All Woodside homes currently listed for sale in Woodside as of 07/19/2019 are shown below. You can change the search criteria at any time by pressing the 'Change Search' button below.
If you have any questions or you would like more information about any Woodside homes for sale or other Woodside real estate, please contact us and one of our knowledgeable Woodside REALTORS® would be pleased to assist you.
"Located in central Woodside, just over one-half mile from the Woodside Village, the remarkable Hilltop House has been masterfully restored over the years retaining the integrity of the circa 1935 chateau originally designed by Gardner Dailey (of Filoli). Presiding on 3.4 acres, surrounded by manicured lawns and lush gardens, Hilltop House is a tranquil oasis spanning more than 10,600 sq.ft. The public rooms represent the romance and artisanship of the era with an emphasis on natural light and space for display of fine art. The palatial dimensions comprise 8 bedroom suites, including a sumptuous master suite and 2 staff quarters. The kitchen and bathrooms are beautifully appointed, a porte cochere recalls the homes early heritage, and a pool and tennis court add resort-inspired amenities. With a wonderful sense of country seclusion, yet just blocks to the Woodside Village, this legendary property is a world-class destination to call home."
"Extraordinary vineyard estate on 6.4 acres located in a premium Silicon Valley location. The property features a stunning contemporary 6,000 square foot main home, a two bedroom guest house and a two room entertainment pavilion with spa facilities and a wine room. Other amenities include a clay tennis court, serene pool area, sport court, dual 3-car garages, and a vineyard with grafted aged vines. The electrical, HVAC, communications, security, and home automation systems are all of unparalleled quality. A 3-tree treehouse awaits smaller guests and puts a finishing touch on this property that can only be described as magical."
"One of the finest locations just over one-half mile to Woodside Village, renowned for restaurants where many Silicon Valley deals have been made. Grand estate on 5.78 acres with ultimate privacy and magnificent views of the western hills. Masterfully renovated over the years with timeless character. Main home, 1-bedroom guest house + quarters for a caretaker, fitness or office. Pool, spa, tennis court, basketball court, golf practice area & custom playhouse. Amazing vegetable gardens, fruit trees & rose gardens. Perfect for gala events, everyday living, or an escape from City life for a weekend getaway. Convenient to venture capital centers, tech companies, Stanford University and international airports. Less than one-half mile to acclaimed Woodside Elementary (K-8)"
* LISTED OVER 120 DAYS
* PRICE LOWERED - $29,900,000 TO $24,500,000
"One of the largest parcels available on the San Francisco Peninsula. Exceptionally rare 32 acres in Woodside Hills just minutes to Menlo Country Club and only 2 miles to Highway 280. Award-winning formal gardens by the owner of the past 67 years, a Master Gardener, surrounded by rolling grassy hills with native oaks and redwoods, orchards, and potential for cattle/horses. Circa 1933 Pennsylvania colonial 7-bedroom main home, secluded oversized pool, multi-room pool house, barn/garage with overhead 1-bedroom apartment, barbecue house, greenhouse, and gardener's workshop. Extraordinary setting of privacy with close-in convenience and easy commute to either San Francisco or Silicon Valley. Zoned RR with possibility for sub-division."
"LOCATION, ARCHITECTURE, LUXURY! Walker Warner Architects masterpiece. 4.5 acre estate on one of the premier streets in central Woodside. Comprised with a series of architecturally significant buildings connected by magnificent level grounds. A world-class destination for luxurious living as well as corporate and/or professional events. 5-bedroom main residence, 1-bedroom guest house, and cabana with Arts and Crafts style, pool, spa, professional golf practice hole and bunker, and pickleball/sport court. A short stroll through the gardens leads to the office/library/spa building, conference/meditation center (or second guest house), and striking yurt, all sanctuaries designed with Zen tranquility inside and out and spaces for gatherings on a large scale. Featured in numerous magazines and solar powered this property is located in one of the most exclusive communities midway between San Francisco and Silicon Valley. Award wining Woodside Schools."
"A Bucolic Masterpiece Perfectly Located. This splendid estate of nearly 3.93 acres (per county) sits on the most coveted street in Woodside and is walking distance to downtown Woodside. The home is every entertainers dream, and includes a recreation room, gym, and guesthouse, for a total of 4 bedrooms, 5.5 bathrooms, and a living area of 10,969 sq. ft. (per drawings). Amenities include a pool, tennis court, exquisite landscape with lush grounds, pergola, and walkways that meander along the creek through wisteria-entwined arbors. Mere moments to Huddart Park, The Horse Park at Woodside, Highway 280, and extensive network of trails for equestrians, hikers, and bikers. Children may attend excellent schools, such as Woodside Elementary (K-8) (#13 Elementary School in California) (buyer to verify eligibility)."
* LISTED OVER 120 DAYS
* PRICE LOWERED - $17,988,000 TO $13,988,000
"Over 12 acres this classic Woodside property is an equestrian lovers dream. Absolute privacy from the street and just across from miles of trails at Wunderlich Park. 17-stall barn, regulation dressage arena, plus an indoor exercise arena. Colorful rose gardens, redwood groves and heritage trees amid the equestrian facilities and open pastures. Traditional 4-bedroom Monterey Colonial home with timeless appeal. Truly a marvelous escape from the fast pace of the Peninsula. Excellent Portola Valley schools, less than 4 miles to Sand Hill Road venture capital centers, and just a short commute to Stanford University and all of Silicon Valley."
"Brilliantly situated on a private level hilltop, this family estate features uninterrupted panoramic views of the Coastal Range with the seclusion and open space that define a Woodside lifestyle. Between Silicon Valley and San Francisco, this 3 acre property offers a 4 bedroom, 5 bath custom-built Mid Century main house, a pool and a guest house surrounded by mature trees in a pastoral setting. The property is bordered to the east by a large private estate that currently has a recorded Conservation Easement prohibiting any new construction on its land. The lot is expansive enough for several equestrian options and building possibilities as well. Hike or bike into some of the Peninsula's most treasured open space preserves and still be within easy reach of lively downtown Redwood City, Palo Alto and picturesque downtown Woodside. Excellent K-8 schools even further enhance this fantastic property. It's not just a home, but a way of life that embraces an irresistible natural setting."
"Gorgeous Woodside 9 AC residential lot w/ approved plans for a thoughtfully designed 6,200 SF luxury home w/ pure and simple lines. Modern feel w/ architectural features that include weathered wood paneling, stucco, and glass outlined by dark steel beams to highlight the angular design. Open floor plan combines a sleek kitchen and roomy family, dining, and living rooms. The master suite is separated by a connecting corridor on the other side of the home for ultimate privacy. Above the main living area are two additional bedrooms w/ ensuite baths. A wine cellar, home theatre, rec room, and bedroom w/ ensuite bath are located on the lower level. 1,000 SF guest house equipped w/ kitchen, living area, bed, and bath. The home was designed around a self-contained courtyard and pool that interacts directly w/ the living spaces on the property while maintaining a quiet and unobstructed views of the surrounding hills. Featuring a 500 SF cabana and 800 SF garage/workshop. Woodside Horse Trail."
"A thoughtfully designed 7,200 SF luxury home with contemporary lines to be built on a gorgeous Woodside 7+ acre parcel scattered with large heritage oaks. The planned home is separated into two structures and connected by a glass walkway leading to an elegantly understated entry. Floor to ceiling windows reveals a self-contained courtyard surrounding the pool and Zen planting garden. The main living area is an open floor concept w/ family room, kitchen, and dining room. Designed w/ two suites on the main floor; a luxurious master and a guest/flex unit with private entrance. Located on the lower level are a second family room, three bedrooms and a home theatre. The mix of natural and structural elements, through the use of wood detailing and exposed concrete, creates expansive architectural spaces in the home's design. Property is connected to the Woodside horse trail and captures amazing views of the Santa Cruz Mountains. Option for Buyer to purchase land and plans only for $5.495M."
"This estate is constructed in the style of a well-aged authentic Italian farmhouse, yet w/all the luxuries for a 21st century lifestyle. Adding authenticity, among other things were 18 containers of materials imported directly from Italy. Beamed ceilings, hand-hewn antique doors, brick finishes & tile floors embody classic, Old World charm. The entire setting of 3.24 acres exemplifies an Italian borgo (village) with its numerous buildings...main residence (~6000 SF) , 2-bedroom guest house (1,342SF) , 1-bedroom caretaker's cottage (745 SF), fitness center (403 SF) & carport/garage (689 SF). A pool and spa, 2 pizza ovens (one indoor, one outdoor), bar-be-cue terrace, clay tennis court, bocce court & putting green invite outdoor entertaining & recreation. The main residence has 3 bedrooms, office (or 4th bedroom), customized wine cellar with tasting room, & media room. Las Lomitas Schools. Located just minutes from Highway 280 for easy commute to San Francisco or Silicon Valley."
* LISTED OVER 120 DAYS
* PRICE LOWERED - $10,900,000 TO $10,450,000
"Rarely is there a residence in the San Francisco Bay Area that is so grand yet also so eminently livable for today's lifestyle. This property offers every state of the art amenity one would expect when residing midway between San Francisco and the Silicon Valley. This just completed, two year, whole-home renovation has resulted in a property equally suited as an executive compound, a second home for international visitors, or a family residence with its close proximity to excellent schools and universities. Minutes to highway 280, the Town of Woodside and nearby Stanford University. The perfectly manicured garden, raised garden beds, infinity pool, full outdoor shower, guest house, 900 sq ft wine tasting room, level-lawn area, plus Cabernet Sauvignon vineyards are just a few of the amenities that make this orly a world-class estate in one of America's most affluent communities."
"A private oasis in central Woodside on more than 3.6 acres with gated cobblestone driveway and motor court. Innate beauty with timeless, classic elegance inside and out. The magnitude of the two-story home accommodates any lifestyle need with main- and upper-level master suites plus 4 bedrooms and 2 shared baths. Executive office with bath, mirrored gym, recreation area for movie nights at home. Five-star grounds with absolute privacy, pool, spa, tennis court, vast terrace, sweeping lawn, playhouse, and tremendous vegetable gardens for your own personal farmers market. Whether hosting gala events, enjoying the sublime privacy every day, or escaping city life for country living on the weekends, this treasured estate offers the best of California living in one of the countrys most affluent towns."
"This classic estate is located on one of the area's premier streets in the highly desirable Hidden Valley neighborhood on approximately 4.18 acres. The sprawling 5-bedroom, 5.5-bath residence spans over 5,000 square feet and offers generously proportioned rooms characterized by high ceilings, expansive windows, hardwood floors and natural stone surfaces. Outside, magnificent trees frame the grounds, ensuring a wonderful sense of seclusion. Equestrians will delight in the 8-stall stable, separate barn, paddock, training ring and proximity to trails. Tennis court, sports court, and swimming pool with adjacent dressing room with full bath and kitchen facility complete the outdoor areas. Offering an array of exciting opportunities this extraordinary property is also convenient to local shopping and dining, and excellent public and private schools; and easy access to Stanford University, venture capital centers on Sand Hill Road, and major commute routes to Silicon Valley and San Francisco."
* LISTED OVER 120 DAYS
* PRICE LOWERED - $8,900,000 TO $7,745,000
"Meticulously maintained every detail appointed to provide the perfect Mediterranean setting for Hobart Villas next family. Beautiful custom tile accents the natural wood cabinets, windows and doors throughout. A modern kitchen opens to the family room exposing full window views of the property. A formal dining room and living room with wine cellar complete this entertaining masterpiece. Three complete bedroom/bathroom suites downstairs. The upper level opens to a large master suite including oversized bedroom, walk in closet, spa inspired bathroom, two private offices plus four outdoor private patios. California living enables full enjoyment of the infinity pool, spa, outdoor kitchen, fire pit, expansive lawns, trails and gardens. Overall, 4,127sqft plus 3.27 acres within walking distance to down town Woodside."
"This recently remodeled residence awaits just beyond a double gated circular driveway, giving access to a resort-like property nestled on 1 Acre in San Mateo County. The main house is comprised of 5 beds and 4.5 baths, a spacious living room with floor to ceiling windows, a massive family room that brings in abundant sunlight via skylights in the high vaulted ceiling, a formal dining room, a wet bar, and a vast state of the art chefs kitchen. The home is installed with surround sound throughout the property and heated floors. The grand layout of this enormous plot of land consists of a heated pool, patio, private garden with a Koi pond and waterfall, childrens playground, and an updated guest house; complete with 1 bed, 1 bath, living room, kitchen, and roofed porch. Located within the Las Lomitas school district,as well as close proximity to Half Moon Bay and Palo Alto."
"Top rated west Menlo Park schools (Las Lomitas & La Entrada) are the bonus with this well constructed newer feeling (built in 2000 / only 19-years old) estate home on a private, gated court! Private flag-lot drive leads to this gorgeous 4-bedroom, 3-bathroom plus 2-half bathrooms 4,290 Sq Ft main home on 1.1.45-acres. There is a full 1-bedroom 1-bathroom guest house attached to the large pool house / cabana with another full bathroom. Also a magical Castle wine cellar building with 2-huge stone patios for entertaining. Wonderful master bedroom suite, large separate dining room, giant step-down living room with built in bar for entertaining, gourmet kitchen with eat-in area as well as a cozy separate family room. Huge back stone patio with sparkling pool and spa, built-in BBQ and bar area, outdoor arbor/trellis for relaxing. Two 2-car garages, one attached and one detached (and set up as a gym now). 1st floor guest suite as well. An estate that must be seen to be appreciated!"
"Ocean View Estate - Peaceful, rural beauty surrounds this estate property. A serene escape from city living yet still within easy commuting distance to Silicon Valley or San Francisco and just one mile from restaurants and shops. Set on almost 24 acres, enhanced by clear-day views reaching out to the Pacific Ocean, this home works equally well as a full-time residence or weekend escape from urban living. Spanning three levels, all connected by elevator, the spacious floor plan is unified with oak floors in the living areas, voluminous ceilings, & tremendous natural light with many French doors opening onto vast view terraces. There are 6 bedrooms, each with en suite bath, arranged over all three levels, including upper and lower-level master suites plus a fully equipped apartment ideal for a caretaker or extended family. This outstanding lifestyle option on the fast-paced Peninsula is a rare opportunity indeed for Silicon Valley living!"
"2005 MODERN MEDITERRANEAN MASTERPIECE - NEVER BEEN LIVED IN! - EXTREMELY RARE OPPORTUNITY to purchase, remodel, & show-off one of San Mateo County's, Very Few, Privately Owned Estates - boasting 17,000+ square feet of living area! This 4-floor, upper Woodside, 5 acre estate is ideal for: developer, contractor, investor, or owner-user. Full architectural plans offered for a current structure remodel, with additions, on this top of the line estate! Planning Dept. approval process is completed. Currently awaiting Building Department review for permit approval. The permit process, once completed, will transform the existing 2005-built home, with an unused, additional 5,769sf of unconditioned/semi-finished interior space, - into a privately gated, whopping 17,204 square foot estate. Future structures: horse stable, tennis court, or accessory building/workshop are subject to planning approval. Surrounded by redwood trees, horse trails, & open space."
"Resort like living - minutes to town!! Overlooking vistas of the western hills & wide open space, this home, situated within a rare gated community, enjoys a wonderful sense of seclusion, yet just minutes to the Woodside Village. Spanning almost 3 acres, this property epitomizes resort living with its stunning pool & spa, tennis court, pool cabana, koi pond & waterfall, & potential for equestrian facilities. Spectacular grounds include prolific fruit trees, meditative paths, & sun swept spaces from which to enjoy Woodside's ideal climate. Main residence features beautiful updates, most apparent in the striking kitchen with its rare granite counters and tremendous wraparound family room with full bar for entertaining. Offers 4 bedrooms, including a romantic master suite comprising the entire upper level & a second main-level suite ideal for guests. Adding the finishing touch are dazzling custom light fixtures, tremendous storage & significant guest parking for grand scale entertaining."
"Gorgeous 3-acre property in Central Woodside with Western Hills views! Huge potenial with this estate as it is less than 1-mile from the Downtown and Woodside School. Existing 3 bedroom 3 bathroom home (1-bedroom could be an office) as well as a 2 bedroom guest house. The former Woodside Winery building is also onsite, used for storage now. Buyer should contact the Town of Woodside regarding potential restictions due to fault lines."
"Prestigious private lane and exceptional views. Extensively renovated home has been transformed into a luxurious showcase for indoor/outdoor living. Approximately 4.7 acres with space for a potential development site and less than 2 miles to Woodside Village and award-winning Woodside School. Oriented to the striking Skyline Ridge views with almost every room opening to the grounds. Tremendous level land boasts a pool, vast lawn, and fabulous deck for outdoor living. With top-of-the-line, just-completed finishes, this country home is an excellent lifestyle option on the fast-paced Peninsula."
"This Amazing Brand New Home has Numerous Velux Skylights Throughout the Entire Property....Come Home to a Natural Tranquil Beauty. This Eco Smart Custom Home Built By Joseph Polati is Almost 4,000 Square Feet. Also Has Flat Lot Size of approximately One Acre of Land. An Open Floor Plan with Vaulted Ceilings Throughout, This Dream Home Boasts Over Sized Duel Paned Windows That Fills the Home with Natural Light and Sweeping Views of Nature at it's Finest. We Also Have an Additional Guest Studio Apartment, With a Full Complete Kitchen and Bath for Your guests or Family Member, Life Time Metal Roof over Radiant Insulation. Two Modern Linear Gas Fire Places one in the Living Room, One in the Master Bedroom Suite. Tank less Water Heater for Endless Hot Water Supply, Property is Zoned for Horses and is Close to Easily Accessible Riding Trails. Property is Landscaped with a Completely Maintenance Free Irrigation System Professionally Installed"
"Charming Woodside Rancher, this 4-bedroom 2.5 bath of 3,050 square feet of living space sits on 2 totally flat acres, & is Move-In ready! It has vaulted ceilings in the great room, a cozy fireplace, bonus room, large master bedroom with a deck, hardwood floors & newer carpet throughout. It was recently upgraded. This central location is of the prestigious Sand Hill Road & is one of the quietest locations in Woodside with no sound & it is premier location midway between San Francisco and Silicon Valley. Highly acclaimed Portola Valley Schools & close proximity to all the high-tech giants & major shopping like the Stanford Mall within 5 miles, & University Ave in Palo Alto. An excellent location to build your dream home, or development opportunity. Stanford owns the acre adjacent (see picture illustration ) & is available for a long lease directly from Stanford."
* PRICE LOWERED - $4,499,888 TO $3,999,888
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