Woodside, CA Homes for Sale with Pool

Set on more than 2.5 acres of quintessential Woodside grounds, this spectacular estate balances timeless elegance with easy comfort. Behind gates and surrounded by mature trees and lush foliage, it conveys a quiet sense of luxurious seclusion. Inside, more than 6,400 total SF includes a dramatic foyer with columns, expansive formal rooms, a chef's kitchen, private office, theater, and five

Michael Repka Deleon Realty

Spectacular Monterey Colonial home on 6+ private acres. Long gated driveway & large motor court. Estate shows tremendous character and beauty. Improvements include a stunning primary bath, a complete new roof & gutters & Exterior paint 2025. 3 expansive levels with grand public rooms, large eat-in kitchen, English Pub bar, recreation/media room and fitness room with sauna, wine room for approx.

Steve Lessard Compass

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc

Scott Dancer Compass

Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning just over 3.4 acres, this expansive property showcases rare Bay views. There is an existing planning study for guidance in future opportunities. Positioned at the end of a private lane, the setting reflects the essence of Woodside

Mary Gullixson Compass

A rare, fully realized legacy compound offering the soul of a European retreat in the heart of Woodside.Hidden within 3.2 acres of curated gardens and ancient oaks, this meticulously renovated sanctuary blends old-world artistry, artisan tile, and beamed ceilings with the peace of mind of enterprise-grade infrastructure. The grounds are a private resort masterpiece designed for serene living,

Erika Demma Compass

This extraordinary Woodside estate spans 6.4 level acres w/sun-swept vineyards & western hill views. The compound comprises multiple architecturally significant buildings, including the main residence, guest house, a multi-room wellness studio w/wine cellar & 6-car garages plus a working lab w/anti-static flooring. Designed for exceptional privacy & self-sufficiency, the property features a 35kW

Mary Gullixson Compass

Evoking the patina & permanence of a residence shaped over generations, this vineyard estate possesses an authenticity rarely achieved in contemporary construction. Completed in 2016 imbued with character of timeless European manor, it received the Julia Morgan Award for Classical Architecture, honoring its exceptional craftsmanship & architectural integrity. Hand-hewn beams, bespoke millwork,

Hugh Cornish Coldwell Banker Realty

This exceptional property spans more than 3 acres with sweeping western hill views and 9,880 square feet of total living space. The main home was completely rebuilt in 2000, and in 2025, an entirely new guest house and entertainment complex was added to the estate. The classically styled main residence features nearly every room opening to the views and includes a state-of-the-art theater and

Mary Gullixson Compass

Set behind private gates on a flat, over 1 acre lot enclosed by a privacy wall, this single-story Tuscan villa offers a rare convergence of architectural integrity and absolute seclusion on one of Athertons most coveted locations with no through traffic-a quiet distinction that speaks to the discretion and privacy this address commands. Just minutes from Sharon Heights Country Club, Sand Hill

Panos Anagnostou Compass