Woodside CA Real Estate & Homes for Sale

Step inside and step back in time to this to this stunning Henrik Bull-style home in Skywood Acres, where classic charm meets modern comfort. Nestled in a sunny tranquil setting, this architectural gem opens into a breathtaking great room with cathedral ceilings and walls of windows that frame sweeping treetop views. This seamless blend of indoor/outdoor living extends to an expansive deck offering a perfect retreat that harmonizes with nature. Reminiscent of a mountain ski lodge, this 2510 sqft private haven enjoys its own sunny microclimate and offers the ultimate escape, just 14 minutes to 280, 25 minutes to Stanford, minutes from Alices Restaurant, and private access to Wunderlick Park, Portola Valley schools. Main home features a primary bedroom that includes bathroom, dressing room and private office. Main level boasts a well-appointed kitchen, custom wood built-ins, opens to a grand living area. Downstairs 2 bedrooms and bath, 3 car garage with wine closet. Detached guest studio with sleeping loft. 1.5 acre lot includes a former sport court ready for new possibilities Make this getaway your private Shangri-La

Western hill views take center stage... at this updated farmhouse on 1.2 acres, just minutes from the heart of Woodside. The multi-level home, set back in complete privacy, is filled with character, featuring gleaming hardwood floors and generous gathering spaces, all with expansive windows oriented to the views. The kitchen and family room combination opens directly to a spacious view-side deck for indoor/outdoor living. There are 4 bedrooms and 2.5 baths, including a main-level primary suite and three bedrooms upstairs. A 3-stall barn connects to fenced pastures, there is ample room for a dog run or chickens, and additional highlights include a charming playhouse and an oversized one-car garage with laundry. Located just 1.5 miles from the town center and with access to acclaimed Woodside Elementary School (K-8), this property celebrates rural tranquility and offers the opportunity to enjoy as-is or thoughtfully renovate for the future.

Perched on a peaceful mountain with breathtaking views of the Pacific Ocean, this updated 3-bed, 2-bath home offers the perfect blend of privacy and convenience. Just minutes from Half Moon Bay and San Mateo, this gated property is tucked within the cozy Kings Mountain community and designed for flexible living. With two spacious living rooms, two kitchens, and a bonus room, the home has excellent potential for separate living spaces; ideal for multigenerational living or guest quarters. The main kitchen features sleek Bosch appliances and modern finishes, while large windows throughout the primary living space capture breathtaking ocean vistas. Enjoy outdoor entertaining and evening sunsets on the deck, soak in the hot tub under the stars, and embrace the quiet, coastal mountain lifestyle. Whether you're looking for a serene full-time residence or a versatile retreat with income potential, this home offers comfort, flexibility, and unmatched views in a truly special setting. Just steps from Purisima Creek Redwoods Open Space Preserve and minutes to local favorites like The Mountain House and Alice's Restaurant, this home offers nature, charm, and versatility in one stunning package.

Delightful 1950 square foot country home with four bedrooms and two bathrooms sits on just over half an acre. This well-loved home has been in the same family for approximately 57 years and is awaiting your vision and loving care to bring her back and make her your own. The focus of the home is the generous living room with soaring beamed ceilings and a massive fireplace creating a dramatic focal point. This room is spacious enough for large gatherings and opens to extensive decks. With the considerable expanses of windows and the natural setting, there is a sense of living in the environment. A formal dining room is light and airy also has enough space for large gatherings and holiday dinners. The downstairs with two bedrooms and one bath also features a family room/central play area ideal for children to have their own space. The downstairs would also function well for office spaces. Includes parcel #075-192-060 to total 22,796 sf. Located in the desirable Skylonda neighborhood of Woodside it is served by the highly sought after Portola Valley and Woodside schools. Stress free commutes to: Stanford- 23 minutes Google Campus- 33 minutes Facebook- 29 minutes San Jose International Airport- 37 minutes SFO- 35 minutes Redwood City- 24 minutes

Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The main floor features a gourmet kitchen with high-end appliances, sleek finishes, dining area, family room and dedicated home office offers the perfect space for remote work or creative pursuits. Upstairs, the bedrooms provide privacy and tranquility. A large, bright family room stands out as a favorite space, filled with natural light and a cozy, welcoming ambiance. Multiple large decks extend the living space outdoors, offering peaceful spots for relaxing, entertaining, or enjoying the majestic redwood surroundings. Additional features include a wine cellar and ample storage. Tucked just off the scenic Skyline Corridor with easy access to Hwy 92, 280/101, SFO, open space trails, restaurants, and award-winning Kings Mtn Elementary, this home offers a rare blend of privacy, convenience, and a strong sense of community fostered by friendly neighbors and the Kings Mtn Volunteer Art Fair.

Nestled on nearly a full acre high above one of Silicon Valleys most affluent neighborhoods, this Luxurious Woodside View Compound includes two homes offering soothing panoramic views spanning the bay with all three bridges from San Francisco to Palo Alto & across to Mt. Diablo. Both homes are meticulously renovated with the finest build quality/finishes & awash with natural light from sunrise to sublime sunsets. At the heart of the compound stands a luxurious 4bd/4ba generous scale home with open concept kitchen/dining/living plus game room with catering station/wet bar all on two levels with expansive walkout view decks. The renovated guest home with street level access was constructed in 1990 and is set on the west side of the estate with panoramic views, spacious open concept kitchen/living/dining design & luxurious master suite + guest bath. Below you will find two additional bonus/flex areas, both with private access perfect for office/gym. This exclusive compound stands as a testament to luxury living, positioned just 30 minutes south of San Francisco and complete with multiple gardens, meandering pathways, unexpected view enclaves, covered terrace with outdoor kitchen w/custom lighting and variant fruit tress, all set amid the expansive grounds.

Morning light pours through redwoods onto white oak floors at this 3BR/2BA retreat on 2.44 private acres. Updated kitchen and marble baths blend comfort and style. A bright barn office and workshop offer flexible use easily converted for equestrian needs with an existing corral. A fenced dog run adds convenience. Enjoy sunrises on the expansive deck or quiet moments on a meditation deck tucked in a redwood fairy ring. Just 10 minutes to Roberts Market, 15 to Stanford, and close to Facebook (20 min), Google (25 min), and Apple (25 min). Top Portola Valley schools and Woodside High.

Mountain Meadow - A Landmark Legacy-Extraordinary in provenance, scale, and preservation, this landmark estate spans nearly 25 acres, located on land protected by Peninsula Open Space Trust and surrounded by Golden Gate National Recreation Area parkland. Offering unmatched privacy yet just 20 minutes from San Francisco International Airport. Commissioned in 1927 as one of the debut residential work of renowned architect Gardner Dailey. Over a period of decades, the entire property has been thoughtfully restored with reverence for its heritage and a commitment to enduring quality. The main residence of almost 9,000 square feet has been brought forward for the next century with seismic retrofitting, state-of-the-art infrastructure, and artisan-level craftsmanship throughout. Continuing beyond the main residence is a 2 story guest/caretaker's house. The heritage grounds are a living piece of California history. Originally designed by the same landscape architect responsible for the adjacent Filoli estate, the gardens include a pool by Thomas Church. This is a once-in-a-lifetime opportunity to live within a rare expanse of natural beauty, wrapped in complete privacy, where historic architecture and legacy gardens have been renewed with clarity of purpose.

Tucked away at the end of a private lane, this beautifully appointed home offers the perfect blend of privacy, contemporary style, & outdoor livability on more than one acre. Refreshed front landscaping & an expansive, partially covered front deck set the tone for the thoughtfully designed spaces within. Beautiful hardwood floors, vaulted ceilings, & walls of glass highlight the home's warm yet modern aesthetic. Two-story layout offers exceptional flexibility with 4 bedrooms, an office, & 4 full baths, including a main-level primary suite. Spacious living room with fossilized limestone fireplace, formal dining room, & a sleek maple kitchen with honed black granite & butcher block finishes, plus a sliding glass door to an expansive wraparound deck. Flexible-use office/den just off the foyer is ideal for remote work. Lower level features a large recreation room with a built-in workstation for two, along with 2 additional bedrooms, one with en suite bath. Terraced rear grounds are designed for both relaxation & adventure, with a free-form pool, barn for potential equestrian use, zip line, & newly refreshed landscaping. Just one-half mile from the heart of downtown Woodside & with access to acclaimed Woodside School, this home offers natural beauty, privacy, and a premier location.

This light-filled country home in the heart of central Woodside, on just over one acre, is privately positioned at the top of a gentle knoll beyond picturesque equestrian facilities. Inside, every room opens to the outdoors through sliding glass doors with views of surrounding redwoods. Formal living room features fireplace & opens to expansive front terrace, while the adjoining formal dining room connects to the rear grounds. Bright & light kitchen with breakfast bar seating opens to the inviting family room with a charming wood stove &access to the rear patio. Separate bedroom wing is arranged for privacy & guest suite with solarium tub that takes full advantage of the redwood views. Luxurious primary suite has access to both front & rear grounds, extensive customized closet space, plus a spa-inspired marble bath with vanities, jetted tub & shower. Equestrian amenities include a 3-stall barn with tack room & white fenced corral amid sun-swept open grounds and perimeter redwoods. An attached 3-car garage & adjoining large covered workshop complete the offering. Located just 1.5 miles from Woodside town center and with access to acclaimed Woodside School, this is a special opportunity to enjoy the best of country living in a premier location.

First time on the market in nearly 50 years. Almost three acres in sought after Central Woodside minutes to Roberts, Village market and horse trails. Original ranch home with newer addition, pool and ADU. Property is suited for complete makeover or reimagine as a new building site. Horses are allowable. Close to sought after Woodside Elementary.

A stately retreat, this exquisite home offers complete privacy just blocks from Town Center and the acclaimed Woodside School. Set behind electronic gates on more than one acre of level land, the property is a showcase of timeless elegance and modern luxury with resort-like amenities. Sustainable living is effortlessly integrated with 32-panel solar power, four Tesla Power walls for energy independence, Tesla charging in the detached 3-car garage, and thermal solar power for the pool. The expansive rear grounds are designed for resort-style living, featuring a 54-foot pool with a beach entrance with water jet, lap lane, spa, plus infinity wall with waterfalls. A state-of-the-art Kalamazoo Outdoor Gourmet kitchen, with Hybrid Fire Grill fueled by any combination of gas, wood and charcoal, gas-fired pizza oven ready in under 45 minutes to make great Neapolitan pizza, and a gravity feed smoker with room for three whole packer briskets, nine whole rib racks or two large turkeys. A fire pit terrace, bocce court, and level lawn provide endless opportunities for entertaining. Offering the best of Californias indoor-outdoor lifestyle, this exceptional property is a rare find so close to the Town.

Nestled in Woodside, The Perch offers 7.7 gated acres of unparalleled privacy and stunning views. The thoughtfully designed home features a spacious two-level floor plan with expansive glass walls that fill the interiors with light and offer seamless outdoor connections. The chef's kitchen, inviting living spaces, and four spacious bedrooms are ideal for both quiet living and entertaining. A separate guest house offers flexibility for visitors, extended stays, or remote work. The expansive grounds include meandering paths, secluded terraces, a pool with a fully equipped pool house, and a tennis court set beneath a canopy of trees. Open lawns provide ample space for gatherings or peaceful relaxation. Just minutes from Woodside's town center, Sand Hill Road, and Highway 280, with easy access to top local schools. This is California living at its finest - private, serene, and perfectly connected to Silicon Valley.