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 are 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

Set on more than 3.6 gated acres of quintessential Woodside grounds, this contemporary masterpiece is surrounded by towering oaks and lush greenery, offering a serene, woodsy retreat. The interiors reflect the natural setting with soaring cherry wood cathedral ceilings, cherry wood floors, and expansive picture windows that flood the home with light and invite the outdoors in. Designed for both

Michael Repka Deleon Realty

Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The

Joakim Bye Ocean Element Real Estate

Nestled in Woodside, The Perch offers 7.7 gated acres of unparalleled privacy and stunning views. The thoughtfully designed home features a spacious two-level floor plan with expansive glass walls that fill the interiors with light and offer seamless outdoor connections. The chef's kitchen, inviting living spaces, and four spacious bedrooms are ideal for both quiet living and entertaining. A

Michael Repka Deleon Realty

Tucked away at the end of a cul-de-sac, this refined home sits on more than an acre of gated grounds and offers over 4,900 square feet of light-filled living space. A circular driveway with a central fountain sets an elegant tone, leading into a residence defined by timeless style - rich hardwood floors, detailed millwork, soaring ceilings, and expansive formal rooms ideal for entertaining. The

Michael Repka Deleon Realty

Known as the Wurster home, this three-lot combination extends across over more than 15 acres and includes as its centerpiece one of the first homes designed by renowned California Architect William Wurster. The house currently spans approx. 4,960 sf with six bedrooms, a beautiful rear lawn and sunny pool area with lovely views of the Western Hills. The lots development options include the

Helen Miller Compass

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.

Keri Nicholas Parc Agency Corporation

Extraordinary residence with stunning panoramic San Francisco Bay views. Opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble staircase

Scott Dancer Compass

Perched on 1.5 acres of beautiful land, this spacious 6-bedroom, 3.5-bathroom home offers panoramic views and room to grow. With generously sized rooms and views from nearly every window, this property combines comfort, versatility, and endless potential. A formal entry leads to a grand living room featuring soaring ceilings, a cozy fireplace, and access to an expansive entertaining deckperfect

Margot and Ricky Lockwood/ Flores Golden Gate Sotheby's International Realty

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

Welcome to Five Acre Woods - A Magical Retreat in Woodside! Nestled on 5.6 private acres, this enchanting property offers sweeping Bay views framed by majestic redwoods. Combining seclusion with convenience, its just minutes from Hwy 280 and the town center of Woodside. Originally built in 1915, this 3-bed,3-bath home has been thoughtfully updated for modern living. With approx. 2,300 SF of

Lisa Keith Golden Gate Sotheby's International 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

Morning light pours through redwoods onto white oak floors at this 3BR/2BA retreat on 2.44 private acres. Updated kitchen and marble baths blend comfort and style. A bright barn office and workshop offer flexible use easily converted for equestrian needs with an existing corral. A fenced dog run adds convenience. Enjoy sunrises on the expansive deck or quiet moments on a meditation deck tucked in

Scott Hayes Compass

First time on the market in nearly 50 years. )ver 2.6 acres in sought after Central Woodside minutes to Roberts, Village market and horse trails. Original 4900 sq ft ranch home with newer addition, pool and ADU. Property is suited for complete makeover or reimagine as a new building site. Horses are allowable. Close to sought after Woodside Elementary. A peaceful setting surrounded by nature,

Andrea Ivarsson Coldwell Banker Realty

Surrounded by natures beauty... on 5.4 acres on a private street yet just 3 miles from Sand Hill Road venture capital centers this home offers complete privacy, organic architecture, and spa-like amenities. Oaks and wildflower-strewn meadows create a serene setting deeply connected to the natural landscape with enchanting walking paths. Inside, warm wood finishes, soaring paneled ceilings, and

Erika Demma Compass

Known as the Craftsman Homes, coupled with the Tennis Court lot, this multi-faceted, independently accessible, two-lot combination extends across over 12 acres and currently includes two homes totaling approx. 2,850 sf (one with 1,515 sf with two bedrooms and a second with 1,335 sf with two bedrooms), a tennis court as well as a two-stall horse stable and grazing area. The numerous development

Helen Miller Compass

Known as the Olive Orchard home, combined with the contiguous Olive Hill East and West lots, this fabulous combination of three parcels totaling just over 23.5 acres, currently includes two homes, one with approx. 3,345 sf and four bedrooms and the other with 1,755 sf with three bedrooms (the Estate Manager's home), each of which present a series of upgrade or redevelopment options. The parcels

Helen Miller Compass

Known as the Oak Grove home, situated on just over 11 acres and including one home of approx. 3,635 sf with five bedrooms, a lovely rear lawn and swimming pool area and intimate views of the Western Hills. This beautifully situated lot and home, nestled near numerous oak trees, is one of the most enchanting locations on the estate. The lots development options include the possibility of either

Helen Miller Compass

The Green Gables Estate, in its entirety, is a 74 acre, spectacular, one of a kind, multi-generation oasis situated within walking distance from the Woodside Town Center. The estate is currently comprised of seven homes and 10 separate lots, featuring significant additional build out potential and may be purchased as a whole or in 6 potential lot combinations (see MLS listings for suggested lot

Helen Miller Compass

Lakeview Lodge: A Storybook Sanctuary with Iconic Views and a Surprisingly Convenient Location. Every now and then, a property comes along that feels pulled from the pages of a storybook. Lakeview Lodge is one of those rare places, loved and nurtured by its owners for 29 years for the simplest reason: its just that special. Perched above the treetops with sweeping views of Stanfords Jasper Ridge,

Ginny Kavanaugh Coldwell Banker Realty

Embrace Nature 5.19 Acre Gated Magical Woodside Retreat. Contemporary style, huge windows, soaring ceilings that reach to amazing heights, pyramid copper roofs, 10 gig network intra-structure, and skylights. Unique style/constructionset in the magical setting of a majestic Redwood grove, surrounded by Silicon Valley Views. 3 bed, 2 bath home of ~2,850 sf. The open plan has a kitchen with custom

Peter Cowperthwaite Golden Gate Sotheby's International Realty

Private retreat with stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside. Custom-built in 2004 on 1.4 acres with incredible quality and seismic integrity, this Craftsman home exudes European flair with imported Spanish tile and walnut floors, 12-foot ceilings, and fireplaces in the formal living and dining rooms. The French kitchen features

Scott Dancer Compass

Situated at the end of a quiet cul-de-sac, this exquisite Woodside property has been tastefully renovated 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

Brian Brunetti Sotheby’s International Realty

Wonderful opportunity to live in your own private forest with views of the bay! This property located in the Skyline area of Woodside offers so many opportunities. This 3 bedroom / 2 bath, 1,460 Sq. Ft. home sits among over 2 acres of land. Property consists of 4 separate parcel numbers: 075-181-100, 075-173-110, 075-173-120 & 075-183-010. Potential to remodel existing home & build 2 more with

Veronica Chaves Quintessential Real Estate Firm, Inc.

Nestled in the tranquility of the redwoods on a cul-de-sac, this amazing open and spacious 4 bedroom, 3.5 bathroom home offers 3110 sq. ft of living space with exposed beams, skylights, soaring ceilings and majestic views. All this value offered on a mostly flat 1.2 acre lot. It boasts a large primary suite, huge walk-in closet, a deck overlooking the forest and a primary bath with jetted hot

Rob Iniguez Keller Williams Thrive