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$4,260,000

Privately positioned on approximately 1.85 acres with unobstructed views of Jasper Ridge Biological Preserve, this custom-built home offers a rare sense of serenity and seclusion just minutes from town. The setting is truly exceptional - vast, mostly level grounds bordered by open sky and native landscape. Designed for indoor/outdoor living, the home features an expansive flagstone terrace and covered front porch, along with a secluded rear terrace and spa - all surrounded by the natural beauty of Woodside and Portola Valley. A striking architectural presence is established with its signature shaped parapet, handcrafted detailing, and richly hued finishes inspired by classic Spanish Revival style. Inside, the warmth continues with red birch floors, wood-paneled cathedral ceilings, and hand-selected tilework from Walker Zanger. Every room captures the views, and the kitchen is appointed for serious cooking with premium appliances, a walk-in pantry with wine storage, and an open connection to the indoor/outdoor dining room. Moments from hiking and biking trails, top-rated schools, and local amenities, this is a home that lives like a country retreat yet remains just minutes from the heart of town and Highway 280.

3 Beds ⋅ 3 Baths ⋅ ML82038786 MLS

Privately positioned on approximately 1.85 acres with unobstructed views of Jasper Ridge Biological Preserve, this custom-built home offers a rare sense of serenity and seclusion just minutes from town. The setting is truly exceptional - vast, mostly level grounds bordered by open sky and native landscape. Designed for indoor/outdoor living, the home features an expansive flagstone terrace and covered front porch, along with a secluded rear terrace and spa - all surrounded by the natural beauty of Woodside and Portola Valley. A striking architectural presence is established with its signature shaped parapet, handcrafted detailing, and richly hued finishes inspired by classic Spanish Revival style. Inside, the warmth continues with red birch floors, wood-paneled cathedral ceilings, and hand-selected tilework from Walker Zanger. Every room captures the views, and the kitchen is appointed for serious cooking with premium appliances, a walk-in pantry with wine storage, and an open connection to the indoor/outdoor dining room. Moments from hiking and biking trails, top-rated schools, and local amenities, this is a home that lives like a country retreat yet remains just minutes from the heart of town and Highway 280.

1439 Portola RD, Woodside

Listed by Kavanaugh Group, 415-377-2924 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of David Kelsey from COMPS

$8,900,000

First time on the market in generations, this rare Woodside property offers a unique opportunity to own a piece of local history. The Victorian home, originally built in 1901 and remodeled in 2010, has remained in the same family for decades and sits on a private 3.4 acre lot, offering potential to split the lot and build your dream home. The home features 4 bedrooms and 2.5 bathrooms, blending classic architectural character with thoughtful updates for comfortable living. The size and location of the property create a distinctive setting that is increasingly rare in Woodside. Ideally located next to Woodside Elementary and just minutes from Woodside Village, with convenient access to Roberts Market, The Village Bakery, Bucks Restaurant, and the Woodside Village Church. A special opportunity offering space, privacy, and historic charm in a highly desirable location.

4 Beds ⋅ 3 Baths ⋅ ML82037417 MLS

First time on the market in generations, this rare Woodside property offers a unique opportunity to own a piece of local history. The Victorian home, originally built in 1901 and remodeled in 2010, has remained in the same family for decades and sits on a private 3.4 acre lot, offering potential to split the lot and build your dream home. The home features 4 bedrooms and 2.5 bathrooms, blending classic architectural character with thoughtful updates for comfortable living. The size and location of the property create a distinctive setting that is increasingly rare in Woodside. Ideally located next to Woodside Elementary and just minutes from Woodside Village, with convenient access to Roberts Market, The Village Bakery, Bucks Restaurant, and the Woodside Village Church. A special opportunity offering space, privacy, and historic charm in a highly desirable location.

3215 Woodside RD, Woodside

Listed by Vivienne Kelvin, 650-291-7241 from Vabrato
(If provided) CoList: Mark Martinho from Vabrato

Sold listing courtesy of Michael Warren from APR

$10,988,000

Set on more than 2.5 acres of quintessential Woodside grounds, this spectacular estate balances timeless elegance with easy comfort. Behind gates and surrounded by mature trees and lush foliage, it conveys a quiet sense of luxurious seclusion. Inside, more than 6,400 total SF includes a dramatic foyer with columns, expansive formal rooms, a chef's kitchen, private office, theater, and five bedrooms, including a sanctuary-like primary suite. Outdoors, resort-style grounds feature a pool, spa, pool house, patio with fireplace and grill, cascading waterfall with bridge, gardens, fruit trees, and a detached bonus studio for work or fitness. Tesla solar panels and 6 Powerwall batteries, a seamless Sonos sound system, and expert craftsmanship enhance every detail. Just minutes from Woodside, Sand Hill Road, Palo Alto, and top schools, it offers the rare blend of privacy, prestige, and proximity.

5 Beds ⋅ 6 Baths ⋅ ML82037743 MLS

Set on more than 2.5 acres of quintessential Woodside grounds, this spectacular estate balances timeless elegance with easy comfort. Behind gates and surrounded by mature trees and lush foliage, it conveys a quiet sense of luxurious seclusion. Inside, more than 6,400 total SF includes a dramatic foyer with columns, expansive formal rooms, a chef's kitchen, private office, theater, and five bedrooms, including a sanctuary-like primary suite. Outdoors, resort-style grounds feature a pool, spa, pool house, patio with fireplace and grill, cascading waterfall with bridge, gardens, fruit trees, and a detached bonus studio for work or fitness. Tesla solar panels and 6 Powerwall batteries, a seamless Sonos sound system, and expert craftsmanship enhance every detail. Just minutes from Woodside, Sand Hill Road, Palo Alto, and top schools, it offers the rare blend of privacy, prestige, and proximity.

160 Phillip RD, Woodside

Listed by DeLeon Team, 650-900-7000 from Deleon Realty
(If provided) CoList: from

$4,295,000

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc countertops. Every bedroom and main living area opens to wraparound decks with sweeping views. Dedicated office for remote work, and a large 2-car garage. Level yard for entertaining, with room for pickle ball court, plus a sunny pool area. Direct walking distance access to scenic hiking on Mid-Pen Open Space trails. Convenient door-to-door bus to top-rated Portola Valley schools.

4 Beds ⋅ 4 Baths ⋅ ML82037717 MLS

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc countertops. Every bedroom and main living area opens to wraparound decks with sweeping views. Dedicated office for remote work, and a large 2-car garage. Level yard for entertaining, with room for pickle ball court, plus a sunny pool area. Direct walking distance access to scenic hiking on Mid-Pen Open Space trails. Convenient door-to-door bus to top-rated Portola Valley schools.

950 Espinosa RD, Woodside

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

$4,000,000

Significant Mid-Century Modern Architecture with Bay Views! Mid-century modern architecture of exceptional pedigree defines this Skywood Acres property designed by renowned furniture maker John Kapel as his own home. Recognized for embodying the distinctive characteristics of mid-century modern design with remarkable artistic value and integrity of workmanship, the home has been featured in numerous publications and described as a masterpiece of artful craftsmanship. A recent renovation honors his original vision while enhancing comfort and energy efficiency for today, including an all-new kitchen and baths, solar panels, three Tesla Powerwalls, and SPAN energy management panels. The home spans 3.16 acres with Bay views and a multi-level floor plan that includes 4 bedrooms, an art studio or playroom, plus a high-end theater and car collectors garage. A separate studio guest house with bath and full kitchen provides added flexibility. Outdoor living spaces are plentiful with a soothing hot tub, heated lounges, and wraparound Bay view decks. This serene location is just one mile from famed Alices Restaurant, 5.5 miles from Woodside town center, and has access to excellent Portola Valley schools.

4 Beds ⋅ 3 Baths ⋅ ML82037542 MLS ⋅ Skywood Acres BLDG.

Significant Mid-Century Modern Architecture with Bay Views! Mid-century modern architecture of exceptional pedigree defines this Skywood Acres property designed by renowned furniture maker John Kapel as his own home. Recognized for embodying the distinctive characteristics of mid-century modern design with remarkable artistic value and integrity of workmanship, the home has been featured in numerous publications and described as a masterpiece of artful craftsmanship. A recent renovation honors his original vision while enhancing comfort and energy efficiency for today, including an all-new kitchen and baths, solar panels, three Tesla Powerwalls, and SPAN energy management panels. The home spans 3.16 acres with Bay views and a multi-level floor plan that includes 4 bedrooms, an art studio or playroom, plus a high-end theater and car collectors garage. A separate studio guest house with bath and full kitchen provides added flexibility. Outdoor living spaces are plentiful with a soothing hot tub, heated lounges, and wraparound Bay view decks. This serene location is just one mile from famed Alices Restaurant, 5.5 miles from Woodside town center, and has access to excellent Portola Valley schools.

80 Skywood WAY, Woodside

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

Sold listing courtesy of Sternsmith Group from APR

$5,750,000

Gorgeous, unobstructed views of the bay and mid-century styling in a private setting in Woodside Hills. Situated on a 1.12-acre lot with 4 spacious bedrooms plus an office and 3 bathrooms, this single level home offers a terrific floor plan. Designed to embrace natural light with dramatic floor-to-ceiling windows and high ceilings that create an airy, open atmosphere while seamlessly connecting indoor and outdoor spaces. The large patio, seen through walls of glass throughout the home, overlooks the views and is the ideal spot for entertaining. The gardens feature mature fruit trees, charming landscaping, spaces for children to play, and a sparkling pool and spa. The 2-car attached garage and additional detached 1-car garage and a generous circular driveway provide ample parking.

4 Beds ⋅ 3 Baths ⋅ ML82037292 MLS

Gorgeous, unobstructed views of the bay and mid-century styling in a private setting in Woodside Hills. Situated on a 1.12-acre lot with 4 spacious bedrooms plus an office and 3 bathrooms, this single level home offers a terrific floor plan. Designed to embrace natural light with dramatic floor-to-ceiling windows and high ceilings that create an airy, open atmosphere while seamlessly connecting indoor and outdoor spaces. The large patio, seen through walls of glass throughout the home, overlooks the views and is the ideal spot for entertaining. The gardens feature mature fruit trees, charming landscaping, spaces for children to play, and a sparkling pool and spa. The 2-car attached garage and additional detached 1-car garage and a generous circular driveway provide ample parking.

51 Cragmont WAY, Woodside

Listed by Monica & Mandy Group, 650-823-8212 from Compass
(If provided) CoList: from

Sold listing courtesy of Judy Citron from COMPS

$2,275,000

A very special home among the trees with peekaboo views towards the ocean. An ideal escape from the bustle just down the hill. The chefs kitchen with center island is open to the spacious family room and breakfast nook. Just outside is an extensive deck and your eyes are drawn out to the natural beauty around. The formal dining room and adjacent living room are light filled with large windows and gracious views. Completing the main floor is a convenient bedroom and nearby full bathroom. Upstairs, the massive primary bedroom has double suite bathrooms, yes, TWO bathrooms attached to the primary. Two additional bedrooms, one decorated as an office/media room, a convenient bathroom with dual sinks, plus the adjacent laundry area with storage round out the second floor. Whether awakening to the mist drifting through the trees or falling asleep listening to the sounds of owls, nature is ever present.

4 Beds ⋅ 4 Baths ⋅ ML82036766 MLS

A very special home among the trees with peekaboo views towards the ocean. An ideal escape from the bustle just down the hill. The chefs kitchen with center island is open to the spacious family room and breakfast nook. Just outside is an extensive deck and your eyes are drawn out to the natural beauty around. The formal dining room and adjacent living room are light filled with large windows and gracious views. Completing the main floor is a convenient bedroom and nearby full bathroom. Upstairs, the massive primary bedroom has double suite bathrooms, yes, TWO bathrooms attached to the primary. Two additional bedrooms, one decorated as an office/media room, a convenient bathroom with dual sinks, plus the adjacent laundry area with storage round out the second floor. Whether awakening to the mist drifting through the trees or falling asleep listening to the sounds of owls, nature is ever present.

6 Megans LN, Woodside

Listed by Janie Barman, 650-759-1182 from Compass
(If provided) CoList: John Barman from Compass

Sold listing courtesy of Alicia Sanguinetti from APR

$10,500,000

Nestled in prime central Woodside, this remarkable estate was designed by Charlie Barnett and includes a modern farmhouse main home accompanied by a guest house and a charming log cabin, all harmonizing beautifully with the areas rural ambiance. Positioned on a level lot with majestic oaks, the estate features a refined, timeless palette with warm gray concrete floors, oak cabinetry, and limestone tile baths that create a sophisticated yet natural feel. French doors open onto surrounding terraces, inviting in soft, filtered light from the surrounding trees, while the perfect Woodside location places you just moments from Woodside Elementary, the library, and nearby shops and restaurants. This is an exceptional opportunity to enjoy life on one of central Woodside's most coveted streets.

5 Beds ⋅ 6 Baths ⋅ ML82035970 MLS

Nestled in prime central Woodside, this remarkable estate was designed by Charlie Barnett and includes a modern farmhouse main home accompanied by a guest house and a charming log cabin, all harmonizing beautifully with the areas rural ambiance. Positioned on a level lot with majestic oaks, the estate features a refined, timeless palette with warm gray concrete floors, oak cabinetry, and limestone tile baths that create a sophisticated yet natural feel. French doors open onto surrounding terraces, inviting in soft, filtered light from the surrounding trees, while the perfect Woodside location places you just moments from Woodside Elementary, the library, and nearby shops and restaurants. This is an exceptional opportunity to enjoy life on one of central Woodside's most coveted streets.

222 Albion AVE, Woodside

Listed by Thomas Werbe, 650-207-9168 from Breakwater Properties, Inc.
(If provided) CoList: from

Sold listing courtesy of Brent Gullixson from COMPS

$8,000,000

One of the most extraordinary properties on the SF Peninsula on 17 acres. The property has endless potential and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. 17 minutes to Woodside town center.

6 Beds ⋅ 9 Baths ⋅ ML82034677 MLS

One of the most extraordinary properties on the SF Peninsula on 17 acres. The property has endless potential and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. 17 minutes to Woodside town center.

16351 Skyline BLVD, Woodside

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

Sold listing courtesy of Kavanaugh Group from CBR

$11,706,000

4 Beds ⋅ 6 Baths ⋅ ML82033323 MLS

151 Eleanor DR, Woodside

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: Andrea Schultz from Coldwell Banker Realty

Sold listing courtesy of Julie Hadidi from COMPS

$23,500,000

Walking distance to all that the Woodside Village has to offer, this just completed masterpiece showcases the brilliant, organic design of architect Steve Simpson and builder Gilson Development, perfectly in tune with the natural setting. The spacious three-story home, connected by elevator, presents cathedral ceilings, custom Portella steel windows and glass doors, and hydronic-heated white oak floors that span all levels. Four bedrooms and five and one-half baths in the main home are complemented by a detached office with bath and a separate one-bedroom guest house with full kitchen. The lower level featuring a sculptural stainless-steel slide that serves as both art and function, along with a theater, fitness center, steam shower, wine cellar, fully loaded HD Golf simulator, and a bunk room. Resort-style amenities unfold outdoors with a fully tiled saltwater pool and therapeutic spa, fire pit, heated terrace, and full outdoor kitchen surrounded by vast synthetic lawn and professionally landscaped gardens with exceptional lighting. Solar power, four Tesla Powerwalls, and home automation. Acclaimed Woodside Elementary School. Habitable footage: 9,406; Main house: 8,261; ADU: 799; Detached office: 346 Plus garage 550. Total all buildings: 9,956 per Seller architect drawings

6 Beds ⋅ 8 Baths ⋅ ML82031620 MLS

Walking distance to all that the Woodside Village has to offer, this just completed masterpiece showcases the brilliant, organic design of architect Steve Simpson and builder Gilson Development, perfectly in tune with the natural setting. The spacious three-story home, connected by elevator, presents cathedral ceilings, custom Portella steel windows and glass doors, and hydronic-heated white oak floors that span all levels. Four bedrooms and five and one-half baths in the main home are complemented by a detached office with bath and a separate one-bedroom guest house with full kitchen. The lower level featuring a sculptural stainless-steel slide that serves as both art and function, along with a theater, fitness center, steam shower, wine cellar, fully loaded HD Golf simulator, and a bunk room. Resort-style amenities unfold outdoors with a fully tiled saltwater pool and therapeutic spa, fire pit, heated terrace, and full outdoor kitchen surrounded by vast synthetic lawn and professionally landscaped gardens with exceptional lighting. Solar power, four Tesla Powerwalls, and home automation. Acclaimed Woodside Elementary School. Habitable footage: 9,406; Main house: 8,261; ADU: 799; Detached office: 346 Plus garage 550. Total all buildings: 9,956 per Seller architect drawings

6 Cedar LN, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: Jenn Gilson from Golden Gate Sotheby's International Realty

Sold listing courtesy of RECIP from RCIP

$16,250,000

Completed in 2021 following a 5-year design and construction process, this extraordinary residence showcases the work of renowned professionals in architecture, interior design, and landscape architecture. Located on a gated corner lot of approximately 0.9 acres surrounded by award-winning heritage oaks, the home has been featured in Luxe and California Homes magazines and honored with awards. Every inch reflects a masterful level of craftsmanship and a meticulous eye for detail. Interiors reveal a refined yet livable luxury, where traditional elements are balanced with a modern aesthetic across three beautifully curated levels. Signature materials, custom finishes, and seamless indoor/outdoor connections define the living experience. With 5 bedrooms, 5 full baths, and 3 half-baths, the home offers exceptional accommodations for a variety of lifestyle needs. A true architectural statement in the heart of Woodside, designed to endure and impress for generations to come.

5 Beds ⋅ 8 Baths ⋅ ML82031334 MLS

Completed in 2021 following a 5-year design and construction process, this extraordinary residence showcases the work of renowned professionals in architecture, interior design, and landscape architecture. Located on a gated corner lot of approximately 0.9 acres surrounded by award-winning heritage oaks, the home has been featured in Luxe and California Homes magazines and honored with awards. Every inch reflects a masterful level of craftsmanship and a meticulous eye for detail. Interiors reveal a refined yet livable luxury, where traditional elements are balanced with a modern aesthetic across three beautifully curated levels. Signature materials, custom finishes, and seamless indoor/outdoor connections define the living experience. With 5 bedrooms, 5 full baths, and 3 half-baths, the home offers exceptional accommodations for a variety of lifestyle needs. A true architectural statement in the heart of Woodside, designed to endure and impress for generations to come.

3490 Tripp RD, Woodside

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

Sold listing courtesy of Scott Dancer from APR

$1,750,000

Forever views of coastal hills and Pacific ocean at the very end of a small country maintained road. Adjacent to hundreds of Open Space acreage. 1,600 + sq. ft. upper floor Great-Room with floor-to-ceiling windows. Large open kitchen / dining area and open living room with wet bar and guest bath. Upper level deck wraps around the entire exterior. Bedrooms are all downstairs each with access to the deck. Bonus room (great for crafts, possible den or bedroom) and laundry utility area. Downstairs is also aprox.1600 sq. ft.. House was being remodeled, but was not completed. Truly a fixer upper. Complete set of remodel plans included.

4 Beds ⋅ 4 Baths ⋅ ML82029010 MLS

Forever views of coastal hills and Pacific ocean at the very end of a small country maintained road. Adjacent to hundreds of Open Space acreage. 1,600 + sq. ft. upper floor Great-Room with floor-to-ceiling windows. Large open kitchen / dining area and open living room with wet bar and guest bath. Upper level deck wraps around the entire exterior. Bedrooms are all downstairs each with access to the deck. Bonus room (great for crafts, possible den or bedroom) and laundry utility area. Downstairs is also aprox.1600 sq. ft.. House was being remodeled, but was not completed. Truly a fixer upper. Complete set of remodel plans included.

47 Forest View RD, Woodside

Listed by Plank or Cline, 650-728-8080 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Richard Beale from BEAL

$7,645,000

Experience the Woodside Lifestyle in this exquisite single-level 5 bedrooms and 5.5 bathroom residence. Fully reimagined and updated in 2025, this thoughtfully designed 3,580 sq. ft. residence offers a modern, open layout that perfectly balances style and comfort. The spacious living areas are ideal for both family gatherings and quiet relaxation. A private lower-level suite includes its own kitchen and bath providing a perfect setup for guests or a live-in au pair (currently staged as a game room). From sunrise to sunset, the captivating views of the Kings Mountain Hills and Skyline will leave you in awe. A home you will never tire of - welcome to Woodside living at its finest.

5 Beds ⋅ 6 Baths ⋅ ML82024868 MLS

Experience the Woodside Lifestyle in this exquisite single-level 5 bedrooms and 5.5 bathroom residence. Fully reimagined and updated in 2025, this thoughtfully designed 3,580 sq. ft. residence offers a modern, open layout that perfectly balances style and comfort. The spacious living areas are ideal for both family gatherings and quiet relaxation. A private lower-level suite includes its own kitchen and bath providing a perfect setup for guests or a live-in au pair (currently staged as a game room). From sunrise to sunset, the captivating views of the Kings Mountain Hills and Skyline will leave you in awe. A home you will never tire of - welcome to Woodside living at its finest.

131 Croydon WAY, Woodside

Listed by David Young, 650-315-8989 from Coldwell Banker Realty
(If provided) CoList: Victoria Surles from Coldwell Banker Realty

Sold listing courtesy of Victoria Surles from CBR

$4,049,000

Refined Country Luxury on a Gated Level Lot Set beyond a gate on a spacious level lot, this newer home offers luxurious quality with an open and bright floor plan. Bamboo floors with a hewn finish, coved crown moldings, solid wood doors, and up-lit tray ceilings exemplify the quality details found throughout. The open design revolves around a spacious foyer with a formal living room, dining area, chefs kitchen with breakfast bar, and family room. There is a dedicated office, perfect for todays work-from-home needs, plus 3 upstairs bedrooms, including the primary suite with Western hill views and marble bath. Outside, the newly landscaped grounds unfold as a private retreat with mature trees and an expansive lawn, all with newly added lighting for evening enjoyment. A vibrant rose garden adds color, a welcoming patio invites effortless al fresco dining and entertaining, plus there is a raised bed succulent garden. Adding to the appeal is the homes close-in convenience just over 2 miles from the Woodside Village and with access to acclaimed Woodside Elementary School.

3 Beds ⋅ 3 Baths ⋅ ML82024793 MLS

Refined Country Luxury on a Gated Level Lot Set beyond a gate on a spacious level lot, this newer home offers luxurious quality with an open and bright floor plan. Bamboo floors with a hewn finish, coved crown moldings, solid wood doors, and up-lit tray ceilings exemplify the quality details found throughout. The open design revolves around a spacious foyer with a formal living room, dining area, chefs kitchen with breakfast bar, and family room. There is a dedicated office, perfect for todays work-from-home needs, plus 3 upstairs bedrooms, including the primary suite with Western hill views and marble bath. Outside, the newly landscaped grounds unfold as a private retreat with mature trees and an expansive lawn, all with newly added lighting for evening enjoyment. A vibrant rose garden adds color, a welcoming patio invites effortless al fresco dining and entertaining, plus there is a raised bed succulent garden. Adding to the appeal is the homes close-in convenience just over 2 miles from the Woodside Village and with access to acclaimed Woodside Elementary School.

750 W California WAY, Woodside

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

Sold listing courtesy of Costantini Team from APR

$4,850,000

Sweeping views across the San Francisco Bay take center stage at this beautifully remodeled home on more than 3 acres of predominantly level land. Minute to downtown Woodside and Stanford. Designed for entertaining and recreation, the property features a large pool and separate spa framed in Connecticut bluestone, an expansive synthetic lawn for recreation and play, and broad decks with built-in seating and cable-strung railings. A brick-walled garden courtyard with Art Deco metal and glass front doors introduces the interiors highlighted by soaring ceilings and skylights. Wall-to-wall windows capture the panorama of the glorious views immediately upon entering. Multiple gathering spaces include a dramatic living room with stone-clad fireplace, a remodeled kitchen and dining area, and a family room with full bar and fireplace. A flexible use room between the foyer and kitchen offers versatility for a home office or playroom. Four bedrooms in a separate wing include a spacious primary suite with Bay views and steam shower, three bedrooms and a remodeled bath, plus there are two half-baths. Solar power with four Tesla Powerwalls, reclaimed San Francisco cobblestone paths, and a three-car garage are added features. Highly Rated Portola Valley Schools. Minutes to Woodside Village.

4 Beds ⋅ 4 Baths ⋅ ML82024655 MLS

Sweeping views across the San Francisco Bay take center stage at this beautifully remodeled home on more than 3 acres of predominantly level land. Minute to downtown Woodside and Stanford. Designed for entertaining and recreation, the property features a large pool and separate spa framed in Connecticut bluestone, an expansive synthetic lawn for recreation and play, and broad decks with built-in seating and cable-strung railings. A brick-walled garden courtyard with Art Deco metal and glass front doors introduces the interiors highlighted by soaring ceilings and skylights. Wall-to-wall windows capture the panorama of the glorious views immediately upon entering. Multiple gathering spaces include a dramatic living room with stone-clad fireplace, a remodeled kitchen and dining area, and a family room with full bar and fireplace. A flexible use room between the foyer and kitchen offers versatility for a home office or playroom. Four bedrooms in a separate wing include a spacious primary suite with Bay views and steam shower, three bedrooms and a remodeled bath, plus there are two half-baths. Solar power with four Tesla Powerwalls, reclaimed San Francisco cobblestone paths, and a three-car garage are added features. Highly Rated Portola Valley Schools. Minutes to Woodside Village.

6 Friars LN, Woodside

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

Sold listing courtesy of Elena Tsukanova from APR

$2,900,000

Perched a top of Skyline Ridge, this gated custom estate offers spectacular views of the San Francisco South Bay, including Mt. Diablo, Stanford, and San Jose. Nestled on a private 5+ acre east-facing parcel near the 942-acre Wunderlich Park, the home features 5 bedrooms, 4.5 bathrooms, 4 large decks, and a 2-car garage. The gourmet kitchen with center island, dining room, and large pantry opens to the great room with vaulted ceiling, skylights, and 3 French doors. Upstairs showcases imported slate floors, a central family/activity room, a guest half bath, a library/office, and a spacious primary suite with a walk-in shower, a 2-person jetted spa, a private deck, double sinks, a bidet, and a walk-in closet. A nearby flexible room could serve as a bedroom, nursery, or den. The laundry area opens to a flat yard suitable for a future pool, tennis court, or stables. Downstairs includes 2 bedrooms, a large bath, a sitting room, and a fully self-contained ADU with private entry and a deck. In the coveted Portola Valley/Woodside School District, the estate feels private yet is minutes from Alice's Restaurant, Fogarty Winery, central Woodside, Stanford, and the Coast.

5 Beds ⋅ 5 Baths ⋅ ML82023275 MLS

Perched a top of Skyline Ridge, this gated custom estate offers spectacular views of the San Francisco South Bay, including Mt. Diablo, Stanford, and San Jose. Nestled on a private 5+ acre east-facing parcel near the 942-acre Wunderlich Park, the home features 5 bedrooms, 4.5 bathrooms, 4 large decks, and a 2-car garage. The gourmet kitchen with center island, dining room, and large pantry opens to the great room with vaulted ceiling, skylights, and 3 French doors. Upstairs showcases imported slate floors, a central family/activity room, a guest half bath, a library/office, and a spacious primary suite with a walk-in shower, a 2-person jetted spa, a private deck, double sinks, a bidet, and a walk-in closet. A nearby flexible room could serve as a bedroom, nursery, or den. The laundry area opens to a flat yard suitable for a future pool, tennis court, or stables. Downstairs includes 2 bedrooms, a large bath, a sitting room, and a fully self-contained ADU with private entry and a deck. In the coveted Portola Valley/Woodside School District, the estate feels private yet is minutes from Alice's Restaurant, Fogarty Winery, central Woodside, Stanford, and the Coast.

16501 Skyline BLVD, Woodside

Listed by Hebe Li, 650-889-6649 from The Agency
(If provided) CoList: from

Sold listing courtesy of Alexandra Gilmartin from GILM

$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

$5,525,000

Set on approximately 1.4 acres with views stretching out to the Bay, this beautifully remodeled 4-bedroom, 3.5-bathroom home offers timeless traditional style with elevated designer finishes. The 3339 sq ft interior features oak hardwood floors with inlaid borders, decorative moldings, and three fireplaces, creating a refined yet comfortable ambiance throughout. The floor plan is ideal for everyday living and entertaining, with formal and casual living spaces, a spacious kitchen, and light-filled rooms that open to the outdoors. Each bedroom offers privacy and flexibility, including options for a home office or guest accommodations. Outside, enjoy the peaceful setting with a sparkling pool, a charming pool house, and beautifully landscaped grounds framed by mature trees. A rare opportunity for style, space, and serenity just a short drive from town and local conveniences.

4 Beds ⋅ 4 Baths ⋅ ML82021333 MLS ⋅ Woodside Hills Home Association BLDG.

Set on approximately 1.4 acres with views stretching out to the Bay, this beautifully remodeled 4-bedroom, 3.5-bathroom home offers timeless traditional style with elevated designer finishes. The 3339 sq ft interior features oak hardwood floors with inlaid borders, decorative moldings, and three fireplaces, creating a refined yet comfortable ambiance throughout. The floor plan is ideal for everyday living and entertaining, with formal and casual living spaces, a spacious kitchen, and light-filled rooms that open to the outdoors. Each bedroom offers privacy and flexibility, including options for a home office or guest accommodations. Outside, enjoy the peaceful setting with a sparkling pool, a charming pool house, and beautifully landscaped grounds framed by mature trees. A rare opportunity for style, space, and serenity just a short drive from town and local conveniences.

155 Normandy LN, Woodside

Listed by Tim Kerns, 650-430-4052 from Coldwell Banker Realty
(If provided) CoList: Kyle Katz from Coldwell Banker Realty

Sold listing courtesy of JJ Team:Jones/Cassel from NTERO

$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

$2,199,000

Nestled among the redwoods, 13630 Skyline Blvd offers the perfect Woodside retreat. Recently refreshed with a brand-new roof, new decks, refinished hardwood floors, and new carpet, this 3,270 sq ft home is move-in ready. The floorplan includes 3 bedrooms plus a dedicated office, a huge main suite, and spacious living areas that balance privacy with flow. A 2-car garage provides convenience, while the 0.56-acre lot delivers peace and room to grow. Located in the Kings Mountain Elementary boundary, this home offers the serenity of mountain living with the accessibility buyers wantjust 15 minutes to Hwy 280 at 92 and 45 minutes to SFO. Whether youre seeking a full-time residence or a weekend retreat, this property combines natural beauty, thoughtful updates, and everyday practicality in one of the Peninsulas most desirable settings.

3 Beds ⋅ 3 Baths ⋅ ML82019950 MLS

Nestled among the redwoods, 13630 Skyline Blvd offers the perfect Woodside retreat. Recently refreshed with a brand-new roof, new decks, refinished hardwood floors, and new carpet, this 3,270 sq ft home is move-in ready. The floorplan includes 3 bedrooms plus a dedicated office, a huge main suite, and spacious living areas that balance privacy with flow. A 2-car garage provides convenience, while the 0.56-acre lot delivers peace and room to grow. Located in the Kings Mountain Elementary boundary, this home offers the serenity of mountain living with the accessibility buyers wantjust 15 minutes to Hwy 280 at 92 and 45 minutes to SFO. Whether youre seeking a full-time residence or a weekend retreat, this property combines natural beauty, thoughtful updates, and everyday practicality in one of the Peninsulas most desirable settings.

13630 Skyline BLVD, Woodside

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

Sold listing courtesy of David Skokan from RMXSP

$18,900,000

A magnificent transformation has redefined this 1929 French chateau into a modern estate of extraordinary light and sophistication. Once known for its European formality and ornate detail, the home has been renewed from top to bottom with the highest level of design, cabinetry, and finishes. Original millwork and moldings were meticulously preserved, now presented in a palette of light tones that elevate rather than overshadow the architecture. Exceptional lighting and carefully curated finishes bring contemporary elegance to every room, creating a residence that feels entirely new while honoring its historic character. The result is a home that stands among the finest expressions of luxury living today. Equally compelling are the dual-gated five acres of formal grounds that frame the estate. Vast lawns, parterre gardens, and farm-to-table gardens accompany resort amenities of a pool, spa, and tennis court, with multiple terraces providing an unparalleled setting for entertaining or private retreat. All of this unfolds within easy reach of Silicon Valley and San Francisco, establishing a rare estate property where history and modern vision meet at the highest level. among the finest expressions of luxury living today.

7 Beds ⋅ 9 Baths ⋅ ML82019556 MLS

A magnificent transformation has redefined this 1929 French chateau into a modern estate of extraordinary light and sophistication. Once known for its European formality and ornate detail, the home has been renewed from top to bottom with the highest level of design, cabinetry, and finishes. Original millwork and moldings were meticulously preserved, now presented in a palette of light tones that elevate rather than overshadow the architecture. Exceptional lighting and carefully curated finishes bring contemporary elegance to every room, creating a residence that feels entirely new while honoring its historic character. The result is a home that stands among the finest expressions of luxury living today. Equally compelling are the dual-gated five acres of formal grounds that frame the estate. Vast lawns, parterre gardens, and farm-to-table gardens accompany resort amenities of a pool, spa, and tennis court, with multiple terraces providing an unparalleled setting for entertaining or private retreat. All of this unfolds within easy reach of Silicon Valley and San Francisco, establishing a rare estate property where history and modern vision meet at the highest level. among the finest expressions of luxury living today.

320 Harcross RD, Woodside

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

Sold listing courtesy of Charles Liu from COMPS

$2,425,000

Discover the perfect blend of space, comfort, and natural beauty in this Woodside retreat. A scenic meadow highlights the property, plus a flat, usable acreideal for recreation, gardening, or expansion. The log cabin exterior with river rock accents evokes timeless curb appeal and a true Tahoe-inspired feel. Inside, the open floor plan, formal dining, breakfast room, and large bonus room provide flexibility for entertaining and everyday living. With 3 bedrooms upstairs and 1 downstairs with separate entry, the layout is perfect for families, guests, or multigenerational living. Enjoy top-of-the-mountain living in a park-like setting with redwoods, meadows, and direct access to hiking and equestrian trails in nearby Huddart Park. Sunset views from the expansive deck, a wood-burning stove, hardwood floors, and spa tub in the primary suite add charm and comfort. Amenities include central AC with dual zones, Generac whole-house generator with propane hookup, RV parking, ADT security, gutter guard filters, and a tranquil fenced yard. Just 6 miles from Hwys 92 and 84, youre minutes from the Peninsula or coast while enjoying the privacy and community spirit of Kings Mountain.

4 Beds ⋅ 3 Baths ⋅ ML82019227 MLS

Discover the perfect blend of space, comfort, and natural beauty in this Woodside retreat. A scenic meadow highlights the property, plus a flat, usable acreideal for recreation, gardening, or expansion. The log cabin exterior with river rock accents evokes timeless curb appeal and a true Tahoe-inspired feel. Inside, the open floor plan, formal dining, breakfast room, and large bonus room provide flexibility for entertaining and everyday living. With 3 bedrooms upstairs and 1 downstairs with separate entry, the layout is perfect for families, guests, or multigenerational living. Enjoy top-of-the-mountain living in a park-like setting with redwoods, meadows, and direct access to hiking and equestrian trails in nearby Huddart Park. Sunset views from the expansive deck, a wood-burning stove, hardwood floors, and spa tub in the primary suite add charm and comfort. Amenities include central AC with dual zones, Generac whole-house generator with propane hookup, RV parking, ADT security, gutter guard filters, and a tranquil fenced yard. Just 6 miles from Hwys 92 and 84, youre minutes from the Peninsula or coast while enjoying the privacy and community spirit of Kings Mountain.

13890 Skyline BLVD, Woodside

Listed by Teri Rossetto Shaughnessy, 650-504-4016 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Gina Nibbi from COMP12

$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 RD, Woodside

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

$2,525,000

Experience the ultimate retreat, where majestic redwoods, sweeping canyon vistas, and ocean views provide a stunning backdrop for everyday living. This 3,323 sq ft custom home features 5 bedrooms and 3.5 bathrooms. The main level boasts soaring ceilings, expansive windows, and skylights that flood the space with natural light, highlighting the breathtaking scenery. The open-concept design connects the spacious living area to the kitchen, featuring Brazilian soapstone countertops, rich wood flooring, and stainless steel appliances, perfect for entertaining or relaxing. An adjoining family room offers more space to unwind. Head downstairs to access the expansive deck, versatile bedrooms, and flexible spaces. Outdoor living takes center stage as you step onto the oversized deck, soak in the hot tub under a canopy of stars, or explore the meticulously terraced yard, offering space to garden, relax, or let your animals roam free. Ideally located, a short walk to miles of open space trails,10 minutes to Hwy 280 with easy access to SFO, Silicon Valley, and the Half Moon Bay coast, this home offers the perfect blend of serenity and convenience. Come experience the lifestyle you've been dreaming of, surrounded by nature, tranquility, and the welcoming community of Kings Mountain.

5 Beds ⋅ 4 Baths ⋅ ML82019381 MLS

Experience the ultimate retreat, where majestic redwoods, sweeping canyon vistas, and ocean views provide a stunning backdrop for everyday living. This 3,323 sq ft custom home features 5 bedrooms and 3.5 bathrooms. The main level boasts soaring ceilings, expansive windows, and skylights that flood the space with natural light, highlighting the breathtaking scenery. The open-concept design connects the spacious living area to the kitchen, featuring Brazilian soapstone countertops, rich wood flooring, and stainless steel appliances, perfect for entertaining or relaxing. An adjoining family room offers more space to unwind. Head downstairs to access the expansive deck, versatile bedrooms, and flexible spaces. Outdoor living takes center stage as you step onto the oversized deck, soak in the hot tub under a canopy of stars, or explore the meticulously terraced yard, offering space to garden, relax, or let your animals roam free. Ideally located, a short walk to miles of open space trails,10 minutes to Hwy 280 with easy access to SFO, Silicon Valley, and the Half Moon Bay coast, this home offers the perfect blend of serenity and convenience. Come experience the lifestyle you've been dreaming of, surrounded by nature, tranquility, and the welcoming community of Kings Mountain.

103 Harkins RD, Woodside

Listed by Joakim Bye, 650-284-2080 from Ocean Element Real Estate
(If provided) CoList: from

Sold listing courtesy of Valerie Trenter from CBR

$7,500,000

Set on a 3.1-acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly-updated residence offers the perfect blend of refined luxury and modern comfort - just minutes from town. Flooded with natural light from expansive floor-to-ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public spaces in +/-5,555sf. The open-concept living room boasts 24-foot ceilings, massive curved windows, a striking fireplace, and flows seamlessly into the sun-filled dining room. The chef's kitchen opens to a huge family room with 10-foot ceilings, a dramatic fireplace, bar, and French doors opening to a patio-perfect for indoor/outdoor living. Designed for everyday comfort and entertainment, the home offers multiple terraces, temperature-controlled wine storage, and an expansive lower level replete with a gym, home theater, and full bath. Outdoor amenities include a pool with spa, tennis court, meandering paths that encircle the property, level lawns, and a vineyard. A detached 2BR/2BA, +/-1,135sf guest house is ideal for extended family or visitors. Access to the top-rated Woodside Elementary School completes this rare opportunity to experience a lifestyle of elegance, privacy, and convenience.

4 Beds ⋅ 5 Baths ⋅ ML82017471 MLS

Set on a 3.1-acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly-updated residence offers the perfect blend of refined luxury and modern comfort - just minutes from town. Flooded with natural light from expansive floor-to-ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public spaces in +/-5,555sf. The open-concept living room boasts 24-foot ceilings, massive curved windows, a striking fireplace, and flows seamlessly into the sun-filled dining room. The chef's kitchen opens to a huge family room with 10-foot ceilings, a dramatic fireplace, bar, and French doors opening to a patio-perfect for indoor/outdoor living. Designed for everyday comfort and entertainment, the home offers multiple terraces, temperature-controlled wine storage, and an expansive lower level replete with a gym, home theater, and full bath. Outdoor amenities include a pool with spa, tennis court, meandering paths that encircle the property, level lawns, and a vineyard. A detached 2BR/2BA, +/-1,135sf guest house is ideal for extended family or visitors. Access to the top-rated Woodside Elementary School completes this rare opportunity to experience a lifestyle of elegance, privacy, and convenience.

333 Raymundo DR, Woodside

Listed by Jim Arbeed, 650-558-4248 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jaswinder Gill from GILLJ

$3,000,000

Perched on 1.5 acres of beautiful land, this spacious 6-bedroom, 3.5-bathroom home offers panoramic views and room to grow. With generously sized rooms and views from nearly every window, this property combines comfort, versatility, and endless potential. A formal entry leads to a grand living room featuring soaring ceilings, a cozy fireplace, and access to an expansive entertaining deckperfect for indoor-outdoor living. The family-style kitchen includes a charming eat-in area, a second fireplace, and plenty of space for gathering. The main level also offers a formal dining room and a functional laundry room with ample storage, conveniently connected to a 2-car garage. Upstairs, youll find four spacious bedrooms, while the lower level has been thoughtfully converted into an ADU, featuring two bedrooms, a full kitchen, bathroom, and its own separate entry and dedicated parking areaideal for extended family, guests, or rental income. This solidly built home is ready for your personal touch and updates. Dont miss the opportunity to make this property your own retreat in a truly special setting.

6 Beds ⋅ 4 Baths ⋅ ML82013538 MLS

Perched on 1.5 acres of beautiful land, this spacious 6-bedroom, 3.5-bathroom home offers panoramic views and room to grow. With generously sized rooms and views from nearly every window, this property combines comfort, versatility, and endless potential. A formal entry leads to a grand living room featuring soaring ceilings, a cozy fireplace, and access to an expansive entertaining deckperfect for indoor-outdoor living. The family-style kitchen includes a charming eat-in area, a second fireplace, and plenty of space for gathering. The main level also offers a formal dining room and a functional laundry room with ample storage, conveniently connected to a 2-car garage. Upstairs, youll find four spacious bedrooms, while the lower level has been thoughtfully converted into an ADU, featuring two bedrooms, a full kitchen, bathroom, and its own separate entry and dedicated parking areaideal for extended family, guests, or rental income. This solidly built home is ready for your personal touch and updates. Dont miss the opportunity to make this property your own retreat in a truly special setting.

495 Summit Springs RD, Woodside

Listed by Margot Lockwood, 650-400-2528 from Golden Gate Sotheby's International Realty
(If provided) CoList: Ricky Flores from Golden Gate Sotheby's International Realty

Sold listing courtesy of Ginna Lazar from LHG

$9,600,000

Set on more than 3.6 gated acres of quintessential Woodside grounds, this contemporary masterpiece is surrounded by towering oaks and lush greenery, offering a serene, woodsy retreat. The interiors reflect the natural setting with soaring cherry wood cathedral ceilings, cherry wood floors, and expansive picture windows that flood the home with light and invite the outdoors in. Designed for both entertaining and everyday living, the residence features grand formal rooms, multiple fireplaces, a chefs kitchen with sunny breakfast nook, a walk-out family room, and a stylish executive office. Four bedrooms include a luxurious primary suite with its own fireplace, balcony, and spa-inspired bath. Outside, sprawling grounds offer a center courtyard with covered deck and fire pit, built-in grill, a separate guest house, and two garages including one with a lift for car enthusiasts as well as an RC car racetrack. Minutes from Portola Valley, top schools, and Silicon Valley tech centers.

5 Beds ⋅ 6 Baths ⋅ ML82013370 MLS

Set on more than 3.6 gated acres of quintessential Woodside grounds, this contemporary masterpiece is surrounded by towering oaks and lush greenery, offering a serene, woodsy retreat. The interiors reflect the natural setting with soaring cherry wood cathedral ceilings, cherry wood floors, and expansive picture windows that flood the home with light and invite the outdoors in. Designed for both entertaining and everyday living, the residence features grand formal rooms, multiple fireplaces, a chefs kitchen with sunny breakfast nook, a walk-out family room, and a stylish executive office. Four bedrooms include a luxurious primary suite with its own fireplace, balcony, and spa-inspired bath. Outside, sprawling grounds offer a center courtyard with covered deck and fire pit, built-in grill, a separate guest house, and two garages including one with a lift for car enthusiasts as well as an RC car racetrack. Minutes from Portola Valley, top schools, and Silicon Valley tech centers.

140 Farm RD, Woodside

Listed by DeLeon Team, 650-900-7000 from Deleon Realty
(If provided) CoList: from

Sold listing courtesy of David Weil from PACT

$4,750,000

Designer Style with Pool and ADU on Large Level Grounds Classic and timeless architecture and beautifully remodeled interiors come together on more than one-half acre of level land with a pool and Accessory Dwelling Unit. Hardwood floors and multiple fireplaces add warmth and character across three levels designed for flexibility and comfort. The chefs kitchen and adjoining family room connect effortlessly to formal living and dining rooms, with glass doors throughout opening to expansive patios and vast rear grounds ideal for large-scale entertaining. There is also a dedicated office plus a lower-level laundry room and recreation room with full bath convenient to the tucked-away pool. Upstairs are four bedrooms, including a spacious primary suite with two full baths and two walk-in closets, plus sweeping western hill views. Just minutes from the natural beauty and trailheads of Edgewood Park, and offering access to top-rated Woodside School, this home balances timeless design with modern livability in a premier setting.

4 Beds ⋅ 5 Baths ⋅ ML82011673 MLS

Designer Style with Pool and ADU on Large Level Grounds Classic and timeless architecture and beautifully remodeled interiors come together on more than one-half acre of level land with a pool and Accessory Dwelling Unit. Hardwood floors and multiple fireplaces add warmth and character across three levels designed for flexibility and comfort. The chefs kitchen and adjoining family room connect effortlessly to formal living and dining rooms, with glass doors throughout opening to expansive patios and vast rear grounds ideal for large-scale entertaining. There is also a dedicated office plus a lower-level laundry room and recreation room with full bath convenient to the tucked-away pool. Upstairs are four bedrooms, including a spacious primary suite with two full baths and two walk-in closets, plus sweeping western hill views. Just minutes from the natural beauty and trailheads of Edgewood Park, and offering access to top-rated Woodside School, this home balances timeless design with modern livability in a premier setting.

490 W Maple WAY, Woodside

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

Sold listing courtesy of Samira Amid-Hozour from SGP

$4,900,000

Surrounded by natures beauty... on 5.4 acres on a private street yet just 3 miles from Sand Hill Road venture capital centers this home offers complete privacy, organic architecture, and spa-like amenities. Oaks and wildflower-strewn meadows create a serene setting deeply connected to the natural landscape with enchanting walking paths. Inside, warm wood finishes, soaring paneled ceilings, and walls of glass establish a tranquil, Zen-like atmosphere that invites the outdoors in at every turn. The layout unfolds with multiple stone fireplaces, outdoor access from nearly every room, and refined materials that reflect the homes high-end craftsmanship. A spa-inspired primary suite features an all-marble bath with cedar-lined sauna and sliding glass doors to the outdoor spa. The flexible floor plan includes one bedroom with a fireplace, en suite bath, and private entrance making it ideal for guest quarters or a possible family room. There is also a detached studio and a lower-level wine cellar with outside access. Outdoor living is equally well considered with a spacious deck overlooking the natural landscape. This one-of-a-kind property offers a close-in location just minutes to miles of hiking and biking trails, town centers, and access to excellent Portola Valley schools.

4 Beds ⋅ 3 Baths ⋅ ML82011671 MLS

Surrounded by natures beauty... on 5.4 acres on a private street yet just 3 miles from Sand Hill Road venture capital centers this home offers complete privacy, organic architecture, and spa-like amenities. Oaks and wildflower-strewn meadows create a serene setting deeply connected to the natural landscape with enchanting walking paths. Inside, warm wood finishes, soaring paneled ceilings, and walls of glass establish a tranquil, Zen-like atmosphere that invites the outdoors in at every turn. The layout unfolds with multiple stone fireplaces, outdoor access from nearly every room, and refined materials that reflect the homes high-end craftsmanship. A spa-inspired primary suite features an all-marble bath with cedar-lined sauna and sliding glass doors to the outdoor spa. The flexible floor plan includes one bedroom with a fireplace, en suite bath, and private entrance making it ideal for guest quarters or a possible family room. There is also a detached studio and a lower-level wine cellar with outside access. Outdoor living is equally well considered with a spacious deck overlooking the natural landscape. This one-of-a-kind property offers a close-in location just minutes to miles of hiking and biking trails, town centers, and access to excellent Portola Valley schools.

19 Preston RD, Woodside

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

Sold listing courtesy of Kemper Ray from COMPS