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$24,995,000
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

$2,995,000
3 Beds ⋅ 3 Baths ⋅ ML82054634 MLS
Woodside Retreat "Beside The Woods in Woodside" Peaceful end-of-road privacy and a rustic, eclectic retreat once featured in the Almanac, cherished by one family for 50+ years. 4 sunny, wooded acres with sweeping hill and redwood views. Private gate opens directly onto the trails of 900+ acre Huddart Park. Close to town and Woodside schools. This rustic 3600+ ft 3 beds/2.5 bths home is a study in Vintage Tahoe-style craftsmanship. The living room anchors the house with wood and brick walls, an open stone fireplace, and terracotta tile underfoot. Wooden beams carry into the country kitchen with Subzero and stainless appliances, and the dining room flows onto an expansive view deck over the gardens and pool. A home office overlooks the gardens, and a skylit staircase leads down to a gallery hallway with a stained glass window and a private family room/bedroom. The showstopper: a dramatic Great Room "tavern," host to gatherings of 150, with 19' ceils and grand fireplace of original SF cobblestones. Custom bar built from salvaged San Carlos post office and pharmacy. A reclaimed-barn-siding full bath with steam shower. Large billiard room completes the tavern vibe. Decks and brick paths trace the contour of the land to the pool, framed by redwoods on all sides. Sep 2-car garage.

496 Raymundo DR, Woodside

Listed by Don DeFranco, 415-722-7259 from Compass
(If provided) CoList: Grayson Martin from Compass
$2,870,000
7 Beds ⋅ 6 Baths ⋅ ML82039818 MLS
A rare opportunity to own an expansive estate with breathtaking panoramic views, exceptional square footage, and incredible potential in a private hillside setting. From the moment you arrive, the home commands attention with its grand entry and impressive scale. Inside, soaring ceilings, dramatic open spaces, and walls of windows flood the home with natural light while showcasing sweeping valley views. The main level is built for both everyday living and entertaining, featuring a spacious living room, multiple gathering areas, and seamless access to a wraparound deckperfect for true indoor-outdoor living. The kitchen offers a large island, ample cabinetry, and a functional layout ready to be elevated into a stunning chefs space. Generous bedrooms and flexible living areas include a primary suite with scenic windows, dual vanities, and a soaking tub, creating a peaceful retreat with beautiful natural surroundings. The lower level offers an expansive bonus/game room with bar area and endless possibilities for entertaining, recreation, or extended living. A dedicated wine cellar adds a rare and desirable touch. Expansive decking and usable outdoor space complete this exceptional offering, blending privacy, scale, and opportunity in a truly unique setting.

245 Heacox RD, Woodside

Listed by Aaron Derbacher, 408-828-8114 from KW Bay Area Estates
(If provided) CoList: Benjamin Frieden from KW Bay Area Estates
$4,588,000
4 Beds ⋅ 4 Baths ⋅ ML82050181 MLS
Nestled among majestic oak trees on nearly 1.2 acres in Woodside Hills, this home is set well back from the street via a long paver driveway. Spanning 4,150 SF, the interiors feature wide-plank hardwood floors, soaring ceilings, and refined finishes that create a light-filled, airy atmosphere in harmony with its natural surroundings. Expansive formal rooms are complemented by multiple fireplaces, a well-appointed kitchen, and a walk-out family room that opens to the outdoors. The four-bedroom layout includes a primary suite with a spa-inspired bathroom designed for comfort and retreat. Outdoor living is equally compelling, with a generous deck and patio featuring an outdoor kitchen, all framed by a verdant, oak-studded backdrop that emphasizes the home's connection to nature. A three-car garage completes the property, while the setting balances privacy with convenience, just minutes to downtown Redwood City, nearby nature preserves and trailheads, and easy access to Highway 280.

61 Oak Haven WAY, Woodside

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(If provided) CoList: from

$12,995,000
7 Beds ⋅ 9 Baths ⋅ ML82045810 MLS
Lowest price per square foot @ $956 in Woodside, Atherton or Portola Valley. Spectacular Monterey Colonial home on 6+ private acres. Long gated driveway & large motor court. Estate shows tremendous character and beauty. Improvements include a stunning primary bath, a complete new roof & gutters & Exterior paint 2025. 3 expansive levels with grand public rooms, large eat-in kitchen, English Pub bar, recreation/media room and fitness room with sauna, wine room for approx. 1,000 bottles. Seven large bedrooms, including two primary suites, a full two bedroom attached apartment, a separate 1 bedroom guest house privately located on the grounds with a separate 2 car garage and parking. Additionally, attached 4 car garage, large swim pool, tennis court and Stable for 5 horses & riding arena, Hay storage, wash rack, multiple areas for parking trailers. Beautiful Western & Southern hills views. Award winning Las Lomitas Elementary Schools K-8. Nearby to town center, easy commute to SF or Silicon Valley. Main house 13,590 sf per county records, 5,560 sf main level , 4,300 sf 2nd level, 3,730 sf lower level includes home theater, wine room, workout/ sauna. Not including guest house, extra 2 car garage, shop & Horse stable. Corral & stable have separate driveway. Seller wants it sold.

389 Moore RD, Woodside

Listed by Steve Lessard, 650-704-5308 from Compass
(If provided) CoList: from

$2,715,000
4 Beds ⋅ 4 Baths ⋅ ML82048252 MLS

320 Grandview DR, Woodside

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

Sold listing courtesy of Julie Hadidi from COMPS
$38,800,000
6 Beds ⋅ 9 Baths ⋅ ML82045742 MLS
This extraordinary Woodside estate spans 6.4 level acres w/sun-swept vineyards & western hill views. The compound comprises multiple architecturally significant buildings, including the main residence, guest house, a multi-room wellness studio w/wine cellar & 6-car garages plus a working lab w/anti-static flooring. Designed for exceptional privacy & self-sufficiency, the property features a 35kW photovoltaic solar system, a 125kW whole-house backup generator, & a 1,600 amp electrical service. A comprehensive, enterprise-grade infrastructure includes a network w/fiber connectivity linking each building to the main racks, supported by a firewall, 26 ethernet switches, & 15 Wi-Fi access points. A whole-house audio system powered by advanced network amplifiers & Lutron-app controlled light further elevate the living experience. The grounds are equally compelling, with a well for irrigation, a clay tennis court, lighted sport court, & approximately 2 acres of Pinot Noir grafted aged vines. A whimsical designed 3-tree playhouse & fort adds a rare & enchanting element to the landscape. The result is a true sanctuary--where architectural beauty , advanced infrastructure and natural surroundings converge in one of Silicon Valley's most exceptional settings.

15 Hidden Valley LN, Woodside

Listed by Brent & Mary Gullixson, 650-888-0860 from Compass
(If provided) CoList: from

$12,000,000
6 Beds ⋅ 5 Baths ⋅ ML82046443 MLS
Designer Transformation on 1.5 Private Acres Steps to Town A remarkable whole-home transformation has elevated this property into a showcase of design, quality, and livability. Spanning approximately 1.5 acres just minutes from the town center, the setting unfolds with park-like grounds that capture the essence of Woodside country living. Inside, a beautifully orchestrated floor plan offers predominantly single-level living with subtle elevation changes that define spaces while maintaining an open, flowing arrangement ideal for both everyday living and entertaining. Every detail reflects a designers eye, with cohesive finishes and thoughtfully selected materials creating a sophisticated yet welcoming atmosphere throughout. A well-appointed 2-bedroom, 1-bath guest house with full kitchen and laundry adds exceptional flexibility for extended family, guests, or even office use. Outdoor amenities are equally compelling, highlighted by a sparkling pool, vast lawn areas, and a bountiful orchard alongside a charming chicken coop that enhances the property's country appeal. All of this plus access to acclaimed Woodside Elementary School, offering a rare combination of privacy, scale, and convenience.

140 Dean RD, Woodside

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

Sold listing courtesy of Matt Zampella from SGP
$8,700,000
4 Beds ⋅ 5 Baths ⋅ ML82044880 MLS ⋅ Woodside Hills BLDG.
A rare opportunity to own an earthy modern estate set in the esteemed Woodside Hills with breathtaking sweeping Bay views. The residence was reimagined with uncompromising attention to detail, offering a truly like-new experience that has never been lived in. Situated on 0.98 acres, the 6,809 sq ft home blends dramatic scale with warm, livable sophistication for true California Living. The thoughtfully designed floor plan includes 4 well-appointed bedrooms, 4 designer bathrooms, 1 powder room, dedicated office, flex studio, media room, laundry/mud room, and luxurious rec room. The designer kitchen serves as both a functional showpiece and an entertainers dream, featuring open steel & beam vaulted ceiling, natural light, custom white oak cabinetry, top-of-the-line appliances, wet bar, pantry, temperature controlled wine cellar, and designer finishes. The grounds include a stunning chefs kitchen, fire pit lounge, abundance of areas to entertain, view decks, and a refreshing pool. Surrounded by other distinguished estates, 150 Brookwood Rd is an iconic offering, combining design-forward architecture, extraordinary views, exceptional outdoor living, and an unparalleled Woodside setting to create a one-of-a-kind luxury retreat. Buyer to verify.

150 Brookwood RD, Woodside

Listed by QL Realty Group, 831-566-0006 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Susan Ferguson from COLD02
$6,561,058
5 Beds ⋅ 5 Baths ⋅ ML82045206 MLS ⋅ Woodside Hills Association BLDG.
Set on a flat acre of gorgeously manicured grounds. This single story home borrows transitional architectural tones from the French countryside. The circular driveway leads up to a large 3 car garage. Five bedrooms that come with a separate guest house, sports court, large pool with covered grotto like spa, adjacent bath with changing room. Outdoor kitchen covered by a palapa, the perfect shade from natural elements while dining al fresco. Backyard is south facing and hosts the perfect weather all year long. The yard is an entertainers paradise. French oak engineered flooring throughout. Kitchen has an open layout with Thermador appliances and tuscan inspired limestone touches. Front living room has custom built shelving and cozy gas fireplace. Knotted Alderwood window and doors. Indoor surround sound. Generous master suite with walk in closet and wardrobes. Heated floors in bath and an oversized shower with tropical garden views. Enjoy the privacy this secluded subdivision provides. Hidden away, yet suburban enough hooked up to city sewer and close proximity to Sand Hill Road, Silicon Valley and San Francisco. Close to Menlo School, Sacred Heart Prep, Phillips Brooks, Woodside Priory amongst many other renown schools. Enjoy sunsets and the nature this lifestyle provides.

330 Ridgeway RD, Woodside

Listed by Mariana Pappalardo, 650-670-7888 from Compass
(If provided) CoList: from

Sold listing courtesy of Agnes Yu from BPRO
$7,495,000
4 Beds ⋅ 6 Baths ⋅ ML82044344 MLS
New Price! Set at the end of a private, gated country lane on approximately 1.11 fully usable acres, this elegant estate with French country architecture offers an exceptional blend of refined living and natural beauty, with sweeping views of the Western Hills and stunning sunsets. The main residence features 4 BR and 5.5 BA and a dedicated office/library with inspiring views. A recently updated chefs kitchen with a sunny breakfast area, main-level primary suite with connecting recreation room, patterned oak hardwood floors, and dual-paned windows throughout create a warm yet sophisticated ambiance. Designed for indoor/outdoor entertaining with expansive terraces and beautifully landscaped gardens this is a one of a kind home. A detached 1 BR 1 BA guest house has a full kitchen, wood-burning fireplace, and high ceilings, perfect for guests, extended family, or independent work space. An additional 520 square feet of garage space and 795 square feet of basement storage provide functionality alongside luxury. Ideally located within walking distance to Woodside Town Centers shops and restaurants, and close to Woodside School (Pre-K8th), Interstate 280, Sand Hill Road, and Stanford University, this home exemplifies the best of serene, convenient, and elegant Woodside living

55 Mission Trail RD, Woodside

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

Sold listing courtesy of Victoria Yang Surles from CBR
$34,995,000
8 Beds ⋅ 7 Baths ⋅ ML82038776 MLS
This exceptional property spans more than 3 acres with sweeping western hill views and 9,880 square feet of total living space. The main home was completely rebuilt in 2000, and in 2025, an entirely new guest house and entertainment complex was added to the estate. The classically styled main residence features nearly every room opening to the views and includes a state-of-the-art theater and temperature-controlled wine cellar. The newly completed guest house showcases authentic European detail with roof tiles handmade in Provence and Genoise eaves, complemented with modern construction and smart home technology. A new saltwater pool and spa, nearly 60 feet in length, is surrounded by an expansive terrace with sound system, outdoor kitchen, pizza oven, and easy catering access. The south-facing grounds are equally impressive, with a 310-vine Cabernet vineyard, heritage olive trees and oaks, a parterre rose garden, bountiful orchard, and raised vegetable beds. Reflecting timeless European elegance and exceptional craftsmanship, the estate is remarkably private, with far-reaching views enhancing the entire setting and all midway between Silicon Valley and San Francisco.

307 Olive Hill LN, Woodside

Listed by Brent & Mary Gullixson, 650-888-0860 from Compass
(If provided) CoList: from

$5,450,000
5 Beds ⋅ 4 Baths ⋅ ML82044125 MLS
Tucked away on a private, gated cul-de-sac, 200 Todo El Mundo in Woodside offers the perfect balance of privacy, convenience, and natural beauty. Situated on approximately 1.5 acres of flat, usable land bordered by a seasonal creek, the property features expansive front and back irrigated lawns and a peaceful, park-like setting. The European-influenced traditional 4,885-square-foot main residence is designed for effortless indoor-outdoor entertaining, with several rooms opening through French doors to two sunny decks. A dramatic living room with soaring two-story ceilings and fireplace anchors the home, complemented by a spacious family room with its own fireplace and wet bar, a cozy kitchen and a private dining room ideal for intimate gatherings. The thoughtful five-bedroom, three-and-a-half-bath layout includes a serene upper-level Primary Suite with a full bath, sauna, fireplace and walk-in closet, two additional upstairs bedrooms and two main-level bedrooms with a full bath and tub. With its proximity to Woodside Town Center, Woodside Plaza shopping, Sand Hill Road, Stanford University, and nearby freeway access to major Silicon Valley destinations, this exceptional property offers a rare opportunity to enjoy the Woodside lifestylequiet, connected, and surrounded by nature

200 Todo El Mundo, Woodside

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

Sold listing courtesy of Larry Liu from APR
$16,000,000
5 Beds ⋅ 6 Baths ⋅ ML82041798 MLS
In one of the best locations in Central Woodside, easy walking distance to Town Center and acclaimed Woodside School (pre-K to 8th); this home captures California Country with East Coast Elegance with its breathtaking views of the Western Hills from the flat one-acre parcel. The open floor plan flows seamlessly for indoor/outdoor entertaining featuring a rear dining patio, built-in BBQ, 50 foot saltwater pool, bocce court, shaded pergola sitting area, spacious rear grass lawn and surrounding array of colorful gardens. Gorgeous oak hardwood floors unify the two-story home, with a comfortable family room adjacent to the chefs kitchen and large combined dining and living room, all with French Doors opening out to the sunny rear entertaining patio. The home has 5 spacious bedrooms, each with its own bath and ideally arranged for a variety of lifestyle needs. The main-level also has a separate home office. Upstairs a primary suite plus 3 additional en-suite bedrooms provide a perfect living area layout. This location offers it all: a private home and property on one of the best country lanes in Woodside while also being within walking distance to Woodside School, Town Center shops and restaurants, and all of the hiking, biking and horseback trails that make Woodside special.

180 Romero RD, Woodside

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

Sold listing courtesy of Katy Thielke Straser from COMPS
$12,750,000
4 Beds ⋅ 8 Baths ⋅ ML82041478 MLS
Extraordinary residence on 5 acres with opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway and sweeping views of San Francisco Bay. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble staircase with hand-forged railings leads to the upper level with formal living room, formal dining room, tremendous kitchen, family room, office, plus grand primary suite with 2 full baths. 3 luxurious bedroom suites plus large office and conference center make up the ground level. Breathtaking views from every room on both levels. Elevator in the main residence. 1-bedroom pool house and studio guest house, each with bath and full kitchen. Sparkling pool and spa plus fireplace terrace for idyllic entertaining in complete privacy.

490 Las Pulgas DR, Woodside

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

Sold listing courtesy of Scott Dancer from APR
$5,388,000
4 Beds ⋅ 4 Baths ⋅ ML82041471 MLS ⋅ Woodside Hills Home Association BLDG.
Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers privacy, scale, and resort-inspired living. Light-filled interiors feature soaring ceilings, refined millwork, and an elegant flow designed for both entertaining and everyday living. Formal living and dining rooms provide distinct gathering spaces, while the well-appointed kitchen with custom cabinetry, stone countertops, and a center island opens seamlessly to the adjacent family room and surrounding outdoor spaces for effortless indoor outdoor living. The spacious primary suite is a private retreat with a view deck and spa-inspired bath. Three additional bedrooms offer flexibility for guests, office space, fitness, or extended living. Resort-style grounds include expansive patios, a pool, covered lounge area, mature landscaping, and multiple vantage points capturing sweeping Bay views and natural beauty throughout. Conveniently located near downtown Woodside and Redwood City, Highway 280, and major Silicon Valley employers. Nearby private schools include Menlo School, Phillips Brooks School, Sacred Heart Schools, and Woodside Priory.

140 Ridgeway RD, Woodside

Listed by Caroline Dinsmore, 650-773-2226 from The Agency
(If provided) CoList: from

Sold listing courtesy of Jennifer Bitter from GGSIR
$2,750,000
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
$10,988,000
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
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

$5,750,000
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
$8,000,000
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
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
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
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
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
$2,900,000
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
$18,900,000
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
$3,088,000
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

$7,500,000
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

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