Woodside CA Real Estate & Homes for Sale

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 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 2 car garage with extra room for storage. This home is located within the Woodside Elementary School District. Don't miss the opportunity to make this lovely Woodside home your own. Call Tammy 650-683-0426

Napa Valley-Like Vineyard Estate with Bay Views. This breathtaking estate has been reimagined in sleek modern style across approximately 3.8 acres with magnificent SF Bay views from each level. The gated grounds showcase 600 Pinot Noir and Syrah vines, with resort-inspired amenities that define a luxurious lifestyle. Meticulous design, from dramatic open-concept interiors to vast outdoor spaces that feature an 82-foot lap pool with an integrated spa, a life-size chess board, expansive lawns, and multiple covered lounges ideal for entertaining or relaxation. The estates amenities are extensive, including a stainless steel kitchen equipped with German appliances, numerous choices for remote office needs, and grand-scale recreation room with a full kitchen and bar. Health and wellness are prioritized with a spa bath and steam shower in the fitness center. The home offers 5 bedrooms and 6.5 baths, including a main-level primary suite with 2 full baths and stunning Bay views. Advanced sustainable features enhance the home, such as solar-powered electricity, a backup generator, and 2 EV charging stations in the attached 4-car garage. Located near town center, this home uniquely combines seclusion with accessibility, alongside proximity to acclaimed Woodside Elementary School.

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.

Situated on a cul-de-sac, this sun-drenched, designer-updated home offers an ideal blend of style, comfort and nature. Just minutes from Town and top-rated 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 a fresh kitchen. Also connected is a 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.

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.

Welcome to these cabins nestled in the quiet, redwood-lined hills of Woodside with the Portola Valley School System! Two vintage cabins (needs work) on a single lot - the perfect blend of rustic charm. Enjoy the peace of a small mountain community without being too far from modern essentials like groceries, shops, and entertainment. The front cabin welcomes you with a large deck, an inviting interior featuring hardwood floors, exposed beam ceilings with skylights, and a cozy wood-burning fireplace. The main living space includes a full kitchen, breakfast nook, a sleeping loft, and a spacious bath with tub. Delight in the forested beauty and fresh mountain air on the lofts wraparound deck. Downstairs, the versatile bonus room is perfect for a studio, home office, or game room, plus a laundry area and unfinished basement for additional storage. Tucked toward the back of the lot is the second cabin a charming studio with a full kitchen, bath, and its own peaceful deck space. Both cabins are older and do need some love, making this a true fixer-upper with incredible upside. Whether you are looking for a weekend escape, a full-time mountain lifestyle, or a unique investment opportunity, this property offers a special kind of retreat that is hard to find. You will LOVE living Here!

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.

Whole-Home Transformation & Amazing Views. This magical setting begins with a wine country-style garden entrance and continues out to sweeping western hill views and amazing privacy. A whole-home transformation created a luxurious indoor/outdoor space with designer finishes and an exceptionally bright and light ambiance. The floor plan is arranged with two distinct lower-level wings for the homes 4 bedrooms, connected by a vast rear terrace with inviting garden paths throughout the grounds of nearly one-half acre. The main living areas, catered by a stunning all-white gourmet kitchen, open to a covered deck for ultimate view enjoyment. A lower-level family room plus offices on each level round out the accommodations. There are 3.5 baths, each beautifully appointed in a selection of Carrara marble and glass tiles. Access to acclaimed Woodside Elementary School and proximity to miles of hiking trails add the finishing touch to this exceptional home.

Imagine a home where every detail invites you to relax and enjoy the peace and privacy of nature, while still offering a perfect space to entertain. This home strikes the ideal balance between indoor and outdoor living, featuring a spacious deck that looks out over majestic redwood trees, creating a serene retreat. The natural materials throughout, including stone and rock finishes, blend effortlessly with the surroundings, giving the home a grounded, earthy feel. Picture yourself hosting unforgettable gatherings around a large dining table that easily accommodates friends and family. And with a walk-out downstairs leading to the side yard, plus a full bathroom on the lower level, this home offers both comfort and convenience in every corner. Wouldnt you love to call this place home?

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

An extended driveway meanders through more than 1.3 acres of Woodside grounds, leading to this spacious and inviting home offering nearly 4,200 SF of space. Bright and airy interiors, adorned with maple floors and intricate millwork, have been thoughtfully updated over the years with modern living in mind, providing ideal spaces for entertaining or quiet evenings at home. Expansive formal rooms, cozy fireplaces, a chefs kitchen, and five bedrooms, including two with en suite bathrooms, create a comfortable and functional layout. Designed for seamless indoor/outdoor living, the all-encompassing grounds feature a pool, outdoor kitchen, drought-friendly synthetic grass, and gorgeous views. Additional highlights include air conditioning, a 2-car garage with an attached workroom, and a prime location near the Atherton border. Youll enjoy convenient access to downtown Menlo Park, Menlo Country Club, the iconic Woodside Pub, Bucks, and top schools (buyer to verify eligibility).

Panoramic Western Hills views set the stage for this stunning Central Woodside estate, nestled on approximately 3.2 flat, fully usable acres just moments from downtown shops, dining, and top-rated Woodside Elementary. Designed for both comfort and function, the primarily single-level layout includes a spacious primary suite, multiple living areas, and a bright eat-in kitchen opening to a large deck overlooking a sprawling lawn, pool, and spa. Work or unwind in the detached office near a private chipping and putting green, while the beautifully crafted barn features a 4-stall stable, tack room, hay storage, riding ring, and fenced turnouts surrounded by peaceful pastures. This estate is brimming with amenities: a rose garden, fountains, sports court, horseshoe area, hidden redwood trails, and vibrant landscaping throughout. The expansive ~2,700 sq ft basement offers incredible storage, along with a wine cellar. Separate guest quarters complete with a second kitchen and private entrance. A rare combination of luxury, land, and locationthis is Central Woodside living at its finest.

Embrace Nature 5.19 Acre Gated Magical Woodside Retreat. Contemporary style, huge windows, soaring ceilings that reach to amazing heights, pyramid copper roofs, 10 gig network intra-structure, and skylights. Unique style/constructionset in the magical setting of a majestic Redwood grove, surrounded by Silicon Valley Views. 3 bed, 2 bath home of ~2,850 sf. The open plan has a kitchen with custom cabinets, luxury appliances, all wrapped by windows. Alfresco dining is just steps away, a tranquil oasis & just one of several venues for entertaining. Separate dining, family and living rooms. Huge primary suite with sitting area & office. Oversized 2-car garage & large workshop/art studio. Extras: Beautiful finishes, radiant heat, Ring doorbell, Advantage lighting system, excellent storage, Boise sound system, hidden panel to finished basement/laundry, whole house vac system, Tesla EV charging, Rumford fireplace, steam shower & much more. Excellent Schools. Just 6 miles from Hwy 280 & Menlo Park. This is just a hint of the treasures this property holds, schedule an appt. with Peter today.

First time on the market in almost 50 years. This unique setting close to horse trails in Central Woodside offers the opportunity to reimagine the potential of almost 3 park like acres. A private oasis for your dream home and minutes away from 280. Proximate to premier local shops and restaurants, Roberts Market, and highly rated Woodside Elementary School.

One of the most extraordinary properties on the SF Peninsula on almost 18 acres. The property has endless potential (including zoning for commercial use) and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. Woodside or PV schools. 17 minutes to Woodside town center.

IN THE HEART OF HORSE COUNTRY, this treasured family farm on 3 acres will provide enjoyment for years to come. Spacious and expansive, the classically simple and refreshed one-level home is designed for effortless indoor/outdoor living. Highlights include a dramatic great room, extra-large kitchen, 4 bedrooms, and seamless access to the pool and enchanting outdoor living spaces. Enhancing the appeal is a separate guest cottage or ADU, equestrian facilities with direct trail access to 973-acre Huddart Park, plus access to acclaimed Woodside School. 3 sunny acres, all usable and ready for planting/farming and/or horses Spacious, refurbished one-level home with a design for indoor/outdoor living ( approx 3340 square feet) 4 bedrooms and 3 baths; approximately 3,340 square feet Guest cottage or ADU with full kitchen, bath, and large deck( approx 640 square feet) 3-car garage with workshop ( approx 970 square feet) Pool plus expansive entertaining patios and decks ( approx storage rooms 215 sq ft, dressing rm 90 sq ft,) Equestrian facilities with two barns ( approx 1175 and 190 sq ft) riding arena ( approx 50x100), and fully fenced horse pastures Woodside Elementary (K-8) School (total structure approximate square feet 6620)

A stately Hamptons-style 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. Extensively remodeled, the interiors feature refinished hardwood floors, fresh paint, and just-completed designer baths. The kitchen showcases classic style with white cabinetry, soapstone and Carrara marble counters, and all Miele appliances. The adjoining family room invites media enjoyment and a wonderful space for everyday living beyond the formal living and dining rooms.

Gated, secluded retreat on over one acre, offering serene privacy and easy access to Silicon Valley. Light-filled, single-level residence features peek-a-boo ocean views and refinished hardwood floors, echoing the clean lines and natural materials of the home. The expansive, open-concept great room complete with a gourmet kitchen and high-end appliances, flows seamlessly into the living area and separate family room, each anchored by a stone fireplace. A dedicated bedroom wing features a primary suite with spa-like bath and heated floors. Shoji-style screens add a touch of balanced aesthetic. Sustainable living with owned solar panels and Tesla Powerwall. An expansive rear deck, curated landscaping with a gas fire pit, and seamless indoor/outdoor spaces are ideal for entertaining. This residence offers unparalleled access to the miles of trails within Purisima Creek. Set back from the scenic Skyline corridor, it provides a peaceful haven while maintaining easy access to Highways 92 and 280, or Woodside Road. A long, private drive provides generous space for parking. Benefit from the award-winning Kings Mountain Elementary School and become part of a warm and rooted community.

Tucked away in the enchanting Woodside Glens neighborhood, this circa mid-1930s cottage is wrapped with lush gardens on a level lot, presenting a rare opportunity not seen on the market in four generations. Thoughtfully maintained and updated, the home showcases its original charm with a leaded glass front door and handcrafted built-ins throughout. A welcoming foyer, inviting living spaces, and a flexible floor plan with four bedrooms on two levels plus a detached secondary structure provide both comfort and versatility. An expansive patio, a soothing spa, and plantings create a peaceful outdoor retreat. Amenities include solar electricity, a portable Generac back-up generator, generous 2-car garage, plus additional off-street parking. Just over one mile from the heart of Woodside for shopping and dining. This home also offers easy access to Highway 280 and the acclaimed Woodside Elementary School. Welcome home!

This exceptional hilltop residence features dramatic bay views from Mt. Diablo to the coastal mountain range. The Hamptons-inspired shingle home has the ambiance of a resort retreat and the privacy that comes with being adjacent to 5000+ acres of Open Space yet minutes from the heart of Silicon Valley, A giant office suite, complete with lounge, meeting area and private deck is perfect for work from home with high speed internet access supplied by Etheric Networks. A separate library, professional gymnasium, and acres of land to run and play makes this a true sanctuary for all ages.. There are 5 bedrooms and 4.5 bathrooms including a stunning master wing with a private master deck. The outdoor spaces include a pool and patio as well as 4000~ square feet of ipe deck, covered porch with fireplace, outdoor kitchen, and lovely native landscaping. Starwood is a gated private road. The end of road privacy is further enhanced by private trail access from your front door to Open Space.

Private retreat with stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside. Custom-built in 2004 on 1.4 acres with incredible quality and seismic integrity, this Craftsman home exudes European flair with imported Spanish tile and walnut floors, 12-foot ceilings, and fireplaces in the formal living and dining rooms. The French 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, backup generator, and 2-car garage with covered access. Sunny level yard for play and entertaining, plus a secluded pool surrounded by redwood groves. Scenic hiking trails right out the door. Family-friendly neighborhood with a convenient door-to-door bus to top-rated Portola Valley schools.

Wonderful opportunity to live in your own private forest with views of the bay! This property located in the Skyline area of Woodside offers so many opportunities. This 3 bedroom / 2 bath, 1,460 Sq. Ft. home sits among over 2 acres of land. Property consists of 4 separate parcel numbers: 075-181-100, 075-173-110, 075-173-120 & 075-183-010. Potential to remodel existing home & build 2 more with ADUs for a total of 3 houses with 3 ADUs (Buyer to verify building options). Just 7 short miles from Hwy 280, this property is conveniently located close to Alices Restaurant and a convenience store; feeds into great schools. Surrounded by redwood trees offering much privacy. There is also a separate entrance from Sequoia Way. These owners have lived at the property for over 50 years...it must be pretty special!

Tucked among towering redwoods, this enchanting log cabin-style home offers a serene retreat in the heart of Woodside's verdant nature. Spread across two levels, this enchanting property features three bedrooms and 3.5 baths. Skylights bathe the interior with natural light, while rich wood floors and a grand stone fireplace create a warm and inviting ambiance. Step out onto the beautiful deck with forest views, establishing a cozy and private retreat. Comprising 3 parcels (075-092-040, 075-092-050, 075-092-060), this 1+ acre property slopes gently down to a tranquil creek. The great outdoors beckons with multiple usable areas, perfect for relaxation or entertaining. And with numerous open space trailheads accessible off Skyline Boulevard, you'll have plenty of opportunities to explore natures beauty. Conveniently located near Alices Restaurant, its just a 13-minute drive to Highway 280, 20 minutes to Stanford University or the San Mateo coast. Dont forget the excellent Portola Valley Schools. Experience the allure of mountain living with the convenience of Silicon Valley and coastal access just moments away.

Stunning Custom Built 3 Level Home with Guest Cottage and Pool on 4.37+/- Acres with Stables and Riding Ring on Private Cul-de-Sac in Central Woodside. 5 Bedrooms. 5.5 Bathrooms. Living Room Features Vaulted Ceilings, Wood Floors, and Floor-to-Ceiling Windows. Spacious Kitchen with Large Island, Peninsula and Views of the Pool and a Pond. Intimate Family Room with Sliding Glass Doors to Pool. Library with Fireplace. Wine Room, 3 Laundry Rooms, and Large Fitness Area with Sauna and Steam Room. Outdoor Cold Plunge. Three-Car Garage. Ipe Decking, Pool, Large Pool House, and Outdoor Kitchen. Guest Cottage. Sand Riding Arena and Horse Stables with 8 Stalls and Loft. Situated Hillside for Amazing Views.

Contemporary luxury with breathtaking western hill views from a close-in location with access to acclaimed Woodside Elementary School (K-8). Whole-home renovation in 2020 to 2022 with open concept design and three levels comprising 3 bedroom suites, dedicated office, 3.5 designer appointed baths, and spacious kitchen. Maple floors on the main level, towering vaulted all-wood ceilings, entire walls of glass presenting the views, plus front balcony. Vast level rear yard for play and entertaining with large deck, synthetic lawns, and gardening area. Fire-resistant Hardie plank siding (newly painted), composite roof and Azek decks, and triple-pane windows. Gated driveway to attached and finished 2-car garage with EV charging. Amazing customized storage throughout, including potential wine cellar and in garage, which can double as a home gym.