Exclusive homes for sale in Woodside

Panoramic views and inspiring design are just the start of what makes this 4,200 sq. ft. Woodside home so exceptional. Enter the breathtaking 5-acre property from a long private driveway toward this grand residence. The elegant two-story entry foyer is an attention-grabber and opens to the formal dining room where large windows frame the stunning view that stretches all the way to the San Mateo bridge. The expansive main level also features a large chef's kitchen, formal dining room, family room, two half baths, and a separate office. Up the open staircase, you'll find four ensuite bedrooms, including a primary suite w/fireplace, sitting area, private balcony, and massive walk-in closet. The 3-car garage, two EV charging outlets, brand new roof, and quality craftsmanship offer modern comfort and convenience. This coveted location is a big draw for families of Woodside Elementary!

Tucked away, yet close-in, this Woodside Glens home is the perfect blend of comfort and country. Set back from the street, and with dedicated off-street parking, the home is surrounded with the natural beauty of the area dotted with colorful foliage from azaleas and rhododendrons. Highlighting the home are hardwood floors and a lovely open design for living, dining, and kitchen. An expansive deck across the rear of the home, accessed from the living room & two of the bedrooms, invites outdoor living and a chance to enjoy the seasonal creek at the bottom of the property. The lower level adds complete flexibility of use with two rooms including recreation room & fitness, office, and/or play space. Located near the end of a cul-de-sac, this beautiful country setting is close-in to the Woodside Village and Woodside Elm. Plus, access to a wonderful trail into Joan Olson Natural Preserve is just two doors away. All this, with an ideal location midway between San Francisco & Silicon Valley.

Majestic Mediterranean and equestrian estate on secluded 8.7 acres in central Woodside. 4 bedroom/4.5 bath in main 6300 sq ft + residence includes expansive great room overlooking grounds with with additional study/5th bedroom option. Primary bedroom includes luxurious bath, two large walk in closets, and private rooftop deck with view of the grounds and western hills. Charming courtyard takes you to 3 studio guest apartments, detached office, gym and pathway to additional office/guest house. Breathtaking grounds feature stone terrace off the great room with outdoor fireplace, pool, spa, tennis court, historic 10 stall barn, paddock and riding arena all surrounded by natural grasses, expansive lawn, apple orchard, and stunning oak and redwood trees. This creekside setting allows for the ultimate in privacy and serenity just minutes to Town, Woodside Schools, and all the amenities of Silicon Valley living.

Nestled on a secluded level half-acre in the heart of Woodside lies an enchanting retreat, sure to captivate your senses. Boasting 4 bedrooms and 3.5 bathrooms, this impeccable residence offers an open and inviting floor plan, ideal for a comfortable lifestyle. The interior of this stunning home is adorned with an open concept gourmet kitchen, and two primary suites. Outside is an entertainer's paradise, featuring a sparkling pool, expansive lawn, built-in gas firepit, and an outdoor kitchen with a barbecue and refrigerator. Perfect for hosting guests or enjoying a tranquil evening alone, this outdoor oasis will take your breath away. The ADU above the 2.5 car garage is equally as impressive, boasting hardwood, fireplace, kitchen, and bath making it the perfect opportunity for additional living quarters, a home office, or a guest suite. This property comes with additional 23,522 sq ft with street. This magnificent property is a stroll away from the renowned Woodside Elementary.

This estate (known as Hilltop House) is a masterful combination of timeless French architecture, by Gardner Dailey circa 1935, and luxurious updates for 21st century living. Spanning ~3.4 acres, the setting is quintessential Woodside, set far back from the street with added layers of privacy from redwood groves and a vast meadow adjoining a conservation easement with unobstructed views. The 3-story residence is classically appointed with hardwood floors, refined millwork, and grand formal rooms complemented by a parlor, entertainment bar, library and chef's kitchen. Personal quarters are many with a total of 8 bedrooms, including the lavish multi-room master suite, plus extended family living quarters with full kitchen, and lower-level staff quarters. The impressive grounds include a pool, tennis court, and sun-swept lawns ready to host family or philanthropic events. Located in the heart of central Woodside just minutes to Stanford, Silicon Valley and 2 airports. Woodside Elementary

Aptly named by the original owner, Ukuthula ~ meaning peace or silent pause is exactly what this property offers. This rare oasis, situated only 20 minutes from Bay Area congestion, provides seclusion and privacy ideal for artists, entrepreneurs, or anyone seeking a break from the hustle and bustle of everyday life. Custom-built with architectural elegance, you can entertain guests or simply retreat, decompress and indulge in picturesque sunsets, Ocean and Half Moon Bay views. Soak in the natural light beaming through the expansive windows and the airiness from the vaulted ceilings. Enjoy house guests with the separate loft area and wet bar. The studio with a private entry and full bath (AKA Ukuthula 2) provides extra opportunities for guests and workspace. Imagine the workshop as an artist's studio or exercise room with dream views. This tranquil setting, nestled amongst the trees, provides a private hiking trail, yoga deck and low maintenance grounds. Take a leisurely stroll to some of the best restaurants in Woodside or drive the short distance to all that Woodside has to offer.

Just completed, this incredible estate blends the beauty of Woodside with tasteful modern living. Set on 10.5 acres this property has it all! Views and sustainability-surrounded by majestic oaks and rolling hills, hiking and incredible horse trails are literally right out your front door. Huddart Park is a short walk away. Get on your bike or take a short 2.7 mile drive to the town of Woodside. Easy access to 280. Brand new construction completed in 2023 with design by Simpson Design Group architects (SDG). -10.5 acres gated and fenced estate-5,580 sq ft of living space-3 levels with 4 bedrooms, 5 full and one half bath, 3 car garage with 2 available Charging stations and professional dog wash station- potentially off grid home with solar panel field, propane, 3 Tesla power walls, well water irrigation -Hardwood floors throughout- Herringbone wood floors on main level -Savant Smart home system -Wolf and Sub Zero kitchen appliances-Additional unit (663 sq ft) can conform to home office, gym or art studio. Bathroom may be added to the scalable septic system. -Waterworks bathroom fixtures -Property is not maxed out on buildability and is scalable to your needs. Room for barn, guest house, etc.- pool and spa

This exceptional Woodside Glens gem was comprehensively renovated down to the studs in 2021! Immerse yourself in nature in this pristine 4 bedroom, 2 bath home just a short walk to town and the award-winning Woodside Elementary School. Top quality construction with chic contemporary style, enjoy peaceful country living with a carefully conceived design aimed to maximize light, space and privacy. Wonderful open floor plan features a gourmet chef's kitchen fitted with top of the line Thermador appliances, customized cabinetry, and Mirage wide plank white oak flooring. Main floor features two brs, incl. spacious primary suite and walk-in closet. Downstairs are 2 more brs, multi-use bonus/storage rooms and state of the art home theatre. Multiple decks for al fresco enjoyment and fenced flat grassed yard provide space to play outdoors and low-traffic street with easy bike, walkability and xlarge .52 ac lot offers amazing potential for expansion, garage + ADU!

Complete privacy set way back from the street on 5.6 acres just one mile from famed Alice's Restaurant. Lodge style ambiance throughout with wood paneled wainscot and towering ceilings plus expansive windows and sliding glass doors. Spacious living room, formal dining room, large family room, and open design kitchen with high-end appliances. 2 offices plus 3 bedrooms and 3.5 baths. Private upstairs wing for primary suite with its own view deck plus second upstairs wing with 2 bedrooms. Numerous detached workshops for storage or hobbies. Professional greenhouse, pond, huge deck for outdoor living plus vast stretch of lawn for recreation. Miles of hiking, biking and equestrian trails nearby. Barn & horse corrals. Large attached 3 car garage plus 1 car detached.

PERMIT READY! EXTREMELY RARE OFFERING! - EXISTING 4-STORY EXQUISITE MASTERPIECE! The BEST forested HOME CAMPUS ideal for Corporate Live/Work/Educate/Entertain! Grand & Awe-Inspiring -blend your own elegant & luxurious dream home w/ your chosen modern corporate component. Own your Private Getaway estate set superbly among majestic California Redwoods. Picturesque & Private, this park-like setting sanctuary perched spectacularly atop Woodside, projects dramatically high entryways, soaring ceilings, a multitude of decks, filtered city views & incredible mountain views from nearly every room! Ahh! moments abound! REMODEL - APPROVED PLANS allow for a total of 7 BR, 8 Full BA, 6 Half BA, & boasting 19,000+/-sf of living space w/ attached (interior) ADU on 5+ acres, above-garage addition, full gym w/ sauna, 20-seat home theater, wine cellar, infinity pool, tennis court & jogging path. (SMC Plan. Dept. approval is recommended for stables, putting green or exterior ADU).

Amazing Western Hill views in the sought after Mountain Home corridor in Central Woodside; this 3.5 acre gated fully fenced estate, offered for the first time in nearly 60 years. Situated at the end of a quiet cul-de-sac, come see this timeless treasure, comprised of a classic two story California Craftsman main home, an adjacent carriage house set up for entertaining, a pool and peaceful pathways through the mostly flat grounds. Ideal for indoor/outdoor entertaining, the main home has large Living and Family rooms with French doors opening out to a spacious entertaining patio framed by mature heritage oaks and world class English Gardens showcasing the spectacular western sunsets. Light-filled kitchen has been recently updated. Upstairs, a spacious primary suite with updated bathroom and home office, near the additional four bedrooms. Unusual privacy and tranquility within close proximity to Town Center shops, restaurants, in close driving distance to Silicon Valley & airports

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 yet minutes from the heart of Silicon Valley, A giant office suite, complete with lounge, meeting area and private deck is perfect for work from home with high speed internet access supplied by Etheric Networks. A separate library, professional gymnasium, and acres of land to run and play make this a true sanctuary for all ages.. 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. Starwood is a gated private road. The end of road privacy is further enhanced by private trail access from your front door to Open Space.

Escape to this peaceful and picturesque property with old-world charm and modern updates. The elevated lot, of approximately 2.41 acres, offers sweeping views of the surrounding natural beauty with shade and sun gardens. The main home boasts newly painted interiors, new carpet, an updated granite kitchen, and numerous skylights that enhance the appeal. There are 4 bedrooms and 3.5 baths, a large lower-level family room that opens to the gardens, plus a separate guest cottage/ADU with 2 bedrooms and 1 bath. Classic white fences border the barn and vintage tennis court, with optional equestrian space if desired, while a pool and cabana stand ready for added recreation and large outdoor gatherings. Whether enjoying today or renovating/building for the future, this location is superb steps from Huddart Park with miles of hiking trails, 2 miles from the town center, and with access to acclaimed Woodside Elementary School. Go to www.265greer.com for more information. Welcome home!

Incredible View of the San Francisco Bay Area on 1.3 acres of very usable land. The home has approximately 3000 square feet of well appointed living space. Large primary suite and many mature fruit trees.

Stately Italian villa sitting on roughly 7.7 acres on one of Woodsides most sought after cul-de-sac locations is now available. Incredible attention to detail and rare, highest end, European finishes makes this home a rare treasure and true sight to behold. Venetian plaster walls, brick barrel ceiling with oak beams, herringbone terra cotta flooring, and 300-year-old terracotta roof tiles imported from Italy to name a few. Majestic park-like grounds offer the ultimate private escape. Resort like amenities include pool, hot tub, tennis court, gym, vast lawns. Have dinner under the stars in your private redwood grove with tranquil creekside setting. Incredible guest house, additional gatehouse. This is one of Woodsides finest. Highly sought after Portola Valley schools.

Introducing 130 Lynn Way, Woodside, CA! This single-story estate offers 3 beds, 2.5 baths, 3,120 sqft. It is situated on 1.7 acres and features incredible views, natural light, and hardwood floors. The open floor plan includes a high-end kitchen, a dining area with scenic views, and a cozy primary suite with a fireplace and sunken tub. Outside, enjoy the pool, BBQ area, and full-sized tennis court. With a newer roof, private setting, and meticulous grounds, this timeless estate invites endless possibilities for luxury living. Don't miss the chance to embrace elegance and tranquility in this Woodside gem!

Through the private driveway at 11 Southgate Drive, something extraordinary awaits. Youre greeted by hand crafted iron gates which open to an expansive front courtyard, meticulously landscaped grounds, and an astounding, Ernest Coxhead designed 5,790-square foot Spanish Colonial home. The classic estate, built in 1929 as the original owners summer retreat, combines timeless design and luxury in a private, California setting with unmatched views of the Woodside hills, the sparkling Bay Area and beyond. Inside, youll find dramatic architecture, spacious living & entertaining areas, and distinct treatments throughout, with four bedrooms and bathrooms for family and guests. Outside, inspired by nearby historic Filoli gardens, youll enjoy the unique trees, plants, and flowers, as well as the resort-like backyard with large pool and entertainment areas. This is an extremely rare opportunity to enjoy the lifestyle of a more refined era all in the heart of world-renowned Silicon Valley. A world away, yet close to everything.

Located in Central Woodside, this premier property offers the best of CA living. A renovated designer home, sun-swept pool & spa, plus ADU above the barn-all on 1.92 gated acres. The spacious floor plan has 4 bedrooms, including a luxe primary suite on the main level plus a bedroom, office, & recreation room on the lower level. Plus, an updated 1-bed, 1-bath ADU is privately located above the 4-stall barn, currently a garage & ideal for a car collector. Highlights include beautiful wood floors on both levels, natural light, & multiple French doors to the rear grounds. The kitchen is a chefs dream in Carrara marble w/ adjoining gathering area & extra-large family room. The grounds are equally compelling & extremely private with the pool & spa, a rock waterfall cascading down the hillside, custom playground, level front yard, & a wonderful picnic area. Offering the best of Woodside living, this home is just over 1-mile to the town center & acclaimed Woodside Elementary as well as trails.

One of the BEST gated estates in Woodside's most prestigious area. This majestic one-of-a-kind estate features an enchanting private lake, a long scenic winding driveway, 7+ lush acres, EXTENSIVELY REMODELED 5 bd/5.5 ba primary residence with guest house. Approximately 8238 sq ft of total living space, an energy efficient metal roof, dual pane windows/doors, sub zero refrigerator/ freezer, 3 separate heating systems, a gourmet kitchen, gym, bocce ball court, pool, greenhouse, 3 wells, a sand beach to launch boats onto the private lake, a 6-stall remodeled horse stable with railed riding area, rose garden & areas for a future tennis court/a riding arena. It is quintessential of fine living where numerous weddings & fundraisers exceeding 500+ people have been hosted. Secluded yet conveniently located to Stanford, Sand Hill Rd, tech companies, SF & San Jose International Airports. This property represents a RARE opportunity to own one of the most unique properties in all of Woodside.

Located at the very end of a long lane, this 1.1 Acre property has complete privacy from the main st, is just 4 blocks from Woodside town center, and has access to acclaimed Woodside Elementary. The setting is quintessential country, the long driveway leads past an open sun-swept meadow & oak trees arriving at the home. The covered front door opens to a traditional foyer; beautiful wide-plank wood floors throughout. Open design for living, dining, & kitchen; a fireplace in ledgestone; windows wrap around two walls. The remodeled kitchen is topped in granite, including breakfast seating at the peninsula; stainless steel appliances and track lighting. 2 bedrooms, each with lighted ceiling fan & glass doors to a spacious rear deck. Attached 2-car garage w/ custom built-ins & laundry area. Quality updates throughout, a lovely spot to move in & enjoy today. Opportunity to expand / build new; adjoining 1-acre parcel, also for sale, increases options for estate living in a superb location.

Extraordinary contemporary estate on over one acre in Woodside Hills with sweeping panoramic views across the Bay from nearly every room. Enjoy your own gated sanctuary in this unique property featuring a 4 bedroom, 4.5 bath residence plus large media room, office & separate gym/flex space. Boasting soaring ceilings and expansive glass windows, stunning views are framed from every window overlooking your own private and flat 1.15 acre landscaped park setting. The gorgeous open chef's kitchen is ideal for entertaining, with a large center island, custom cabinetry, & high-end appliances. The spacious primary bedroom features a generous walk-in closet, a luxurious en suite bathroom, access to a private balcony with Bay views. All additional bedrooms have en suite bathrooms. The level rear yard overlooks astonishing views from the pool, fire pit, garden, & a pergola-covered terrace. Approximately 5,000 sq.ft. of interior living space are arranged over 2 levels. Attached 3-car garage.

Competitive price per sqft! A great home on 5.5+ acres with so much potential! Enjoy the stunning views from the living room, dining room, kitchen, primary bedroom, and outdoor patios! Move in, transform or potentially build new in this private setting. The two-story house has 5 spacious bedrooms, and 4.5 bathrooms. Upon entering, you are greeted by soaring ceilings and expansive windows and skylights that offer ample natural light and a view into the private backyard. The eat-in kitchen is highlighted by a huge center island, peninsula with extra seating, and large glass doors leading to the outdoor patio. The large patio is perfect for BBQs, alfresco dining or star gazing in the summer time. The main level has the master suite with dual vanities, shower , spa stub and private balcony. The lower level has a total of 2 bedrooms and 2 full bathrooms, including an in-law unit with kitchen , bathroom, and a separate entry. Excellent Portola Valley schools. Perfect for vacation rental.

This exceptional home is situated on approx. 3/4 +acre, sunny usable lot and designed for indoor/outdoor living. Established natural landscape infuses the home through soaring windows, many skylights and French doors. The effect leaves one feeling far away from the hustle and bustle while just minutes from the Peninsula. Ideal for family living and entertaining. The gourmet kitchen is the heart of the home with an abundance of cabinets, extra-large center island, AGA stove and sun-filled eating nook. Open floor plan seamlessly connects the kitchen to living room on one side and cozy family room on the other. The large master suite found upstairs is a restful oasis with French doors and a private deck looking to the beautiful setting, spacious walk-in closet, and dreamy master bath with tub and sep. custom shower. Outdoor living at its finest with expanses of decks and garden sitting areas graced by majestic redwoods and established landscaping. Desirable Woodside/PV schools

Custom built, this architectural masterpiece with clean-lined modern style has it all. Sweeping San Francisco Bay and Menlo Country Club golf course views in a 1.5 acre park-like setting, bright & light interiors spanning two levels, a floor plan for indoor/outdoor living, and a design for eco-friendly sustainability. Walnut or travertine spans the radiant-heated floors, Venetian plaster finishes the main-level walls, & European glass doors and windows, with tilt & slide operation, connect to the grounds & views at every turn. The open & flowing floor plan boasts gently vaulted ceilings dotted with LED lighting that accentuates the lofty height of many rooms and is designed for display of fine art. Outside, the magnificent setting of approximately 1.5 acres boasts vast terraces, a pool more than 60 feet long, plus a spa, barbecue kitchen, and full bath. Highly acclaimed Las Lomitas schools and minutes to Menlo Country Club and town center.