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$24,995,000

Evoking the patina & permanence of a residence shaped over generations, this vineyard estate possesses an authenticity rarely achieved in contemporary construction. Completed in 2016 imbued with character of timeless European manor, it received the Julia Morgan Award for Classical Architecture, honoring its exceptional craftsmanship & architectural integrity. Hand-hewn beams, bespoke millwork, artisanal detailing, & imported Italian patterned terra cotta tile flooring define the interiors, while Mediterranean Revival influences create an atmosphere that is grand & welcoming. Arranged across two levels with elevator access, lower-level storage room with wine cellar potential, residence offers 4 bedrooms, dedicated office, & detached guest house. Formal & informal living spaces center around a chef's kitchen with a generous butlers pantry, while arched windows & French doors frame surrounding landscape. Set on approximately 4.33 acres in Woodsides coveted Hidden Valley, the estate enjoys sweeping views of Jasper Ridge, the Santa Cruz Mountains, the Western Hills, & Westridge. A pool, spa, rose gardens, crushed stone paths, dual-fuel backup generator, & professionally managed Pinot Noir vineyard producing up to 50 cases annually complete this extraordinary Silicon Valley retreat.

4 Beds ⋅ 5 Baths ⋅ ML82054839 MLS

Evoking the patina & permanence of a residence shaped over generations, this vineyard estate possesses an authenticity rarely achieved in contemporary construction. Completed in 2016 imbued with character of timeless European manor, it received the Julia Morgan Award for Classical Architecture, honoring its exceptional craftsmanship & architectural integrity. Hand-hewn beams, bespoke millwork, artisanal detailing, & imported Italian patterned terra cotta tile flooring define the interiors, while Mediterranean Revival influences create an atmosphere that is grand & welcoming. Arranged across two levels with elevator access, lower-level storage room with wine cellar potential, residence offers 4 bedrooms, dedicated office, & detached guest house. Formal & informal living spaces center around a chef's kitchen with a generous butlers pantry, while arched windows & French doors frame surrounding landscape. Set on approximately 4.33 acres in Woodsides coveted Hidden Valley, the estate enjoys sweeping views of Jasper Ridge, the Santa Cruz Mountains, the Western Hills, & Westridge. A pool, spa, rose gardens, crushed stone paths, dual-fuel backup generator, & professionally managed Pinot Noir vineyard producing up to 50 cases annually complete this extraordinary Silicon Valley retreat.

180 Farm RD, Woodside

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

$4,625,000

Located in the highly desirable Woodside Hills, this exceptional gated estate offers the perfect blend of privacy, luxury, and bay views. Set on a level one-acre lot, the property features a thoughtfully designed main residence and a fully separate guest house, ideal for extended family, guests, or work-from-home flexibility. The main house offers approximately 3,247 square feet of living space with three bedrooms and two and half bathrooms, complemented by a three-car garage. Designed for both comfort and entertaining, the home opens to expansive outdoor amenities including a pool, hot tub, and sports court, all surrounded by mature landscaping and serene views. The guest house provides approximately 1,254 square feet, featuring two bedrooms, two full baths, its own one-car garage, and complete privacy from the main residence with its own private yard. Additional highlights include solar power, a gated entry, and sweeping Bay and mountain views, making this a rare opportunity to own a versatile estate property in one of Woodside's most sought-after neighborhoods.

3 Beds ⋅ 3 Baths ⋅ ML82033724 MLS

Located in the highly desirable Woodside Hills, this exceptional gated estate offers the perfect blend of privacy, luxury, and bay views. Set on a level one-acre lot, the property features a thoughtfully designed main residence and a fully separate guest house, ideal for extended family, guests, or work-from-home flexibility. The main house offers approximately 3,247 square feet of living space with three bedrooms and two and half bathrooms, complemented by a three-car garage. Designed for both comfort and entertaining, the home opens to expansive outdoor amenities including a pool, hot tub, and sports court, all surrounded by mature landscaping and serene views. The guest house provides approximately 1,254 square feet, featuring two bedrooms, two full baths, its own one-car garage, and complete privacy from the main residence with its own private yard. Additional highlights include solar power, a gated entry, and sweeping Bay and mountain views, making this a rare opportunity to own a versatile estate property in one of Woodside's most sought-after neighborhoods.

300 Ridgeway RD, Woodside

Listed by Gregory Garcia, 650-771-0656 from Sequoia Realty Services
(If provided) CoList: from

Sold listing courtesy of Anuja Krishnan from KWPEN

$3,195,000

Luxury retreat offers a serene escape on 9+ acres, secured by an electronic gate. Under 2 miles and just minutes to Alices restarant. Stunning style on one level, the home features dramatic light-filled interiors with an open-concept design, SOARING CEILINGS, and abundant sliding glass doors and skylights. Bamboo floors, vertical grain cabinetry, and polished concrete counters. The main rooms revolve around a central patio with a stunning heritage oak tree, while an expansive rear deck with a large spa beneath the redwoods and a sunswept front yard for gardening enhance the outdoor experience. Three privately located bedrooms, each with its own bath, ensure comfort and flexibility. An equally well-appointed ADU above the garage includes a kitchen, bath, and laundry. Total privacy directly adjacent to MidPen open space. Flat useable grounds with large vegetable garden, ample of paved parking, large ground level deck and heritage oak entertainment area for large parties. Open sunny side toward views and beauty of Redwood forest on the oposite side of the house with heated spa under the redwoods. Main house 2870 sq.ft, plus ADU 550 sq.ft., plus attached garage 525 sq.ft for total of 3945 sq.ft.

3 Beds ⋅ 3 Baths ⋅ ML82045702 MLS

Luxury retreat offers a serene escape on 9+ acres, secured by an electronic gate. Under 2 miles and just minutes to Alices restarant. Stunning style on one level, the home features dramatic light-filled interiors with an open-concept design, SOARING CEILINGS, and abundant sliding glass doors and skylights. Bamboo floors, vertical grain cabinetry, and polished concrete counters. The main rooms revolve around a central patio with a stunning heritage oak tree, while an expansive rear deck with a large spa beneath the redwoods and a sunswept front yard for gardening enhance the outdoor experience. Three privately located bedrooms, each with its own bath, ensure comfort and flexibility. An equally well-appointed ADU above the garage includes a kitchen, bath, and laundry. Total privacy directly adjacent to MidPen open space. Flat useable grounds with large vegetable garden, ample of paved parking, large ground level deck and heritage oak entertainment area for large parties. Open sunny side toward views and beauty of Redwood forest on the oposite side of the house with heated spa under the redwoods. Main house 2870 sq.ft, plus ADU 550 sq.ft., plus attached garage 525 sq.ft for total of 3945 sq.ft.

1100 Old La Honda RD, Woodside

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

$2,250,000

Set on 2.6+ wooded acres in the hills, this warm & beautifully renovated home offers something genuinely rare on the Peninsula: complete privacy amid towering redwood trees, a profound sense of forest immersion, and less than 15 minutes to Sand Hill & 280. The updated & open floor plan kitchen flows into generous dining and living spaces, all oriented towards sweeping forest views. Natural light fills the space, and wraparound decks extend living outdoors, with a hot tub just off the primary suite. A flexible two bedroom wing can accommodate children, teens, guest rooms, or office and studio space. An independent 1-bdrm ADU with its own kitchen / bath is ideal for rental income, an au pair, or an aging parent. The kitchen, secondary bathrooms, finishes, HVAC, roof, and water heater - have all been recently renovated, and pre-sale inspections were completed with virtually all items addressed. Hiking, cycling & equestrian trails connect directly to the property, and the land is zoned for horses. Stanford's campus is a short, predictable 25 min commute away. Zoned for Portola Valley El / Mid schools and Woodside HS, with several excellent private schools nearby. Soaring redwoods, architectural warmth & effortless access to the heart of Silicon Valley - come see it for yourself.

4 Beds ⋅ 4 Baths ⋅ ML82041849 MLS

Set on 2.6+ wooded acres in the hills, this warm & beautifully renovated home offers something genuinely rare on the Peninsula: complete privacy amid towering redwood trees, a profound sense of forest immersion, and less than 15 minutes to Sand Hill & 280. The updated & open floor plan kitchen flows into generous dining and living spaces, all oriented towards sweeping forest views. Natural light fills the space, and wraparound decks extend living outdoors, with a hot tub just off the primary suite. A flexible two bedroom wing can accommodate children, teens, guest rooms, or office and studio space. An independent 1-bdrm ADU with its own kitchen / bath is ideal for rental income, an au pair, or an aging parent. The kitchen, secondary bathrooms, finishes, HVAC, roof, and water heater - have all been recently renovated, and pre-sale inspections were completed with virtually all items addressed. Hiking, cycling & equestrian trails connect directly to the property, and the land is zoned for horses. Stanford's campus is a short, predictable 25 min commute away. Zoned for Portola Valley El / Mid schools and Woodside HS, with several excellent private schools nearby. Soaring redwoods, architectural warmth & effortless access to the heart of Silicon Valley - come see it for yourself.

12 Summit RD, Woodside

Listed by Alexander Nichols, 650-575-4069 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Susanne Bohl from RDFIN

$2,750,000

This Custom built home is perched high on the Skyline ridge (approx. 2000' elevation) with the Pacific Ocean on one side the SF Bay on the other. Located in the exclusive Woodside neighborhood of Kings Mountain, this modern retreat was built with natural filtered light through the Redwoods in mind surrounded by about an acre of wooded privacy. Think open floor plan flow, soaring ceilings, and a wall of glass framing endless redwood canopies. Gourmet kitchen opens to a family gathering area with wood burning stone fireplace. Spa-like baths with a steam shower in the master bathroom, large deck in back for your entertainment needs, a private heated lap pool below, and a separate entrance to an attached ADU/art studio/private office with it's own kitchen and bathroom - it's all here, your own mountain retreat wrapped on a rare level lot where hi-tech meets tranquility and serenity. Woodside's hidden gem where you can become part of a true community - minutes from a top rated elementary school, very active and vibrant community. Only 10-15mins drive to either San Mateo or Half Moon Bay, 20 min to SFO, 25 min to Stanford and 30-40mins to SF - yet worlds away from the chaos. Perfect for remote execs/workers, nature lovers, hikers/bikers, or anyone craving Elevation - literally!

4 Beds ⋅ 4 Baths ⋅ ML82041075 MLS

This Custom built home is perched high on the Skyline ridge (approx. 2000' elevation) with the Pacific Ocean on one side the SF Bay on the other. Located in the exclusive Woodside neighborhood of Kings Mountain, this modern retreat was built with natural filtered light through the Redwoods in mind surrounded by about an acre of wooded privacy. Think open floor plan flow, soaring ceilings, and a wall of glass framing endless redwood canopies. Gourmet kitchen opens to a family gathering area with wood burning stone fireplace. Spa-like baths with a steam shower in the master bathroom, large deck in back for your entertainment needs, a private heated lap pool below, and a separate entrance to an attached ADU/art studio/private office with it's own kitchen and bathroom - it's all here, your own mountain retreat wrapped on a rare level lot where hi-tech meets tranquility and serenity. Woodside's hidden gem where you can become part of a true community - minutes from a top rated elementary school, very active and vibrant community. Only 10-15mins drive to either San Mateo or Half Moon Bay, 20 min to SFO, 25 min to Stanford and 30-40mins to SF - yet worlds away from the chaos. Perfect for remote execs/workers, nature lovers, hikers/bikers, or anyone craving Elevation - literally!

13370 Skyline BLVD, Woodside

Listed by Jonathan Lee, 650-619-9255 from A 2 M Real Estate
(If provided) CoList: from

Sold listing courtesy of Brent Walsh from COMPS

$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

$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

$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

$1,924,911

Welcome to this charming updated 3-bedroom, 2-bathroom home located in the beautiful city of Woodside. This inviting residence sits on a spacious 15,400 sq ft lot, offering plenty of room to enjoy the outdoors. Inside, the well-appointed updated kitchen features modern amenities including a gas cooktop, dishwasher, microwave, oven range, and refrigerator, making meal preparation a breeze. The dining area, conveniently situated in the living room, creates a cozy atmosphere perfect for entertaining. Updated ADU with additional 3rd bathroom separate entrance. Large barn-like 2 car garage with extra room for storage workshop/office or more. This home is located within the Woodside Elementary School District. Lush and serene grounds with quiet and privacy inside this beautifully done home. Easy access to HWY 280 and downtown Woodside, close proximity to the Filoli Historic House and Garden. Don't miss the opportunity to make this lovely Woodside home your own. Large price reduction..Motivated Sellers!

3 Beds ⋅ 2 Baths ⋅ ML82002229 MLS

Welcome to this charming updated 3-bedroom, 2-bathroom home located in the beautiful city of Woodside. This inviting residence sits on a spacious 15,400 sq ft lot, offering plenty of room to enjoy the outdoors. Inside, the well-appointed updated kitchen features modern amenities including a gas cooktop, dishwasher, microwave, oven range, and refrigerator, making meal preparation a breeze. The dining area, conveniently situated in the living room, creates a cozy atmosphere perfect for entertaining. Updated ADU with additional 3rd bathroom separate entrance. Large barn-like 2 car garage with extra room for storage workshop/office or more. This home is located within the Woodside Elementary School District. Lush and serene grounds with quiet and privacy inside this beautifully done home. Easy access to HWY 280 and downtown Woodside, close proximity to the Filoli Historic House and Garden. Don't miss the opportunity to make this lovely Woodside home your own. Large price reduction..Motivated Sellers!

789 Canada RD, Woodside

Listed by Tammy T-Cole, 650-683-0426 from Compass
(If provided) CoList: from

Sold listing courtesy of Sharad Gupta from LY55V

$2,700,000

Lakeview Lodge: A Storybook Sanctuary with Iconic Views and a Surprisingly Convenient Location. Every now and then, a property comes along that feels pulled from the pages of a storybook. Lakeview Lodge is one of those rare places, loved and nurtured by its owners for 29 years for the simplest reason: its just that special. Perched above the treetops with sweeping views of Stanfords Jasper Ridge, and originally named for its view of Searsville Lake, this peaceful retreat offers a front-row seat to natures changing beauty. From golden sunrises to dusky twilight, the vistas inspire reflection. Located near the bottom of Old La Honda Rd at Portola Rd, your minutes from Stanford, top schools, commute routes, and dining - seclusion without sacrifice. Nearby Dennis Martin Creek trails offer tranquil walks under the redwoods. The main home features 2BD/2BA, and a private-entry suite below with kitchen, living area, bedroom, and bathideal for guests or a home office. With high-speed internet, you can Zoom by day and stargaze by night. Lakeview Lodge is more than a home, its a soulful escape with a country feel and unbeatable convenience.

3 Beds ⋅ 3 Baths ⋅ ML82003150 MLS

Lakeview Lodge: A Storybook Sanctuary with Iconic Views and a Surprisingly Convenient Location. Every now and then, a property comes along that feels pulled from the pages of a storybook. Lakeview Lodge is one of those rare places, loved and nurtured by its owners for 29 years for the simplest reason: its just that special. Perched above the treetops with sweeping views of Stanfords Jasper Ridge, and originally named for its view of Searsville Lake, this peaceful retreat offers a front-row seat to natures changing beauty. From golden sunrises to dusky twilight, the vistas inspire reflection. Located near the bottom of Old La Honda Rd at Portola Rd, your minutes from Stanford, top schools, commute routes, and dining - seclusion without sacrifice. Nearby Dennis Martin Creek trails offer tranquil walks under the redwoods. The main home features 2BD/2BA, and a private-entry suite below with kitchen, living area, bedroom, and bathideal for guests or a home office. With high-speed internet, you can Zoom by day and stargaze by night. Lakeview Lodge is more than a home, its a soulful escape with a country feel and unbeatable convenience.

171 Old La Honda RD, Woodside

Listed by Kavanaugh Group, 650-850-1046 from Coldwell Banker Realty
(If provided) CoList: Steven Gray from Coldwell Banker Realty

Sold listing courtesy of Alexander Nichols from EXPCA

$5,750,000

Welcome to a breathtaking estate crafted from heart redwood, where timeless elegance meets modern luxury. The beautifully updated main residence features four spacious bedrooms along with a renovated kitchen and baths, designed for both comfort and style. Two inviting guest houses provide flexible living options, while a third guest unit serves as a bright, inspiring studio/gym. Soak up the sun by the luxurious pool, unwind in the private spa just off the primary suite, or find serenity on one of the many garden patios. Skylights throughout the home flood the interiors with natural light, creating a warm and welcoming ambiance. For outdoor entertainment, enjoy friendly competition on the bocce ball court or stroll through the storybook grounds, complete with sweeping lawns and majestic oaks. Set on fully fenced, gated, and alarm-secured acreage with garage parking for three, this rare retreat offers privacy, beauty, and convenienceall within the acclaimed Portola Valley school district. A truly magical and one-of-a-kind offering.

4 Beds ⋅ 4 Baths ⋅ ML82002115 MLS

Welcome to a breathtaking estate crafted from heart redwood, where timeless elegance meets modern luxury. The beautifully updated main residence features four spacious bedrooms along with a renovated kitchen and baths, designed for both comfort and style. Two inviting guest houses provide flexible living options, while a third guest unit serves as a bright, inspiring studio/gym. Soak up the sun by the luxurious pool, unwind in the private spa just off the primary suite, or find serenity on one of the many garden patios. Skylights throughout the home flood the interiors with natural light, creating a warm and welcoming ambiance. For outdoor entertainment, enjoy friendly competition on the bocce ball court or stroll through the storybook grounds, complete with sweeping lawns and majestic oaks. Set on fully fenced, gated, and alarm-secured acreage with garage parking for three, this rare retreat offers privacy, beauty, and convenienceall within the acclaimed Portola Valley school district. A truly magical and one-of-a-kind offering.

1477 Portola RD, Woodside

Listed by Kristin Cashin, 650-387-2603 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Ankur Luthra from CATAPULT

$4,480,000

This fantastic new price makes it possible to create your own dream property on 2 tranquil acres! Conveniently located in true central Woodside with 2 homes, 2 private driveways and so much room to grow. The main house is 3,090 square feet, has 5 bedrooms, and 3 bathrooms. The large living room has huge windows overlooking the expansive lawn and pool area. The primary bedroom upstairs features a walk-in closet, fireplace, and a balcony with a jacuzzi overlooking your 2-acre property. The cottage can be accessed off of the first driveway and has been thoroughly remodeled. There is a lush green pasture, and pathways leading to the pool and patio area. 2 natural gas generators connected to each house. Experience the tranquility of Woodside, just 2 minutes from the town center and renowned horse trails. This is your chance to embrace a relaxed lifestyle in the heart of Woodside!

6 Beds ⋅ 4 Baths ⋅ ML81987106 MLS

This fantastic new price makes it possible to create your own dream property on 2 tranquil acres! Conveniently located in true central Woodside with 2 homes, 2 private driveways and so much room to grow. The main house is 3,090 square feet, has 5 bedrooms, and 3 bathrooms. The large living room has huge windows overlooking the expansive lawn and pool area. The primary bedroom upstairs features a walk-in closet, fireplace, and a balcony with a jacuzzi overlooking your 2-acre property. The cottage can be accessed off of the first driveway and has been thoroughly remodeled. There is a lush green pasture, and pathways leading to the pool and patio area. 2 natural gas generators connected to each house. Experience the tranquility of Woodside, just 2 minutes from the town center and renowned horse trails. This is your chance to embrace a relaxed lifestyle in the heart of Woodside!

8 Oakhill DR, Woodside

Listed by Costantini Team, 650-430-8425 from Compass
(If provided) CoList: from

Sold listing courtesy of Rachel Hardyck from DWELL

$4,887,500

Woodside Gem! This expansive one+ acre property is a versatile estate offering endless potential to renovate, re-imagine entirely, or simply move in and enjoy. The property includes a light-filled ranch home with vintage details intact, blending classic appeal with modern upgrades, including fresh interior and exterior paint throughout. The main residence offers 4 spacious bedrooms and 3 and half bathrooms, formal dining, separate living room and kitchen / family combo providing ample space for family and guests. Additionally, a 1-bedroom, 1-bath ADU, complete with a full kitchen, is ideal for guest stays or rental opportunities. The vast grounds feature multiple outdoor zones, including a separately fenced pool and plenty of open space to accommodate equestrian use or future enhancements. Located within the acclaimed Woodside Elementary School district, this rare property captures the essence of rural tranquility with suburban convenience. Just minutes from the town center and school.

4 Beds ⋅ 3 Baths ⋅ ML81986602 MLS

Woodside Gem! This expansive one+ acre property is a versatile estate offering endless potential to renovate, re-imagine entirely, or simply move in and enjoy. The property includes a light-filled ranch home with vintage details intact, blending classic appeal with modern upgrades, including fresh interior and exterior paint throughout. The main residence offers 4 spacious bedrooms and 3 and half bathrooms, formal dining, separate living room and kitchen / family combo providing ample space for family and guests. Additionally, a 1-bedroom, 1-bath ADU, complete with a full kitchen, is ideal for guest stays or rental opportunities. The vast grounds feature multiple outdoor zones, including a separately fenced pool and plenty of open space to accommodate equestrian use or future enhancements. Located within the acclaimed Woodside Elementary School district, this rare property captures the essence of rural tranquility with suburban convenience. Just minutes from the town center and school.

155 Ravine DR, Woodside

Listed by Christienne Hadley, 650-533-3766 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Bharath "Kumar" Talluri from NTERO

$1,935,000

Welcome to tranquil home with an ocean view among the lush Redwood Forest off Skyline Blvd. in Woodside! Located about 15 minutes from HWY92, less than a minute from Kings Mt Road, you'll enjoy winding down on the multi-level deck on a warm afternoon or next to a cozy fire on a cold brisk night. Oak hardwood flooring throughout the main home with vaulted ceilings adding lots of natural light. The kitchen is equipped for a chef with a Wolf gas range, new quartz countertops, stainless steel sink, and goose neck faucet. The main house has 3 Bedrooms and 2.5 Baths encompassing 2,260sf of the 3,180 total including the dining room, 2 office spaces, a laundry room, and walk-in closet. The secondary unit is situated on the bottom floor with its own private deck, separate laundry, and walk-in closet in the primary bedroom. At 920sf there is plenty of space in the ADU; 2 Bedrooms and 1 Bathroom. New quarts counter tops and appliances, stainless steel sink and faucet. Motivated Seller

5 Beds ⋅ 4 Baths ⋅ ML81949920 MLS

Welcome to tranquil home with an ocean view among the lush Redwood Forest off Skyline Blvd. in Woodside! Located about 15 minutes from HWY92, less than a minute from Kings Mt Road, you'll enjoy winding down on the multi-level deck on a warm afternoon or next to a cozy fire on a cold brisk night. Oak hardwood flooring throughout the main home with vaulted ceilings adding lots of natural light. The kitchen is equipped for a chef with a Wolf gas range, new quartz countertops, stainless steel sink, and goose neck faucet. The main house has 3 Bedrooms and 2.5 Baths encompassing 2,260sf of the 3,180 total including the dining room, 2 office spaces, a laundry room, and walk-in closet. The secondary unit is situated on the bottom floor with its own private deck, separate laundry, and walk-in closet in the primary bedroom. At 920sf there is plenty of space in the ADU; 2 Bedrooms and 1 Bathroom. New quarts counter tops and appliances, stainless steel sink and faucet. Motivated Seller

14732 Skyline BLVD, Woodside

Listed by Angela Burnett, 650-743-4950 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Allen Nazari from PKLNC

$6,850,000

Central Woodside / Woodside Knolls beauty! 4-bd, 3.5ba, 4,000 sq ft, 1,000+ sq ft ADU, pool & spa, flat backyard with full edible garden and kennels! Huge 3-car garage with workshop. Rebuilt and added onto in 2001-2004 so looks and feels newer! This property will not disappoint!!

4 Beds ⋅ 4 Baths ⋅ ML81952476 MLS

Central Woodside / Woodside Knolls beauty! 4-bd, 3.5ba, 4,000 sq ft, 1,000+ sq ft ADU, pool & spa, flat backyard with full edible garden and kennels! Huge 3-car garage with workshop. Rebuilt and added onto in 2001-2004 so looks and feels newer! This property will not disappoint!!

240 Laning DR, Woodside

Listed by Sean Foley, 650-207-6005 from Compass
(If provided) CoList: from

Sold listing courtesy of Christina Hengehold from CBR

$8,850,000

Custom rebuilt Hidden Valley / Farm Rd estate will not disappoint! On just over 3.25-acres, this 5,253 sq ft estate home was taken down to the studs, remodeled, expanded and structurally retrofitted over the years. The main residence has a spacious office loft and 4 bedrooms, including a main-level primary suite with 2 couture closet rooms and sumptuous marble bath. The large, detached building with executive office and overhead studio guest house, each with bath and kitchenette. Spacious terrace, pool, and vast stretches of lawn intertwined with walking paths encircling the entire property. Also suitable for up to 6 horses. This magical Woodside area is just minutes to 280, Sand Hill Road, Stanford University, and excellent Portola Valley schools. Luxurious livability, acreage, privacy, and every amenity needed for today.

5 Beds ⋅ 4 Baths ⋅ ML81939228 MLS

Custom rebuilt Hidden Valley / Farm Rd estate will not disappoint! On just over 3.25-acres, this 5,253 sq ft estate home was taken down to the studs, remodeled, expanded and structurally retrofitted over the years. The main residence has a spacious office loft and 4 bedrooms, including a main-level primary suite with 2 couture closet rooms and sumptuous marble bath. The large, detached building with executive office and overhead studio guest house, each with bath and kitchenette. Spacious terrace, pool, and vast stretches of lawn intertwined with walking paths encircling the entire property. Also suitable for up to 6 horses. This magical Woodside area is just minutes to 280, Sand Hill Road, Stanford University, and excellent Portola Valley schools. Luxurious livability, acreage, privacy, and every amenity needed for today.

165 Farm RD, Woodside

Listed by Sean Foley, 650-207-6005 from Compass
(If provided) CoList: from

Sold listing courtesy of Derek Timm from DTIMM

$5,075,000

Welcome to The Barrel House. This distinctive property was built in 1973 and designed by Sidney Hoover, a distinguished local architect that was influenced by Frank Llyod Wright. The private two-story home boasts three bedrooms and two and a half baths along with an ADU which is attached to a two-car garage. The inspiration for this home came from the beauty of four enormous redwood water barrels that were used as the cornerstones of the residence. The abundant natural light is drawn through massive windows and skylights throughout to give you the feeling of living in the forest. An abundance of trees are scattered across the beautiful 1+acre parcel. The quiet serenity of the property is enhanced by the location which is accessed by a flag lot lane. The home is within a short distance to Woodside Elementary School and the Town Center for upmost convenience. If you have ever envisioned living in nature The Barrel House could be your dream come true!

3 Beds ⋅ 3 Baths ⋅ ML81938892 MLS

Welcome to The Barrel House. This distinctive property was built in 1973 and designed by Sidney Hoover, a distinguished local architect that was influenced by Frank Llyod Wright. The private two-story home boasts three bedrooms and two and a half baths along with an ADU which is attached to a two-car garage. The inspiration for this home came from the beauty of four enormous redwood water barrels that were used as the cornerstones of the residence. The abundant natural light is drawn through massive windows and skylights throughout to give you the feeling of living in the forest. An abundance of trees are scattered across the beautiful 1+acre parcel. The quiet serenity of the property is enhanced by the location which is accessed by a flag lot lane. The home is within a short distance to Woodside Elementary School and the Town Center for upmost convenience. If you have ever envisioned living in nature The Barrel House could be your dream come true!

3364 Woodside RD, Woodside

Listed by Chris Anderson, 650-207-7105 from Compass
(If provided) CoList: Grayson Martin from Compass

Sold listing courtesy of Dennis Phan from EXPCA