Woodside CA Real Estate & Homes for Sale

Step inside and step back in time to this to this stunning Henrik Bull-style home in Skywood Acres, where classic charm meets modern comfort. Nestled in a sunny tranquil setting, this architectural gem opens into a breathtaking great room with cathedral ceilings and walls of windows that frame sweeping treetop views. This seamless blend of indoor/outdoor living extends to an expansive deck offering a perfect retreat that harmonizes with nature. Reminiscent of a mountain ski lodge, this 2510 sqft private haven enjoys its own sunny microclimate and offers the ultimate escape, just 14 minutes to 280, 25 minutes to Stanford, minutes from Alices Restaurant, and private access to Wunderlick Park, Portola Valley schools. Main home features a primary bedroom that includes bathroom, dressing room and private office. Main level boasts a well-appointed kitchen, custom wood built-ins, opens to a grand living area. Downstairs 2 bedrooms and bath, 3 car garage with wine closet. Detached guest studio with sleeping loft. 1.5 acre lot includes a former sport court ready for new possibilities Make this getaway your private Shangri-La

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.

Perched on a peaceful mountain with breathtaking views of the Pacific Ocean, this updated 3-bed, 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.

Delightful 1950 square foot country home with four bedrooms and two bathrooms sits on just over half an acre. This well-loved home has been in the same family for approximately 57 years and is awaiting your vision and loving care to bring her back and make her your own. The focus of the home is the generous living room with soaring beamed ceilings and a massive fireplace creating a dramatic focal point. This room is spacious enough for large gatherings and opens to extensive decks. With the considerable expanses of windows and the natural setting, there is a sense of living in the environment. A formal dining room is light and airy also has enough space for large gatherings and holiday dinners. The downstairs with two bedrooms and one bath also features a family room/central play area ideal for children to have their own space. The downstairs would also function well for office spaces. Includes parcel #075-192-060 to total 22,796 sf. Located in the desirable Skylonda neighborhood of Woodside it is served by the highly sought after Portola Valley and Woodside schools. Stress free commutes to: Stanford- 23 minutes Google Campus- 33 minutes Facebook- 29 minutes San Jose International Airport- 37 minutes SFO- 35 minutes Redwood City- 24 minutes

Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The main floor features a gourmet kitchen with high-end appliances, sleek finishes, dining area, family room and dedicated home office offers the perfect space for remote work or creative pursuits. Upstairs, the bedrooms provide privacy and tranquility. A large, bright family room stands out as a favorite space, filled with natural light and a cozy, welcoming ambiance. Multiple large decks extend the living space outdoors, offering peaceful spots for relaxing, entertaining, or enjoying the majestic redwood surroundings. Additional features include a wine cellar and ample storage. Tucked just off the scenic Skyline Corridor with easy access to Hwy 92, 280/101, SFO, open space trails, restaurants, and award-winning Kings Mtn Elementary, this home offers a rare blend of privacy, convenience, and a strong sense of community fostered by friendly neighbors and the Kings Mtn Volunteer Art Fair.

Nestled on nearly a full acre high above one of Silicon Valleys most affluent neighborhoods, this Luxurious Woodside View Compound includes two homes offering soothing panoramic views spanning the bay with all three bridges from San Francisco to Palo Alto & across to Mt. Diablo. Both homes are meticulously renovated with the finest build quality/finishes & awash with natural light from sunrise to sublime sunsets. At the heart of the compound stands a luxurious 4bd/4ba generous scale home with open concept kitchen/dining/living plus game room with catering station/wet bar all on two levels with expansive walkout view decks. The renovated guest home with street level access was constructed in 1990 and is set on the west side of the estate with panoramic views, spacious open concept kitchen/living/dining design & luxurious master suite + guest bath. Below you will find two additional bonus/flex areas, both with private access perfect for office/gym. This exclusive compound stands as a testament to luxury living, positioned just 30 minutes south of San Francisco and complete with multiple gardens, meandering pathways, unexpected view enclaves, covered terrace with outdoor kitchen w/custom lighting and variant fruit tress, all set amid the expansive grounds.

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.

Mountain Meadow - A Landmark Legacy-Extraordinary in provenance, scale, and preservation, this landmark estate spans nearly 25 acres, located on land protected by Peninsula Open Space Trust and surrounded by Golden Gate National Recreation Area parkland. Offering unmatched privacy yet just 20 minutes from San Francisco International Airport. Commissioned in 1927 as one of the debut residential work of renowned architect Gardner Dailey. Over a period of decades, the entire property has been thoughtfully restored with reverence for its heritage and a commitment to enduring quality. The main residence of almost 9,000 square feet has been brought forward for the next century with seismic retrofitting, state-of-the-art infrastructure, and artisan-level craftsmanship throughout. Continuing beyond the main residence is a 2 story guest/caretaker's house. The heritage grounds are a living piece of California history. Originally designed by the same landscape architect responsible for the adjacent Filoli estate, the gardens include a pool by Thomas Church. This is a once-in-a-lifetime opportunity to live within a rare expanse of natural beauty, wrapped in complete privacy, where historic architecture and legacy gardens have been renewed with clarity of purpose.

Tucked away at the end of a private lane, this beautifully appointed home offers the perfect blend of privacy, contemporary style, & outdoor livability on more than one acre. Refreshed front landscaping & an expansive, partially covered front deck set the tone for the thoughtfully designed spaces within. Beautiful hardwood floors, vaulted ceilings, & walls of glass highlight the home's warm yet modern aesthetic. Two-story layout offers exceptional flexibility with 4 bedrooms, an office, & 4 full baths, including a main-level primary suite. Spacious living room with fossilized limestone fireplace, formal dining room, & a sleek maple kitchen with honed black granite & butcher block finishes, plus a sliding glass door to an expansive wraparound deck. Flexible-use office/den just off the foyer is ideal for remote work. Lower level features a large recreation room with a built-in workstation for two, along with 2 additional bedrooms, one with en suite bath. Terraced rear grounds are designed for both relaxation & adventure, with a free-form pool, barn for potential equestrian use, zip line, & newly refreshed landscaping. Just one-half mile from the heart of downtown Woodside & with access to acclaimed Woodside School, this home offers natural beauty, privacy, and a premier location.

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.

First time on the market in nearly 50 years. Almost three acres in sought after Central Woodside minutes to Roberts, Village market and horse trails. Original ranch home with newer addition, pool and ADU. Property is suited for complete makeover or reimagine as a new building site. Horses are allowable. Close to sought after Woodside Elementary.

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.

Nestled in Woodside, The Perch offers 7.7 gated acres of unparalleled privacy and stunning views. The thoughtfully designed home features a spacious two-level floor plan with expansive glass walls that fill the interiors with light and offer seamless outdoor connections. The chef's kitchen, inviting living spaces, and four spacious bedrooms are ideal for both quiet living and entertaining. A separate guest house offers flexibility for visitors, extended stays, or remote work. The expansive grounds include meandering paths, secluded terraces, a pool with a fully equipped pool house, and a tennis court set beneath a canopy of trees. Open lawns provide ample space for gatherings or peaceful relaxation. Just minutes from Woodside's town center, Sand Hill Road, and Highway 280, with easy access to top local schools. This is California living at its finest - private, serene, and perfectly connected to Silicon Valley.

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.

Zen-Inspired Close-in Retreat on 5.4 Acres. 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. 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 a 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. All this plus a close-in location just minutes to miles of hiking and biking trails, town centers, and access to excellent Portola Valley schools.

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.

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.

Known as the Craftsman Homes, coupled with the Tennis Court lot, this multi-faceted, independently accessible, two-lot combination extends across over 12 acres and currently includes two homes totaling approx. 2,850 sf (one with 1,515 sf with two bedrooms and a second with 1,335 sf with two bedrooms), a tennis court as well as a two-stall horse stable and grazing area. The numerous development options of these combined lots include the possibility of expanding and/or possibly relocating the homes, as well as adding swimming pools and accessory dwellings.

Known as the Wurster home, this three-lot combination extends across over more than 15 acres and includes as its centerpiece one of the first homes designed by renowned California Architect William Wurster. The house currently spans approx. 4,960 sf with six bedrooms, a beautiful rear lawn and sunny pool area with lovely views of the Western Hills. The lots development options include the possibility of expanding the main home as well as adding at least one accessory building.

Known as the Olive Orchard home, combined with the contiguous Olive Hill East and West lots, this fabulous combination of three parcels totaling just over 23.5 acres, currently includes two homes, one with approx. 3,345 sf and four bedrooms and the other with 1,755 sf with three bedrooms (the Estate Manager's home), each of which present a series of upgrade or redevelopment options. The parcels also include a beautiful vegetable and flower garden, the iconic Greene & Greene designed Tea and Dairy House, as well as a large barn and storage facility, both of which can be expanded and repurposed. The lot combination features fabulous vistas and a variety of development options, including the potential for relocating and expanding the homes as well as adding accessory structures and swimming pools.

Known as the Oak Grove home, situated on just over 11 acres and including one home of approx. 3,635 sf with five bedrooms, a lovely rear lawn and swimming pool area and intimate views of the Western Hills. This beautifully situated lot and home, nestled near numerous oak trees, is one of the most enchanting locations on the estate. The lots development options include the possibility of either expanding the main home or even completely rebuilding it, as well as adding at least one accessory building to meet ones growing needs.

Known as The Main House and Historic Gardens, representing the magnificent central, architectural jewel of the entire estate. The main home and gardens, situated on approx.11.7 acres, were designed by renowned Craftsman era architects Greene & Greene and include a two-story English-inspired existing. 9,890 sf home (with additional lower-level square footage), and an estimated 11,945 potential future total square footage, extraordinary lawns, trees and gardens, all of which overlook the stunning 100 yard long Roman Pool which beautifully frames the spectacular views of the Western Hills. The homes beautiful motor court is connected to the wonderfully situated large free form swimming pool with lovely oak trees and vistas along with three bath houses, as well as separate barbecue and kitchen areas.

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.

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.

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.