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

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

Sweeping, unobstructed San Francisco Bay views define this contemporary estate set on more than an acre in Woodside Hills, with dramatic scenery enjoyed from nearly every room. Walls of glass, soaring ceilings, and refined finishes including marble, granite, and travertine floors create a striking yet warm aesthetic throughout approximately 4,800 square feet across two levels. The expansive

Michael Repka Deleon Realty

Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers a rare blend of privacy, scale, and resort inspired living. Thoughtfully designed to balance formal and casual living, the home features a gracious entry introducing light filled interiors with high ceilings, refined millwork, and an elegant flow throughout. The living and dining

Caroline Dinsmore The Agency

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, hand-painted murals, artisan tile, and beamed ceilings with the peace of mind of enterprise-grade infrastructure. The grounds are a private resort masterpiece designed

Erika Demma Compass

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

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 by Pacific Peninsula Architects for guidance in future opportunities. Positioned at the end of a private lane, the setting

Mary Gullixson Compass

Designer Transformation on 1.5 Private Acres Steps to Town A remarkable whole-home transformation has elevated this property into a showcase of design, quality, and livability. Spanning approximately 1.5 acres just minutes from the town center, the setting unfolds with park-like grounds that capture the essence of Woodside country living. Inside, a beautifully orchestrated floor plan offers

Erika Demma 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

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

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

Tucked away on a private, gated cul-de-sac, 200 Todo El Mundo in Woodside offers the perfect balance of privacy, convenience, and natural beauty. Situated on approximately 1.5 acres of flat, usable land bordered by a seasonal creek, the property features expansive front and back irrigated lawns and a peaceful, park-like setting. The European-influenced traditional 4,885-square-foot main residence

Helen Miller Compass

One of Woodside's premier estates, encompassing nearly 10,000 square feet across all structures, this property offers exceptional scale, quality, and lifestyle, highlighted by a classically styled main residence and a brand-new guest house crafted with authentic European detail. The main home is luxuriously appointed across two levels, with nearly every room opening to the outdoors. A

Mary Gullixson Compass

Enjoy exceptional indoor-outdoor living in this stunning single-story ranch home in Redwood City. Spanning approx. 3,000 sq ft on a generous 13,000 sq ft lot, this home showcases sweeping Bay Area views, abundant natural light, and a seamless open floorplan with high ceilings and stylish tile floors. Walls of windows connect the main living spaces to the backyard oasis, featuring a pool with

Vicky Costantini Compass