Woodside CA Real Estate & Homes for Sale

Located in the highly desirable Woodside Heights on a vast 41,000 sq ft lot! Featuring an open concept floor plan, soaring ceilings and an abundance of natural light this 4 bedroom, 3 bathroom, 2,990 sq ft villa sets the stage for gracious living and entertaining! Formal living room, fireplace and custom cabinets with access to the beautiful stone terrace. The large kitchen with dining bar opens to an inviting family room and adjacent spacious dining room. Paces away you have a separate laundry room, perfectly placed space for a home gym and beautiful wine cellar. Rounding out this level is a wonderful library/office and full bathroom. Just upstairs you have a private and spacious primary suite retreat with walk-in closet and spa-like bath! Down the hall, three additional bedrooms share a full hall bathroom. Relax or entertain outside in the elaborate yard with lush mature, landscaping boasting sweeping views and several seating areas. Located just minutes to Town Center, great schools and streamlined commute routes!

Stunning Custom Built 3 Level Home with Guest Cottage and Pool on 4.37+/- Acres with Stables and Riding Ring on Private Cul-de-Sac in Central Woodside. 5 Bedrooms. 5.5 Bathrooms. Living Room Features Vaulted Ceilings, Wood Floors, and Floor-to-Ceiling Windows. Spacious Kitchen with Large Island, Peninsula and Views of the Pool and a Pond. Intimate Family Room with Sliding Glass Doors to Pool. Library with Fireplace. Wine Room, 3 Laundry Rooms, and Large Fitness Area with Sauna and Steam Room. Outdoor Cold Plunge. Three-Car Garage. Ipe Decking, Pool, Large Pool House, and Outdoor Kitchen. Guest Cottage. Sand Riding Arena and Horse Stables with 8 Stalls and Loft. Situated Hillside for Amazing Views.

Relax and restore yourself at this charming one-of-a-kind updated log-cabin retreat that sits on over an acre of Woodside redwoods and still gets plenty of sun! Built in 1934, this location for decades has held weddings, outdoor concerts, retreats & family gatherings. It also has a trail that leads into the 6100+ acre La Honda Creek Open Space Preserve. You can walk over to Alice's Restaurant and enjoy some local musicians or enjoy a relaxing evening on the 4 deck areas attached to the main house and feel 'away from it all'. The property is a 2-story, 3-bedroom, 2-bath craftsman cabin home that opens to the great room with ample seating and a stove fireplace. The upstairs has both the vaulted master bedroom as well as an ample 2nd bedroom that accommodates two queen beds comfortably. The new extension has the dining area, and a vaulted updated kitchen with all amenities and giant windows that will leave you staring out at the redwoods right in front of you. Downstairs has been updated and has a second full bathroom, a very large family room and the 3rd bedroom, with double doors that open up onto its own private patio area. There is an abundance of outdoor seating and eating areas to enjoy as well. Detached studio/cottage - has been rented before for additional income.

Majestically situated on 5 flat acres in central Woodside, sits this magnificent Tudor manor close to Silicon Valley, San Francisco, Stanford University, and Filoli Mansion, which hosted President Biden and President Xi Jing Ping at the recent APEC summit. A gated entrance and brick wall surrounds the entire property. A cobblestone driveway flanked by parterre gardens of boxwoods and roses, leads to the grand entrance. The gallery with soaring 24-foot ceilings, is flanked by formal dining and living rooms, with 3 bedrooms & 4 baths on the ground floor including a primary suite. Two family rooms open to the indoor 2,200-square-foot pool pavilion. This rare 16,000-square-foot home with 7 bedrooms and 9 baths, offers limitless possibilities. The city of Woodside no longer approves homes of this size within the city limits. The property also has a rustic and historic three-bedroom guest house and barn, with loft above and horse stalls below. Arched doorways, leaded glass windows, coffered ceilings, heavy wainscotting, rich wood paneling, deep moldings, turreted open beam ceilings & pool pavilion create a refined balance of dramatic formality, yet comfortable ambiance. Perfect for entertaining, or family gatherings, this impressive landmark property is ready for a new legacy!

Rare opportunity ready to create your dream estate in the heart of central Woodside! "The Old Apple Orchard" offers 3 flat sun-drenched acres of quintessential country living, with mature trees, rolling pasture, equestrian expanse with existing barn, chicken coop and enclosed garden, and a private pool oasis in a seasonal creekside setting! Remodel existing mid-century home or build this state of the art luxury modern farmhouse compound- INCLUDES FULLY APPROVED plans for ~12,000 sq ft luxury multi-building estate including ~6800 sq ft main residence, accessory units, pool house, office and gym. Two entrances, one from Canada Rd and secondary access from Olive Hill Ln, this special property is primed with amazing possibilities, all within walking distance to town and Woodside Elementary School.

Located on 3 acres with complete privacy, and close-in convenience, this exceptional property epitomizes luxury living. The elegant sophistication of the interiors rivals luxury resorts with an extensive use of natural stones that transform walls into works of art. Book-matched precision is showcased on fireplaces, countertops, and shower walls. Grand entertaining spaces are designed for hosting gatherings large or small, served by a fabulous all-white kitchen, temperature-controlled wine storage, and numerous terraces for outdoor enjoyment. The home spans 3 levels with 4 spacious bedrooms, each with its own en suite bath, plus there are 2 versatile offices, a fitness center, and a home theatre. Additionally, a detached guest house provides 2 bedroom suites for visitors. The outdoor areas, complete with vineyard, are designed with health and wellness in mind, featuring a pool, spa, tennis court, and a path that wraps around the property for walking or jogging. Adding the finishing touch is the homes access to acclaimed Woodside Elementary School just two miles away.

Located at the end of a quiet Woodside lane, this four-acre estate designed by the highly acclaimed architect, Howard J. Backen, was inspired by Mexican architects Luis Barragan & Ricardo Legoretta, masters of shapely geometric buildings that embrace their natural settings. The home offers a truly seamless indoor-outdoor living experience with staggering views of the Santa Cruz Mountains. The approach to the residence is marked by a dramatic entrance with a long stone path leading to a light-filled atrium. Inside, rectilinear architecture featuring floor-to-ceiling glass doors transforms the living areas into expansive outdoor spaces with limestone terraces and a reflective pool that enhances the connection to the scenic backdrop. Outdoors, a lap pool with an infinity edge and an antique French fireplace create a peaceful setting. Interior finishes include parchment-colored limestone floors, stunning Texas shell stone walls and Venetian plaster. The state-of-the-art kitchen and bathrooms feature marble countertops. The primary suite offers dual bathrooms and panoramic mountain views. Near Woodside town center, bordering Huddart Park on one side and private open space on the other. This private oasis provides easy access to Stanford University, Silicon Valley and San Francisco.

Situated in the heart of premier central Woodside, this magnificent estate combines the elegance of a classic country manor with boundless possibilities to live the lifestyle of your dreams. This is a rare opportunity to obtain a spacious & versatile home on a large, 3-acre plot of prime, level land just one-half mile from Woodside Town Center. The property is replete with resort-style amenities catering to a variety of alluring lifestyles, including outdoor living, entertaining, fitness, equestrian pursuits, gardening, & farm-to-table dining. Estate features a spacious main residence with classic Tudor architecture. Other rooms provide flexible space for additional offices, fitness rooms, & recreation. Tucked away on the lower level is an extraordinary 3,000-bottle wine cellar designed in European fashion with a dining & tasting area to uniquely entertain guests. Extensive grounds also include a magnificent, recently built barn with 4 stalls for horses, 2 work rooms, restroom, & extra space to store a horse trailer, extensive patio with bbq area, pergola, social fire pit surrounding a newly refinished pool & spa. An ideal retreat for the quintessential Woodside lifestyle, this exceptional property's offering of luxury, amenities, size, & location won't soon be seen again.

An exquisite modern farmhouse in Woodside, where luxury, comfort & functionality blend seamlessly amongst the verdant setting. Bordering Open Space & spanning over 3,800 sq ft & 1.5 acres, this stunning estate offers an unparalleled retreat with breathtaking views & top-notch amenities. Every bedroom is a private sanctuary with ensuite bathroom. The primary suite is a true oasis featuring a fireplace, custom walk-in closet & a spa-like bathroom with a BainUltra freestanding tub & walk-in shower. The gourmet kitchen is equipped with a Viking Tuscany range, marble countertops & chef favorites such as a built-in espresso machine, pot filler, microwave drawer, wine fridge & pantry. A statement temperature-controlled wine room, conveniently located off the kitchen, is perfect for wine enthusiasts. Elegant elements throughout include floor-to-ceiling windows throughout, trim & wall detailing, electric linen blinds, built-in Sonos system & designer fixtures. The 6+ car garage with a workshop & soaring ceilings is a dream come true for car aficionados. Outdoor serenity is epitomized by the center courtyard adorned with a koi pond & cascading waterfall. The surrounding low-maintenance landscaping & garden beds further enhance the natural beauty. Woodside Elementary.

Nestled in the serene landscape of Woodside, this charming turnkey 2 bed, 2 bath residence with attached 1 bed, 1 bath apartment boasts breathtaking views of Stanford's Biological Preserve, Jasper Ridge. Conveniently located at the bottom of Old La Honda Road, near Portola Road, and is just minutes from global financial/tech centers on Sand Hill Rd & Stanford University. The home offers a beautiful authentic rustic design and is completely hidden from the road. This 1.06-acre property delivers rare seclusion utilizing its natural setting that promotes a peaceful and conducive at-home work environment, complemented with its enhanced WiFi / internet service. Excellent Portola Valley schools.

Contemporary luxury with breathtaking San Francisco Bay views in Central Woodside. Extensively renovated open concept design on two levels, including modern kitchen, white oak floors, new metal roof, and designer baths. Tesla solar power, 5 battery backups, EV charging, and synthetic lawn. Every room opens to a deck for Bay or western hill views or just the natural beauty of the surrounding grounds. Elevated and private pool plus meditation/yoga area with sweeping views. Separately fenced farm with large barn and space for animals or garden. Direct access to hiking and equestrian trails at Wunderlich County Park. Excellent Woodside Elementary School (K-8). Recent upgrades over 500K of improvements including new standing seam metal roof, solar system & storage, HVAC systems, structural upgrades, plumbing, home A/V systems. Every detail updated and ready to be enjoyed!

This beautiful estate is nestled on nearly a 1.50 acre lot and is surrounded by beautiful redwood trees. This amazing, two-story mountain home offers unparalleled tranquility & privacy in a majestic setting. This rustic retreat boasts handcrafted wood features throughout the home, from the gorgeous detailing of the cabinetry in the loft, to the decorative pieces around the fireplace, to the beautiful wood beams adorning the ceilings. The first level features the kitchen that seamlessly flows into the dining room, a spacious and cozy living room, 2 bedrooms & 1 bathroom. The second level features a large, open loft, the primary bedroom suite & bathroom & two outdoor decks. While this home captivates so much history & exuberates timeless beauty, there is abundant potential to add in your own touches & transform this residence into your dream home. This property also offers a second dwelling unit with its own septic tank. The second dwelling is an unpermitted 2 bedroom, 2 bath unit with its own outdoor deck. Located in close proximity to the tech hubs of Silicon Valley, Stanford & the serene beauty of the Pacific coastline, this is an opportunity not to be missed. Don't let this chance slip away to own a slice of paradise in one of the most coveted neighborhoods in the area!

Experience country living just 30 minutes from the heart of Silicon Valley. Nestled in California's majestic Redwood Forest, this horse-zoned property blends natural beauty and equestrian potential. Set on a 2-acre lot with a HUGE open grass field, this home offers ample space for just about every lifestyle. Surrounded by lush greenery and open skies, it's a perfect retreat for those seeking a serene, private lifestyle. The expansive grounds provide endless possibilities for gardening, recreation, or creating your own outdoor oasis. Despite its secluded feel, youre close to top-rated schools and the 280 freeway, ensuring easy access to everything you need. The property is fenced, gated, and obscured by trees. The well-designed home features a fully equipped kitchen, spacious living room, high ceilings, and a welcoming family room, ideal for daily living and entertaining. Inside, cozy bedrooms offer a perfect haven after a long day. Tall windows and glass doors flood the floor plan with natural light. A bonus room under the house is perfect as a gym, recreation room, or playroom. Outside, a huge patio and wraparound deck overlook the expansive lot. Come live the life you deserve in this peaceful retreat.

Welcome to 277 Grandview Drive, a contemporary Craftsman style haven in Woodside, CA offering privacy near Silicon Valley. The 4-bed, 4-bath main house with 2 offices spans 4920 sq ft on a 10+ acre lot. A 996 sq ft guest house, with an additional 1 bedroom and 1 bath, adds versatility (currently used as a music studio). The gated entrance reveals a welcoming design which includes an 8.4 kW solar system with battery backup. Inside, discover radiant heating, a chef's kitchen and two living rooms with surround sound. Outside, a fireplace, porch and deck offer relaxation and entertainment spaces, not to mention ultimate privacy. Adjacent to Thornewood Open Space, and built in 2008, this residence seamlessly combines modern amenities with eco-conscious features. Explore the harmonious blend of modern living and natural beauty.

Originally conceived by the visionary architect Gardner Dailey in 1934, this exceptional estate is a testament to his architectural brilliance updated with a complete comprehensive renovation. The classic style of a country manor is presented, creating a visual symphony from the slate tile roof to the leaded glass windows and exceptional gardens. The views offered are nothing short of dazzling, encompassing verdant views of the bordering Menlo Country Club golf course, the sweeping panorama of San Francisco Bay, and the majestic silhouette of the East Bay hills. Set within a gated sanctuary of 1.5 acres, the home is adjacent to a 2.8 acre lot available for separate acquisition, enhancing the promise of exclusivity or with potential for further development. The palatial home spans more than 10,000 square feet of grace and sophistication. The journey into the home begins with a unique entrance a pedestrian gate beyond the gated driveway opens into a vast front courtyard with a magnificent heritage oak tree, lawns and patios, and a sparkling pool, creating an enchanting space for grand celebrations or private relaxation. Adjacent 2.8 acre parcel also available for sale. This is a once-in-a-lifetime property!

Welcome to your dream home at 250 Hardwick Rd in Woodside. Situated at the end of a quiet cul-de-sac, this exquisite property just completed a high-end, studs-out renovation and boasts stunning views of the Bay and East Bay hills. With dual oversized primary suites (4 bedrooms, 4 full bathrooms total), this home offers ample space for your growing family or those considering multigenerational living. As you step into the proper foyer, you'll be greeted by warm ambiance and stunning views that continue throughout the entire home. The open-plan kitchen is a chef's delight, featuring high-end appliances, integrated gas range, oversized kitchen island, and a walk-in pantry for all your culinary needs. The spacious family room is perfect for entertaining guests, with its vaulted ceilings and massive windows allowing for an abundance of natural light and stunning Woodside views! Both primary suites have been totally remodeled to perfection, featuring luxurious ensuite bathrooms, large walk-in closets, walk-in showers, and a gorgeous free-standing tub. The 1.6 acres of usable land, provides plenty of private outdoor space to enjoy the beautiful California weather. Just a short distance away, you'll find top-rated schools ensuring an excellent education for your children.

Perfectly and privately situated on nearly 9 sun-filled acres of land, options abound at this very special property: remodel the charming home or build new to create your own dream vision. The choice is yours. The land enjoys breathtaking 180 degree views of the Western Hills and there is a pool, spa, guest house and vast gardens. There is also a 1.2 mile hiking/biking trail encircling the property for a no-excuses healthy lifestyle right out the front door. Explore the endless possibilities. Approximately 9 acres (389,760 square feet; buyer to verify) Existing circa 1930 home with 4 bedrooms and 3 baths plus a one bedroom guest/pool house. Exceptional privacy and rural beauty Western hill views ~1 mile to Woodside town center. Woodside Elementary (K-8) School

Majestic home set on 1.96 acre lot boasting with mature redwood trees, beautiful lush grounds with stunning views! Quaint entry porch & front door invites you into the spacious living room with cozy brick fireplace. Separate dining area, chefs kitchen with gas range and breakfast bar. Updated baths, recessed lighting, gorgeous hardwood flooring, dual-paned windows, 2 side storage sheds, large walkin basement accsessible from back yard under deck. Perfectly located in Central Woodside; this home is minutes to town center for convenient shopping, dining and the acclaimed Woodside School. Easy access to hiking trails, biking and horse back riding. Expansive deck to entertain guest while enjoying breathtaking views.

Location, location! This lush jewel estate is located along central Woodside's most exclusive Mountain Home Road corridor. A rarely available opportunity to own a 1.25 flat acre property in the heart of the town's most prestigious neighborhood, discover an effortless blend of fine craftsmanship with luxurious elements and a touch of Hollywood style: 4(+1) brs, 4.5 ba plus an array of multi-functional spaces: a main-level suite easily converts to lounge/5th bedroom, the primary suite is enhanced by a private library/office/ walk-in closet, nursery or 2nd bedroom. Venture to the wine cellar with its own tasting room through a potential home theatre. An entertainer's dream for elegant al fresco afternoons by the pool and easy indoor/outdoor living, and the expansive grassed yard is as well suited for ball play as larger events, all framed for utmost privacy by pristine mature landscaping, a romantic rose garden, olive and fruit orchards. A short walk to town and the Woodside Elementary School, this garden estate balances peaceful seclusion with close proximity to all commuter routes and less than 20 minute drive to SFO Airport.

Exceptional half acre+ with bay views in sought after Emerald Hills custom home built with meticulous attention to detail. Local artisan designed stone and ironwork. Outstanding floor plan with a focus on indoor-outdoor living the home seamlessly extending from the family room to a mostly covered, tiled deck with a fireplace, lounge, dining area and well-equipped outdoor kitchen offering a serene and inviting space for everyday living. Vaulted ceilings including living room with fireplace, formal dining room with fireplace, sun room and main floor bedroom suite. Granite chefs kitchen with views, breakfast room with outdoor patio, plus adjacent family room with fireplace. Upstairs luxurious primary suite with fireplace, vaulted ceiling, views and sitting room, plus two additional bedrooms and adjoining lounge or office. Lower-level flexible-use room for office, 2-car garage PLUS 735 square feet studio including half bath-possible ADU conversion. Approximately 5,173 square feet of conditioned space plus 2-car garage. Mostly float lot with vast lawn, huge entertaining spaces, privacy and views. Excellent Roy Cloud School, views and vast lawn, mostly flat land. One-of-a-kind enchanting home resting on gentle knoll-a must see.

Updated and renovated, this home is ideally located opposite the picturesque Kite Hill permanent open space, on a double lot of approximately 0.41 acres. Introducing the home is a spacious great room that encompasses a living room, with modern stone gas fireplace, and a step-down seating area with an impressive wall-to-wall window view of the rock and cactus garden. Adjacent to this is a formal dining room and newly remodeled kitchen with quartz counters and all new stainless steel appliances. There are 4 bedrooms and 2 baths plus a detached bonus room ideal for today's remote office, or for a game room or fitness center. Outside, are sun-drenched spaces, a stunning rock and cactus garden complete with pathways and a seating area, plus a private rear garden with large deck for entertaining around the sparkling pool. Adding the finishing touch is this homes access to the highly regarded Woodside School (K-8) and proximity to the Woodside Village.

Expanded by home owner to 2,479sq feet. This beautiful mission style, four bedroom smart home was built for both luxurious entertainment and family fun. From the imported knotty alder doors to the 50 speaker home entertainment system, attention has been given to each detail. A residence door separates the front house from the bedrooms for privacy. Enter through the double door to an open kitchen and dining which area leads into a sitting room and large office. The full guest bath features an exquisite Orinoco granite slab shower while the living room centers around the gorgeous wood burning fireplace. Behind the residence door are three bedrooms, two baths, a nursery/multi-use room and a dog run. The master bath boasts exotic Tanzanian Onyx stone slabs and an oversized Moen spa shower. The kids' bath has Alaskan white granite and an extra long jet tub. Nestled up against the Santa Cruz mountains just above Silicon Valley, with easy access to San Francisco, San Jose and Palo Alto, Woodside boasts California's top elementary school with 11 students per teacher.

Welcome to Woodside Whisper, a fully gated property stands as an epitome of refined luxury & tranquil living.This distinguished single-family home spans across 4050 square feet of meticulously crafted living space on a 1 acre parcel. Boasting 4 spacious beds & 4.5 baths, this residence offers ample room for both relaxation & entertainment. Upon entering, guests are greeted by an inviting formal entrance characterized by abundant natural light & tasteful finishes. The gourmet kitchen, equipped w/high-end appliances & custom cabinetry, serves as the heart of the home, inspiring culinary creativity & gatherings. The primary suite exudes sophistication & serenity, featuring a luxurious en-suite bath w/huge walk-in closet. Additional bedrooms offer comfort & privacy, each thoughtfully appointed to ensure restful nights & rejuvenating mornings. Get your game on at the on-site sports court, perfect for basketball, pickleball, or tennis. Post-match, plunge into the saltwater pool or jacuzzi, or detox in the outdoor sauna it's wellness on your doorstep. The outdoor space is a dreamy landscape for enjoying the Californian sunshine. Chill on the vast patios, gather around the fire pit under the stars, or wander through the lush gardens it's all about serene outdoor living.

Plenty of space to build an ADU-Horse property- Circular driveway leads to this luxuriously appointed home atop a gentle knoll. Views encompass a glorious sunrise, Windy Hill, Huddart Park. Level backyard, in-ground pool, fabulous outside entertaining patio w/ built-in BBQ, pizza oven & refrigerator. The classic lines and timeless architecture welcome you to the formal entry w/Chestnut floors in the spacious LR with high ceilings,impressive gas FP and mantle,formal DR. Chef's dream- Granite counters, wine refrigerator, 2 dishwashers, sub-zero refrigerator, trash compactor, microwave, 6 burner gas Dacor,double ovens,stainless steel dual sinks + a vegetable sink. BB + eating area.FR boasts a gas FP, window seat, ceiling fan, built-in book shelves. Relax in the library. There are 2 en-suite bedrooms down the hall, + a convenient half bath & full laundry facilities. Ascend the elegant staircase to the primary bedroom featuring double door entry, gas fireplace, sitting areas, black out shades, outside European roller shades, ceiling fan. Primary bath is replete with dual sinks, steam shower, jetted tub, water closet & verandah. Office upstairs w/ a window seat + the 4th en-suite bedroom. 2 AC & 2 Furnaces-solar enabled whole house battery back-up system rated 25KWH-Woodside Elementary

This fantastic new price makes it possible to create your own dream property on 2 tranquil acres! Conveniently located in true central Woodside with 2 homes, 2 private driveways and so much room to grow. The main house is 3,090 square feet, has 5 bedrooms, and 3 bathrooms. The large living room has huge windows overlooking the expansive lawn and pool area. The primary bedroom upstairs features a walk-in closet, fireplace, and a balcony with a jacuzzi overlooking your 2-acre property. The cottage can be accessed off of the first driveway and has been thoroughly remodeled. There is a lush green pasture, and pathways leading to the pool and patio area. 2 natural gas generators connected to each house. Experience the tranquility of Woodside, just 2 minutes from the town center and renowned horse trails. This is your chance to embrace a relaxed lifestyle in the heart of Woodside!