Woodside CA Real Estate & Homes for Sale

3 level acres Prime Central Woodside with a very nice single level Ranch home and accessory structures. Pinot and Merlot wine vineyards which can be easily removed for a larger yard. Very convenient location near central town and commuting. Excellent Schools. Surrounded by larger estates of much higher value.

Priced to sell! Picture yourself, immersed in nature, living amongst the redwoods and fruit trees in your own fully fenced, secluded compound. Hidden from the road allowing you the ultimate in privacy. Enjoy the fragrance of fresh air and the Coastal breeze. Sink into soulful bliss and surround yourself in the beauty of nature while enjoying your morning beverage or your telecommute on the sun filled deck. The large great room with stone fireplace is the perfect space to entertain, an additional fireplace in the primary bedroom. Bonus room downstairs. No freeways here, far enough away from the hustle and bustle of the Silicon Valley, yet a short drive to Highways 92 and 280. With a little TLC, this lovely, private and secluded, quiet home would transform into a true gem. Sitting on over a half an acre, this is a real opportunity for the buyer who wants to keep the history and nostalgia of the area while creating a beautiful sanctuary to call their own, bring your vision and your contractor. Live here or make this your vacation home away from home, moderate drive from the East Bay or San Francisco. Forget Tahoe, live Woodside!

This fantastic new price makes it possible to create your own dream property on 2 tranquil acres! Conveniently located in true central Woodside with 2 homes, 2 private driveways and so much room to grow. The main house is 3,090 square feet, has 5 bedrooms, and 3 bathrooms. The large living room has huge windows overlooking the expansive lawn and pool area. The primary bedroom upstairs features a walk-in closet, fireplace, and a balcony with a jacuzzi overlooking your 2-acre property. The cottage can be accessed off of the first driveway and has been thoroughly remodeled. There is a lush green pasture, and pathways leading to the pool and patio area. 2 natural gas generators connected to each house. Experience the tranquility of Woodside, just 2 minutes from the town center and renowned horse trails. This is your chance to embrace a relaxed lifestyle in the heart of Woodside!

Amazing price for this stunning completely remodeled home! Located on 3 acres with complete privacy, and close-in convenience, this exceptional property epitomizes luxury living. The elegant sophistication of the interiors rivals luxury resorts with an extensive use of natural stones that transform walls into works of art. Natural light throughout. Book-matched precision is showcased on fireplaces, countertops, and shower walls. Grand entertaining spaces are designed for hosting gatherings large or small, served by a fabulous all-white kitchen, temperature-controlled wine storage, and numerous terraces for outdoor enjoyment. The home spans 3 levels with 4 spacious bedrooms, each with its own en suite bath, plus there are 2 versatile offices, a fitness center, and a home theatre. Additionally, a detached guest house provides 2 bedroom suites for visitors. The outdoor areas, complete with vineyard, are designed with health and wellness in mind, featuring a pool, spa, tennis court, and a path that wraps around the property for walking or jogging. Adding the finishing touch is the homes access to acclaimed Woodside Elementary School. Move right in!

Welcome to Woodside Big View Ranch! This legacy 162+ acre ranch has been in the same family for nearly a century - can now be yours. The large country home has a barn, workshop, huge pond for swimming and fishing and an unofficial,but well used air strip. The house is appx 4230 sq ft with amazing western views of the ocean.Built in 1983 by the patriarch of the family, it features 4 bedrooms 3 full and 1 half baths. A large, casual kitchen has views of the gardens and a spacious area for a big table. The formal dining room has paneled walls and looks out the back to the pond area and gardens. The living room is huge and takes a minute to believe that this beautiful of a setting is possible. You can feel the memories, the music and the possibilities for entertaining.There is a magnificent center veranda which has clear views of the pond and air strip. It is a remarkable view. There library that also can be used as a bedroom, with access to a full bathroom. Unfinished basement with laundry that has exterior access. One of the best fishing spots in all of Woodside, is the pond on this property. It is also a great swimming pond with a quaint deck for relaxing. Exuding personality and joy, this ranch is right out of an old Western movie - minutes to Sand Hill/Stanford. Williamson Act.

Welcome to Serenity Hill Haven, a once-in-a-lifetime opportunity to own a stunning estate in the coveted Woodside Hills. A 6,200 sq.ft., 5-bedroom, 6.5-bathroom estate, perched on 2.180 acres & engulfs breathtaking Panoramic Bay Views. A sophisticated LR, highlighted by a fireplace & large windows that invite natural light, large walkout w/water feature & spectacular views. Separate DR & chef's eat-in kitchen, complete w/a center island & high-end Thermador appliances. The kitchen opens into a spacious FR w/another fireplace. The main level of Serenity Hill Haven boasts a luxurious Jr. suite, a convenient PR, & a separate office. The primary suite retreat features its own fireplace, walk-in closet, & a spa-like bath w/oversized tub & a separate shower. In addition there are 3 more spacious jr. suites & 5.5 bathrooms, ensuring ample space & privacy for all. The estate also includes a family/recreation room, a sauna, laundry room & lots of closet/storage space. The beautifully landscaped over 2-acre grounds include walking paths, a rear great lawn, & a large natural pond. The property features a wrap-around driveway leading to a 3-car garage w/cabinetry. Experience luxury living with stunning views & unparalleled amenities in this magnificent Woodside Hills estate.

Mountain Retreat with Valley Views, Ultimate Privacy, and Open-Concept Living! This 3-bedroom, 2-bath home offers the best of both worldsclose enough for a quick Silicon Valley commute, yet it feels like a secluded mountain escape. The open-concept design connects the kitchen, dining, and living spaces, creating an airy flow perfect for relaxing and entertaining. Enjoy stunning valley views from the kitchen, living room, upstairs bedroom, and spacious decks. The largest bedroom, with a private entrance, offers ADU potentialideal for a guest suite, rental, or a teens private space.The sun-drenched backyard features mature oaks, fruit trees, berry bushes, a greenhouse, and irrigated planting beds. The front yard, with a redwood ring and native plants, enhances the peaceful retreat feel. Inside, the home boasts updated bathrooms, wood floors upstairs, and heated tiles in the downstairs bedroom and bath. Skylights and double-pane windows fill the home with light, while fresh paint and newer decks make it move-in ready. Walking distance to Skywood Trading Post and Alices Restaurant, this home has a small-town vibe. With top-rated Portola Valley schools and nearby trails, and only 25 minutes from the beach, its a perfect blend of nature and convenience.

Ideal setting to build your dream home. Large 3000 sq. ft metal shop on site. Building sites for house, guest house, and barn. The most spectacular views in all directions and total privacy. Minutes to Skylonda center and Alices restaurant. Quiet setting off highway 84 on a quiet country lane. These sites rarely come available in this premium location with views and privacy.

Completed in 2023 on Woodside's most premier central corridor, a Cul De Sac off Mountain Home Road. This 3 - acre Tuscan inspired estate property is a masterpiece of design that blends the finest materials from around the globe. Breathtaking displays of quartzite evoke artful elegance, while floors of marble and French oak exude timeless sophistication. Every detail is crafted with precision- French oak cabinetry, ceilings, and trim, coupled with Venetian plastered walls in the grand public rooms, and softly illuminated by chandeliers from Spain. Designed to perfection for toady's lifestyle, the great room serves as the heart of the home, offering a magnificent kitchen and a seamless flow to the loggia and vast private grounds. Five bedroom suites, including for both main and upper level primary suites, provide ultimate flexibility and privacy. The guest house mirrors the main residence's impeccable standards, complete with a full kitchen, bedroom, two baths, and a sauna. the estate's grandeur extends outdoors with a wrap around loggia with fireplace, 60 foot pool and spa with canopy jets, fully fenced tennis court, and expansive lawns and meadows. Located in one of the country's most exclusive zip codes, nearby Venture capital hub Sandhill Road, Stanford Univ. & Silicon Valley.

GATED COMMUNITY HOSTS A MODERN ARCHITECTURAL STATEMENT ON 6.44 ACRES! Impeccable showing condition and integrity of its Modern DNA! Custom designed in 1991 by celebrated architect Paul Gilger, it's no wonder this home takes on cinematic qualities: around the same time Gilger was crafting this modern opus, he was masterminding the film studio of George Lucas, the legendary Industrial Light and Magic in San Rafael. * 3 bed/3 ba main house + ADU with bed area, office area, kitchen & full bath * Lower level of main home makes an inspiring Office, Art or Music Zone * Stunning Open Concept * Unobstructed water views * Extensive new landscaping * 2-Story Staircase nearly 30 feet high as work of art * Indoor/Outdoor w/ view dining decks & flat pad to rear * Immersive privacy beyond circular motor court * Detached ADU/Office overlooks new Fountain Courtyard * Architecturally significant bespoke caliber * Central Woodside lifestyle w/ Woodside Elem, just 20-30 min to Sand Hill, Stanford, & Silicon Valley* THIS GATED PRIVATE ROAD HAS TWO GATES: ONE AT CENTRAL WOODSIDE'S BEAR GULCH, AND A SECOND AT SKYLINE, NOT FAR FROM MOUNTAIN HOUSE RESTAURANT AND EASY HWY 92 CONNECTION!

PRICE DROP! Discover this charming home built with love and designed to stand out. This unique 'round house' offers soaring open-beam wood ceilings and panoramic views of the stunning nature that envelops it. Built in 1978 and ready for you to renovate, or take advantage of the 1.6-acre lot and build your dream home. (Permits would be SMC, not City of Woodside.) Key features... Spacious Living: 2400 sq ft of living space with 4 bedrooms downstairs and 1 den/study/bedroom on the main level, providing ample room for family & guests. Outdoor Oasis: Wrap-around decks allow you to fully embrace the beauty of the surrounding landscape. This property also backs up to open space & Wunderlich Park, perfect for hiking enthusiasts. Expansive Lot: 1.6 acres adorned with a variety of beautiful trees, providing a harmonious balance of sun and shade. Prime Location: Located on a developed street with beautiful homes, you're just 5 minutes from the iconic Alice's Restaurant, local wineries & other attractions. Don't miss the opportunity to own this one-of-a-kind home in a desirable community! Take advantage of the price reduction and make this unique property yours today! (Note: Some images are digitally enhanced, with virtual staging to show furniture configurations. 3 bedrooms on record.)

Chic & Luxurious Retreat with Ocean Views. offering an unparalleled living experience, high-end luxury throughout, just 20 minutes to Woodside Village. Set on more than 8.2 acres with vast level areas, the entire home was extensively remodeled just 12 years ago and features a grand entrance via a long cobblestone-lined driveway. The open and flowing interiors showcase oak hardwood floors and a blend of modern / rustic design elements, including vaulted wood-paneled ceilings, paneled walls in some rooms, and contemporary designer light fixtures. Every room overlooks the ocean, accessing decks on each level lined in clear glass for unobstructed views. The home includes 4 spacious bedrooms, with the primary suite on the upper level and a second primary suite plus two additional bedrooms on the lower level revolving around a central lounge. Outside offers expansive decks, an ocean-view spa plus a regulation sand volleyball court for added relaxation and recreation. Nearby are miles of hiking and biking trails at Open Space Preserves plus acclaimed restaurants, such as Alices and Mountain House with a Michelin-star chef, along with a convenience market, deli, and gas station, all enhancing the lifestyle at this luxurious coastal-view retreat.

Plans are conditionally accepted to build an appx 3000 (+,-) square foot home, an appx 715 square foot ADU and a full 2 car garage with beautiful views of the bay, city and mountains. Conveniently located right off of Woodside Road.

Welcome to 55 Bigtree, an enchanting retreat nestled among the towering redwoods of Woodside. This historic cabin, beautifully remodeled and thoughtfully expanded, seamlessly blends rustic charm with modern elegance. The original cabin has been significantly remodeled, featuring a substantial addition that enhances the living space while preserving its timeless character. The new great room is the heart of the home, with soaring ceilings, abundant natural light, and picturesque views of the surrounding redwoods. The brand-new kitchen boasts state-of-the-art appliances, custom cabinetry, and a large center island, making it a chefs dream. Adjacent to the kitchen, the family room offers a cozy area for gatherings, with easy access to outdoor living spaces. Enjoy a serene, partial bay view, adding a touch of charm to this woodland retreat. Set on nearly half an acre, the property provides ample space for outdoor activities, gardening, or simply soaking in the natural beauty of the redwoods. The lush landscape creates a private oasis, perfect for unwinding. Don't forget the wonderful Portola valley schools. Experience the peaceful ambiance of a redwood forest with modern amenities. Don't miss your chance to make this extraordinary home yours.

A sanctuary of refinement and grace nestled on nearly 4.4 AC on a prestigious street. Almost 10,000 SF total space. Structures designed by Ugo Sap and Thomas Church, renowned for supreme craftsmanship. Floors of walnut and imported French limestone. Soaring ceilings and towering windows. Opulent formal rooms, gourmet kitchen, family room, well-appointed study, temperature-controlled wine and cigar storage. All bedrooms en suite, with the primary offering a retreat-like oasis. Six total fireplaces throughout the property. Lush, sprawling grounds with flourishing vineyards, olive orchard, lily pond, pool, stunning foliage, and ample outdoor spaces for entertaining. Extended, gated driveway, ample parking, 3-car garage. French-style copper gutters. Detached structures include pool house, studio/office, and storage. Walk to Village Pub, Robert's Market and Bucks. Woodside Elementary (buyer to verify). An estate of supreme distinction in the heart of Silicon Valley. Seller has informed us that the cost of reconstruction in 1997 adjusted for inflation was approximately $29M (orig home built 1977, completely reconstructed in 1997).

First time on the market in almost three decades, the Lakeview Lodge is more than just a home its a sanctuary, embraced by stunning natural surroundings and offering spectacular views. Its well-chosen name was inspired by the serene sight of Stanford's Searsville Lake, and todays breathtaking views include the picturesque landscape of Stanford's Biological Preserve, Jasper Ridge. Perfectly capturing the essence of this tranquil retreat, the updated and refreshed residence, complete with an attached separate apartment, provides a unique blend of rustic charm and modern features. Despite its secluded ambiance, the home is conveniently located at the bottom of Old La Honda Road, near Portola Road, just minutes from the global financial and tech centers on Sand Hill Road, Silicon Valley, and Stanford University. Beyond its natural beauty and prime location, the Lakeview Lodge also promotes a peaceful and conducive at-home work environment, enhanced by upgraded WiFi and internet service, making it an ideal balance of tranquility and modern convenience. For an opportunity to tour this special property call Steve at 650.850.1046.

Originally conceived by the visionary architect Gardner Dailey in 1934, this exceptional estate is a testament to his architectural brilliance updated with a complete comprehensive renovation. The classic style of a country manor is presented, creating a visual symphony from the slate tile roof to the leaded glass windows and exceptional gardens. The views offered are nothing short of dazzling, encompassing verdant views of the bordering Menlo Country Club golf course, the sweeping panorama of San Francisco Bay, and the majestic silhouette of the East Bay hills. Set within a gated sanctuary of 1.5 acres, the home is adjacent to a 2.8 acre lot available for separate acquisition, enhancing the promise of exclusivity or with potential for further development. The palatial home spans more than 10,000 square feet of grace and sophistication. The journey into the home begins with a unique entrance a pedestrian gate beyond the gated driveway opens into a vast front courtyard with a magnificent heritage oak tree, lawns and patios, and a sparkling pool, creating an enchanting space for grand celebrations or private relaxation. Adjacent 2.8 acre parcel also available for sale. This is a once-in-a-lifetime property!

Welcome to your dream home at 250 Hardwick Rd in Woodside. Situated at the end of a quiet cul-de-sac, this exquisite property just completed a high-end, studs-out renovation and boasts stunning views of the Bay and East Bay hills. With dual oversized primary suites (4 bedrooms, 4 full bathrooms total), this home offers ample space for your growing family or those considering multigenerational living. As you step into the proper foyer, you'll be greeted by warm ambiance and stunning views that continue throughout the entire home. The open-plan kitchen is a chef's delight, featuring high-end appliances, integrated gas range, oversized kitchen island, and a walk-in pantry for all your culinary needs. The spacious family room is perfect for entertaining guests, with its vaulted ceilings and massive windows allowing for an abundance of natural light and stunning Woodside views! Both primary suites have been totally remodeled to perfection, featuring luxurious ensuite bathrooms, large walk-in closets, walk-in showers, and a gorgeous free-standing tub. The 1.6 acres of usable land, provides plenty of private outdoor space to enjoy the beautiful California weather. Just a short distance away, you'll find top-rated schools ensuring an excellent education for your children.

Perfectly and privately situated on nearly 9 sun-filled acres of land, options abound at this very special property: remodel the charming home or build new to create your own dream vision. The choice is yours. The land enjoys breathtaking 180 degree views of the Western Hills and there is a pool, spa, guest house and vast gardens. There is also a 1.2 mile hiking/biking trail encircling the property for a no-excuses healthy lifestyle right out the front door. Explore the endless possibilities. Approximately 9 acres (389,760 square feet; buyer to verify) Existing circa 1930 home with 4 bedrooms and 3 baths plus a one bedroom guest/pool house. Exceptional privacy and rural beauty Western hill views ~1 mile to Woodside town center. Woodside Elementary (K-8) School

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.

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.

Extraordinary residence on 5.32 acres with opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway and sweeping views of San Francisco Bay. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble staircase with hand-forged railings leads to the upper level with formal living room, formal dining room, tremendous kitchen, family room, office, plus grand primary suite with 2 full baths. 3 luxurious bedroom suites plus large office and conference center make up the ground level. Breathtaking views from every room on both levels. Elevator in the main residence. 1-bedroom pool house and studio guest house, each with bath and full kitchen. Sparkling pool and spa plus fireplace terrace for idyllic entertaining in complete privacy.