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1190 Bear Gulch RD, Woodside
$2,995,000
6 Beds ⋅ 7 Baths ⋅ ML82066176 MLS
A unique opportunity awaits to restore this significant contemporary estate on approximately 7.1 acres with dramatic San Francisco Bay & East Bay hill views from all three levels. Built in 1991 & spanning more than 7,000 square feet of living space, the home is distinguished by commanding architecture with soaring ceilings, expansive walls of glass, skylights, steel cable-strung railings, & glass-block details. Some rooms currently have no finished flooring, drywall has been removed in select areas, & some doors & windows are in need of repair presenting the opportunity to restore & reimagine the interiors while retaining the home's distinctive architectural framework. Numerous terraces & balconies take full advantage of the Bay views & surrounding wooded setting. Level tiered front grounds, deck, & playground provide additional outdoor space. Reached via private gated road, the parklike setting feels exceptionally secluded & adjoins 942-acre Wunderlich Park with miles of hiking & riding trails, yet Woodside Town Center is just 15 minutes away. Access to acclaimed Woodside Elementary School further enhances this exceptional opportunity to restore a substantial Woodside estate to its full potential.

1190 Bear Gulch RD, Woodside

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

118 Hillside DR, Woodside
$4,195,000
6 Beds ⋅ 3 Baths ⋅ ML82066102 MLS
Set in Woodside Glens and the K-8 Woodside Elementary School District, about a mile from Town Center, this light-filled ~3,000 sq ft home has six bedrooms, three full baths, and a skylit office. A 2024 addition joined the 1920s home, giving you room for everyone, whether you need kids' bedrooms, home offices, guests, or a gym. Iron-and-glass front doors open to a cathedral entry and a living room with vaulted ceilings and exposed wood beams. The great room includes a white quartz kitchen with a peninsula and Bosch gas range, a sitting area, and glass-walled dining. The main level includes three bedrooms, a bath with a marble-topped vanity, and a closet ready for a second stacked washer/dryer. Upstairs, the skylit primary suite has a loft, walk-in closet, heated bath floors, curbless shower for two, and a balcony for sunsets over the hills. Downstairs, a bonus lounge with a beverage cooler, 65-inch TV, and in-wall audio opens through stacking glass doors to the terrace, alongside two bedrooms, the office, a full bath, and the main laundry room. Relax on the front porch, or entertain on the terrace by the heritage oak, with a pergola and outdoor kitchen. Includes smart lighting, audio, fire sprinklers, RV hookups, and a 50-amp outlet for EV in the garage.

118 Hillside DR, Woodside

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

307 Olive Hill LN, Woodside
$29,995,000
8 Beds ⋅ 7 Baths ⋅ ML82065658 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

643 W Glen WAY, Woodside
$5,200,000
4 Beds ⋅ 4 Baths ⋅ ML82065037 MLS
Framed by majestic trees w/ sweeping views of Woodside & the Santa Cruz mountains, this remodeled California Mediterranean home brings the outdoors in. A bright foyer w/ custom millwork & Spanish tile stair risers leads to a private office w/ garage access & live-edge sit/stand desk. Upstairs, the formal living room offers 13' ceilings, arched windows & a floor-to-ceiling fireplace. The chefs kitchen features peninsula seating for four, Caesarstone quartz, a pantry, dual refrigerators & ovens, & opens to dining & family rooms w/ custom wood ceilings & mountain vistas. The family room has a wet/coffee bar & opens to a glass-walled sunroom w/ curved dry bar, made for game night. Three main-level bedrooms include an en suite & a shared 4-piece bath, plus a generous laundry room. The top-level primary suite offers mountain views, a sitting area w/ fireplace, a 6-piece bath w/ marble shower & jetted tub, & a walk-in closet. Dimmable lighting, Bluetooth sound, zoned HVAC & a 3-car garage w/ Tesla charger. Outside: fenced rear yard, built-in grill, lit walkways, shade awning & irrigated redwoods. Major remodel 2019-2020, fully permitted, w/ updates through 2026. A move-in-ready Woodside retreat. Close to the Town of Woodside & the 280 freeway. Woodside Elementary & Sequoia High School.

643 W Glen WAY, Woodside

Listed by Ginna Lazar, 650-302-6666 from Lazar Homes
(If provided) CoList: from

12520 Skyline BLVD, Woodside
$3,495,000
3 Beds ⋅ 4 Baths ⋅ ML82064329 MLS
Spectacular views of the Pacific Ocean, Half Moon Bay, and San Francisco highlight this exceptionally private property just 3 miles from Highway 92. On the market for the first time in 50 years the home is set well back from the road on more than 11 acres with vast level areas and potential for additional structures like an ADU or equestrian facilities. The spacious one-story home is ready to enjoy. Vaulted natural wood ceilings, hardwood floors, and a two-sided brick fireplace enhance the main living areas. The eat-in kitchen has stainless steel appliances and a breakfast room plus there is a separate family room. 3 bedrooms include the primary suite, a second suite, and bedroom with dual-entry bath plus there is a privately located spacious room for an office or gym. An expansive deck spans the home and looks out to the views. Additional amenities include a 3-car garage, central air conditioning, a fenced vegetable garden, and greenhouse. Just 8 miles from downtown Half Moon Bay and a 24-minute drive to SFO. Kings Mountain Elementary School.

12520 Skyline BLVD, Woodside

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

235 Harcross RD, Woodside
$19,950,000
5 Beds ⋅ 7 Baths ⋅ ML82064103 MLS
Newly constructed modern residence by Keightley Builders defined by exceptional architecture, abundant natural light, and a private knoll-top setting. 8,275 sf of living space and 1,055 sf garage pair elegant design with a sense of calm in a private, park-like setting. Enter the main floor to walls of glass, a sculptural floating staircase, an inviting living room, a guest bedroom and a great room comprised of a spacious chefs kitchen with adjacent dining and family rooms separated by a striking two-way gas fireplace. Fleetwood sliding doors open to an entertaining deck, pool with spa, Baja shelf and lap lane and a BBQ seating area around gas fed fireplace. Upstairs, privacy and tranquil views define the luxurious primary suite and three additional en-suite bedrooms. The lower level creates a more private dimension for work, wellness and recreation with dedicated rooms for fitness, yoga, a home office, a spacious media room and a temperature controlled wine cellar. Refined aesthetics throughout include wide plank white oak hardwood floors, custom lighting, natural stonework and designer fixtures. A beautifully appointed detached 2 BR guesthouse and adjoining pool house create an independent retreat for family and friends. Come see this spectacular one of a kind estate!

235 Harcross RD, Woodside

Listed by Helen Miller, 650-400-3426 from Compass
(If provided) CoList: from

160 Redland RD, Woodside
$2,750,000
4 Beds ⋅ 3 Baths ⋅ ML82063276 MLS
Some houses announce themselves, this one settles quietly into the redwoods of Skylonda, a 1967 mid-century modern by architect Edwin Wadsworth where the light comes first, then the trees, and only after that the house itself. High wood ceilings and heavy beams carry the eye through walls of glass to the forest beyond, the sunken living room feels sheltered beside a stone fireplace, and the dining room opens to the decks through floor to ceiling windows and a sliding door, with a pass through to the island kitchen and a sunny breakfast area warmed by a freestanding wood-fired stove. Upstairs, the primary suite sits in the canopy like a separate apartment, with its own outside entrance, walk-in closet, and balconies on either side. The recreation room has its own entrance from the gravel courtyard, and a small detached office offers a quiet place to work. Approximately 3,420 square feet, 4 bedrooms, 3 baths, and approximately 0.91 acres, expanded in 1989 and refreshed with new flooring through much of the home, interior paint, updated lighting, and deck repairs, with Alice's, the Skywood Trading Post, and County Fire Station 58 close by.

160 Redland RD, Woodside

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

775 W California WAY, Woodside
$4,850,000
4 Beds ⋅ 3 Baths ⋅ ML82063093 MLS
775 West California Way is calling you home! Located in the highly regarded Woodside School District and ideally situated near Woodside Town Center, this meticulously maintained retreat has been loved by the same family for more than 50 years. Set on nearly an acre, this approx. 3,060 sq ft oasis offers 4 bedrooms, 2.5 baths, oversized garage space, abundant storage and an expansive lower-level bonus room with separate entrance. Natural light and gleaming hardwood floors fill the formal living room, dining room and family room. Create memorable meals with a Wolf cooktop, host holiday gatherings, or spend summer days around the beautiful pool. Enjoy the charm of Woodside with local favorites including Roberts Market, Roberts Hardware, Bucks Restaurant, The Village Bakery and The Village Pub nearby. Private yet convenient to San Francisco and Silicon Valley, this is more than a house - it's a place to make memories and call home!

775 W California WAY, Woodside

Listed by Alex Lehr, 650-766-5300 from Guide Real Estate
(If provided) CoList: from

55 Mission Trail RD, Woodside
$8,000,000
4 Beds ⋅ 6 Baths ⋅ ML82060993 MLS
Privately positioned at the end of a gated country lane, this elegant French Country estate combines sweeping Western Hills and sunset views with the convenience of a prime Central Woodside location. Set on approximately 1.11 acres, the grounds feature expansive terraces, mature landscaping, and inviting spaces for indoor-outdoor living and entertaining. The main residence features four bedrooms, five-and-a-half bathrooms, a dedicated office/library, a main-level primary suite with an adjoining flexible-use room, and a recently updated chefs kitchen with a sunny breakfast area. Patterned oak floors, high ceilings, and abundant natural light create a warm, sophisticated atmosphere throughout. A detached one-bedroom, one-bath guest house with a full kitchen, fireplace, and high ceilings provides an ideal setting for guests, extended stays, or a private workspace. Just moments from Woodside Town Center, Woodside School, Interstate 280, Sand Hill Road, and Stanford University, this exceptional property offers a rare combination of privacy, usable acreage, inspiring views, and close-in convenience.

55 Mission Trail RD, Woodside

Listed by Victoria Yang Surles, 415-818-3603 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Sally Li from CBR
160 Crest RD, Woodside
$5,988,000
5 Beds ⋅ 4 Baths ⋅ ML82062056 MLS
Set on a private acre in Woodside Hills, this exceptional midcentury residence offers more than 4,600 square feet of living space, spectacular Bay views, and a wonderful connection between indoors and out. Walls of glass, hardwood floors, and expansive living areas create a distinctive setting, complemented by two fireplaces and a stylish kitchen with black granite and appliances from top brands. The family room provides a comfortable gathering space, while five bedrooms plus an office offer flexibility for family, guests, and work. Multi-level grounds showcase the views with a large deck, inviting pool, and broad lawn, creating an ideal setting for entertaining and everyday enjoyment. Conveniently located near shops, restaurants, parks, nature preserves, and Interstate 280, the home is also just five minutes from acclaimed Woodside High School (buyer to verify eligibility).

160 Crest RD, Woodside

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

7 Blue Ridge LN, Woodside
$65,000,000
5 Beds ⋅ 6 Baths ⋅ ML82032838 MLS
Completed in 2023 on Woodside's most premier central corridor, a Cul De Sac off Mountain Home Road. This 3 acre Tuscan inspired estate property is a masterpiece of design that blends the finest materials from around the globe. Breathtaking displays of quartzite evoke artful elegance, while floors of marble and French oak exude timeless sophistication. Every detail is crafted with precision- French oak cabinetry, ceilings, and trim, coupled with Venetian plastered walls in the grand public rooms, softly illuminated by chandeliers from Spain. Designed to perfection for today's lifestyle, the great room serves as the heart of the home, offering a magnificent kitchen with a seamless flow to the loggia and vast private grounds. Five bedroom suites, including both main and upper level primary suites, provide ultimate flexibility and privacy. The guest house mirrors the main residence's impeccable standards, complete with a full kitchen, bedroom, two baths, and sauna. The estate's grandeur extends outdoors with a wrap around loggia with fireplace, 60 foot pool and spa with canopy jets, fully fenced tennis court, expansive lawns and meadows. Located in one of the country's most exclusive Silicon Valley zip codes, nearby Venture Capital hub Sandhill Road, Stanford Univ. & Silicon Valley.

7 Blue Ridge LN, Woodside

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

600 Moore RD, Woodside
$14,900,000
7 Beds ⋅ 9 Baths ⋅ ML82057953 MLS
A rare, fully realized legacy compound offering the soul of a European retreat in the heart of Woodside. Hidden within 3.2 acres of curated gardens and ancient oaks, this meticulously renovated sanctuary blends old-world artistry, artisan tile, and beamed ceilings with the peace of mind of enterprise-grade infrastructure. The grounds are a private resort masterpiece designed for serene living, anchored by a rare clay tennis court, a waterfall grotto, a pool and spa, a pitch-and-putt green, and a bocce court. The main residence features four refined suites, a professional grade kitchen, a magnificent wine cellar,and a private executive office. Multi-generational living is perfected with a 2-bedroom family cottage, a 1-bedroom guest house, and a detached fitness center with sauna and Tonal strength training equipment.Beyond the charm, the estate offers total autonomy with redundant internet access, a backup generator, and advanced surveillance. This is the ultimate turnkey acquisition: an impossible-to-replicate blend of character and modern high-performance living, perfectly positioned minutes away from Silicon Valleys entrepreneurial eco-systems most iconic hubs.

600 Moore RD, Woodside

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

180 Farm RD, Woodside
$21,995,000
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

496 Raymundo DR, Woodside
$3,175,000
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

Sold listing courtesy of James Horn from JHORN
245 Heacox RD, Woodside
$2,750,000
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

Sold listing courtesy of Adam Touni from COMPS
144 Alta Mesa RD, Woodside
$4,625,000
4 Beds ⋅ 4 Baths ⋅ ML82051662 MLS
Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

144 Alta Mesa RD, Woodside

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

Sold listing courtesy of Joan Cattermole from APR
17001 Skyline, Woodside
$3,150,000
4 Beds ⋅ 3 Baths ⋅ ML82049733 MLS
Truly extraordinary 10+ acre retreat offers a rare combination of privacy, usability, and natural beauty. Tastefully updated home sits on an elevated, level setting surrounded by mature trees and abundant sunshine, creating a peaceful sanctuary that feels far removed from the pace of everyday life. A private road winds down through the property, crossing a seasonal creek before opening to a spectacular sunny meadow below & connects to Horse and Hiking trails. This expansive area presents endless possibilities, from horses, barns, and riding facilities to orchards, gardens, recreational uses, or simply enjoying the open space. Outdoor enthusiasts will appreciate direct access to miles of nearby trails for hiking, horseback riding, and mountain biking right from the property. Combining turnkey living with exceptional land, tremendous sun exposure, remarkable privacy, and a setting that inspires exploration and relaxation, this is a truly special opportunity to own one of Skylines most compelling lifestyle properties

17001 Skyline, Woodside

Listed by Nino Gaetano, 650-207-1986 from The Agency
(If provided) CoList: from

Sold listing courtesy of Greg Damelio from SGP
61 Oak Haven WAY, Woodside
$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

199 Brookwood RD, Woodside
$4,075,000
4 Beds ⋅ 4 Baths ⋅ ML82050010 MLS
One Acre with Sweeping Bay Views in Woodside Hills! Sweeping San Francisco Bay views take center stage at this exceptional Woodside Hills property with fresh updates throughout. Spanning one acre, the elevated corner lot is positioned to capture the expansive views while also providing generous level areas for outdoor living. Enhancing the setting is the gentle sound of a meandering creek and strolling paths that create a distinctly parklike ambiance. Fresh interior updates include new paint, refinished hardwood floors, and new carpet, all complementing the living rooms signature vaulted ceiling, handcrafted with layered redwood cedar rising to a dramatic center peak. Multiple fireplaces add warmth and character, while glass doors open to several outdoor spaces oriented to enjoy the Bay views. The formal living room and dining room each have Bay views, plus there is a large open kitchen and family room for everyday gatherings. Four bedrooms, an office, and 3.5 baths are well arranged, featuring a main-level primary suite and a second suite comprising the entire lower-level with outside access and flexibility for future ADU conversion. An attached two-car garage and abundant off-street parking complete this inviting retreat with close-in convenience.

199 Brookwood RD, Woodside

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

Sold listing courtesy of Erika Demma from APR
300 Ridgeway RD, Woodside
$4,625,000
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
320 Grandview DR, Woodside
$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
103 Toyon CT, Woodside
$4,950,000
4 Beds ⋅ 4 Baths ⋅ ML82046648 MLS
More than one-third acre creates an exceptional setting for this spacious home with 4 bedrooms, 3.5 baths, and multiple living areas designed for today. There are formal living and dining rooms, a designer kitchen with Carrara marble finishes and wine bar, a welcoming family room, a lower-level recreation and media room, and a private bedroom with its own entrance and adjacent bath that is ideal for guests or office use. The primary suite is privately located and features a steam shower and jetted tub. Outdoor living is equally inviting with an arbor-covered deck, newly planted lawns, terraced gardens, play area, and raised vegetable beds. Located on a cul-de-sac street less than one mile from the Woodside town center and served by renowned Woodside Elementary School (TK-8). Additional highlights include abundant storage, optional RV parking with hookups, and refreshed landscaping throughout.

103 Toyon CT, Woodside

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

15 Hidden Valley LN, Woodside
$35,000,000
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 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

140 Dean RD, Woodside
$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
150 Brookwood RD, Woodside
$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
330 Ridgeway RD, Woodside
$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
55 Mission Trail RD, Woodside
$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
200 Todo El Mundo, Woodside
$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
180 Romero RD, Woodside
$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
490 Las Pulgas DR, Woodside
$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

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