Woodside CA 1750+ Sq. Ft. Real Estate, Homes, Condos for Sale

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

$1,888,000

4 Beds ⋅ 4 Baths ⋅ ML82056831 MLS

An exceptional opportunity to own a premier property in the heart of Woodside, one of the Peninsula's most prestigious and sought-after communities. Located at 26 Big Tree Rd, this unique offering combines privacy, natural beauty, and convenient access to Silicon Valley, making it ideal for homeowners, investors, or those seeking a legacy property. Surrounded by mature trees and Woodside's renowned rural charm, it offers a peaceful retreat just minutes from downtown Woodside, Stanford University, Sand Hill Road, and major employment centers. Residents enjoy a rare balance of tranquility, open space, and access to world-class dining, shopping, and recreation. Whether creating a private estate, preserving a long-term investment, or capitalizing on one of the Bay Area's most desirable locations, 26 Big Tree Rd presents a rare opportunity in a market where exceptional properties are seldom available. Woodside remains one of Northern California's premier residential destinations, known for expansive estates, an equestrian lifestyle, enduring property values, and unmatched privacy, prestige, and long-term appreciation.

26 Big Tree RD, Woodside

Listed by Matthew Dapolito, 408-202-9202 from Intero Real Estate Services
(If provided) CoList: Scott Bishop from Intero Commercial

$2,175,000

3 Beds ⋅ 2 Baths ⋅ ML82055302 MLS

Set upon an extraordinary 3.25-acre setting, and just west of Palo Alto sits this charming one-story home which offers a rare sense of seclusion and natural beauty, further enhanced by its adjacency to a protected 6-acre parcel that ensures enduring privacy. The grounds are a true sanctuary, featuring a 40-year-old native garden that blooms nearly year-round, and a spacious rear deck overlooks this serene landscape, creating a seamless connection between indoor comfort and outdoor living. The property is graced with mature fruit trees, including pear, cherry and peach trees that add both charm and seasonal delight. Inside, the living room is a striking centerpiece, featuring a grand stone fireplace with a wood stove insert, complemented by soaring redwood-beam ceilings that add warmth and character to the space. A generously sized family room offers flexibility for relaxation, entertaining, or extended living. Modern convenience meets country tranquility with reliable high-speed internet, making this an ideal retreat without compromise. Surrounded by scenic, horse- and dog-friendly trails and supported by a welcoming, close-knit neighborhood, this is a setting that offers both peaceful escape and a genuine sense of community.

188 Martinez RD, Woodside

Listed by Mercedes Roses, 650-766-3910 from Compass
(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

$3,195,000

4 Beds ⋅ 2 Baths ⋅ ML82054316 MLS

Nestled on nearly two private acres in a coveted Woodside setting, this Mid-Century Modern home offers a rare blend of rustic charm, natural beauty, & breathtaking panoramic views. Thoughtfully designed to embrace its spectacular surroundings, the four-bedroom, two-bath residence features a sun-drenched living room framed by a dramatic wall of floor-to-ceiling windows that capture sweeping vistas & create an effortless connection to the outdoors. Adjacent to the living room, the open kitchen & dining area also flow seamlessly onto the expansive view deck which is an ideal setting for entertaining, sunset gatherings, or quiet mornings overlooking the horizon. The main level features the primary bedroom & a full bathroom, offering the ease and convenience of single-level living. Downstairs, three additional bedrooms, a full bath, dedicated laundry room, and a spacious bonus family room provides exceptional flexibility for a media lounge, home office, or recreation space. Set on 1.95 acres of serene grounds, the property offers a true sense of privacy and includes a charming barn, adding authentic Woodside character. Lots of possibilities! With access to acclaimed Woodside schools, this special property creates a lifestyle defined by tranquility, scenic beauty, and timeless appeal.

3635 Partition RD, Woodside

Listed by Jennifer Alfaro, 650-888-8338 from Compass
(If provided) CoList: Kimm Terpening 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

$3,895,000

4 Beds ⋅ 3 Baths ⋅ ML82053870 MLS

Central Woodside Opportunity on 1.11 Acres. Just over one mile from Woodside town center this 1.11-acre property presents an increasingly rare opportunity in a desirable Central Woodside setting. A seasonal creek at the rear of the property and stunning western hill views that may be further enhanced create a beautiful natural environment that reflects the scenic character for which Woodside is renowned. A secondary access point from Hillside Drive to the barn further enhances the property's flexibility and future potential. The mid-century ranch-style home has been recently refreshed with new paint inside and out, refinished hardwood floors, new carpet, and refreshed landscaping. Comfortable living spaces, flexible lower-level quarters with a bonus kitchen, and a detached two-stall barn with expansive upper-level space provide immediate enjoyment while offering numerous possibilities for the future. The true appeal extends beyond the home itself. Generous acreage, a close-in location, access to acclaimed Woodside Elementary School, and surrounding estate properties create an exceptional setting for renovation, expansion, or the creation of a significant new residence all while immediately enjoying the freshly updated home.

136 Jane DR, Woodside

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

$4,750,000

4 Beds ⋅ 5 Baths ⋅ BE41140473 MLS

Tucked at the end of a peaceful cul-de-sac in Woodside Hills, this beautifully reimagined single-level retreat pairs timeless ranch design with an unbeatable connection to nature. Panoramic views stretch across Hoover Tower, Moffett Field, the Dish, and Mount Hamilton - a backdrop that changes with the light throughout the day. Set on a full acre with a creekside property line, the grounds feel like a private nature escape. Deer and songbirds pass through regularly, while four terraced garden beds await your green thumb. Outdoor living is at the heart of this property, with a spacious private deck, a bocce ball court, horseshoes, a swing set, and even a chicken coop - space to entertain, play, and unwind in equal measure. A large paved driveway offers ample parking for hosting guests with ease. Inside, the open floor plan is anchored by a custom kitchen featuring a large center island, stainless steel appliances, and timeless leathered granite countertops, prized for their easy maintenance, complete with a pantry for extra storage - all flowing seamlessly into the home's entertaining spaces. The thoughtfully remodeled layout (2013) also offers true separation between private and social areas. Two en-suite bedrooms and a Jack-and-Jill bath provide flexibility for family or guests,

140 Sheridan Way, Woodside

Listed by Ella Naylor, (650) 520-9864 from Compass
(If provided) CoList: Daniel Boot from Compass

$4,795,000

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

$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

$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

$3,950,000

3 Beds ⋅ 2 Baths ⋅ ML82050036 MLS

Set on 1.5 acres at the end of a quiet cul-de-sac in Central Woodside, the property offers a beautifully completely updated estimated 2,105 sq ft retreat in the highly regarded Woodside School District. The refreshed home features wide-plank oak hardwood floors, new dual-pane windows, LED lighting, and a new metal roof with added skylights. The renovated kitchen showcases shaker cabinetry, white marble countertops, a Wolf induction range, Sub-Zero refrigerator, dual Wolf ovens, a deep corner pantry with microwave, and an island with seating, plus a Dutch door to the spacious rear patio. Enjoy a cozy family room with wood-burning fireplace, large-screen TV, and articulating door to outdoor entertaining and dining. The primary suite includes an expansive sleeping area with French doors to the nearby native plant garden and majestic Redwoods, a Mitsubishi split A/C, and an upgraded and spectacular bath with marble counters, freestanding tub, new shower, and improved walk-in closet. Additional highlights: new central forced-air system with Nest controller, Level 2 EV charger, security cameras, new septic system and gated trail access to Teague Preserve.

855 Patrol RD, Woodside

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

$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

$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

$4,999,950

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

$2,999,000

4 Beds ⋅ 3 Baths ⋅ ML82049221 MLS

Sunlit Sanctuary on 3.7 beautiful acres. Sky Hill Farm, a rare, retreat-like property that blends natural beauty, indoor-outdoor living & modern luxury minutes from the heart of Silicon Valley. This beautifully renovated home has been completely reimagined w/high-end finishes & exceptional craftsmanship, offering a lifestyle of comfort, privacy & effortless elegance. Seamlessly flowing open floor plan, refined aesthetics and meticulously upgraded systems that enhance comfort, efficiency and long-term peace of mind. Sun-filled living spaces open naturally to the outdoors. The heart of the home is a gourmet kitchen featuring premium appliances, custom cabinetry, expansive counter space and functional layout. Huge deck extends the living space outward. Set on 3.7 very usable acres provides endless possibilities gardens, play areas, outdoor lounges, or simply room to breathe. The primary suite feels like a private retreat, with serene views and redwood finishes, huge walk-in closet and luxurious bath. Charming 2 bed guest house w/kitchen. Historic updated carriage house can be used as 6-car garage, workshop a dream for car collectors, hobbyists, or anyone needing serious workspace. At the back of the property sits a restored barn for storage, projects ,animals. Plans show 2427 s.f.

260 Grandview DR, Woodside

Listed by Karin Bird, 650-207-0940 from Compass
(If provided) CoList: from

$4,050,000

3 Beds ⋅ 3 Baths ⋅ ML82048231 MLS

Nestled on a quiet, beautifully wooded lot in desirable Woodside Hills, this meticulously updated residence blends timeless elegance with modern comfort. Light-filled interiors showcase expansive windows, refined finishes, custom window coverings and seamless indoor-outdoor flow. The remodeled chef's kitchen (2019) features a quartz-topped island, custom cabinetry, and premium Thermador, Bosch, and LG appliances, while opening to inviting dining and family spaces. A gracious living room with a redesigned gas fireplace and access to a deck creates an ideal setting for entertaining. Up the grand staircase, a serene primary suite offers high ceilings, dual walk-in closets, and a spa-inspired bath with soaking tub, curb-less shower, and designer finishes. Two additional bedrooms enjoy natural light and peaceful views. Extensively renovated, the backyard presents a resort-like retreat with multiple entertaining areas, a saltwater pool, AZEK decking, stamped concrete patios, gazebo and stone retaining walls and box planters, all surrounded by majestic oaks. Smart home features throughout the home include an EV charger. This exceptional home is situated in a premier, ultra-private location while being close to the Town of Woodside, Redwood City, schools, shopping, dining and Hwy 280.

345 Harcross RD, Woodside

Listed by Jane Dew, 650-353-8899 from The Agency
(If provided) CoList: from

Sold listing courtesy of Carol Koffel from COMP41

$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

$3,645,000

3 Beds ⋅ 3 Baths ⋅ ML82047690 MLS

Access to renowned Woodside Elementary School, an end of cul-de-sac location with underground utilities, and just one mile from the Woodside town center set this home apart. Newly built in 2007, the home has soaring cathedral ceilings, hardwood floors, expansive windows, and an open floor plan that flows to generous outdoor living spaces. The flexible layout includes 3 bedrooms and a dedicated office, including a spacious primary suite with fireplace, customized walk-in closet, and newly remodeled bath. The open kitchen features custom cabinetry, granite slab counters, a BlueStar gas range, Liebherr wine cooler, and counter seating at a center island. A large deck, level lawn, paver stone terrace, and spa create exceptional outdoor living on fully fenced grounds. Additional features include central air conditioning, wiring for EV charging, plus expansion and ADU potential (subject to Town approval & applicable development standards).

63 Ridge CT, Woodside

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

$4,300,000

3 Beds ⋅ 2 Baths ⋅ ML82047585 MLS

For Comp Purposes Only

180 Phillip RD, Woodside

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

Sold listing courtesy of Costantini Team from APR

$5,495,000

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

$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

$3,195,000

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

$3,650,000

3 Beds ⋅ 3 Baths ⋅ ML82045699 MLS

A setting of extraordinary natural beauty defines this distinctive redwood retreat, where architecture and environment exist in quiet harmony. Designed by renowned builder Jerry Ellis, the home is masterfully engineered above a seasonal creek, where the gentle movement of water enhances the serene surroundings of more than 2 acres. Dramatic ceilings and expansive walls of glass create a seamless connection to the landscape. Sunlight filters through the trees and skylights above, casting an ever-changing interplay of light and shadow throughout the day. Spacious decks and winding paths extend the living experience outdoors. The result is a home with a rare sense of place, offering a living experience that feels both peaceful and architecturally compelling while being just minutes from the Town Center, acclaimed Woodside School, and all of Silicon Valley.

573 Patrol RD, Woodside

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

Sold listing courtesy of Scott Dancer from APR

$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

One of Woodside's premier estates, encompassing nearly 10,000 square feet across all structures, this property offers exceptional scale, quality, and lifestyle, highlighted by a classically styled main residence and a brand-new guest house crafted with authentic European detail. The main home is luxuriously appointed across two levels, with nearly every room opening to the outdoors. A state-of-the-art theatre and a temperature-controlled wine cellar are just two of many standout features. The newly completed guest house pairs handmade roof tiles and Genoise eaves inspired by the South of France with state-of-the-art smart home technology. Designed for entertaining, the guest house opens to a new saltwater pool and spa and expansive limestone terrace with a full outdoor kitchen and easy catering access. A 310-vine Cabernet vineyard anchors the south-facing gardens, while heritage olive trees and oaks, a fragrant parterre rose garden, bountiful orchard, and raised vegetable beds enhance the estates agrarian beauty. The result is a property where timeless elegance and refined European living are masterfully expressed in an extraordinary private setting of more than 3 acres with western hill views. Main Residence 6,485 | Guest House 1,505 | Garage One 560 | Garage Two 520 | Gym 560

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

$5,350,000

4 Beds ⋅ 4 Baths ⋅ ML82043727 MLS

Set at the end of a private lane on more than one acre, this stylish contemporary retreat offers a rare sense of privacy just moments from downtown Woodside. Refreshed landscaping & a spacious, partially covered front deck introduce interiors defined by clean lines, hardwood floors, vaulted ceilings, & expansive walls of glass that fill the home with natural light. The flexible two-level floor plan features 4 bedrooms, an office, & 4 full baths, including a main-level primary suite. A dramatic living room with a fossilized limestone fireplace, formal dining room, & streamlined maple kitchen with honed black granite & butcher block surfaces create a modern yet inviting backdrop for everyday living & entertaining. Sliding glass doors open to a wraparound deck for seamless indoor-outdoor flow. The lower level expands the living space with a large recreation room with a built-in workstation for two, plus 2 additional bedrooms, one with an en suite bath. Terraced rear grounds include a free-form pool, barn with potential equestrian use, zip line, & refreshed landscaping, along with additional usable outdoor areas suited for recreation, play, or future possibilities. Just one-half mile from downtown Woodside & within the acclaimed Woodside School District.

35 Neuman LN, Woodside

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

Sold listing courtesy of Erika Demma from APR

$5,080,000

3 Beds ⋅ 4 Baths ⋅ ML82041730 MLS

This is the forever home everyone hopes for! Exceptionally quiet and private, this gated single-level ranch home spans approximately 3,000 sq ft on over one acre of rare, level land in a prestigious Woodside Hills cul-de-sac. Offering a unique combination of serenity and convenience, the property is just minutes from Highway 280 for easy commuting. A gated entry opens to an expansive front yard with ample parking and a spacious motor court. This lot is ready for a pool, lawn games or an ADU. The home features a well-designed floor plan highlighted by a grand-scale living room, a separate formal dining room, and a sun-filled kitchen with wraparound windows overlooking the backyard. The kitchen flows seamlessly into the family room, creating an open-concept great room ideal for everyday living and entertaining. The bedroom wing includes three generously sized bedrooms, each with its own connected bathroom, including a primary suite. The grounds are park-like, featuring a large, flat lawn, mature trees, and partial view-an uncommon offering in this area. An exceptional opportunity to enjoy a peaceful setting with easy access to commute routes and nearby amenities.

140 Northridge, Woodside

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

Sold listing courtesy of Linda Wang from AGNC

$2,195,000

3 Beds ⋅ 3 Baths ⋅ ML82042155 MLS

Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.

20255 Skyline BLVD, Woodside

Listed by Jennifer Paulson, 650-996-7147 from Christie's International Real Estate Sereno
(If provided) CoList: from

$4,500,000

4 Beds ⋅ 4 Baths ⋅ ML82041987 MLS

Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a quiet part of the sought-after Woodside Glens neighborhood, features a host of thoughtful upgrades by long time owners. They created a floor plan which showcases views from nearly every room and which, with its ipe hardwood spacious rear decks, presents a host of seamlessly flowing indoor/outdoor entertainment options. All new appliances were added in the chefs kitchen, the hardwood floors were recently refinished, new dual paned windows installed, high end finishes and touches were made throughout and the outside grounds sport attractive low maintenance, water-conserving plantings. Designed around light and nature, the home currently has three bedrooms on the main level and a lower level with an expansive family room and adjacent primary suite, all of which provide a range of configuration alternatives for home office, workout or entertainment setups. Come see this amazing home!

175 Alta Mesa RD, Woodside

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

Sold listing courtesy of Lucy Goldenshteyn from RDFIN

$2,250,000

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

$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

$6,500,000

3 Beds ⋅ 2 Baths ⋅ ML82041776 MLS

This is an idyllic Woodside property on over 1 level acre, where open land, equestrian facilities, and close-in convenience come together just one-half mile from the Town Center and highly acclaimed Woodside School. The expansive, level grounds set the tone complete with a 1 bedroom and 1.5 bath guest house, barn, fenced paddocks, pool, and broad stretches of lawn that capture the true spirit of country living. The home has been beautifully remodeled with a fresh, cohesive design that includes all-new lighting, a fully renovated kitchen, and beautifully updated bathroom. The interiors feel bright, current, and immediately livable, and a remodeled 1 bedroom guest house adds valuable flexibility for extended stays, office use, or possible rental. Beyond what is already in place, the scale and level nature of the property presents outstanding opportunity. Expansion, further personalization, or even the creation of a new estate can all be envisioned here, making this property as compelling for today as it is for the future.

3362 Woodside RD, Woodside

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

Sold listing courtesy of Michael Warren from APR

$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

$3,998,000

4 Beds ⋅ 3 Baths ⋅ ML82039737 MLS

Tranquil Woodside Retreat Nestled within one of Woodside's most sought-after enclaves, this enchanting single-family residence offers a rare blend of privacy, natural beauty, and timeless appeal. Set on expansive, level to gently sloping grounds, the property is ideal for equestrian use, featuring serene open spaces framed by mature trees and lush, thoughtfully designed landscaping. Bathed in dappled sunlight, the home exudes warmth and charm throughout. The well-appointed floor plan includes 4 bedrooms and 2.5 bathrooms, with inviting living spaces that seamlessly connect to the outdoors perfect for both relaxed everyday living and elegant entertaining. Step outside to your own private oasis, complete with a pool, lush lawns, barn and meandering brick walkways. Whether enjoying quiet mornings or hosting gatherings, the setting offers unmatched serenity and beauty. Located within the boundaries of the highly acclaimed Woodside Elementary School, this exceptional property combines rural tranquility with convenient access to nearby amenities. A rare opportunity to experience the quintessential Woodside lifestyle.

425 Summit Springs RD, Woodside

Listed by Christienne Hadley, 650-533-3766 from Foundation Real Estate
(If provided) CoList: from

$11,000,000

2 Beds ⋅ 4 Baths ⋅ ML82039836 MLS

Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning just over 3.4 acres, this expansive property showcases rare Bay views. There is an existing planning study for guidance in future opportunities. Positioned at the end of a private lane, the setting reflects the essence of Woodside country living, with lush perimeter trees and vast open land that offer a serene and private natural environment. The gated property includes an existing one-level home, a pool, and an original tennis court. Just one mile from Woodside Town Center and acclaimed Woodside Elementary School, and only minutes to Stanford University, Sand Hill Road venture capital firms, and the heart of Silicon Valley, this location offers both seclusion and convenience.

309 Olive Hill LN, Woodside

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

$4,260,000

3 Beds ⋅ 3 Baths ⋅ ML82038786 MLS

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

1439 Portola RD, Woodside

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

Sold listing courtesy of David Kelsey from COMPS

$3,600,000

3 Beds ⋅ 2 Baths ⋅ ML82038616 MLS

A Private Setting with Sweeping Western Hill Views! Architectural character with a strong connection to the outdoors define this inviting Woodside home set on more than one-third of an acre. Across the front of the home, a dramatic wall of glass rises to a beamed and paneled cathedral ceiling, framing sweeping western hill views and tranquil garden outlooks. Living, dining, and kitchen spaces come together in a generous open area that extends out to a crushed stone patio oriented to the views. Three bedrooms and two baths are arranged for comfort and privacy. The primary suite is positioned just off the foyer and opens directly to the rear yard. Two additional bedrooms are located on the opposite side of the home, including one with an adjoining office or art studio and direct outdoor access. The grounds offer expansive gardens, a level lawn, and a detached studio with flexible use, creating inviting spaces for relaxation, creativity, or entertaining. A close-in setting near the center of town, along with access to highly regarded Woodside Elementary School, completes the appeal of this distinctive property.

665 W Glen WAY, Woodside

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

Sold listing courtesy of DeLeon Team from DLRPA

$8,900,000

4 Beds ⋅ 3 Baths ⋅ ML82037417 MLS

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

3215 Woodside RD, Woodside

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

Sold listing courtesy of Michael Warren from APR

$10,988,000

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

$4,000,000

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

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

80 Skywood WAY, Woodside

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

Sold listing courtesy of Sternsmith Group from APR

$5,750,000

4 Beds ⋅ 3 Baths ⋅ ML82037292 MLS

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

51 Cragmont WAY, Woodside

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

Sold listing courtesy of Judy Citron from COMPS

$2,275,000

4 Beds ⋅ 4 Baths ⋅ ML82036766 MLS

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

6 Megans LN, Woodside

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

Sold listing courtesy of Alicia Sanguinetti from APR

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