Woodside CA Real Estate & Homes for Sale

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.

"Discover this rustic log cabin-style home nestled among the towering redwoods. Spread across two levels, this enchanting property features three bedrooms and 3.5 baths. Skylights flood the interior with natural light, while 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. The .85 acre lot, comprising 3 merged parcels(075-092-040, 075-092-050, 075-092-0600 slopes 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!"

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.

Welcome to this charming Woodside home, cradled amongst a cathedral of Redwood trees, and loaded with character. Enjoy the relaxing ambiance of this home, featuring Pella windows, vaulted wood ceilings, skylights, and pine wainscoting. With the perfect balance of updated convenience and country charm, this lovely home boasts an open kitchen with an adjacent dining nook, a loft perfect for storage, guests, or office, and a living room with vaulted ceiling, perfect for curling up by the wood burning stove. Outdoor eating area, flagstone patio w/arbor, built-in benches, large shed, extra storage, detached garage

Nestled in a serene redwood grove in the hills above Woodside, this 4-bedroom, 2.5-bath home offers a tranquil retreat with modern convenience. Set on a spacious mostly level 1/2-acre, this property blends the beauty of nature with sophisticated living. The open concept living area features vaulted ceilings, large windows, & a cozy fireplace, filling the space with natural light and framing breathtaking views of the towering redwoods. The kitchen boasts stainless steel appliances with granite countertops. The primary suite offers a private sanctuary with two story cathedral windows looking out onto the private back yard. Adjacent to it is an enclosed downstairs porch with a built-in hot tub with 3 additional bedrooms providing ample space for guests, or a home office. Outside, the half-acre lot offers endless opportunities for relaxation & recreation, with pathways, fruit trees a garden area and plenty of space to create your vision. Located just a short drive from the city, this home provides the perfect balance of seclusion and convenience, offering a unique lifestyle for those who value nature and privacy without sacrificing proximity to urban amenities. A rare find in the Bay Area, this home invites you to experience the perfect blend of rustic charm and modern luxury.

Situated in a tranquil yet accessible location, this Woodside home seamlessly combines comfort with modern design. Gleaming hardwood floors and fully remodeled features add a contemporary flair, while expansive windows and glass doors capture breathtaking views of the surrounding landscape. The large deck is ideal for entertaining, enhanced by the calming sounds of a nearby seasonal creek, creating a serene escape. Located in a charming country setting, the property offers direct trail access to Woodside Village, just over a mile away, and falls within the highly regarded Woodside Elementary School district. Ideally positioned between San Francisco and Silicon Valley, this home provides a truly exceptional living experience.

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.

SKY HOUSE: INNOVATIVE BAY-VIEW ESTATE! WOODSIDE ELEMENTARY! Once in a great while, a destination comes along that is not just a home or an address, but a meeting place: a harmony of nature and design: a meeting place that is at once timeless and forward thinking. Adjacent to Wunderlich Park on a gated private road, Sky House at 33 Bear Glen is one such unforgettable experience. 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*

NEW LOWER PRICE! Discover the charm and uniqueness of 76 Morse Lane, a home built with love and designed to stand out. This two-story '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 large 1.6 acre lot and build your own dream home. (Permit process would be SMC, not City of Woodside.) Here is just a sampling of the key features... Spacious Living: With 2400 sq ft of living space, this home has 4 bedrooms (3 per tax records) and 1 den/study, providing ample room for family and guests. Outdoor Oasis: Wrap-around decks that allow you to fully embrace the beauty of the surrounding landscape. This property also backs up to open space and Wunderlich Park, perfect for hiking enthusiasts. Expansive Lot: Nestled on a 1.6-acre lot 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 and other attractions. Don't miss the opportunity to own this one-of-a-kind home in a desirable community! Take advantage of the recent price reduction and make this unique property yours today!

Contemporary Woodside. Designed by William A. Churchill and inspired by Frank Lloyd Wright - an extraordinary architectural masterpiece. One of the most sophisticated living and entertainment homes in Silicon Valley! Private, located on 3.38 gated acres, expansive entry is surrounded by a professionally managed vineyard of over an acre of Pinot Noir, Cabernet Sauvignon and Vermentino grape varietals. Open floor plan, 35-foot ceilings. The approximate 8,660 sq ft home has 5 bedrooms/ 6 full/2 half baths. Primary suite - stunning retreat w/fireplace, secluded outdoor terrace and dramatic ceiling.All bedrooms have unique features - ceilings of glass, views of the gardens and large adjoining bathrooms. Living room has views of the magnificent grounds and Santa Cruz Mountains. Five seat wet bar and game area. Library/office includes hand crafted bookcases and fireplace. Formal dining room. Openkitchen has granite counters and top of the line appliances.Family room.Outdoor entertainment area w/big western hill views, cascading pool and spa, verandas, barbecue and dining areas. Garden vegetable planters.Private spa/massage room, wet and dry saunas, gym room, and a private entry office w/kitchen and bath.Temperature-controlled wine cellar for 1,000 bottles, 4 car garage w/EV charger.

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.

Discover the endless possibilities with this exceptional home set on over 5.5 acres of serene land! This property offers breathtaking views from the living room, dining area, kitchen, primary bedroom, and outdoor patios. Whether youre looking to move in, renovate, or even build new, this private retreat is brimming with potential.This two-story residence features 5 spacious bedrooms and 4.5 bathrooms. Upon entering, you are welcomed by soaring ceilings, expansive windows, and skylights that flood the home with natural light, showcasing views of the private backyard. The eat-in kitchen is a chefs dream, with a large center island, additional peninsula seating, and large glass doors that open to the patio.The expansive patio is ideal for BBQ, alfresco dining, or summer stargazing. The main level includes a luxurious master suite with dual vanities, a spa tub, a shower, and a private balcony. The lower level features 2 bedrooms and 2 full bathrooms, including a fully equipped in-law unit with a kitchen, bathroom, and separate entrance. Located within the highly regarded Portola Valley school district.

$72,000 Reduction!!! Discover this exceptional 3-bedroom, 2-bathroom home that perfectly combines an ideal location and comfort. The home is a tranquil place to unwind and savor the calming views. The spacious living room features soaring vaulted ceilings and rich hardwood floors, creating a warm and welcoming ambiance. Enjoy cozy evenings by the fireplace, perfect for relaxing and entertaining. With an atrium, wrap around deck, two-car garage and an expansive paved lot to extend the house. Total lot size is 14,767. (Needs TLC.) Dont miss the chance to make this beautiful Woodside Retreat your own!

Amazing opportunity to build a beautiful new home in Woodside just 2 miles from the town center and with access to acclaimed Woodside School (Pre K-8). Architectural plans, by the renowned firm, Mason Architects, have already been paid & approved by the City of Woodside. The plans include a 3,214 sf main home and 512 sq. ft ADU. The main level of the home features a formal living and dining room combination plus a great room kitchen, powder room, and mud room. Upstairs area includes a spacious primary suite, a second bedroom suite, the other two bedrooms/office connect to a shared balcony & laundry room. The 512 sq. ft ADU above the 717 sq. ft. garage has a living area, full kitchen, bedroom, and bath. Comprising two separate parcels, the total lot is approximately three-quarters of an acre (30,681 sf) with existing rustic home and garage. The entire setting is serene with sun swept spaces and a backdrop of wooded grounds that exemplify Woodside's charm. Just down the street are miles of hiking and biking trails as well as easy access to Highway 280 to all of Silicon Valley and San Francisco. *Note the 3D rendering is only for illustration purposes.

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).

Majestically situated on 5 flat acres in central Woodside, sits this magnificent Tudor manor close to Silicon Valley, San Francisco, Stanford University, and Filoli Mansion, which hosted President Biden and President Xi Jing Ping at the recent APEC summit. A gated entrance and brick wall surrounds the entire property. A cobblestone driveway flanked by parterre gardens of boxwoods and roses, leads to the grand entrance. The gallery with soaring 24-foot ceilings, is flanked by formal dining and living rooms, with 3 bedrooms & 4 baths on the ground floor including a primary suite. Two family rooms open to the indoor 2,200-square-foot pool pavilion. This rare 16,000-square-foot home with 7 bedrooms and 9 baths, offers limitless possibilities. The city of Woodside no longer approves homes of this size within the city limits. The property also has a rustic and historic three-bedroom guest house and barn, with loft above and horse stalls below. Arched doorways, leaded glass windows, coffered ceilings, heavy wainscotting, rich wood paneling, deep moldings, turreted open beam ceilings & pool pavilion create a refined balance of dramatic formality, yet comfortable ambiance. Perfect for entertaining, or family gatherings, this impressive landmark property is ready for a new legacy!

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. 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 just two miles away.

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.

Contemporary luxury with breathtaking San Francisco Bay views in Central Woodside. Extensively renovated open concept design on two levels, including modern kitchen, white oak floors, new metal roof, and designer baths. Tesla solar power, 5 battery backups, EV charging, and synthetic lawn. Every room opens to a deck for Bay or western hill views or just the natural beauty of the surrounding grounds. Elevated and private pool plus meditation/yoga area with sweeping views. Separately fenced farm with large barn and space for animals or garden. Direct access to hiking and equestrian trails at Wunderlich County Park. Excellent Woodside Elementary School (K-8). Recent upgrades over 500K of improvements including new standing seam metal roof, solar system & storage, HVAC systems, structural upgrades, plumbing, home A/V systems. Every detail updated and ready to be enjoyed!

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