Woodside CA Real Estate & Homes for Sale

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!

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).

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.

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.

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)