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$3,088,000
4 Beds ⋅ 8 Baths ⋅ ML82017325 MLS
SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase | 4 levels of destinations inspire your finishing details | Library off the lobby | Two Enormous Primary Suites (one main level, one upstairs) | Multiple Offices | Immense walk-in closets | Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest | Flat rear grounds inspire a future pool & ADU | Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage | Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.

1 Reids Roost RD, Woodside

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

$2,525,000
5 Beds ⋅ 4 Baths ⋅ ML82019381 MLS
Experience the ultimate retreat, where majestic redwoods, sweeping canyon vistas, and ocean views provide a stunning backdrop for everyday living. This 3,323 sq ft custom home features 5 bedrooms and 3.5 bathrooms. The main level boasts soaring ceilings, expansive windows, and skylights that flood the space with natural light, highlighting the breathtaking scenery. The open-concept design connects the spacious living area to the kitchen, featuring Brazilian soapstone countertops, rich wood flooring, and stainless steel appliances, perfect for entertaining or relaxing. An adjoining family room offers more space to unwind. Head downstairs to access the expansive deck, versatile bedrooms, and flexible spaces. Outdoor living takes center stage as you step onto the oversized deck, soak in the hot tub under a canopy of stars, or explore the meticulously terraced yard, offering space to garden, relax, or let your animals roam free. Ideally located, a short walk to miles of open space trails,10 minutes to Hwy 280 with easy access to SFO, Silicon Valley, and the Half Moon Bay coast, this home offers the perfect blend of serenity and convenience. Come experience the lifestyle you've been dreaming of, surrounded by nature, tranquility, and the welcoming community of Kings Mountain.

103 Harkins RD, Woodside

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

Sold listing courtesy of Valerie Trenter from CBR
$3,125,000
3 Beds ⋅ 2 Baths ⋅ ML82019083 MLS
A rare and private 15+ acre estate blending equestrian excellence, vineyard living, and natural beauty. Perfect for riders, vintners, or those seeking peaceful country living. The Barn Pros barn includes 4 matted stalls with Euro fronts, individual runs, a heated wash rack with hot/cold water, tack room, and enclosed feed/hay storage. Above, a spacious apartment with 2 sleeping areas, tall ceilings, and sweeping viewsideal for guests, caretakers, or rental income. Equestrian features include 2 fenced pastures with matted double run-ins, a paddock with a single matted shed, ~95x198 Olympia Footing arena (fenced with sand/rubber footing), and a ~60 round pen. The vintage 3BR, 1.5BA farmhouse offers rustic charm, storage, a cellar, and a relaxing front porch with serene views. A newer guest house (separately addressed) features 1BR + office/bonus roomideal for family, guests, or rental. Enjoy ~1 acre of Pinot Noir vines, fully fenced and producing excellent estate wineperfect for personal use or boutique winemaking. Mid Pen has plans to add a lot and access to the La Honda Open Space Perserve, that is right across the street. This is more than a propertyits a lifestyle sanctuary just ~20 mins to Hwy 280 and 30 mins to Half Moon Bay.

11120 La Honda RD, Woodside

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

Sold listing courtesy of David Cline from CBR
$3,800,000
4 Beds ⋅ 3 Baths ⋅ ML82019068 MLS
Great cul-de-sac location, this sunny, designer-updated home is as charming as it is comfortable. Just minutes from downtown Woodside and top-rated K-8 Woodside School, this location in the Glens is coveted. Step inside to discover the main level, featuring three bedrooms, including two with en-suite baths. The primary suite is a peaceful sanctuary with a generous footprint, sitting area, and direct access to the deck. A third full bath accommodates guests and the third bedroom. The heart of the home is open-concept, with a family room that flows seamlessly into an updated kitchen. Flow into the formal dining room and the inviting living room, where picture windows, custom built-ins, and one of two elegant stone fireplaces create a welcoming atmosphere. Step outside onto the expansive deck for effortless indoor-outdoor living and entertaining. Downstairs, discover a flexible fourth bedroom that can also serve as a home office or bonus room. With exposed beam ceilings, French doors leading to a private patio and fire pit, this may become your favorite space. A separate laundry room and two-car garage add functionality. The landscaped, tiered, and fenced backyard is perfect for entertaining, playing, or enjoying the serene natural surroundings.

115 Toyon CT, Woodside

Listed by Kimberly Hansen, 415-806-8230 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Ginna Lazar from LHG
$4,000,000
5 Beds ⋅ 5 Baths ⋅ ML82018950 MLS
Private ~half-acre property is prime for redevelopment with an existing 3,365+/- sf house and ADU* with 5BDs and 5BAs, a carriage house with studio, paddock, two access gates and multiple outbuildings. This highly coveted location is within 0.5 mile of Woodside Village with Roberts Market, Bucks, the library, The Village Pub (Michelin starred), Village Hub and Village Bakery and Cafe, and near top rated schools, miles of hiking, biking and horseback riding trails and surrounding open space preserves. Nestled in the foothills of the Santa Cruz Mountains between the Pacific Ocean and SF Bay, Woodside is one of the wealthiest communities in Silicon Valley and the U.S. It is renowned for its natural beauty, redwood forests, equestrian culture, sprawling estates, high-profile residents and proximity to Stanford, venture capital firms and tech hubs like Palo Alto and Menlo Park. It is about 30 minutes from San Francisco and the coast, 1.5 hours from Napa Valley and located between two international airports and private jet centers. Affluent, private and understated, this scenic rural town of about 5,100 residents offers a low-key lifestyle and tranquil retreat within easy reach of thriving epicenters. *Some structures may have been built without permits; buyer to investigate.

120 Miramontes RD, Woodside

Listed by Michael Silva, 650-515-2388 from Compass
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS
$699,000
2 Beds ⋅ 1 Baths ⋅ ML82018470 MLS ⋅ Kings Mountain Association BLDG.
Tucked along Skyline Boulevard, this 2-bedroom, 1-bath Woodside condo with its own private one car garage and laundry offers a lifestyle thats becoming increasingly hard to find: quiet, privacy, and nature; without giving up proximity to Silicon Valley and the Peninsula. Only 10-15 minutes to hwy 280 and set among towering redwoods, open sky, an ocean view and steps away from trails. This home features a spacious, light-filled layout with comfortable living areas that feel both grounded and welcoming. Whether youre starting your morning surrounded by nature or coming home after a long day below the hill, this property delivers a sense of retreat that most condos simply cant. This is Woodside living at an attainable level; ideal for a first-time buyer, down-sizer, or anyone craving a peaceful escape with real long-term value. Inventory in this area is limited, and opportunities like this dont come along often. If youve been waiting for the right way into Woodside; this is it.

14826 Skyline BLVD 3, Woodside

Listed by Stephanie Nash, 650-995-3820 from Compass
(If provided) CoList: from

$7,500,000
4 Beds ⋅ 5 Baths ⋅ ML82017471 MLS
Set on a 3.1-acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly-updated residence offers the perfect blend of refined luxury and modern comfort - just minutes from town. Flooded with natural light from expansive floor-to-ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public spaces in +/-5,555sf. The open-concept living room boasts 24-foot ceilings, massive curved windows, a striking fireplace, and flows seamlessly into the sun-filled dining room. The chef's kitchen opens to a huge family room with 10-foot ceilings, a dramatic fireplace, bar, and French doors opening to a patio-perfect for indoor/outdoor living. Designed for everyday comfort and entertainment, the home offers multiple terraces, temperature-controlled wine storage, and an expansive lower level replete with a gym, home theater, and full bath. Outdoor amenities include a pool with spa, tennis court, meandering paths that encircle the property, level lawns, and a vineyard. A detached 2BR/2BA, +/-1,135sf guest house is ideal for extended family or visitors. Access to the top-rated Woodside Elementary School completes this rare opportunity to experience a lifestyle of elegance, privacy, and convenience.

333 Raymundo DR, Woodside

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

Sold listing courtesy of Jaswinder Gill from GILLJ
$1,500,000
1 Beds ⋅ 1 Baths ⋅ ML82016775 MLS

4214 Jefferson AVE, Woodside

Listed by Sternsmith Group, 650-678-5455 from Compass
(If provided) CoList: from

Sold listing courtesy of Zach Arrington from 991248
$3,000,000
6 Beds ⋅ 4 Baths ⋅ ML82013538 MLS
Perched on 1.5 acres of beautiful land, this spacious 6-bedroom, 3.5-bathroom home offers panoramic views and room to grow. With generously sized rooms and views from nearly every window, this property combines comfort, versatility, and endless potential. A formal entry leads to a grand living room featuring soaring ceilings, a cozy fireplace, and access to an expansive entertaining deckperfect for indoor-outdoor living. The family-style kitchen includes a charming eat-in area, a second fireplace, and plenty of space for gathering. The main level also offers a formal dining room and a functional laundry room with ample storage, conveniently connected to a 2-car garage. Upstairs, youll find four spacious bedrooms, while the lower level has been thoughtfully converted into an ADU, featuring two bedrooms, a full kitchen, bathroom, and its own separate entry and dedicated parking areaideal for extended family, guests, or rental income. This solidly built home is ready for your personal touch and updates. Dont miss the opportunity to make this property your own retreat in a truly special setting.

495 Summit Springs RD, Woodside

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

Sold listing courtesy of Ginna Lazar from LHG
$450,000
BE41106236 MLS
Tucked into the tranquil forested hills of Woodside, this serene 5.64-acre parcel offers an immersive escape into nature. Surrounded by mature trees, quiet trails, and peaceful open space, the property is perfect for those seeking solitude, fresh air, and natural beauty-just minutes from the 280 freeway and an easy route to Silicon Valley. Enjoy hiking, biking, or simply relaxing beneath the canopy in a setting that feels miles away from it all. This property is ideal for buyers who value privacy, recreation, and a deep connection to the outdoors. Adjacent 13.72-acre parcel also available (APN 075-220-280) offering a rare opportunity to acquire over 19 acres of pristine forest land in one of the Bay Area's most desirable rural communities.

LOT27 Old La Honda Rd, Woodside

Listed by Mike Continillo, (925) 519-0794 from Villa Propertes
(If provided) CoList: from

$750,000
BE41106235 MLS
Tucked away in the serene hills of Woodside, this extraordinary 13.72-acre parcel offers a rare opportunity to immerse yourself in the natural beauty of a mature forest. Surrounded by towering trees, meandering trails, and peaceful wildlife, it's a private haven for those seeking quiet reflection, outdoor adventure, or a personal retreat. Enjoy the feeling of complete seclusion while still being minutes from the 280 freeway, offering easy access to Silicon Valley and beyond. Whether you're hiking, biking, or simply unwinding under the canopy of trees, this land provides an unmatched connection to nature. A truly special slice of Woodside-offering space, solitude, and endless potential for those who value privacy and the forest lifestyle. Adjacent 5.68 Acre lot (APN 075-220-290) also currently for sale. Offering a rare opportunity to acquire over 19 acres of pristine forest land in one of the Bay Area's most desirable rural communities.

Lot26 Old La Honda Rd, Woodside

Listed by Mike Continillo, (925) 519-0794 from Villa Propertes
(If provided) CoList: from

$9,600,000
5 Beds ⋅ 6 Baths ⋅ ML82013370 MLS
Set on more than 3.6 gated acres of quintessential Woodside grounds, this contemporary masterpiece is surrounded by towering oaks and lush greenery, offering a serene, woodsy retreat. The interiors reflect the natural setting with soaring cherry wood cathedral ceilings, cherry wood floors, and expansive picture windows that flood the home with light and invite the outdoors in. Designed for both entertaining and everyday living, the residence features grand formal rooms, multiple fireplaces, a chefs kitchen with sunny breakfast nook, a walk-out family room, and a stylish executive office. Four bedrooms include a luxurious primary suite with its own fireplace, balcony, and spa-inspired bath. Outside, sprawling grounds offer a center courtyard with covered deck and fire pit, built-in grill, a separate guest house, and two garages including one with a lift for car enthusiasts as well as an RC car racetrack. Minutes from Portola Valley, top schools, and Silicon Valley tech centers.

140 Farm RD, Woodside

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

Sold listing courtesy of David Weil from PACT
$4,750,000
4 Beds ⋅ 5 Baths ⋅ ML82011673 MLS
Designer Style with Pool and ADU on Large Level Grounds Classic and timeless architecture and beautifully remodeled interiors come together on more than one-half acre of level land with a pool and Accessory Dwelling Unit. Hardwood floors and multiple fireplaces add warmth and character across three levels designed for flexibility and comfort. The chefs kitchen and adjoining family room connect effortlessly to formal living and dining rooms, with glass doors throughout opening to expansive patios and vast rear grounds ideal for large-scale entertaining. There is also a dedicated office plus a lower-level laundry room and recreation room with full bath convenient to the tucked-away pool. Upstairs are four bedrooms, including a spacious primary suite with two full baths and two walk-in closets, plus sweeping western hill views. Just minutes from the natural beauty and trailheads of Edgewood Park, and offering access to top-rated Woodside School, this home balances timeless design with modern livability in a premier setting.

490 W Maple WAY, Woodside

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

Sold listing courtesy of Samira Amid-Hozour from SGP
$4,900,000
4 Beds ⋅ 3 Baths ⋅ ML82011671 MLS
Surrounded by natures beauty... on 5.4 acres on a private street yet just 3 miles from Sand Hill Road venture capital centers this home offers complete privacy, organic architecture, and spa-like amenities. Oaks and wildflower-strewn meadows create a serene setting deeply connected to the natural landscape with enchanting walking paths. Inside, warm wood finishes, soaring paneled ceilings, and walls of glass establish a tranquil, Zen-like atmosphere that invites the outdoors in at every turn. The layout unfolds with multiple stone fireplaces, outdoor access from nearly every room, and refined materials that reflect the homes high-end craftsmanship. A spa-inspired primary suite features an all-marble bath with cedar-lined sauna and sliding glass doors to the outdoor spa. The flexible floor plan includes one bedroom with a fireplace, en suite bath, and private entrance making it ideal for guest quarters or a possible family room. There is also a detached studio and a lower-level wine cellar with outside access. Outdoor living is equally well considered with a spacious deck overlooking the natural landscape. This one-of-a-kind property offers a close-in location just minutes to miles of hiking and biking trails, town centers, and access to excellent Portola Valley schools.

19 Preston RD, Woodside

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

Sold listing courtesy of Kemper Ray from COMPS
$1,790,000
3 Beds ⋅ 3 Baths ⋅ ML82011144 MLS
Welcome to Five Acre Woods - A Magical Retreat in Woodside! Nestled on 5.6 private acres, this enchanting property offers sweeping Bay views framed by majestic redwoods. Combining seclusion with convenience, its just minutes from Hwy 280 and the town center of Woodside. Originally built in 1915, this 3-bed,3-bath home has been thoughtfully updated for modern living. With approx. 2,300 SF of single floor space, recent upgrades include a new metal roof, fresh paint, & flooring. The open kitchen flows into a great room that leads to a wrap-around deck, perfect for entertaining or enjoying the serene setting. 2 en-suite bedrooms are off the great room, while a 3rd bedroom & bath open directly to the deck. An office/bonus room offers inspiring redwood views, and the lower level features large, partially finished spaces ideal for a workshop, gym, or studio. Outside, explore your own stream, swing, and private trail connecting to the Thornewood Open Space Preserve. The ppty enjoys a mostly fog-free climate, making outdoor living a year-round pleasure. Located just 2 minutes from Four Corners, home to Alices Restaurant, gas station, and Skywood Trading Post -this home is also in the PV Sch Dist. Offering charm, privacy, and potential, this classic Woodside retreat is a rare find.

125 Grandview DR, Woodside

Listed by Lisa Keith, 650-703-8644 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Disen Cai RE Group from KWPEN
$3,005,000
4 Beds ⋅ 3 Baths ⋅ ML82009528 MLS
Western hill views take center stage... at this updated farmhouse on 1.2 acres, just minutes from the heart of Woodside. The multi-level home, set back in complete privacy, is filled with character, featuring gleaming hardwood floors and generous gathering spaces, all with expansive windows oriented to the views. The kitchen and family room combination opens directly to a spacious view-side deck for indoor/outdoor living. There are 4 bedrooms and 2.5 baths, including a main-level primary suite and three bedrooms upstairs. A 3-stall barn connects to fenced pastures, there is ample room for a dog run or chickens, and additional highlights include a charming playhouse and an oversized one-car garage with laundry. Located just 1.5 miles from the town center and with access to acclaimed Woodside Elementary School (K-8), this property celebrates rural tranquility and offers the opportunity to enjoy as-is or thoughtfully renovate for the future.

1207 Godetia DR, Woodside

Listed by Erika Demma, 650-888-6558 from Compass
(If provided) CoList: Deborah Kehrberg from Compass

Sold listing courtesy of The Patty Dwyer Group from APR
$2,037,000
4 Beds ⋅ 2 Baths ⋅ ML82008982 MLS
Perched on a peaceful mountain with breathtaking views of the Pacific Ocean, this updated 4-bedroom, 2-bath home offers the perfect blend of privacy and convenience. Just minutes from Half Moon Bay and San Mateo, this gated property is tucked within the cozy Kings Mountain community and designed for flexible living. With two spacious living rooms, two kitchens, and a bonus room, the home has excellent potential for separate living spaces; ideal for multigenerational living or guest quarters. The main kitchen features sleek Bosch appliances and modern finishes, while large windows throughout the primary living space capture breathtaking ocean vistas. Enjoy outdoor entertaining and evening sunsets on the deck, soak in the hot tub under the stars, and embrace the quiet, coastal mountain lifestyle. Whether you're looking for a serene full-time residence or a versatile retreat with income potential, this home offers comfort, flexibility, and unmatched views in a truly special setting. Just steps from Purisima Creek Redwoods Open Space Preserve and minutes to local favorites like The Mountain House and Alice's Restaurant, this home offers nature, charm, and versatility in one stunning package.

12960 Skyline BLVD, Woodside

Listed by David Skokan, 650-200-7420 from RE/MAX Gold Redwood Shores.
(If provided) CoList: from

Sold listing courtesy of Emily Baratzadeh from CBR
$7,125,000
4 Beds ⋅ 4 Baths ⋅ ML82008127 MLS
Located in the desirable Woodside Heights neighborhood adjacent to Atherton, this dramatic Mid-Century Modern home on 1.05-acres showcases a top-to-bottom designer transformation that elevates every aspect of the home's features. Single-level floor plan offers 4 bedrooms & 4 baths, 2 spacious bedroom suites (one with its own separate office) positioned at opposite ends of the home for optimal privacy with guests or extended family. High-end Walker-Zanger Italian porcelain tile floors throughout provide the look of hardwood with the superior durability & easy maintenance of porcelain. Outdoor designed for entertaining & everyday enjoyment & landscaped to enhance privacy. Sparkling pool, expansive lawn, flagstone terrace with firepit, & separate-level flagstone terrace with fireplace for gatherings. Large poolside cabana open on three sides with its own stone fireplace adds architectural interest & functionality, while the vast undeveloped space at the bottom of the property extends the sense of space & privacy & provides great potential for additional use. Private front courtyard includes an antique marble fountain & a large, wisteria-covered arbor. Complete privacy, a close-in location, & access to top-rated Las Lomitas schools further elevate this one-of-a-kind designer home.

275 Eleanor DR, Woodside

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

Sold listing courtesy of Sanaz Khalili Malek from CBR
$1,875,000
3 Beds ⋅ 2 Baths ⋅ ML82008056 MLS
Morning light pours through redwoods onto white oak floors at this 3BR/2BA retreat on 2.44 private acres. Updated kitchen and marble baths blend comfort and style. A bright barn office and workshop offer flexible use easily converted for equestrian needs with an existing corral. A fenced dog run adds convenience. Enjoy sunrises on the expansive deck or quiet moments on a meditation deck tucked in a redwood fairy ring. Just 10 minutes to Roberts Market, 15 to Stanford, and close to Facebook (20 min), Google (25 min), and Apple (25 min). Top Portola Valley schools and Woodside High.

350 Grandview DR, Woodside

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

Sold listing courtesy of Jennifer Pollock from COMPS
$3,935,000
4 Beds ⋅ 3 Baths ⋅ ML82007527 MLS
This light-filled country home in the heart of central Woodside, on just over one acre, is privately positioned at the top of a gentle knoll beyond picturesque equestrian facilities. Inside, every room opens to the outdoors through sliding glass doors with views of surrounding redwoods. Formal living room features fireplace & opens to expansive front terrace, while the adjoining formal dining room connects to the rear grounds. Bright & light kitchen with breakfast bar seating opens to the inviting family room with a charming wood stove &access to the rear patio. Separate bedroom wing is arranged for privacy & guest suite with solarium tub that takes full advantage of the redwood views. Luxurious primary suite has access to both front & rear grounds, extensive customized closet space, plus a spa-inspired marble bath with vanities, jetted tub & shower. Equestrian amenities include a 3-stall barn with tack room & white fenced corral amid sun-swept open grounds and perimeter redwoods. An attached 3-car garage & adjoining large covered workshop complete the offering. Located just 1.5 miles from Woodside town center and with access to acclaimed Woodside School, this is a special opportunity to enjoy the best of country living in a premier location.

3570 Tripp RD, Woodside

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

Sold listing courtesy of Christina Hengehold from CBR
$3,500,000
4 Beds ⋅ 4 Baths ⋅ ML82006889 MLS
Bring your builder and architect!! First time on the market in 50 years - incredible value, priced to sell. Four beds and 4 baths in original ranch home plus more recent addition and ADU above garage. Beautiful in ground pool. Horses allowable and close to Woodside trails. Almost three acres!!!! Close to all Central Woodside has to offer including highly desirable Woodside elementary school.

380 La Questa WAY, Woodside

Listed by Andrea Ivarsson, 949-933-0219 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Andrea Ivarsson from CBR
$8,849,000
4 Beds ⋅ 5 Baths ⋅ ML82006723 MLS
A stately retreat, this exquisite home offers complete privacy just blocks from Town Center and the acclaimed Woodside School. Set behind electronic gates on more than one acre of level land, the property is a showcase of timeless elegance and modern luxury with resort-like amenities. Sustainable living is effortlessly integrated with 32-panel solar power, four Tesla Power walls for energy independence, Tesla charging in the detached 3-car garage, and thermal solar power for the pool. The expansive rear grounds are designed for resort-style living, featuring a 54-foot pool with a beach entrance with water jet, lap lane, spa, plus infinity wall with waterfalls. A state-of-the-art Kalamazoo Outdoor Gourmet kitchen, with Hybrid Fire Grill fueled by any combination of gas, wood and charcoal, gas-fired pizza oven ready in under 45 minutes to make great Neapolitan pizza, and a gravity feed smoker with room for three whole packer briskets, nine whole rib racks or two large turkeys. A fire pit terrace, bocce court, and level lawn provide endless opportunities for entertaining. Offering the best of Californias indoor-outdoor lifestyle, this exceptional property is a rare find so close to the Town.

3295 Woodside RD, Woodside

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

Sold listing courtesy of Jennifer Alfaro from COMPS
$2,100,000
4 Beds ⋅ 4 Baths ⋅ ML82006263 MLS
Discover the tranquility of Woodside living in this beautifully designed 4-bedroom, 3.5-bath home, nestled on 1.5 private acres with sweeping views of mountains and lush trees. Backing directly onto open space, this home offers unmatched peace and seclusionyet is just minutes from the heart of town. The spacious open floor plan is ideal for modern living, providing seamless flow between the living, dining, and kitchen areas. In addition to the main residence of 2 bed, 2 bath and loft , the property features a charming 2 bed, 1 bath guest unit and a versatile artists studio with half bath, offering two additional income-producing or creative spaces. Located within the award-winning Woodside Elementary School District (K8), this home is perfectly positioned for families seeking top-tier education and a strong sense of community. Enjoy the nearby outdoor treasures such as the scenic trails of Huddart Park, and explore the history of the area at the iconic Woodside Store. Dine at the legendary Bucks Restaurantfamous as the meeting place where many Silicon Valley startups were born. With convenient access to Highway 280, you're just a short drive from both Silicon Valley and San Francisco. Come experience the peaceful charm and timeless appeal of Woodside.

885 Patrol RD, Woodside

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

Sold listing courtesy of Brendan Callahan from COMPS
$85,000,000
34 Beds ⋅ 26 Baths ⋅ ML81985961 MLS
The Green Gables Estate, in its entirety, is a 74 acre, spectacular, one of a kind, multi-generation oasis situated within walking distance from the Woodside Town Center. The estate is currently comprised of seven homes and 10 separate lots, featuring significant additional build out potential and may be purchased as a whole or in 6 potential lot combinations (see MLS listings for suggested lot combinations with Albion addresses 329-A, 329-AA, 329-C, 331, 333). The complete estates homes currently include 34 bedrooms, 26 bathrooms across approx. 23,900 existing square feet, with numerous options for expansion and/or redevelopment. The vast landscape includes world class gardens, magnificent vistas of the Western hills, its own large reservoir, three swimming pools, a tennis court and a breathtaking 100-yard Roman pool. Situated in the heart of Silicon Valley at the epicenter of venture capital, technology, and renowned educational institutions, the estates elegant blend of English and Italian design offers a bounty of elegant spaces to host retreats, social events, and cultural gatherings or to simply be a world class refuge from the pressure of the outside world. Green Gables is a truly remarkable estate and welcomes its next owner to the latest chapter of its amazing legacy.

329 Albion AVE, Woodside

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

Sold listing courtesy of from

$1,768,000
4 Beds ⋅ 2 Baths ⋅ ML81989321 MLS
Imagine a tranquil sanctuary highlighted by the splendor of nature, perfect for hosting gatherings in a lovely outdoor setting. This 4 BD & 2 BA home integrates indoor & outdoor living, boasting generous decks that overlook majestic redwood treeslocated just 20 minutes from Stanford! The living room & kitchen have vaulted ceilings & large picture windows throughout. The kitchen is equipped with premium SST appliances and custom cabinetry. Throughout the home, neutral tones & designer touches create a timeless and tranquil ambiance. The master bedroom serves as a private sanctuary, offering lush mountain views through oversized windows. Each additional bedroom also features large windows, providing peaceful views of the surrounding forest. Enjoy a built-in BBQ station, a private hot tub, and plenty of space for dining and loungingideal for soaking under the stars or enjoying quiet moments in nature's embrace. Conveniently located near Alice's Restaurant, local trails, and parks, midway between SF and San Jose, in the heart of Peninsula. Ormondale TK-3, Corte Madera 4-8, Woodside High School (buyer to verify all schools). This home is truly a Woodside gem!

13499 La Honda RD, Woodside

Listed by Wen Guo RE Group, 650-867-1128 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Paul Sabbagh from ZHB2X
$1,924,911
3 Beds ⋅ 2 Baths ⋅ ML82002229 MLS
Welcome to this charming updated 3-bedroom, 2-bathroom home located in the beautiful city of Woodside. This inviting residence sits on a spacious 15,400 sq ft lot, offering plenty of room to enjoy the outdoors. Inside, the well-appointed updated kitchen features modern amenities including a gas cooktop, dishwasher, microwave, oven range, and refrigerator, making meal preparation a breeze. The dining area, conveniently situated in the living room, creates a cozy atmosphere perfect for entertaining. Updated ADU with additional 3rd bathroom separate entrance. Large barn-like 2 car garage with extra room for storage workshop/office or more. This home is located within the Woodside Elementary School District. Lush and serene grounds with quiet and privacy inside this beautifully done home. Easy access to HWY 280 and downtown Woodside, close proximity to the Filoli Historic House and Garden. Don't miss the opportunity to make this lovely Woodside home your own. Large price reduction..Motivated Sellers!

789 Canada RD, Woodside

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

Sold listing courtesy of Sharad Gupta from LY55V
$4,850,000
5 Beds ⋅ 4 Baths ⋅ ML82004201 MLS
Completely transformed with sophisticated designer style, this home showcases luxury living at every turn, elevated by panoramic views that stretch from the San Francisco Bay & East Bay hills to the western hills. A striking front entrance, reimagined with cable-strung railings & beautiful landscaping, sets the tone for the more contemporary interiors. Located on just over one-half acre, the setting offers exceptional privacy along with expansive outdoor space designed for both relaxation & play, with vast level lawn, custom treehouse & playground, & expansive view-facing decks. A crisp white palette & refinished hardwood floors are complemented by sleek modern lighting & a reimagined kitchen. Multiple fireplaces enhance the ambiance, while vaulted ceilings & skylights infuse the home with natural light. Open-concept floor plan is designed for formal & casual living, including a lower-level family room & separate recreation room with fitness zone & rock climbing wall, plus a full kitchenette, all with direct access to outdoor play & entertaining space. Adding the finishing touch is a close-in location just minutes from town center & within the highly sought-after Woodside Elementary School District.

83 Tum Suden WAY, Woodside

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

Sold listing courtesy of Lynne Mercer, CRS from APR
$14,250,000
6 Beds ⋅ 8 Baths ⋅ ML82004065 MLS
Masterfully Renovated Bay-View Vineyard Estate. This extraordinary estate presents a masterfully executed whole-home renovation, captivating San Francisco Bay views, and resort-style amenities. Encompassing 1.8 acres of fully landscaped grounds, the property also includes a Chardonnay vineyard, two wine cellars, and expansive indoor and outdoor entertaining spaces designed for grand gatherings. The main residence was taken down to the studs with both levels reimagined with the ultimate in designer sophistication. Highlights include bespoke lighting, custom wall coverings, premium fixtures, exquisite finishes, and white oak floors throughout. The main residence has 6 bedrooms, 6 full baths, and 2 half-baths. As part of the renovation, an equally well-appointed 2-bedroom, 1-bath guest house was added along with a pool house with indoor barbecue center and ample space for entertaining.

140 Eleanor DR, Woodside

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

Sold listing courtesy of Pamela Culp from COMP32
$12,600,000
4 Beds ⋅ 5 Baths ⋅ ML82003378 MLS
Striking Modern Retreat near Town Center. In the heart of central Woodside, this modern home retains secluded privacywith convenience to shopping & dining just down the road. On a private country lane off the main road, the just over 1-acre setting presents sweeping western hill views from its gentle knoll beyond custom gates. Sophisticated architecturalelements define the home, from Ann Sacks tiles and radiant-heated French oak and marble floors to dazzling designerlighting and Fleetwood doors and windows. The open floor plan balances spacious gathering areas with options for privacyand flexibility plus indoor/outdoor living all around. A dramatic fireplace is shared by the family room with the living anddining room, all oriented to the majestic views. The open kitchen is a hallmark of the design, blending warm wood toneswith French limestone and designer tiles, while an adjacent den/study center offers versatility. There are 4 bedrooms and4.5 baths plus an equally well-appointed 1-bed, 1-bath guest house with full kitchen and laundry, perfect as an ADU orpoolside entertaining. At the center, a sparkling infinity-edge pool is surrounded by level lawn and sun-drenched terraces.A rare combination of modern luxury, a premier location, plus access to Woodside School (K-8).

1491 Canada LN, Woodside

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

Sold listing courtesy of Michael Warren from APR
$2,700,000
3 Beds ⋅ 3 Baths ⋅ ML82003150 MLS
Lakeview Lodge: A Storybook Sanctuary with Iconic Views and a Surprisingly Convenient Location. Every now and then, a property comes along that feels pulled from the pages of a storybook. Lakeview Lodge is one of those rare places, loved and nurtured by its owners for 29 years for the simplest reason: its just that special. Perched above the treetops with sweeping views of Stanfords Jasper Ridge, and originally named for its view of Searsville Lake, this peaceful retreat offers a front-row seat to natures changing beauty. From golden sunrises to dusky twilight, the vistas inspire reflection. Located near the bottom of Old La Honda Rd at Portola Rd, your minutes from Stanford, top schools, commute routes, and dining - seclusion without sacrifice. Nearby Dennis Martin Creek trails offer tranquil walks under the redwoods. The main home features 2BD/2BA, and a private-entry suite below with kitchen, living area, bedroom, and bathideal for guests or a home office. With high-speed internet, you can Zoom by day and stargaze by night. Lakeview Lodge is more than a home, its a soulful escape with a country feel and unbeatable convenience.

171 Old La Honda RD, Woodside

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

Sold listing courtesy of Alexander Nichols from EXPCA

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