Woodside Real Estate, Homes and Condos for sale

All Woodside homes currently listed for sale in Woodside as of 06/27/2017 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.


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$48,800,000
1550 Portola Road, Woodside CA 94062
5
BEDS
8
BATHS
6,305
SQFT
$7,740
$/SQFT
7.02
ACRES
1915
BUILT
"Welcome to Canardia, one of the most enchanting properties in all of Lower Woodside. This storybook property, originally belonging to prominent socialite Adelade Kirkbride, boasts 7+ majestic acres of lush landscaping and serene gardens, including horse stables and its own private lake. The main residence includes 5BR and 7.5BA with over 6,000 sq. ft. of living space, including a gourmet chef's kitchen, game room, and large master bedroom wing. An entertainer's dream house, with pool, pool house, fire pits, outdoor kitchen, gardens, and more. A premiere horse property, with stables and box stalls, zoned for 14+ horses. Minutes away from both Downtown Woodside and the Rosewood Sand Hill, the property is perfectly located in the middle of the SF Peninsula, between San Francisco and San Jose. It sits in close to proximity to San Francisco International Airport an San Jose International Airport, and companies Apple, Google, Facebook, Sand Hill Road VC firms and Stanford University."
* NEW LISTING 
$39,500,000
309 Manuella Avenue, Woodside CA 94062
4
BEDS
6
BATHS
8,082
SQFT
$4,887
$/SQFT
5.78
ACRES
1928
BUILT
"Deemed to be one of the absolute best settings in all of Woodside; a spectacular estate on almost 6 acres of mostly level land with breathtaking views of the western hills. The home, built in 1928, presents a masterful renovation with grand main residence, guest house, plus quarters for caretaker, fitness studio, or office - a total of over 10,000 square feet. Magnificent grounds for resort living with pool, spa, tennis court, basketball court, golf practice area, and custom playhouse. Tremendous vegetable gardens, fruit trees, rose garden. A close-in country home perfect for Silicon Valley or San Francisco commutes."
* LISTED OVER 120 DAYS 
$25,495,000
140 Winding Way, Woodside CA 94062
5
BEDS
7
BATHS
11,055
SQFT
$2,306
$/SQFT
3.64
ACRES
2012
BUILT
"Built just 5 years ago, this is quintessential Woodside living â? spectacular western hill views, luxurious appointments, and ultimate privacy on 3.6 pristine sun-filled acres in central Woodside. Detailed craftsmanship is integrated at every turn with no expense spared for finishing touches. Behind the scenes, a commitment to LEED standards for sustainable design and environmental stewardship is a hallmark of the property. The result of this thoughtfully crafted Woodside estate is a warm and inviting escape midway between the Silicon Valley and San Francisco. This bucolic property includes: a 2 bedroom guest/pool house, studio guest house with bath, garages for 5 cars, pool, spa, custom playhouse and gorgeous landscaped grounds with vast lawn level lawn areas for outdoor entertaining. Award winning Woodside School. All of this, plus a location on one of Woodside's most sought after streets."
$24,995,000
45 Roberta Drive, Woodside CA 94062
5
BEDS
7
BATHS
12,500
SQFT
$2,000
$/SQFT
4.08
ACRES
2017
BUILT
"Located on one of central Woodside's most exclusive private roads, this stunning newly constructed country estate is framed by over 4 acres of lush landscaping, heritage oaks and a picturesque olive grove. State of the art fully automated 3 level residence features 5 br plus (6th or) separate office (all en-suite), gourmet kitchen and separate back kitchen, elevator, entertainment room and home theatre, 2000+ bottle temperature-controlled wine room and heated exterior living room overlooking the pool and spa in an expansive private park setting. Two garages (6 car) with ample off-street parking, plus 3 stall barn, large flat grassed play area and spacious 2 br, 2 ba guest cottage accessible by second gated driveway. Custom designed to enhance family life with relaxed sophistication, this unique property is simultaneously equipped for large scale entertaining, combining elegance and comfort in quintessential Woodside style."
$20,000,000
450 Mountain Home Road, Woodside CA 94062
6
BEDS
8
BATHS
10,326
SQFT
$1,937
$/SQFT
3.00
ACRES
2005
BUILT
"One of Woodside's finest properties with expansive views of the western hills. French farmhouse completed in 2005 on 3 beautifully landscaped acres featured in Garden Design Magazine and the esteemed American Garden Conservancy's California garden tours. Towering ceilings, modern custom lighting, hardwood floors, and Venetian plaster walls. 6-bedroom main residence and self-sufficient 2-bedroom guesthouse, plus barn currently used as an art studio. Library, playroom, theatre, gym, and wine cellar. Magnificent country setting has stonewall fountains, tucked away lap pool and spa, numerous terraces with fireplace, fire pit, and barbecue center, custom chicken coop, vegetable garden, roses, and fruit trees. Well for irrigation. Acclaimed Woodside School. The best of California living on Woodside's most prestigious scenic corridor."
* PRICE LOWERED - $24,500,000 TO $20,000,000 
$17,850,000
700 Kings Mountain Road, Woodside CA 94062
4
BEDS
6
BATHS
12,000
SQFT
$1,488
$/SQFT
3.07
ACRES
1988
BUILT
"This Estate boasts an award winning park like setting adjacent to the 1,000 acre Huddart Park, an expansive motor court, awe inspiring arch of showy, mature flowering plum trees, including a 100 ft lap pool with fountains and gazebo, w/majestic stately Oaks and Redwood trees, +/- 1,200 sf carriage house and +/- 1,000 sf Single Level Guest House (please see aerial and home interior video)."
$14,995,000
155 Kings Mountain Road, Woodside CA 94062
5
BEDS
5
BATHS
10,000
SQFT
$1,500
$/SQFT
5.00
ACRES
1985
BUILT
"Five level sun filled acres with magnificent landscaping in Central Woodside. Minutes to town and highly acclaimed Woodside School. Renovated and expanded this 5 acre property boasts sunshine all day. Beautiful pool, outdoor kitchen, 1-bedroom guest house, 8-stall barn, large recreation area with full bar and full bath. Amazing horse facilities, 3-car garage with finished space below. Tennis court, orchards, children's playground, batting cage. Park like setting in a prime location. Gourmet kitchen and a separate caterer's kitchen make this a perfect home for entertaining. Close to Stanford, Silicon Valley and San Francisco. Too many details to mention, this is a must see property!"
$14,995,000
1250 Canada Road, Woodside CA 94062
4
BEDS
5
BATHS
8,250
SQFT
$1,818
$/SQFT
4.93
ACRES
2000
BUILT
"Once in a lifetime opportunity to own a postmodern masterpiece. Designed by Ettore Sottsass, founder of the Memphis Group, for David Kelley, founder of IDEO and the Stanford Design School. A home built to challenge your sense of convention while still providing an intimate and functional dwelling. On almost 5 acres, the property includes a working equestrian center complete with stables, tack room, birthing shed, barn, riding ring and turnouts. Excellent, quiet Woodside location, set back off road yet walking distance to town."
$13,900,000
4105 Woodside Road, Woodside CA 94062
4
BEDS
4
BATHS
4,580
SQFT
$3,035
$/SQFT
12.05
ACRES
1979
BUILT
"This classic Woodside property is an equestrian lover's dream. Over 12 acres with 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."
* LISTED OVER 120 DAYS 
$12,395,000
835 La Honda Road, Woodside CA 94062
4
BEDS
4
BATHS
7,274
SQFT
$1,704
$/SQFT
7.70
ACRES
1958
BUILT
"Escape the pace of Silicon Valley to almost 8 acres yet less than 10 minutes to Highway 280. Easy commute to Google, FB, Apple, venture cap row or San Francisco tech centers. Architecturally significant and completely renovated magical retreat. San Francisco Bay views, Pinot Noir vineyard, pool, tennis, guest house, pool house, fitness studio. Fabulous for entertaining with lots of room for parking. Everything you need is right here. One-of-a-kind luxury living midway between San Francisco and Silicon Valley. Excellent schools."
$11,995,000
307 Olive Hill Lane, Woodside CA 94062
6
BEDS
5
BATHS
7,080
SQFT
$1,694
$/SQFT
3.08
ACRES
1977
BUILT
"This exceptional Central Woodside property enjoys the utmost in privacy on just over three sun-swept acres at the end of a private lane with sweeping views of the western hills. From every room, French doors open to private courtyards, balconies, or terraces- all overlooking the glorious gardens and western views and surrounding countryside. The grounds are an idyllic setting for outdoor living with a pool, a vast main terrace, sunken spa and pathways that meander through the property. This outstanding retreat set midway between Silicon Valley and San Francisco, is truly unique and has access to acclaimed Woodside School!"
* NEW LISTING 
$8,788,000
17900 Skyline Boulevard, Woodside CA 94062
6
BEDS
8
BATHS
9,800
SQFT
$897
$/SQFT
23.84
ACRES
2004
BUILT
"Look no further, this large custom home has it all. Behind the private gated entrance and down the driveway, come experience over 23-acres of tranquility, redwoods and privacy with this large custom home built by the current owner in 2004. There are soaring 22-foot ceilings upon entering in the grand foyer. There is a large formal living room, dining room, gourmet kitchen with stainless steel appliances, granite counters, double ovens and tranquil views from every window. There is an open office and room used as a gym that completes the main floor. The floorpan is very light and bright and open. There are 3 bedrooms en-suite on the second floor with spectacular Southern views including the ocean on clear days! The bottom floor features a guest suite, workshop and mud-room. There are stairway and elevator access on all three levels. There is a private guest suite above the spacious 6-car attached garage."
* LISTED OVER 120 DAYS 
$8,599,900
280 Family Farm Road, Woodside CA 94062
4
BEDS
5
BATHS
5,765
SQFT
$1,492
$/SQFT
6.02
ACRES
1922
BUILT
"Incredible hilltop views of Western Hills on one side and Jasper Ridge Preserve on the other in this one-of-a-kind centrally-located private retreat surprisingly close to it all! Only minutes from I-280 freeway access, this unique compound sits atop a 6.02-acre quiet, rolling property and comprises approx. 5,765 sq ft of living space, including an updated 4,680 sf two-story 4 BR/4.5 BA main home, two 1 BR guesthouses (approx. 565 sf & 460 sf), a pool, spa & cabana, a 3-car garage and 2-car carport. In award-winning Portola Valley School District, near to both central Woodside and Portola Valley restaurants and shopping and just up the road from Stanford University."
$7,995,000
618 Manzanita Way, Woodside CA 94062
4
BEDS
4
BATHS
5,730
SQFT
$1,395
$/SQFT
2.67
ACRES
1987
BUILT
"This exceptional property has it all, a beautifully remodeled home, equestrian facilities, plus a private pool and spa, all on more than 2.6 magnificent landscaped acres. Light, bright and airy with attention to detail. This property is perfect for indoor outdoor entertaining. Located on one of Woodside's most sought after streets, this beautiful estate offers the private and rural feel of Woodside, yet is close to the town center. Set between San Francisco and Silicon Valley, Woodside is known for its friendly small-town community, miles of shaded hiking and riding trails, and quiet country lanes that bikers dream about. Highly Acclaimed Portola Valley Schools."
* PRICE LOWERED - $8,695,000 TO $7,995,000 
$7,488,000
290 Winding Way, Woodside CA 94062
5
BEDS
5
BATHS
4,830
SQFT
$1,550
$/SQFT
1.25
ACRES
1926
BUILT
"Privacy, Comfort, and Prestige. Gated, beautifully manicured grounds of approx. 1.25 acres (per county) surround this alluring yet private 5 bedroom, 4.5 bath residence of approx. 4,800 sq. ft. (per county). Built in the 1920s, this elegantly updated manor effortlessly blends fine craftsmanship with luxurious elements, and includes a potential home theater, a wine cellar with a tasting room, and a main-level bedroom suite easily convertible to a pool lounge. A romantic rose garden and a pool with a spa augment the pristine grounds. Located off prestigious Mountain Home Road, this garden estate balances peaceful seclusion with close proximity to shopping, dining, and commuter routes, plus highly desired Woodside Elementary (API 965) (buyer to verify eligibility)."
$6,995,000
170 Josselyn Lane, Woodside CA 94062
3
BEDS
6
BATHS
4,636
SQFT
$1,509
$/SQFT
3.38
ACRES
1999
BUILT
"A long, gated driveway at the end of a private lane heightens the sense of seclusion that envelops this country residence and guest house. Custom built in 1999, the 3.38-acre property pays tribute to the classic beauty of Woodside with an ambiance that is decidedly country elegance. Stunning black oak floors, rustic wood beams and subtle finishes define the warm and inviting venues for gatherings. At the heart of it all is a great room with chef's kitchen, while the bedrooms are privately arranged in their own wing. Every room has direct access to the grounds where wraparound decks overlook the western hills and a sun-swept rear yard integrates a pool that blends in harmony with the natural setting. All around, heritage oaks, bountiful rose gardens provide color and fragrance, and numerous trees are ready to spring forth in full bloom. This quintessential Woodside setting is located on one of its most sought-after streets, just one mile to acclaimed Woodside School and the Village."
* PRICE LOWERED - $7,250,000 TO $6,995,000 
$6,995,000
100 Phillip Road, Woodside CA 94062
4
BEDS
4
BATHS
4,520
SQFT
$1,548
$/SQFT
3.14
ACRES
1997
BUILT
"A masterpiece of Craftsman architecture, this home was custom built by the current owners on a magnificent property of more than 3 acres in central Woodside. The kitchen is a chef's dream with a signature La Cornue range and the adjoining family room is certain to be the home's central gathering place, while a separate recreation room is perfect for poolside entertaining. A studio apartment over the garage provides added accommodations for guests or an au pair. Equally stunning are the level grounds with sun-swept venues that invite outdoor living - a pool and spa, custom sculpted fire pit, and even an authentic pizza oven. Vast expanses of level lawn are perfect for play, an olive grove produces ~5 gallons of oil, & the bonded vineyard boasts ~150 cases of fine Pinot Noir a year, found in local markets and restaurants. Remarkable beauty & incredible livability, all in a premier location midway between San Francisco and Silicon Valley. Highly Acclaimed Portola Valley Schools"
$6,399,000
133 Old La Honda Road, Woodside CA 94062
4
BEDS
3
BATHS
4,505
SQFT
$1,420
$/SQFT
6.39
ACRES
1982
BUILT
"Modern design in a country setting with sleek architectural lines, incredible San Francisco Bay views, and captivating setting of more than 6 acres. Sophisticated, open floor plan with views from every room, towering ceilings, and amazing natural light. Flexible floor plan with up to 4 bedrooms and 3 full baths. Gorgeous grounds with lavender, tulips, and parterre garden, all inspired by gardens in the south of France. Excellent equestrian property with direct trail access, a gardener's delight for your own farmer's market, and potential vineyard site. Just 5 minutes to Highway 280 and venture capital centers. Excellent Portola Valley schools."
$5,975,000
661 Kings Mountain Road, Woodside CA 94062
3
BEDS
4
BATHS
4,994
SQFT
$1,196
$/SQFT
1.52
ACRES
1999
BUILT
"This private, gated residence takes place in a stunning park-like setting on over 1.5 acres in Woodside.  Inside and out the craftsmanship and design create the perfect confluence of high style and timeless architecture. The multi-level floor plan is traditional with all bedrooms upstairs and living areas on the two floors below. This creates the perfect balance between private and entertaining space.  A lofty arched ceiling entry and expansive windows bring in tons of natural light which highlights dark ebony stained walnut floors throughout. Three bedrooms, three and a half baths, a nursery, plus a versatile lower level guest suite / media room accommodates any homeowner's needs, be it a movie night or a place for extended family to stay. Equally impressive are the fully-landscaped grounds which include indoor / outdoor living, a flagstone entertaining area, salt water pool and spa, as well as a lower level lawn area for play."
$5,750,000
340 Jane Drive, Woodside CA 94062
6
BEDS
6
BATHS
6,465
SQFT
$889
$/SQFT
3.14
ACRES
1987
BUILT
"This updated, expansive 6 BR/5.5 BA approx. 6,465 sq ft home on 3.14+ acres offers an enviable blend of privacy, proximity to open space and elegant living. Situated at the end of a private and gated cul-de-sac, this property is minutes from Town Center shopping, restaurants, 280 freeway access and the acclaimed Woodside School (preK-8th). The home features two offices (one is possible 6th bedroom) and large common areas which include separate living, dining and dual family rooms each connected to a light-filled kitchen & breakfast room. Set up for entertaining, a large outside deck & patio with built-in BBQ overlook a luxurious custom pool & spa with views of the adjacent open space hills."
$5,488,000
5 Cedar Lane, Woodside CA 94062
5
BEDS
5
BATHS
3,900
SQFT
$1,407
$/SQFT
1.01
ACRES
2001
BUILT
"Timeless Allure in Famed Location. Located off exclusive Mountain Home Road, this custom 4 bedroom, 4 bath residence of 3,900 sq. ft. (per county) and 1 bedroom, 1 bath guesthouse blend classic finishes, modern luxury, and vibrant gardens of over an acre (per county) within a coveted, highly walkable cul-de-sac. Though built in the 21st century, the home offers stained glass, exposed-beam ceilings, and reclaimed fixtures, creating an ambience of timeless charm. Multiple French doors open to enticing gardens with footpaths and terraces. From the natural privacy of these seemingly secluded grounds, stroll to shopping, dining, and top-ranking Woodside School (API 965), and quickly reach scenic open spaces and Highway 280 (buyer to verify eligibility)."
$4,998,000
22 Starwood Drive, Woodside CA 94062
5
BEDS
5
BATHS
7,300
SQFT
$685
$/SQFT
5.00
ACRES
1984
BUILT
"Hamptons transitional in Woodside! 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. Minutes from the heart of the Peninsula and Silicon Valley, this sprawling 7300 square foot home features generous living and entertaining spaces. Comprehensively renovated in 2016, this home has meticulous craftsmanship and beautiful details through-out with fine woodwork, and exceptional use of stone. 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. The end of road privacy is further enhanced by the private trail access from your front door to Open Space."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $5,498,000 TO $4,998,000 
$4,650,000
662 Glen Way, Woodside CA 94062
3
BEDS
6
BATHS
4,430
SQFT
$1,050
$/SQFT
1.28
ACRES
2008
BUILT
"Gorgeous home renovated in 2011 with classic, timeless appeal and luxurious appointments. Gentle knoll-top position on approx. 1.28 acres with sweeping views across the Peninsula, Windy Hill, and Huddart Park. Two-stories with hand-hewn hickory floors, grand entry, and formal rooms plus tremendous kitchen and family room that opens to the rear grounds, pool and views. 5 bedrooms (1 used as den, 1 used fitness rm), each with en suite bath, including upstairs master suite and adjacent suite ideal for a fitness center or nursery. Large loft for office or study needs. Classic Woodside with space for horses, open fields, and abundant privacy. Acclaimed Woodside School."
$3,999,999
12424 Skyline Boulevard, Woodside CA 94062
4
BEDS
4
BATHS
3,650
SQFT
$1,096
$/SQFT
5.00
ACRES
1960
BUILT
"Stunning ocean views abound from this gorgeous home set on 5 acres and surrounded by miles of open space. A spacious, open floorplan showcases the view and the home features hardwood floors throughout with a large great room that opens to a huge deck and stone patio area with an outdoor kitchen. Additionally, there is an eat in chef's kitchen with a suite of top of the line appliances, formal dining room, gorgeous step down living room, beautiful master suite, separate office or media room, 3 car attached garage and separate 4 car garage for a total of 7 cars, tennis court and beautifully landscaped grounds with flat, usable land. A one of a kind property that does not come on the market often"
* LISTED OVER 120 DAYS 
 
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