Woodside CA Real Estate & Homes for Sale

Central Woodside Oasis with Resort-Like Amenities. Located in Central Woodside within the esteemed Tripp Road neighborhood, this cherished property presents indoor/outdoor living in a glorious setting on more than one acre. Owned by the same family for 63 years, the home has been beautifully updated over the years with an organic designer style that includes oak and hickory floors, knotty alder cabinetry, and towering paneled wood ceilings. Almost every room opens to the grounds where a resort-inspired setting amid 200-year-old redwood trees unfolds with a sun-swept pool, secluded barn, putting green, and sport court. The home spans one level, with just a few steps between some rooms, and is filled with natural light from walls of glass and numerous skylights. A spacious formal living room & formal dining room are complemented by a fabulous chefs kitchen & open family room, where a secret door leads to the oversized primary suite with ample space for a nursery, office, and/or fitness center. In a separate wing of the home, there are two additional en suite bedrooms plus a fourth bedroom customized for an office. All around is the beauty of the setting in secluded privacy, yet close to town center and Woodside School, plus proximity to renowned scenic hiking and biking trails.

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).

Chic & Luxurious Retreat with Ocean Views. offering an unparalleled living experience, high-end luxury throughout, and a serene country setting, 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.

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.

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!

Rare opportunity ready to create your dream estate in the heart of central Woodside! "The Old Apple Orchard" offers 3 flat sun-drenched acres of quintessential country living, with mature trees, rolling pasture, equestrian expanse with existing barn, chicken coop and enclosed garden, and a private pool oasis in a seasonal creekside setting! Remodel existing mid-century home or build this state of the art luxury modern farmhouse compound- INCLUDES FULLY APPROVED plans for ~12,000 sq ft luxury multi-building estate including ~6800 sq ft main residence, accessory units, pool house, office and gym. Two entrances, one from Canada Rd and secondary access from Olive Hill Ln, this special property is primed with amazing possibilities, all within walking distance to town and Woodside Elementary School.

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.

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.

Nestled in the serene landscape of Woodside, this charming turnkey 2 bed, 2 bath residence with attached 1 bed, 1 bath apartment boasts breathtaking views of Stanford's Biological Preserve, Jasper Ridge. Conveniently located at the bottom of Old La Honda Road, near Portola Road, and is just minutes from global financial/tech centers on Sand Hill Rd & Stanford University. The home offers a beautiful authentic rustic design and is completely hidden from the road. This 1.06-acre property delivers rare seclusion utilizing its natural setting that promotes a peaceful and conducive at-home work environment, complemented with its enhanced WiFi / internet service. Excellent Portola Valley schools.

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!

This beautiful estate is nestled on nearly a 1.50 acre lot and is surrounded by beautiful redwood trees. This amazing, two-story mountain home offers unparalleled tranquility & privacy in a majestic setting. This rustic retreat boasts handcrafted wood features throughout the home, from the gorgeous detailing of the cabinetry in the loft, to the decorative pieces around the fireplace, to the beautiful wood beams adorning the ceilings. The first level features the kitchen that seamlessly flows into the dining room, a spacious and cozy living room, 2 bedrooms & 1 bathroom. The second level features a large, open loft, the primary bedroom suite & bathroom & two outdoor decks. While this home captivates so much history & exuberates timeless beauty, there is abundant potential to add in your own touches & transform this residence into your dream home. This property also offers a second dwelling unit with its own septic tank. The second dwelling is an unpermitted 2 bedroom, 2 bath unit with its own outdoor deck. Located in close proximity to the tech hubs of Silicon Valley, Stanford & the serene beauty of the Pacific coastline, this is an opportunity not to be missed. Don't let this chance slip away to own a slice of paradise in one of the most coveted neighborhoods in the area!

Experience country living just 30 minutes from the heart of Silicon Valley. Nestled in California's majestic Redwood Forest, this horse-zoned property blends natural beauty and equestrian potential. Set on a 2-acre lot with a HUGE open grass field, this home offers ample space for just about every lifestyle. Surrounded by lush greenery and open skies, it's a perfect retreat for those seeking a serene, private lifestyle. The expansive grounds provide endless possibilities for gardening, recreation, or creating your own outdoor oasis. Despite its secluded feel, youre close to top-rated schools and the 280 freeway, ensuring easy access to everything you need. The property is fenced, gated, and obscured by trees. The well-designed home features a fully equipped kitchen, spacious living room, high ceilings, and a welcoming family room, ideal for daily living and entertaining. Inside, cozy bedrooms offer a perfect haven after a long day. Tall windows and glass doors flood the floor plan with natural light. A bonus room under the house is perfect as a gym, recreation room, or playroom. Outside, a huge patio and wraparound deck overlook the expansive lot. Come live the life you deserve in this peaceful retreat.

Welcome to 277 Grandview Drive, a contemporary Craftsman style haven in Woodside, CA offering privacy near Silicon Valley. The 4-bed, 4-bath main house with 2 offices spans 4920 sq ft on a 10+ acre lot. A 996 sq ft guest house, with an additional 1 bedroom and 1 bath, adds versatility (currently used as a music studio). The gated entrance reveals a welcoming design which includes an 8.4 kW solar system with battery backup. Inside, discover radiant heating, a chef's kitchen and two living rooms with surround sound. Outside, a fireplace, porch and deck offer relaxation and entertainment spaces, not to mention ultimate privacy. Adjacent to Thornewood Open Space, and built in 2008, this residence seamlessly combines modern amenities with eco-conscious features. Explore the harmonious blend of modern living and natural beauty.