Woodside CA Real Estate & Homes for Sale

This private compound presents close-in country living combined with a whole-home remodel that is chic & stylish. Property comprises three separate living quarters on approximately 1.4 acres, offering options for a variety of lifestyles including guests, extended family, rental income, and/or home office space. From the opaque glass front gate to the all-white interiors and espresso-hued hardwood floors, the entire ambiance of the main residence is bright and contemporary. Floor-to-ceiling windows reach the peak of the cathedral ceiling that spans the main living area, which has been entirely reconfigured for an open concept design. Remarkable in its incredible livability, flexible use, and glorious setting, this home also benefits from rare Woodside access to acclaimed Las Lomitas schools and all in one of the most sought-after towns midway between San Francisco and Silicon Valley.

One of the most unique properties in all of Woodside... a rare 7-acre lake estate in the heart of Silicon Valley. Substantially transformed for today's modern lifestyle, the property has been extensively updated by the current owner, all while retaining its original storybook charm. The main residence has been improved with new windows, a new metal roof, and new kitchens and bathrooms. Complete with serene gardens, a guest house, pool, fountains, and a horse stable and paddock. Endless possibilities for further expansion, with the only limit being the new owner's imagination. Located in one of the best locations on the San Francisco Peninsula, a short drive to famed Sand Hill Road, Stanford University, and the headquarters of world-renowned tech, bioscience, and financial companies. Welcome to "Canardia", a magical place to call home. (Square Footage Per County Records - 5,030 Sq Ft)

Located in the sought-after neighborhood of Woodside Hills, this unique property sits on an acre of land at the end of a beautiful cul-de-sac. This home has the feel of a mountainside retreat, with an expansive living room and dining room, ideal for both entertaining and daily living. Highlights include a fireplace in both the living room and family room, and gorgeous vistas of the surrounding majestic trees. Just moments from Stanford Shopping Center, downtown Redwood City, and major transportation arteries, this serene and private home integrates beautifully with the surrounding natural landscape. Walk the path around the home and you find a hidden gem - a private and secluded black bottom swimming pool. Features include two bedrooms, three bathrooms, family room, living room, dining room, kitchen, breakfast room, and massive lower level room, designed to accommodate two bedrooms. Original owners used lower level as an office and exercise room and did not need additional bedrooms.

Serene, very private and quiet 3+/- acre property, only 5 minutes to Woodside town center surrounded by oaks, redwood and manzanita trees. Set on a knoll the property backs up to Huddart Park and watershed property extending down to West Union creek and has beautiful western hill views. The 3-bedroom, 2-bath (current 3rd bedroom used as office), inviting home has rustic tones with wood burning fireplace and an abundance of natural light. Large main bedroom with walk in closet and recently updated en-suite bathroom. Light and bright, well laid out kitchen and updated second bathroom. Multiple outdoor dining and seating areas to enjoy this peaceful natural setting and views. 2 covered horse stalls with runouts, tack room, sand arena/turnout area, larger main barn/workshop, outdoor shower. Barn is aprox. 20'x34' Direct private trail access into Huddart Park, Woodside Elementary School, 10 mins to Sand Hill Road, close access to I280. Buyer to verify sq. ft.

Vieni a Casa Toscano. Unforgettable 2.3 acre Woodside property boasts expansive grounds & an impeccably maintained 3 BD/3.5 BA main house plus 2 BD/2 BA guest house. Luxury radiates through the recently constructed custom home, where broad vaulted living spaces feature authentic wood beams & skylights illuminate white oak floors. Cafe doors flex open to bring the outdoors into the open-plan living room with gas fireplace & kitchen with massive marble island, high-end appliances & floor-to-ceiling climate controlled wine storage. French doors from the stunning Primary Suite open to the backyard. From the main house, acreage reveals a professional riding ring, barn, stately pool with hot tub, vineyard and outdoor covered kitchen. Oaks and redwood trees dot the terrain alongside myriad fruit trees & roses. Here you're close to Wunderlich County Parks many hiking and biking trails amongst the redwoods, but steps to Sand Hill Road and Silicon Valley too. The perfect sanctuary to call home.

Exceptionally well built custom estate featuring complete privacy and stunning views! Sited on almost 24 acres of scenic forested land in the hills of Woodside, this spacious estate offers serene tranquility while still being in close reach of town and Silicon Valley. The generous floor plan offers approx. 9,800 square feet of living space w/ soaring ceilings in the formal entry way, a gourmet kitchen, 6 en-suite bedrooms, home office, & a fully equipped attached guest/caretaker's apartment above the 6 car garage. Breathtaking views from almost every room w/ expansive decks on every level to take in the surrounding beauty of this mountain retreat. This gated home was incredibly well engineered and built in 2004 with 6 heating and air conditioning systems, air and water filtration systems, an individual well, & a back up generator. An exceptionally private retreat property & yet it is still an easy commute to San Francisco, Palo Alto, or San Jose.

A park-like setting of more than 1/3-acre sets the stage for this 3-bedroom, 2.5-bathroom home with more than 2,200 sf of living space. This home enjoys a timeless farmhouse aesthetic with fresh, airy interiors crowned by soaring ceilings. Both the living room and family room offer a centerpiece fireplace, while the dining room adjoins the eat-in kitchen with appliances from Bosch and GE Profile. All of the bedrooms reside upstairs, highlighted by the primary suite with 2 closets and a spa-inspired bathroom. And for true indoor/outdoor living, the expansive backyard offers outstanding space with a large terrace, lawn, and views of the Western hills. Plus, this home also includes a detached shed perfect for use as an office. This neighborhood will leave you with an overwhelming sense of privacy, yet you will still be just 2.5 miles to The Village of Woodside, and a 5-minute drive to Interstate 280, with access to sought-after Woodside Elementary (buyer to verify eligibility).

Quintessential Woodside grounds of 1.1 AC encircle this expansive home that offers luxurious living space and a bright, airy ambiance. With 6 bedrooms, 5.5 bathrooms, and 4,911 square feet of space, including a guest house & gym. The main home floorplan enjoys refreshed interiors with high-end appointments, with highlights that include 4 fireplaces, large formal rooms, a chefs kitchen, office, and an inviting family room beneath a soaring cathedral ceiling. The remodeled primary suite offers a relaxing retreat with a spa-inspired bathroom, while an additional primary suite provides private space for friends & family. Peaceful grounds offer a true indoor/outdoor lifestyle with a gorgeous pool, spa, sauna & built-in grill. And though you will feel far removed from the hustle and bustle of Silicon Valley, this home is just a 5-minute drive to The Village of Woodside, convenient to Interstate 280, and offers access to highly sought-after Woodside Elementary.

A great home on 5.5+ acres with so much potential! Enjoy the stunning views from the living room, dining room, kitchen, primary bedroom, and outdoor patios! Move in, transform or potentially build new in this private setting. The two-story house has 5 spacious bedrooms, and 4.5 bathrooms. Upon entering, you are greeted by soaring ceilings and expansive windows and skylights that offer ample natural light and a view into the private backyard. The eat-in kitchen is highlighted by a huge center island, peninsula with extra seating, and large glass doors leading to the outdoor patio. The large patio is perfect for BBQs, alfresco dining or star gazing in the summer time. The main level has the master suite with dual vanities, shower ,spa stub and private balcony. The lower level has a total of 2 bedrooms and 2 full bathrooms, including an in-law unit with kitchen ,bathroom, and a separate entry. Excellent Portola Valley schools. Perfect for vacation rental. Rental income ~$18K-$20K/month

CUSTOM BUILT IN 2019 BY ALLWOOD CONSTRUCTION, THIS EXTREMELY HIGH-END MODERN PROVINCIAL FRENCH FARMHOUSE IS LOCATED IN CENTRAL WOODSIDE, A SHORT WALKING DISTANCE TO TOWN. 6 BEDROOMS + OFFICE +GYM, AND 4.5 BATHROOMS MAKES THIS THE PERFECT FAMILY HOME. INCREDIBLE CHEF'S KITCHEN OPENS TO GREAT ROOM WITH VAULTED CEILINGS, RUSTIC BEAMS AND VIEWS OF THE WESTERN HILLS. SEPARATE SPACIOUS FAMILY ROOM, GUEST ROOM, AND PRIVATE TOP FLOOR OFFICE. THIS HOME BOASTS MODERN LINES AND WALLS OF GLASS, PLUS OLD-WORLD MATERIALS! SOUGHT AFTER WOODSIDE ELEMENTARY SCHOOL, NOTHING IN WOODSIDE COMPARES TO THIS MODERN FARMHOUSE!

Situated on the cul-de-sac of Eleanor Drive on just over 1.4 acres, this mid-century modern has been exquisitely remodeled for the most discerning in design and taste. The large front pivot door opens to a light-filled home with 9-inch, wide plank European Rustic Oak floors. Recessed lights and 19 custom skylights welcome light throughout the home. The 4BR/3BA home has an ideal floorplan that includes an office, oversized large living room featuring a dramatic bay windows with built-in seating and exquisite marble wood burning fireplace. An adjacent family room opens to a large patio area and lawn for outdoor entertaining. The state of the art chef's kitchen has been designed with attention to form and function. Soft touch cabinets accent the Carrera marble with Miele appliances including an energy efficient induction cooktop for even and fast heating. The primary suite includes a large sitting area, spa like bathroom with walk-in closet. Award winning Las Lomitas School District.

Discreetly nestled at the end of a cul-de-sac in coveted Woodside lies 340 Laning, a non-traditionally shaped 1.69 acre parcel ripe for reimagining and with tons of potential. With three separate structures including a main house with attached atrium-style pool and three separate attached garages, a 1BR apartment attached to what was once used as a barn with huge standing-room attic storage space above, and a studio apartment over an oversized three car double-height garage, this unique property in the Woodside school district abuts the 280 freeway and includes a full-sized North/South tennis court, two driveways including one leading to a parcel perfect for development, and has tremendous upside potential. Take advantage of SB9 to build additional units, build a working barn/stables/corral, or plant a vineyard or orchard...the sky's the limit!

Inviting and private home in an idyllic park-like setting in Woodside Hills. Perfectly sited on one+/- acre with views of the western hills, this easy and comfortable home offers 5 bedrooms, 3.5 baths, a spacious cook's kitchen and separate living, family and dining rooms all oriented to the outdoors. The grounds are captivating, soothing, and fun with something for everyone. Lush lawns, sparkling pool, custom outdoor kitchen, an outdoor fireplace, covered pavilion, dining and entertaining areas, an orchard, a swing set, a bocce ball court and more....

Just 10 minutes from town! "CLOUDVIEW" is absolutely stunning and will impress the most discerning buyer. 3 outbuildings + Main House. Modern art by known artists included throughout the property. Renovated by its current owners whom are an art curator and a home builder. Botanical garden spans the entire property. Dreamlike views. The property flanks the national park and offers permanent protected views and privacy . Beautiful white and blue kitchen remodeled in a current and utilitarian design that opens to an ample dining room and veranda seating with views surrounding. 3rd bedroom is being used as a magazine ready formal living room. Downstairs there is a large & beautiful bedroom with large windows on each side that showcase the botanical garden and view. In addition there is a second bedroom, laundry room, sitting or office area, and second bathroom.Outside there is an outdoor living room/gazebo for outdoor entertaining.

First time on the market in over 4 decades, this gated treasure is situated on a private street on just over 2 acres. Surrounded by nature, this home is a one-of-a-kind retreat. The fountains and koi pond set a stage upon entry that is both calm and comforting. Dramatic large wood beams and a high ceiling welcome you into the main great room. Windows highlight the natural surroundings from almost all of the rooms. The main residence contains 4 bedrooms and 2.5 bathrooms. Adjacent to the garage is a 2-bedroom guest house with a living room and kitchen. There is an additional Studio under the Primary bedroom with a separate entrance. There are multiple structures that all contain living areas. If tranquility and nature are important, this healing retreat is something you must come and experience.

This exceptional hilltop residence features dramatic bay views from Mt. Diablo to the coastal mountain range. The Hamptons-inspired shingle home has the ambiance of a resort retreat and the privacy that comes with being adjacent to 5000+ acres of Open Space yet minutes from the heart of Silicon Valley, A giant office suite, complete with lounge, meeting area and private deck is perfect for work from home with high speed internet access supplied by Etheric Networks. A separate library, professional gymnasium, and acres of land to run and play make this a true sanctuary for all ages.. There are 5 bedrooms and 4.5 bathrooms including a stunning master wing with a private master deck. The outdoor spaces include a pool and patio as well as 4000~ square feet of ipe deck, covered porch with fireplace, outdoor kitchen, and lovely native landscaping. Starwood is a gated private road. The end of road privacy is further enhanced by private trail access from your front door to Open Space.

Woodside Home on 1.1 Private Acres with Outstanding Potential. Located at the very end of a long lane, this property has complete privacy from the main street, is just 4 blocks from Woodside town center, and has access to acclaimed Woodside Elementary School (K-8). The setting is quintessential country with a vast open meadow at the front and extending gently sloping terrain toward the rear, all dotted with beautiful trees. The 2-bedroom, 1-bath home features quality updates throughout and is a lovely spot to move in and enjoy today. Opportunity also prevails to remodel and expand or to build new; the adjoining 1-acre parcel, also for sale, increases the options for estate living in a superb location.

Perfect Woodside Home & Barn on One Level Acre with STUNNING WESTERN HILL VIEWS! Set almost at the end of a long, private lane for complete privacy from the street, this home feels miles away from everything, yet is just 4 blocks from Woodside town center. An enchanting 2-bedroom, 2-bath country home and equestrian facilities span the one-acre lot, which is fully level and has views out to the western hills offering all kinds of possibilities. Enjoy the property today or while planning for building an entirely new home for the future. The adjoining 1.1-acre lot, at the end of the lane, is also available for sale providing even more options at this exceptional location. Adding the finishing touch, this property has access to acclaimed Woodside Elementary School (K-8).

One of Americas grandest estates, the Green Gables Estate is a fabulous combination of mans and natures best, including its exquisitely scaled main residence, world class gardens, six additional homes, a stunning 100+ yard Roman Pool, three swimming pools, a beautiful stone tea house, a large spring-fed reservoir (sustaining much of the estates irrigation needs) and bountiful vegetable and flower gardens. The estate also offers opportunities to create new residential structures, develop vineyards, add an equestrian center or expansive orchards. With its two private roads, wooded trails, and endless tranquility, this incredible estate is the ultimate family compound or inspiring corporate retreat. With its seven homes situated on 74 private acres, featuring breathtaking panoramic views of the Western Hills, it is remarkably situated in the heart of Silicon Valley and is blessed with an idyllic climate as well as location; San Francisco international airport is just 20 minutes away.

Custom-built w/hand-crafted quality,exceptional attention to detail. Spanish Colonial architecture appointed w/hand-selected materials incl tiles,counters, flooring, columns, ironwork, custom-finished walls. Primary suite incl fitted walk-in closet, custom cabinets, stacked W&D, fireplace, charming office/sitting room+very wide terrace w/awning. 2 BR+ 2 BA +powder rm on main level. Veranda w/garden views. Basement w/wet bar, TV area, sleeping/sitting /game area, gym (w/glass doors-wall),laundry room,full bath + 2 lg. store-rooms. Amazing custom-designed garage interior includes heat/air-cond, cabinets all around,custom lighting+attached cottage/office w/fireplace,wet bar, full bath, French doors. Landscape incl citrus trees, lg wildlife resistant garden area, parking court, sitting areas, patio off kitchen. SOLAR + 2 back-up generators. See to appreciate. (Size shown is all insulated / climate conditioned space - house,garage, cottage.). For privacy-images of some rooms withheld.

Enchanting Creekside acreage with 3 bed 2 bath ranch style home. Huge sun-filled deck overlooks the creek and offers an incredible outdoor experience. Very private yet easily accessible. Large meadow amongst the redwoods has potential for additional structure. The open concept kitchen/dining/family room combo with large stone fireplace is an inviting gathering space and features large glass doors leading to the deck door an indoor/outdoor living experience. Separate living room. Master with private bath. Generac whole house generator. Hot-tub on deck overlooking creek. The setting 3+ acre setting is stunning! An inviting combination of majestic heritage redwoods, open meadow space, and lovely trails and almost 900' of creek frontage. This property was built in 1982 by owners for themselves and has never previously been on the market.

This four bedroom, 3 1/2 bath, remodeled, single level home features an open floorplan with a 24 foot slider to the back patio for entertaining. The open kitchen and great room features a large island with a gas range. Thoughtful details include abundant storage under cabinet lighting for evenings and even a smart refrigerator. Three bedrooms, one en suite, are clustered at one end of the home, and a primary suite with a dressing room and luxurious, spa like bath with soaking tub and spacious open shower sit at the other end. A slider to the back yard completes this sanctuary. The large lot offers three yard areas plus a large driveway with plenty of parking. The side yard to the left of the house has direct access to the driveway and parking area, and is a great potential ADU site. A spacious paving stone patio area off the great room is a great spot for entertaining, and a future outdoor kitchen. Finally the spacious back yard features a large grassy area and potential pool site.

Panoramic views and inspiring design are just the start of what makes this 4,200 sq. ft. Woodside home so exceptional. Enter the breathtaking 5-acre property from a long private driveway toward this grand residence. The elegant two-story entry foyer is an attention-grabber and opens to the formal dining room where large windows frame the stunning view that stretches all the way to the San Mateo bridge. The expansive main level also features a large chef's kitchen, formal dining room, family room, two half baths, and a separate office. Up the open staircase, you'll find four ensuite bedrooms, including a primary suite w/fireplace, sitting area, private balcony, and massive walk-in closet. The 3-car garage, two EV charging outlets, brand new roof, and quality craftsmanship offer modern comfort and convenience. This coveted location is a big draw for families of Woodside Elementary!

This estate (known as "Hilltop House") is a masterful combination of timeless French architecture and luxurious updates for 21st century living. Spanning ~3.31 acres, the setting is quintessential Woodside set far back from the street with added layers of privacy from redwood groves and a vast meadow adjoining a conservation easement with unobstructed views. The lower and upper level have been freshly painted. This classically appointed home has hardwood floors, refined millwork, grand formal rooms complimented by a parlor, entertainment bar, library and chef's kitchen. Personal quarters are many with 7-bedrooms, including a multi-room primary suite and extended family quarters with full kitchen. The impressive grounds include a pool, tennis court, and sun-swept lawns ready to host family or philanthropic events. Located in the heart of central Woodside just minutes to Stanford, Silicon Valley and 2 international airports. Woodside Elementary

This boutique building offers entry at ground level! This single level home is the comfortable lifestyle you're looking for! Step inside the open layout where numerous windows frame breathtaking canyon and ocean panoramas while filling nearly every corner w abundant natural light. High vaulted ceilings w exposed beams tower over the well-sized living room that invites you to curl up in front of the fire during cooler seasons. Taking inspiration from its natural surroundings, the interior displays gorgeous wood finishes. Ultra-wide-plank flooring in the dining area and 4-seat bar anchored by striking reclaimed columns. While the 2nd bdr comes w a multifunctional loft, the primary suite has a fireplace. Other noteworthy features include a large laundry room w tons of extra storage complemented by a butcher block tabletop and water is included in the HOA. Highly acclaimed Kings Mountain Elementary school is mere moments away. 9.8 miles to Hwy 280 6.4 miles to the Town of Woodside