Woodside, CA Homes for Sale with Acreage

Discover this exceptional opportunity to own a generational estate spanning 7 acres across 3 separate parcels, each with its own APN. Through a private gate & down a long winding driveway, you're greeted by a circular motor court with incredible views of the Santa Cruz Mountains. The main residence offers 4,340 sqft featuring 6 beds & 5.5 baths, with exceptional upgrades throughout. On the east

Kia Amini Compass

A rare offering on one of Central Woodsides most prestigious streets, just off Mountain Home Road, this extraordinary estate showcases architectural excellence, vineyard beauty, & a luminous natural setting. Spanning almost 4.4 acres with an optional adjacent 3-acre parcel also available, the grounds have been thoughtfully opened to invite abundant sunlight, enhancing both the ambiance and the

Mary Gullixson Compass

7.7 gated acres with Views, Pool, Tennis Court, & Guest house. Bordered by Thornewood Open Space Preserve, and with incredible San Francisco Bay and western hill views. Main home with dramatic formal rooms, walls of glass, and tile or hardwood floors. Sleek modern kitchen with oversized island seating. Main level primary suite with views and spa-like bath plus secondary suite. Lower-level

Scott Dancer Compass

Set on a flat acre of gorgeously manicured grounds. This single story home borrows transitional architectural tones from the French countryside. The circular driveway leads up to a large 3 car garage. Five bedrooms that come with a separate guest house, sports court, large pool with covered grotto like spa, adjacent bath with changing room. Outdoor kitchen covered by a palapa, the perfect shade

Mariana Pappalardo Compass

Set on a 3.1-acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly-updated residence offers the perfect blend of refined luxury and modern comfort - just minutes from town. Flooded with natural light from expansive floor-to-ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public

Jim Arbeed Coldwell Banker Realty

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

James Milton Coldwell Banker Realty

Nestled in the prestigious Woodside Hills, 61 Oak Haven Way is a private estate offering a rare blend of serenity, architectural volume, and thoughtful modern upgrades. Surrounded by majestic oaks on a beautifully landscaped 1.175-acre lot, the home is approached via a long paver driveway that offers privacy and presence. Fully remodeled in 2000 and tastefully updated since, the house includes

Alex Comsa Coldwell Banker Realty

Contemporary single-level main residence with attached two-story ADU on 1.1+ private acres finished in 2021, offering direct Windy Hill views and walking distance to Portola Valley Town Center, library, restaurants, farmers market, and trailheads. Striking modern architecture features walls of glass, soaring ceilings, skylights, and white oak floors throughout. The dramatic great room opens to

Hugh Cornish Coldwell Banker Realty