Woodside CA Real Estate & Homes for Sale

Tucked away in tranquility, this delightfully inviting Woodside Hills jewel offers the discerning buyer an entertaining oasis and 2 homes - a rare opportunity indeed! The 2nd home is stunningly completed introducing a "sneak peek" of how the main residence will shine after just a little sweat equity. Situated to take advantage of summer sun fun from morning to night, all will enjoy the expansive backyard and exquisitely detailed outdoor amenities including large pool, fully equipped outdoor kitchen and seating area protected under an expansive lanai, fire pit, 4 hole putting green and 200'+ walking path. Main residence boasts a 700sqft exercise/game room, dedicated office, soothing master suite with walk-in closet, master bath boasting a 5'x 6' beach entry shower with 3 shower heads and opening skylight. Completed in 2012 the 2nd home is a miniature version exquisitely appoint with many of the same amenities including heated floors. Main residence partially remodeled. Sold as-is.

Classic French country ambiance with extensive remodeling. Ivy covered walls, ornamental iron railings, and expansive brick terraces with pool. A standing seam copper roof complements a signature conservatory by renowned Amdega of England. Interior plaster walls, hand-hewn hardwood floors, and 4 antique stone fireplaces. Formal living and dining rooms, fabulous kitchen and family room combination, dedicated office, and media room with projector/cinema screen. Main- & upper-level primary suites, the latter of which is served by a lavish remodeled bath with steam shower and jetted tub. Formal parterre garden, 2-stall barn, and manicured trails, which continue on an adjacent 3.62-acre property (also for sale at 3600 Partition Road; both properties back up to 624 acres of Teague Hill Preserve, permanently conserved land) for the ultimate private meditation & fitness venue. Architectural character, extraordinary setting, and close-in location less than one mile to Woodside Elementary (K-8).

Country charm with expansive views of the western hills. Open living/dining area with large picture windows providing wonderful southern views, wood-burning fireplace, old-growth vertical grain fir floors, and French doors to the patio area for outdoor entertaining. Gourmet kitchen with breakfast bar, custom knotty alder cabinets, marble counters, Sub-Zero refrigerator, Bosch dishwasher, Garland gas range, and built-in office area with lots of storage and a desk that looks out onto the oak trees. Downstairs bedroom with updated adjacent bath. Upstairs family room has vaulted ceilings and skylights. Master bedroom has large windows looking into the oaks, walk-in closet, and a secondary closet. The third bedroom has two closets, one large enough to be used as a playroom/study. Plus an additional bonus room that is currently being used as a nursery. Detached garage. Space for a horse or possibly your own vineyard. Convenient location and Award-winning Woodside Elementary school.

Tucked away from the street and framed by a wonderful canopy of trees, this home exudes a classic and timeless farmhouse ambiance with front balcony and covered porch. The entire home is light and bright with signature arched windows or transoms, and hardwood floors extend throughout the main level. The traditional two-story floor plan is arranged with formal venues plus the kitchen and family room with built-in office on the ground floor. Upstairs, there are 3 bedrooms, two with direct access to a shared bath, plus the primary bedroom with front balcony and en suite bath. Outside, there is plenty of room for play, entertaining, and gardening on just over one-third acre. Adding to the appeal is the homes close-in convenience just 2.5 miles from Woodside town center and with access to acclaimed Woodside Elementary School.

Just two miles from the Woodside Village, this magical setting begins with a wine country-style garden entrance and continues out to sweeping western hill views and amazing privacy. A whole-home transformation created a luxurious indoor-outdoor space with designer finishes and an exceptionally bright and light ambiance. The floor plan is arranged with two distinct lower-level wings for the homes 4 bedrooms, connected by a vast rear terrace with large spa, garden paths, and even a chicken coop on the lower grounds. The main living areas, catered by a stunning all-white gourmet kitchen, open to a covered deck for ultimate view enjoyment. A lower-level family room plus an office on the main level round out the accommodations. There are 3.5 baths, each beautifully appointed in a selection of Carrara marble and glass tiles. Access to acclaimed Woodside Elementary School and proximity to miles of hiking trails add the finishing touch to this exceptional home.

5+ acres in prime central Woodside, this estate offers exceptional serenity & privacy, minutes to town center. The main residence has been renovated w/extraordinary 5-star interiors. Every detail, light fixture & surface is remarkable-all radiating sophisticated elegance & absolute designer style. The two-story floor plan comprises 5 bedrooms, including a main-level primary suite, 2 executive offices, entertainment lounge, main & upper-level family/media rooms, plus 5 full baths & 2 half-baths. The accommodations continue with a detached 1 bedroom guest house & one-bedroom apartment, each with full kitchen. This home has been meticulously designed around the beauty of the outdoors & the brilliant sunlight that envelopes. A pool blends w/the ground's natural beauty, which extend to vast level lawn, a fireplace terrace adjoining a full outdoor kitchen & pool house. Extraordinary setting with finishes & amenities that are second-to-none. Truly an exceptional home & perfect location.

ESCAPE TO THIS DREAMY TOTALLY REMODELED SANCTUARY IMMERSED IN A MAJESTIC REDWOOD FOREST. GATED FOR ADDL PRIVACY, THIS HOME ON KINGS MOUNTAIN HAS BEEN COMPLETELY UPDATED TO COMBINE MODERN FLAIR W/ THE PEACE & CHARM OF ITS WOODLAND ENVIRONMENT. GATHERING AREAS PAVED W/ HARDWOOD SHARE AN OPEN LAYOUT TOPPED BY CATHEDRAL CEILINGS. MULTIPLE SKYLIGHTS & OVERSIZED WINDOWS GIVE THE SENSE OF LIVING IN A LUXURY TREEHOUSE. A CENTRAL DECK W/ SURROUND SOUND IS PERFECT FOR INDOOR-OUTDOOR LEISURE. GRANITE COUNTERTOPS SURROUND A REMODELED KITCHEN W/ BAR SEATING, S/S APPLIANCES. TWO BEDROOMS ARE EN-SUITE, INCLUDING A SPRAWLING MASTER W/ SPA-LIKE BATH. ENJOY LUXURY BATHS, A LAUNDRY CENTER, GARAGE W/ STORAGE ROOM, LOW-MAINTENANCE LANDSCAPING + CENTRAL AC FOR THOSE HOT SUMMER NIGHTS. HIKE ALONG NEIGHBORING TRAILS, EXPLORE SCENIC NATURE PRESERVES, OR VISIT GETAWAYS LIKE ALICES RESTAURANT & THE MTN HOUSE; YOULL BE MIDWAY BETWEEN SHOPPING & DINING AT WOODSIDE VILLAGE & THE COASTAL HAVEN OF HALF MOON BAY

Tucked among lush landscaping this beautiful two-level home is as chic as it is comfortable. Tall picture windows showcase spectacular vistas of the western hills and views of the surrounding area's natural beauty. The 3-bedroom, 2-bath floor plan is designed with convenience in mind. The primary suite on the main level has a private, sunny balcony. The updated eat-in kitchen is well-appointed with stainless appliances and has direct access to a welcoming deck which offers the perfect place for outdoor entertaining and dining al fresco. Two additional bedrooms, full bath, and laundry are located on the lower level. Raised vegetable beds and fruit trees dot the landscape of this cheerful property. Conveniently located midway between San Francisco and Silicon Valley, with easy access to the town of Woodside, Roberts Market, Bucks Restaurant, and acclaimed Woodside Elementary school.

WOODSIDE AT THIS PRICE??? Versatile & ideal floor plan. A home for a big family OR 2 families, with separate entrances... on a BUILDABLE PAVED LOT, a rarity in the area. In law unit non coforming but can easily be restored to the original traditional family home.1 of 3 full baths non conforming. Sunroom off the living room opens to nature and wrap around deck. Two additonal smaller balconies off the 2 bedrooms. MUSt SEE TO APPRECIATEAMAZING PROPERTY!.

Custom built in 2012, this Mediterranean style villa offers plentiful indoor and outdoor space as well as a separate guest house with a full kitchen and bath. This home welcomes you with an enclosed front yard and beautiful tile work at the entry and sits on one level. The expansive living room features vaulted ceilings and an elegant fireplace The gourmet kitchen boats high quality cabinets with an island and beautiful stone countertops. An adjacent family room opens to the kitchen as well as access out to the side yard. The primary bedroom features a large walk-in closet and a luxurious bath a dual vanity, large soaking tub and a separate stall shower. There's also a 2 car attached garage with a laundry area.. A separate guest houses offers a bright living room and chic kitchen, as well as a full bath and sleeping area. The grounds of this property have been meticulously manicured and offer a hot tub, a small play house, beautiful vegetable beds and mature landscaping.

Santa Barbara inspired home sits on 3 private acres and is connected to the Woodside trail system. The red tile roof, ubiquitous French doors and wrought iron balconettes all exemplify the architectural style and indoor/outdoor living. hand-carved front door depicts scenes of Woodside. Home spans one level with a lower-level garage that is a car collectors dream with space for 6 cars along with a workshop and ample storage space. The home has 4 bedrooms and 4 full baths as well as a separate family room that could work equally well as a dedicated office if needed for todays work-from-home lifestyle. The primary suite is remodeled, complete with a separate office for two and a sumptuous book-matched Italian marble bath with curb less shower, free-standing tub, and heated floors. This sublime sanctuary offers the best of California living. Plus, the acclaimed Woodside Elementary School, Roberts Market and town center are only blocks away. .

NEW PRICE! Wonderful opportunity! Great location less than a mile from scenic Highway 84 and on from there to the coast or Silicon Valley, with a stop at Alice's Restaurant along the way. Approximately seven miles / 15 minutes to Highway 280 at Sand Hill Road. Highly acclaimed Portola Valley Schools! The living /dining room combination enjoys a high ceiling with skylights, a gas fireplace with an elevated hearth, and an enormous window presenting a view out to a beautiful garden of ferns and rhododendrons. Tucked in the entry is a cozy office nook next to the kitchen. Highlighted by a brick wall, the dine-in kitchen includes a large eating area opening to a lovely patio. The main level also includes a powder room and a large office or family room. Upstairs are two bedrooms and a full bath. Large windows throughout. Very private. Large parking area with room for a boat or RV. Additional 12' x 15' workshop.

On Woodside's most prestigious street, close to town center, this estate property was built in 2012. Spanning more than 3 acres with privacy, the property comprises a 3 level 4 bed and 5 full bath main residence and separate 1 bed 2 full bath guest house. Every amenity for today's lifestyle of working from home, multiple office spaces for distance learning, entertainment, fitness, and wellness is built right in. The lower recreation level provides a retractable cinema screen, separate game table area, an exceptional full bar, temperature controlled wine cave and fitness center with spa bath. A pool and spa, golf practice area, outdoor barbecue kitchen, and cabana, fenced dog kennel, inground trampoline plus vegetable gardens and fruit trees complete this wonderful estate. Access to acclaimed Woodside Elementary School and midway proximity between San Francisco and Silicon Valley.

A Tuscan retreat on one of Woodside's most coveted streets. This private compound is comprised of a 3-story main residence with elevator, built in 2010, along with a 1-bedroom, pool-side, guest house, built in 2019 & an enchanting casita, both with full kitchen & which could also serve as an executive office for work-from-home needs. Finely crafted details abound - from floors of hand-finished French tile & hand-scraped hickory to disappearing glass walls for a seamless transition to the outdoors. With a western hill backdrop, gentle waterfalls & ponds fill the home with sounds of nature. There are 5 bedrooms in the main residence, with options for a main or upper-level primary suite, 2 offices, fitness center, recreation room with built-in cinema & 1,500 bottle wine cellar. Outside, the lavish amenities include a solar-heated pool w/spa, fire pit, outdoor kitchen, 250+ roses, raised vegetable beds, orchard & barn. Near both Woodside town center & Woodside Elementary School.

Let your mind unwind, under the majestic Redwood Trees. This 3 bed/2 bath, approx. 1,645 sf home sits on approx. 17,816 sf of well utilized land. There is an approx. 500 sf basement for storage or whatever you heart may desire. Separate from the main home, sits an approx. 180 sf additional structure, currently being used as a workout room. Could be a wonderful home office. As you enter the home, you are greeted by tall wooden beam ceilings, and a beautifully updated kitchen with granite countertops, stainless steel appliances, and white cabinetry. Separate step down family room, which can serve many purposes. The spacious master bedroom suite has views of nature outside, a walk in closet, and a bathroom with a stall shower, tub, and dual vanity. The approx. 1,400 sf deck is ideal for entertaining, or even just relaxing. Just minutes down the road from Alice's Restaurant and hiking/biking trails. Top Portola Valley schools (Buyer to confirm).

Scenic Tahoe-like setting! Surrounded by soaring Redwood Trees this darling 2 bedroom, 2 bath home is a mountain paradise yet close to local conveniences and the famed, Alice's restaurant. Skylonda Dr is just off Skyline Blvd, which runs along the crest of the Santa Cruz Mountain range. Naturally landscaped and private, fenced, front yard. Enter into a spacious living room with high beamed ceilings and hardwood floors. Gourmet, eat in kitchen with stunning Redwood views. Master bedroom on main level leads out to spacious deck and backyard views, perfect for morning Yoga, coffee and entertaining. Additional room on main level makes a great office. Stairs to lower level lead to second bedroom and bath and laundry room. Access to backyard from both levels of the home. 1 car detached garage with storage and additional storage area. Do not miss this chance to own a charming home in Woodside!

A rare downtown property on one fully fenced acre with rear access gate to Prospect Street. Spanish hacienda main home with walnut floors, huge living room with fireplace, formal dining room, separate office, remodeled gourmet kitchen, and 2 bedrooms, each with en suite bath. Custom stained glass window, stained glass ceiling lights, decorative Spanish tile accents, and rain chain downspouts. Detached Accessory Dwelling Unit with full kitchen and newly remodeled bath. Huge 3-bay workshop with 4 roll-up doors is perfect for a collector or hobbyist. 1985 barn has 2 stalls, tack room, feed room, hot water, fly system, and paddocks. Irrigated grounds and sprinklered paddocks, beautiful gardens, and fruit trees. House remodeled in 2003, including foundation and seismic retrofit.

On a verdant 3.15-acre lot (per county) in Woodside, this stunning estate presents superb privacy, timeless luxury, and incredible space for entertaining on a grand scale. Lofty ceilings craft an airy atmosphere throughout the home and tall, wide windows allow an abundance of natural light. Expansive formal rooms enjoy elegant appointments, the kitchen is sure to inspire your inner Top Chef, the handsome office can meet all work-from-home needs, and the lower level includes a theater. Offering 6 bedrooms, 5.5 baths, and 7,168 sq. ft. of living space (per county), including a 1-bed, 1-bath guest house, this home will have you feeling a million miles away from it all thanks to grounds that include a pool, barbecue patio, and pathways that wind their way to Bear Gulch Creek, yet you will still enjoy the convenience of being close to Interstate 280 for Bay Area commuting. Children may attend the acclaimed Woodside Elementary School (buyer to verify eligibility).

Perhaps Americas grandest estate, certainly an architectural, natural and historic treasure, Green Gables Estate is extraordinary on multiple levels. With its seven homes situated on 74 private acres, featuring breathtaking panoramic views of Californias Pacific Coast range, it is remarkably situated in the heart of Silicon Valley. Its unique combination of mans and natures best are brilliantly on display from the exquisitely scaled main residence and its world class gardens, the six additional homes, a stunning Roman Pool, three swimming pools, a tennis court, a beautiful stone tea house, a large spring-fed reservoir (sustaining much of the estates irrigation needs) and a glorious vegetable and flower garden. Portions of the estate offer the potential for a myriad of uses, including vineyards, 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 corporate retreat

PRICE IMPROVEMENT!! Reduced by $1,000,000 & Ready for your Clients! Remarkable in so many ways, this extraordinary Hidden Valley property on 3+ acres is extensively remodeled, structurally retrofitted, and expanded over the years. Every inch is beautifully appointed with sophisticated designer elegance. Main residence has a spacious office and 4 bedrooms, including a main-level primary suite with 2 couture closet rooms and sumptuous marble bath. Large detached building with executive office and overhead studio guest house, each with bath and kitchenette. Spacious terrace, pool, and vast stretches of lawn intertwined with walking paths encircling the entire property. Also suitable for up to 6 horses. This magical Woodside area is just minutes to 280, Sand Hill Road, Stanford University, and excellent Portola Valley schools. Luxurious livability, acreage, privacy, and every amenity needed for today. Property is NOT on Leased Land.

Just minutes from Town Center, this Woodside property of approx. ten acres inspires a world of possibilities. The topography is pure rustic beauty-equestrian areas & sprawling pastures are arranged around an existing central home site, as well as a scenic upper plateau overlooking the Western Hills. Charming 1 bedroom cottage with living room, office & eat in kitchen. The current paddocks and grazing areas are just a hint of the multi faceted potential. Ideally sited near riding trails and the heart of Silicon Valley, this land will equally entice the horse lover & homebuilder. At the elevated plateau, which features possible building sites, the unobstructed mountain vistas take on a dramatic dimension. A convenient roadway winds around the property, providing easy service access to the facilities. Nearby Highway 280 links San Francisco, Silicon Valley, & two international airports- proving once again this property within the Woodside School District offers the best of Town & Country.

Location, Location, Location!!! Exceptional Woodside Estate offering Views, Privacy and Tranquility just minutes from the center of Silicon Valley. Superbly situated at the end of a cul-de-sac and steps from the bucolic village. Poised on a knoll top enjoying vistas of Western hills with over an acre of serene flowering gardens epitomizing the essence of California living. Sophisticated and infused with natural light and an ideal lay-out for time together and quiet moments. Outside you'll find dining terraces, barbecue grill, swimming pool, fireplace and meandering paths, all perfect for indoor-outdoor living. The property also includes a full versatile 2 bedroom guesthouse with kitchen. This beautiful property has everything required for a world class retreat. A rare opportunity awaits the next owner an uncompromising lifestyle. View Website 140DeanRd

Privately nestled amidst 3+/- acres of coveted land in Central Woodside sits a home filled with 63 years of memories. The home was custom built by the family in 1958. The formal living room opens to a large patio, and a beautiful pool. The family room, adjoined by the kitchen, is a great spot for entertaining, with a wet bar, and doors opening the pool areas as well. The tranquil home is very secluded from the rest of the world, the view from every window is a park like setting. There are 3 bedrooms, and the 4th bedroom can be an office. There are 3 full baths, and the floor plan allows a retreat for everyone in the family. There is a detached 3 car garage, and easy access to the Woodside Village, and to Portola Valley, for schools, shopping, and dining.

2+ acres on Woodside's most renowned country lane. Beautifully appointed sophisticated and chic design with every room opening to the rear deck overlooking a Cabernet Sauvignon vineyard. Hardwood floors, custom cabinetry, cathedral ceiling, and amazing natural light. Open living, dining, and kitchen plus separate office or wine room. Gorgeous primary suite has indoor and outdoor bathtubs. Built-in desk area in second bedroom. Detached studio on lower grounds offers flexible space for art, hobbies, or wine needs. Meandering paths wind through lush foliage passing the vineyard, level side and rear lawns, and raised beds for vegetables.

Enjoy today, renovate for the future, or build new on 3 level acres with a secondary gate from Olive Hill Lane and less than one mile from the center of town. Amazing vegetable and fruit gardens, equestrian facilities with direct trail access, tucked-away pool, seasonal stream, and lush spring color all around. Warm and inviting home has Old Woodside character, cobblestone fireplace, remodeled chef's kitchen with family room, plus ample office space on main and upper levels. A wealth of opportunity close to acclaimed Woodside School, Robert's Market, restaurants, and hiking, biking, and horse trails.