All Woodside homes currently listed for sale in Woodside as of 08/23/2019 are shown below. You can change the search criteria at any time by pressing the 'Change Search' button below.
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"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 sp"
"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"
"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 tree"
"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 overhe"
"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/spor"
"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"
"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 "
"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 livin"
"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"
"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 (1,34"
"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, playho"
"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"
"Gorgeous, well constructed & newer feeling (built in 2000 / only 19-years old!) estate home on a private, gated court with a bonus of top rated west Menlo Park schools (Las Lomitas & La Entrada)! 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 s"
"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. Cur"
"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 ove"
"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-c"
"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 Ap"
"Striking Central Woodside 4 BR/3 Full and 1 Half BA mainly one-level home (approx. 3,105 sq ft) located within walking distance to Town Center shops, restaurants and acclaimed Woodside School (pre-K to 8th) in a private, pastoral setting on a quiet, sunny cul-de-sac in enviable location near entrance to Woodside Glens; Wonderful floor plan designed for entertaining includes chefs kitchen, separate living, family & dining rooms and large rear deck; Master has Jacuzzi tub, steam shower and radiant"
"Three homes on one lot. The main house (3 bedrooms/2 bathrooms) is approximately 2670 square feet. The guest house (1 bedroom/1 bath) is approximately 1100 square feet and the cottage (1 bedroom/ 1 bath) is approximately 591 square feet. All of this on approximately 2.65 acres with amazing views of the bay and the redwoods."
1975 Portola Road, Woodside CA 94062
"HUGE PRICE REDUCTION! 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 "
"A true Woodside gem, this gorgeous home boasts unobstructed views of the Pacific ocean, coastal mtn. ranges and even Mavericks surf break on a clear day, all while being in close proximity to Silicon Valley, SF, and SFO. This four bedroom, three bathroom home is updated and modern and each room is spacious and has picturesque view. The home is situated on top of a bluff and receives full sunshine. Fabulous home for entertaining & relaxing. Large open concept kitchen with modern amenities and hig"
"Country living on one of the neighborhoods largest lots, one-half acre, yet just one mile to the Woodside Village. Peaceful setting surrounded by majestic redwoods, rich wood finishes and beautiful hardwood floors. Dramatic living room with redwood framed cathedral ceiling and classic stone fireplace, formal dining area, and updated kitchen with granite slab counters and quality stainless steel appliances. 3 bedrooms each with its own bath including a separate apartment with outside entrance, li"
"Remodeled with a sophisticated country ambiance, this home offers complete privacy and abundant tranquility, yet is still within easy commuting distance to Silicon Valley or San Francisco. Natural betray envelopes the property on approximately 3.6 acres, which includes level areas for play, a spacious deck for entertaining, and a hot tub and outdoor shower for unwinding. The home is exceptionally bright and light and features a remodeled kitchen and baths, and a master suite that comprises the u"
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