extended family or as a rental unit. A rare opportunity on a large scenic lot presents a great opportunity to create a brand-new beautiful home in central Woodside with a private setting. Close to the heart of Silicon Valley and just minutes to Stanford shopping and medical center. Award winning Woodside Schools are a short walk from the site as well as restaurants and shopping in the Village of Woodside. 3615 total sq. ft. consisting of 3,175 livable & 440 garage. All public utilities available.

221 Highland Terrace, Woodside