Woodside CA Real Estate & Homes for Sale

Set upon an extraordinary 3.25-acre setting, this charming one-story home offers a rare sense of seclusion and natural beauty, further enhanced by its adjacency to a protected 6-acre parcel that ensures enduring privacy. The grounds are a true sanctuary, featuring a 40-year-old native garden that blooms nearly year-round, and a spacious rear deck overlooks this serene landscape, creating a seamless connection between indoor comfort and outdoor living. The property is graced with mature fruit trees, including pear, cherry and peach trees that add both charm and seasonal delight. Inside, the living room is a striking centerpiece, featuring a grand stone fireplace with a wood stove insert, complemented by soaring redwood-beam ceilings that add warmth and character to the space. A generously sized family room offers flexibility for relaxation, entertaining, or extended living. Modern convenience meets country tranquility with reliable high-speed internet, making this an ideal retreat without compromise. Surrounded by scenic, horse- and dog-friendly trails and supported by a welcoming, close-knit neighborhood, this is a setting that offers both peaceful escape and a genuine sense of community and exceptional opportunity to experience refined rural living at its finest.

Designer Transformation on 1.5 Acres Steps to Town! A remarkable whole-home transformation has elevated this property into a showcase of design, quality, and livability. Modern and full of sun lit spaces, the setting unfolds with park-like grounds that capture the essence of Woodside country living. Offering a stunning 4 bedroom 3.5 bath main house and a well-appointed 2 bedroom guest house with full kitchen and laundry adds exceptional flexibility for extended family, guests, or even office use. Inside, a beautifully orchestrated floor plan offers predominantly single-level living with subtle elevation changes that define spaces while maintaining an open, flowing arrangement ideal for both everyday living and entertaining. Outdoor amenities are equally compelling, highlighted by a sparkling pool, vast lawn areas, and a bountiful orchard alongside a charming chicken coop that enhances the propertys country appeal. All of this plus access to acclaimed Woodside Elementary School, offering a rare combination of privacy, scale, and convenience. Attached 3-car garage with 2 EV outlets. This home is a must see with too many amenities to mention.

Tucked at the end of a cul-de-sac, this meticulously maintained 2,235 sq ft modern Craftsman sits on a 7,800 sq ft lot framed by soaring redwoods and mature Japanese maples. Inside: vaulted ceilings, gleaming hardwood floors, two fireplaces, a chef's kitchen with BlueStar range and wine fridge, a cherry-paneled office with built-ins, and central heat and air throughout. The primary suite opens directly to a deck with fire table and serene garden views. Three bedrooms, 2.5 baths, two-car garage with storage steps from Woodside Elementary and downtown. Homes like this don't come along twice.

Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.

Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a quiet part of the sought-after Woodside Glens neighborhood, features a host of thoughtful upgrades by long time owners. They created a floor plan which showcases views from nearly every room and which, with its ipe hardwood spacious rear decks, presents a host of seamlessly flowing indoor/outdoor entertainment options. All new appliances were added in the chefs kitchen, the hardwood floors were recently refinished, new dual paned windows installed, high end finishes and touches were made throughout and the outside grounds sport attractive low maintenance, water-conserving plantings. Designed around light and nature, the home currently has three bedrooms on the main level and a lower level with an expansive family room and adjacent primary suite, all of which provide a range of configuration alternatives for home office, workout or entertainment setups. Come see this amazing home!

Set on 2.6+ wooded acres in the hills, this warm & beautifully renovated home offers something genuinely rare on the Peninsula: complete privacy amid towering redwood trees, a profound sense of forest immersion, and less than 15 minutes to Sand Hill & 280. The updated & open floor plan kitchen flows into generous dining and living spaces, all oriented towards sweeping forest views. Natural light fills the space, and wraparound decks extend living outdoors, with a hot tub just off the primary suite. A flexible two bedroom wing can accommodate children, teens, guest rooms, or office and studio space. An independent 1-bdrm ADU with its own kitchen / bath is ideal for rental income, an au pair, or an aging parent. The kitchen, secondary bathrooms, finishes, HVAC, roof, and water heater - have all been recently renovated, and pre-sale inspections were completed with virtually all items addressed. Hiking, cycling & equestrian trails connect directly to the property, and the land is zoned for horses. Stanford's campus is a short, predictable 25 min commute away. Zoned for Portola Valley El / Mid schools and Woodside HS, with several excellent private schools nearby. Soaring redwoods, architectural warmth & effortless access to the heart of Silicon Valley - come see it for yourself.

This is an idyllic Woodside property on over 1 level acre, where open land, equestrian facilities, and close-in convenience come together just one-half mile from the Town Center and highly acclaimed Woodside School. The expansive, level grounds set the tone complete with a 1 bedroom and 1.5 bath guest house, barn, fenced paddocks, pool, and broad stretches of lawn that capture the true spirit of country living. The home has been beautifully remodeled with a fresh, cohesive design that includes all-new lighting, a fully renovated kitchen, and beautifully updated bathroom. The interiors feel bright, current, and immediately livable, and a remodeled 1 bedroom guest house adds valuable flexibility for extended stays, office use, or possible rental. Beyond what is already in place, the scale and level nature of the property presents outstanding opportunity. Expansion, further personalization, or even the creation of a new estate can all be envisioned here, making this property as compelling for today as it is for the future.

Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. Spanning approximately 2,200 sq. ft. on a nearly 0.5 acre lot, this home features verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows which bring the natural beauty of the Glens inside. The floor plan includes a vintage kitchen, a dining area overlooking the oaks, and two bedrooms -- one featuring its own fireplace. Central air-conditioning provides year-round comfort. Upstairs is a versatile loft with a storage area. The lower level features a large bedroom with a bathroom and shower, an oversize 2-car garage, plus driveway space for 2 additional vehicles. With the large lot, an ADU is possible (buyer to confirm with the town). Located in the district for top-rated Woodside Elementary (K-8) and Woodside High, this home is moments from Woodside Village and offers a convenient commute to the entire Bay Area via Hwy 280. Experience the quintessential Woodside lifestyle in this timeless woodland sanctuary.

Set on a beautifully landscaped setting with sweeping Bay views, this impeccably maintained Woodside residence offers a rare blend of privacy, scale, and resort-inspired living. Spanning approximately 3,520 square feet, the 4-bedroom, 3.5-bathroom home is thoughtfully designed with a seamless balance of formal and casual spaces. A gracious entry introduces light-filled interiors with high ceilings, refined millwork, and an elegant flow throughout. The living and dining rooms open effortlessly to the outdoors, while the well-appointed kitchen complete with custom cabinetry, stone countertops, and a central island anchors the homes gathering spaces. The primary suite is a true retreat, featuring generous proportions, a private view deck, and a spa-like bath. Additional bedrooms offer flexibility for guests, office, or extended living. Designed for both everyday living and entertaining, the grounds are exceptional featuring expansive patios, manicured landscaping, a sparkling pool, and a covered lounge area. Multiple vantage points capture the surrounding natural beauty and distant views, creating a sense of tranquility throughout. A rare opportunity to enjoy elevated living in one of Woodsides most sought-after settings, with convenient access to top Peninsula amenities.

Extraordinary residence on 5.32 acres with opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway and sweeping views of San Francisco Bay. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble staircase with hand-forged railings leads to the upper level with formal living room, formal dining room, tremendous kitchen, family room, office, plus grand primary suite with 2 full baths. 3 luxurious bedroom suites plus large office and conference center make up the ground level. Breathtaking views from every room on both levels. Elevator in the main residence. 1-bedroom pool house and studio guest house, each with bath and full kitchen. Sparkling pool and spa plus fireplace terrace for idyllic entertaining in complete privacy.

This Custom built home is perched high on the Skyline ridge (approx. 2000' elevation) with the Pacific Ocean on one side the SF Bay on the other. Located in the exclusive Woodside neighborhood of Kings Mountain, this modern retreat was built with natural filtered light through the Redwoods in mind surrounded by about an acre of wooded privacy. Think open floor plan flow, soaring ceilings, and a wall of glass framing endless redwood canopies. Gourmet kitchen opens to a family gathering area with wood burning stone fireplace. Spa-like baths with a steam shower in the master bathroom, large deck in back for your entertainment needs, a private heated lap pool below, and a separate entrance to an attached ADU/art studio/private office with it's own kitchen and bathroom - it's all here, your own mountain retreat wrapped on a rare level lot where hi-tech meets tranquility and serenity. Woodside's hidden gem where you can become part of a true community - minutes from a top rated elementary school, very active and vibrant community. Only 10-15mins drive to either San Mateo or Half Moon Bay, 20 min to SFO, 25 min to Stanford and 30-40mins to SF - yet worlds away from the chaos. Perfect for remote execs/workers, nature lovers, hikers/bikers, or anyone craving Elevation - literally!

Hidden gem on nearly half an acre behind a private gated entry with professionally landscaped grounds, mature orchard trees, & year-round blooms. The exceptional single-level 3 bedroom, 3 bath 1,842 sqft main residence was completely renovated in 2017 & features an open, light-filled floor plan with skylights & French Oak floors throughout. The entry opens to a spacious living room with custom built-ins & designer lighting, flowing seamlessly into the chef's kitchen with a large center island, Thermador appliances, & dining area. Multiple glass doors open to a stunning 400+/-sq ft lanai, creating effortless indoor/outdoor living. The primary suite retreat with spa-like bath featuring Italian porcelain tile, mosaic marble floors, chandelier, & custom closet. Outdoor living spaces include multiple seating areas, an outdoor kitchen, & gas fire pit, ideal for entertaining year-round. A detached garage offers approx. 687 sqft of flexible space for guest suite or home office, plus an additional 600+/- sqft basement. Additional features include a private well & potential to add an ADU or expand further. Ideally located moments from Village shops & restaurants, hiking & biking trails, Edgewood Park, Stanford University, major tech campuses, & Interstate 280. Excellent Woodside schools.

Nestled in a highly sought-after Woodside neighborhood, this single-family home offers the rare combination of privacy, space, & future potential. Situated on an expansive ~0.340.37 acre lot (15,000+ sq. ft.), the property provides generous outdoor space ideal for entertaining, expansion, or the opportunity to build your custom dream home. The residence features a remodeled kitchen & an upgraded 150-amp electrical panel (completed in 2011), offering a solid foundation for comfortable living or further enhancements. Located in a low-density, established community, this home enjoys a serene, mature setting with exceptional privacy. Zoned for top-rated Woodside Elem., & Woodside High, its an excellent choice for those seeking both tranquility and access to quality education. Convenience meets location with just a 1015 minute drive to Downtown Redwood City, where youll find an array of dining, shopping, & everyday amenities. Commuters will appreciate the close proximity to Redwood City Caltrain Station and easy access to Highway 101 & I-280 via Woodside Road. A unique opportunity to own in one of Woodsides most desirable areas with endless potential.

Tranquil Woodside Retreat Nestled within one of Woodside's most sought-after enclaves, this enchanting single-family residence offers a rare blend of privacy, natural beauty, and timeless appeal. Set on expansive, level to gently sloping grounds, the property is ideal for equestrian use, featuring serene open spaces framed by mature trees and lush, thoughtfully designed landscaping. Bathed in dappled sunlight, the home exudes warmth and charm throughout. The well-appointed floor plan includes 4 bedrooms and 2.5 bathrooms, with inviting living spaces that seamlessly connect to the outdoors perfect for both relaxed everyday living and elegant entertaining. Step outside to your own private oasis, complete with a pool, lush lawns, barn and meandering brick walkways. Whether enjoying quiet mornings or hosting gatherings, the setting offers unmatched serenity and beauty. Located within the boundaries of the highly acclaimed Woodside Elementary School, this exceptional property combines rural tranquility with convenient access to nearby amenities. A rare opportunity to experience the quintessential Woodside lifestyle.

Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning just over 3.4 acres, this expansive property showcases rare Bay views. There is an existing planning study by Pacific Peninsula Architects for guidance in future opportunities. Positioned at the end of a private lane, the setting reflects the essence of Woodside country living, with lush perimeter trees and vast open land that offer a serene and private natural environment. The gated property includes an existing one-level home, a pool, and an original tennis court. Just one mile from Woodside Town Center and acclaimed Woodside Elementary School, and only minutes to Stanford University, Sand Hill Road venture capital firms, and the heart of Silicon Valley, this location offers both seclusion and convenience.

7.7 gated acres with Views, Pool, Tennis Court, & Guest house. Bordered by Thornewood Open Space Preserve, and with incredible San Francisco Bay and western hill views. Main home with dramatic formal rooms, walls of glass, and tile or hardwood floors. Sleek modern kitchen with oversized island seating. Main level primary suite with views and spa-like bath plus secondary suite. Lower-level recreation room, customized wine cellar room, plus two beds and bath. Partially enclosed hallway to the pool house with oversized bar, fireplace, 1.5 baths, and retractable glass doors fully opening to the pool. Detached guest house/ADU with full kitchen and bedroom suite plus separate fitness studio. Large circular pool, tennis court, stainless-steel outdoor kitchen, Pinot Noir vineyard, and vast level lawn. Portola Valley schools and direct access to miles of open-space trails.

Set on quiet Native Sons Road, this approximately 3.63-acre property offers privacy, natural beauty, and an opportunity to restore or reimagine a home in one of the Peninsulas most beloved mountain communities. A charming cottage surrounded by mature trees and near El Corte de Madera Open Space Preserve, the setting feels peaceful and inspiring. The existing residence is ready for a new vision, whether as a creative retreat, writer's paradise, weekend escape, or future custom home. With vintage character and a truly special setting, this property invites its next owner to reimagine and create a personal sanctuary in the heart of Woodside's beloved Kings Mountain.

This property scores high on the unique scale! Just 5 minutes drive from Alice's Restaurant, nestled in a sorrel, fern and redwood gorge, this two bedroom, two bath home is an engineering feat to behold. Outstanding vehicular accessibility as the .87 acre property enjoys a horse-shoe looped driveway off Highway 84 which would be ideal for heavy equipment operators, or motorcycle enthusiasts. There is a large shop and multiple outbuildings. 20 minutes drive to Palo Alto yet a world away; think clubhouse, weekend get-a-way, or create your own Dwell Magazine worthy abode.

Sweeping, unobstructed San Francisco Bay views define this contemporary estate set on more than an acre in Woodside Hills, with dramatic scenery enjoyed from nearly every room. Walls of glass, soaring ceilings, and refined finishes including marble, granite, and travertine floors create a striking yet warm aesthetic throughout approximately 4,800 square feet across two levels. The expansive kitchen and family room anchor the main level, complemented by gracious formal living and dining spaces that provide multiple areas for entertaining. The upper level offers additional gathering space including a media room, along with four bedroom suites highlighted by a luxurious primary retreat with a spa-inspired bath. Outside, the grounds feature a pool and pergola-covered terrace, all oriented toward the views. Climate control ensures year-round comfort, while a gated setting offers privacy close to parks, nature preserves, and convenient commute options.

Set on more than 2.5 acres of quintessential Woodside grounds, this spectacular estate balances timeless elegance with easy comfort. Behind gates and surrounded by mature trees and lush foliage, it conveys a quiet sense of luxurious seclusion. Inside, more than 6,400 total SF includes a dramatic foyer with columns, expansive formal rooms, a chef's kitchen, private office, theater, and five bedrooms, including a sanctuary-like primary suite. Outdoors, resort-style grounds feature a pool, spa, pool house, patio with fireplace and grill, cascading waterfall with bridge, gardens, fruit trees, and a detached bonus studio for work or fitness. Tesla solar panels and 6 Powerwall batteries, a seamless Sonos sound system, and expert craftsmanship enhance every detail. Just minutes from Woodside, Sand Hill Road, Palo Alto, and top schools, it offers the rare blend of privacy, prestige, and proximity.

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc countertops. Every bedroom and main living area opens to wraparound decks with sweeping views. Dedicated office for remote work, and a large 2-car garage. Level yard for entertaining, with room for pickle ball court, plus a sunny pool area. Direct walking distance access to scenic hiking on Mid-Pen Open Space trails. Convenient door-to-door bus to top-rated Portola Valley schools.

Welcome to your peaceful redwood retreat with stunning forest views in the desirable Skyline area of Woodside. Surrounded by majestic redwoods, this beautifully remodeled home offers privacy, nature, and convenient access to nearby towns. Upper Level: A light-filled 2-bedroom, 2.5-bath home designed to bring the outdoors in, with expansive windows showcasing breathtaking forest and canyon views. The open layout is ideal for relaxing and entertaining, featuring a remodeled chefs kitchen with modern finishes and generous space for gathering. Lower Level: A separate unit with its own full kitchen, living room, and bathroomperfect for guests, extended family, or a private workspace. Enjoy peaceful redwood living just minutes from town, with easy access to hiking trails, Woodside Village, Highway 280, Stanford Shopping Center, and downtown Palo Alto

Significant Mid-Century Modern Architecture with Bay Views. Sweeping San Francisco Bay views take center stage at this exceptional Woodside Hills property with fresh updates throughout. Spanning one acre, the elevated corner lot is positioned to capture the expansive views while also providing generous level areas for outdoor living. Enhancing the setting is the gentle sound of a meandering creek and strolling paths that create a distinctly parklike ambiance. Fresh interior updates include new paint, refinished hardwood floors, and new carpet, all complementing the living rooms signature vaulted ceiling, handcrafted with layered redwood cedar rising to a dramatic center peak. Multiple fireplaces add warmth and character, while glass doors open to several outdoor spaces oriented to enjoy the Bay views. The formal living room and dining room each have Bay views, plus there is a large open kitchen and family room for everyday gatherings. Four bedrooms, an office, and 3.5 baths are well arranged, featuring a main-level primary suite and a second suite comprising the entire lower-level with outside access and flexibility for future ADU conversion. An attached two-car garage and abundant off-street parking complete this inviting retreat with close-in convenience.

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.

Mid-Century Modern enthusiasts will be delighted by this truly special Woodside retreat. Nestled in The Glens and surrounded by trees, this home sits atop an expansive preserve with access to hiking trails. Built in 1959, the home showcases iconic mid-century design with floor to ceiling glass that fills the upper level with natural light and opens to an expansive 900+ sq ft deck, seamlessly blending indoor-outdoor living and creating an ideal setting for entertaining. The modern kitchen is thoughtfully appointed with Carrara marble countertops and premium stainless steel appliances, including Bertazzoni, Viking, and Fisher & Paykel. The upper level features a spacious living room with fireplace, a motorized awning for the deck along with two bedrooms and a full bath. The lower level offers a versatile family room, generous storage, and carport access. The primary suite provides a peaceful retreat with its own bathroom and direct access to a secluded patio, perfect for relaxing among the natural surroundings. Other features and updates within the last year include a new roof, new deck, new A/C, new landscaping and a new driveway. A rare opportunity to enjoy timeless architecture, privacy, and the beauty of nature.