Portola Valley CA Real Estate & Homes for Sale

Welcome to the extraordinary lifestyle of Portola Valley w/ this brand new modern build ready for your enjoyment.3,497SF of open sunlit space & ultra tall ceilings w/ 3 ensuite BD's, 4.5BA's + 2 bonus flex rm's, perfect for use as a media rm, game rm, home theatre, playroom, gym, WFH office, or additional guest quarters. Picture yourself living in a place where the equestrian scene mingles w/ stunning natural beauty & breathtaking views while a stone's throw away from Silicon Valley's buzzing energy. This is where luxury meets elite, but in a serene, peaceful setting. Explore the trails on horseback, soak in the awe-inspiring scenery, enjoy quant local restaurants like Rossotti's Alpine Inn, the ThursdayFarmer's Market just steps away, & the acclaimed top-rated schools. Portola Valley has it all! A perfect blend of equestrian adventure, mesmerizing nature, academic excellence while minutes away from all the major tech giants, & a tight knit community atmosphere that's second to none. Welcome Home!

Step into this stunning single-level remodeled modern home nestled in the desirable Ladera neighborhood. Blending contemporary design with everyday comfort, this thoughtfully renovated home is the ultimate expression of California living. Dream chef's kitchen featuring a large center island, high-end appliances, custom cabinetry, & a walk-in pantry. This home has radiant heating, custom concrete floors, & large picture windows that flood the space with natural light, seamlessly blending indoor & outdoor living. Two spacious bedrooms share a Jack & Jill bathroom. A versatile bonus room perfect for a media room, home office, or even a fourth bedroom. Your own private resort awaits outside. Relax or entertain in the lush backyard, complete with a sparkling pool, mature landscaping, and multiple outdoor living areas. Convenienty located to the Ladera Rec Center, 5 miles to Stanford, near Silicon Valley, commute routes, and midway between San Francisco & San Jose international airports.

Stunning 3 Bedroom 3 Bathroom Home with Amazing Views. Formal Entry. Chef's Eat-in Kitchen with Breakfast Bar. Dining Area. Living Room with Fireplace. Separate Family Room with Built-ins. 3 Spacious Bedrooms. 3 Bathrooms. Primary Suite Retreat with Built-ins, Stall Shower, and Ample Storage. Interior Features Include Vaulted Ceilings, Multi-Zone Heating and Air Conditioning, and Japanese-Inspired Aesthetics. Lovely Landscaped 2.31+/- Acres with Breathtaking Views. Award Winning Portola Valley Schools

Come see this modern marvel. With a variety of recent updates, this spacious two bedroom bungalow is a wonderful country living retreat. Views of open space hills and near to Coal Mine Open Space Preserve and a host of scenic hiking trails. Situated on a 7,440 sf lot with ample off street parking on newly paved driveway, the home features a new roof, a main floor living room with high ceilings, hardwood floors, large wood white-washed beams, large glass picture windows and a scenic deck for having your morning coffee. The recently updated kitchen is conveniently located near a sunny series of rear decks, framed with gardens, mature oak trees and a sloping backyard, making a picturesque setting for outdoor entertaining. The primary suite is on the main level and includes space for a small office set up and an updated bathroom with dual sinks and a spa tub. A second bedroom upstairs has views of the nearby open space hills and features another recently updated bathroom. Los Trancos Woods neighborhood is only minutes from a host of amenities which include Roberts Market, Windy Hill Open Space Preserve, Rossottis Alpine Inn, Stanford University and Hospital and Silicon Valley business activities. It is in the acclaimed Portola Valley School District. This is your next home!

Beautifully remodeled and remarkably bright, this home is a rare find in Los Trancos Woods. In an area known for its wooded hillside terrain, this property offers a refreshing contrast with abundant natural light, expansive level outdoor areas, and thoughtfully updated interiors. High-quality finishes, cathedral ceilings with skylights, and newly refinished hardwood floors enhance the inviting ambiance, while numerous French doors on both levels open to multiple sun-swept decks and terraces. The elevated main level features an expansive great room kitchen and three well-appointed bedrooms with three baths, including a luxurious primary suite with fireplace and private outdoor shower plus a second suite. The lower level offers exceptional flexibility with interior or exterior access, a full kitchen, living area, bedroom, and bath, making it ideal as an Accessory Dwelling Unit or private quarters for extended family or guests. Additional highlights include laundry on each level, a temperature-controlled wine cellar, backup generator, and a spacious rooftop deck for even more outdoor living options. Spanning more than one-third acre, the home also benefits from adjoining more than 3 acres of open space.

Stunning views are yours from this delightful 3 bedroom, 2 bath country home on half an acre of all usable land, a gardener's paradise. The main level has two bedrooms, one bath while the primary bedroom suite is tucked away downstairs. The spacious kitchen has a high ceiling & includes a generous eating area plus glass slider & windows all around to take in the beauty of the trees and colorful garden. The living/dining area captures the most spectacular views toward the east over Portola Valley. Every sunrise is different, and the moon is captivating. Outside, extensive decking includes an inviting wisteria covered arbor while winding paths lead to an amazing variety of plantings and sitting areas. Nature is all around. Quail, hummingbirds, hawks and many other birds are abundant. In spring and summer, watch out for a doe and her fawns crossing the road. Separate from the main house is a two car garage with an outside stairway to a lovely second level bonus space. All of this, plus the amenities of Portola Valley's fine schools, trail system, vibrant Town Center with playing fields, pickle ball courts and library, and quick access to Hwy 280, make this a wonderful place to call home.

Welcome to a remaining piece of Portola Valley history, full of possibilities! The charming and rustic original structure, with its tall brick fireplace, high ceiling, and exposed rafters, rests on a sunny, gently sloped, half acre lot. Later additions include a very large primary bedroom and bath. A wide veranda wraps around two sides of the house, perfect for relaxing while taking in the expansive view over Portola Valley and on to the East Bay hills. Colorful sunrises, full moons, and an occasional complete rainbow are yours to enjoy. An additional deck provides another viewing spot, with access from both the primary bedroom and the dining room. Nestled in the Woodside Highlands neighborhood, this location offers Portola Valley's excellent schools and provides nearby access to Portola Valley's hiking trails and to the popular Town Center with its library, children's playground, tennis and pickle ball courts, playing field, a redwood grove, and farmers' market. The half acre lot is all usable. Old stonework lines paths and a pond, and off street parking is plentiful. Bring your imagination and make this lovely space your own!

This 1.25+/- ac. lot has been landscaped to perfection. It is a private, restorative environment that provides seasonal color, nourishment, room to play, & entertain. The home is embraced by the venue in a way that blurs the line between indoors and out. Every window frames lush vistas, the solar-heated pool, majestic redwoods, & level lawn. The home has 3-levels with 5 bed, 3.5 baths, a great room with chefs kitchen, large dining room & cozy sitting room...all opening to yard & pool. Need a home office, bookshelf lined library complete with desk, large family room, and a lower-level with space for a gym/game or media room/separate craft or homework center, large office with custom built-ins, (the lower-level has a private stairway & entrance). In addition there is a guest cottage with a full kitchen, living/dining area, 2 bedrooms, and full bath (separately accessible for pool area). The home has 2 entrances, ample extra parking, a 2-car garage, separate 1-car garage, plus a storage shed. The central Portola Valley location convenient to local shopping, Alpine Hills Swim & Tennis club, The Alpine Inn, excellent PV schools, & just 4 min. to Hwy. 280.

Discover unparalleled luxury in this spectacular modern estate offering 5,560 livable sq feet and ideally positioned atop a 2.5-acre knoll in the heart of Portola Valley. Expertly re-envisioned by Handa Developers Group, this residence offers sweeping western hill views, privacy & expansive flat grounds for seamless indoor-outdoor living. A gated motor court leads to a dramatic glass entryway opening to elegant living & dining spaces that frame picturesque vistas - ideal for intimate gatherings or grand entertaining. The heart of the home is an expansive kitchen-family great room featuring a large center island, Wolf & Sub-Zero appliances, a sleek wet bar & doors that extend effortlessly to the outdoors. The main home offers 6 beds & 4.5 baths, including a luxurious primary suite with a spa-inspired bath. A main-level guest suite & dedicated office add flexibility. Outdoors, resort amenities include a sparkling pool, a covered outdoor dining/kitchen pavilion, fully equipped guest house with bedroom, bath, full kitchen & laundry, plus a pool house with gym & full bath. The expansive flat turf lawn & putting green complete the idyllic grounds. Benefitting from Portola Valley schools & close to Stanford, Sand Hill Rd & top tech campuses, this is an exceptional Silicon Valley estate.

On nearly 2 acres in the prestigious Blue Oaks community, an enclave of custom homes surrounded by 217 acres of open space, this custom-built home showcases Mediterranean design and sweeping views from most rooms. Outside, the Terracotta clay tiled roof makes a striking first impression while inside, lofty ceilings, deep crown moldings, and floors in antique French tiles and fine oak exude timeless appeal. The two-story floor plan, plus lower-level garage, comprises formal living and dining rooms, a cherry-paneled office, and an updated kitchen with custom cabinetry, natural stone countertops, and high-end appliances. The adjacent family room has a focal point stone fireplace and built-in media center and most rooms open to the grounds where heritage oaks, bluestone patios, and a citrus orchard are surrounded by beautiful grounds and vistas. Upstairs, the primary suite is a luxurious retreat alongside a second suite that is ideal for guests, plus two additional bedrooms and a bath. A community pool, spa, and clubhouse are added bonuses, along with miles of hiking trails and access to top-rated Portola Valley schools. Welcome to the Blue Oaks lifestyle.

Contemporary masterpiece with spectacular Windy Hill views designed by architect Ana Williamson. Featuring steel I-beams, soaring ceilings create openness & strategically placed windows fill the space with light highlighting the natural setting. The modern open floor plan includes chef's kitchen with high-end appliances, custom Italian cabinetry & Dekton ceramic countertops. Floor to ceiling walls of sliding Fleetwood glass doors make for easy indoor/outdoor entertaining, extending on to the covered patio with heated floors, fireplace, & Italian pizza oven. The private primary suite upstairs has expansive views, walk-in closet & large chic bathroom. Built with fire safety in mind with a metal roof, no exposed eaves, fire sprinklers, owned solar & backup generator. Detached guest house with full kitchen, 1.5 bathrooms & large bedroom. Bonus detached workshop with extra storage provides a multitude of possibilities. Over 1 acre fully fenced with drought resistant Mediterranean native landscaping, mini orchard, ipe trellis with mature wisteria, 100 sq ft garden shed & raised garden beds. This thoughtfully designed luxury home offers privacy, stunning views, proximity to town, access to commute routes in Silicon Valley & serene hiking trails in the rolling hills of Portola Valley.

Luxury Silicon Valley Getaway in Portola Valley, updated single family craftsman/rustic with modern interior, move-in ready on a large 11,500 square foot lot with panoramic views of western hills, surrounded by nature, natural beauty and network of trails. Open floor plan with natural light throughout, skylights, hardwood floors, built in bookshelves, new kitchen and appliances, eat-in kitchen and sliding glass doors to the expansive deck from living room and primary bedroom, outdoor Jacuzzi. Bonus room below can be used for guests, entertainment, media room, hobbies, workshop or possible JDU. Existing carport and large 11,500 sq ft lot with area to expand. Short drive to Roberts Market, the library, local tennis and swim club, equestrian clubs, bike routes, golfing, Rossottis, Ladera Shopping Center, Bianchinis and Stanford University less than 5 miles without getting on the freeway. Sunrise trail is just two doors down, with access to 650+ acres open space and trails. Also, direct access to Arastradero Preserve and Los Trancos Open Space with over 1500 acres of more hiking trails.

This exquisite Cape Cod-style residence is nestled on a serene cul-de-sac in central Portola Valley. Set on an acre lot w/ captivating western hill views, this home offers a sophisticated and flexible living space. On entering, find a spectacular living room flooded with natural light from floor to ceiling windows. The spacious family room has vaulted ceilings, stone fireplace & dedicated dining area open to the large chef's kitchen equipped w/ 2 dishwashers, dual ovens, sub-zero refrigerator, walk-in pantry, wet bar & island. Opening onto the lush patio, this space is ideal for both everyday living & entertaining. The main level also features 1.5 bthrms, laundry, an office and a versatile den/game room w/ direct access to the yard. Upstairs, discover 5 bdrms, 3 bthrms & additional office offering ultimate functionality. The primary suite is a luxurious retreat boasting two walk-in closets, fireplace, darling window seating & large bthrm with soaking tub. The backyard is a private haven w/ lawn area, mature trees, play structure, & direct access to hiking trails. Short walk to award-winning Portola Valley schools and Woodside Priory. The house is wired for high-speed internet, wifi lighting/security & EVs. Elegant design meets modern amenities in an unparalleled natural setting.

Villa del Prato is a singular gem among Silicon Valley estates. Nestled in the woodlands of Portola Valley on nearly 12 acres of tranquil, private, flat land, the estate comprises three structures: a main house (12,000 sf); an entertainment or business building (6,500 sf); and a pool house (2,000 sf). Inspired by classic Palladian Italian architecture, each structure is reminiscent of a Tuscan villa, featuring soaring arches, 20-foot ceilings, dramatic skylights, solid stone columns direct from Italy, and the finest-quality finishes. The main home, built on two levels, features a one-of-a-kind 900-square-foot dressing suite that doubles as a safe room. Unseen are advanced systems for the comfort and security of residents and guests. The entertainment/business building provides an opportunity for customization. With its towering columns, airy loggia, and spacious ballroom, it could be utilized for entertaining, as a home office, conference center, staff housing, or a home for your next startup. Electrical, plumbing, HVAC, and other key systems are fully fitted out. This grand estate is centrally located close to Hwy 280 mid-way between San Francisco and San Jose, with easy access to major airports and technology and business centers. (All sf info per plans).

Nestled on more than 1.5 acres, this exquisite home has been thoughtfully transformed to deliver an unparalleled living experience. With more than 4,200 sf, the home exudes luxury, from its soaring ceilings and impeccable finishes to the dramatic use of glass. Expansive living areas, multiple fireplaces, a gourmet kitchen, and an executive office offer both comfort and style. Four bedrooms are highlighted by a private, retreat-like primary suite, complete with a spa-inspired bathroom. Outside, multi-level grounds provide the perfect venues for enjoying the idyllic setting, and this home also includes air conditioning, and a 3-car garage. Located just moments from trails, nature preserves, and Roberts Market, this home offers tranquility and convenience, while easy access to Interstate 280 ensures the entirety of the Bay Area is within easy reach. Plus, children may attend acclaimed schools such as Ormondale Elementary and Corte Madera Middle (buyer to verify eligibility).

Welcome to 1 Hayfields Road! Motivated Seller - best price on the flats of Portola Valley!!! Nestled in a serene and peaceful country setting, this inviting rancher offers the perfect balance of privacy and convenience. With stunning access to nearby trails, you can enjoy the natural beauty right outside your doorstep, whether you're hiking, biking, or simply soaking in the outdoors. Inside, this lovely, updated home are multiple living areas, including 4 bedrooms and 2 bathrooms. Featuring soaring cathedral ceilings, skylights, and expansive windows, the home is filled with natural light, creating a bright, open atmosphere. Updated kitchen with stainless appliances. Separate laundry with top of the line LG washer and dryer. Solar panels and 240 outlet in garage for EV charging. The yard offers a natural retreat with seating and dining areas, and is partially fenced for either a dog run or a child's playground. Located just 3 miles from 280, and close to the Portola Valley Schools, and local amenities, you won't have to sacrifice accessibility for country living.

This rare offering truly has it all 2.5 acres in the prestigious Westridge area with complete privacy set back from the street, San Francisco and foothill views, a regulation-size tennis court, resort-style pool with elevated spa and waterfall, and a poolside sauna with an outdoor shower. The well-appointed classic ranch home features bright and light interiors with fine hardwood floors throughout its effortless single-level design. Recent updates, including crisp white paint, refinished floors, new lighting, and newer appliances, make this home move-in ready while also presenting an excellent opportunity to further transform it into your dream vision. Four spacious bedrooms, each with an en suite bath, include one that is privately located and perfect for guests or a home office. In a premier location, with 2.5-acre minimum parcels, and access to top-rated Portola Valley schools, this property offers an unparalleled lifestyle of sophistication, serenity, and endless potential.

Discover unparalleled modern living in this ultra-modern Portola Valley home, where exceptional design harmonizes with the surrounding natural landscape. An island-stone waterfall welcomes you at the grand entry, flanked by a home office & flexible guest suite with a convenient kitchenette. Ascend the staircase to reach the heart of the home: a vaulted great room that opens to a chefs kitchen featuring custom walnut cabinetry, leathered Cote D'Azur countertops, a walk-in pantry & luxury integrated appliances. Expansive telescoping glass doors open to a spacious deck & beautifully landscaped yard, complete with a relaxing hot tub for the ultimate outdoor retreat. At days end, retreat to the primary suite, featuring a private balcony, spacious walk-in closet & a spa-like bathroom with a walk-in shower framed by a skylight and luxurious rain shower head. This property is the ultimate blend of exclusive luxury & functional family living, with amenities including a library, wine room, mudroom, office & spacious guest suite with kitchenette all set on nearly a third of an acre. Owned solar & EV charger. Ideally located just minutes from Alpine Rd, 280 & top-rated Portola Valley schools. Ideally located just minutes from Alpine Rd, 280 & top-rated Portola Valley schools.

Welcome home to a brand new exquisitely designed contemporary residence. This stunning luxury home includes 4 bedrooms, 5 bathrooms and 4 decks with spectacular bay views from the master bedroom and roof deck. Situated on top of a hill across the street from a serene lake and steps from Old Spanish Trail into the Windy Hill Preserve, this new home is perfect for those who love the woods. The roof deck sits at the oak canopy with impressive views of the Bay Area, Fogarty vineyards and Los Trancos Woods' majestic oaks. At night, enjoy the glittering city lights and star gazing. Features include oak hardwood floors throughout, a chef's kitchen with a Delmare leather quartzite island, Thermador appliances include a standing wine fridge, double oven, electric range and hood. Designed with Brizo fixtures, storage room wine cellar, Tesla Powerwall 3 Battery with new 8KW solar system, great room sound system, vaulted ceilings, skylights, master bedroom deck, master slab shower with Brizo fixtures, and an attached ADU that could be used as nanny quarters, home office, guest suite, or rental unit. The craftsmanship and sophisticated design in this residence are exemplary. Roberts Market, Alpine Inn and top-rated schools are minutes away. This modern home is a must-see!

Build your dream home on this approx. 4.2-acre undeveloped country parcel situated adjacent to Portola Valley on Santa Clara County land just up from the Ladera Shopping Center shops and restaurants. The lot is surrounded by open space, Stanford lands and the gently flowing Los Trancos Creek and is in the Palo Alto Unified School District.

Exceptional opportunity for a developer or end user to build on this flat .77 acre lot, out of the flood zone (LOMA issued) with preliminary plans, land survey, geotechnical report, contractor bids and etc in a tranquil setting assigned to award-winning Palo Alto schools. Property is on a quiet lane off of Alpine Road so there is no traffic (punch in 4133 Alpine Road in GPS, property is next door). Plans are for a 5 bed, 4.5 bath modern two-story residence, designed by renowned M Design Architects. Though it feels removed, this one of a kind property is moments away from the Alpine Hills Swim and Tennis Club, Ladera Country Shopper, Stanford University & Shopping Center and vibrant Menlo Park and Palo Alto, while children may attend top-ranked Palo Alto schools, including Nixon Elementary (#6 Elementary School in California), Fletcher Middle (#8 Middle School in California), and Gunn High (#1 High School in California).

Completed in 2006, this magnificent vineyard estate is the perfect place to escape from the fast daily pace of Silicon Valley. The approximately 41 acres are as peaceful as they are beautiful, with spectacular top-of-the-world San Francisco Bay views. Arriving on the front terrace is as if stepping into the Italian countryside. The scale of the home is destined for grand entertaining spilling out to exceptional front and rear terraces. The kitchen is a culinary retreat with commercial-quality appliances, and the wine cellar awaits a sizable collection. Multiple rooms for everyday living, a theatre, plus a well-being center with spa, steam, and sauna add luxurious touches. Both 5660 Alpine Road and APN 080-040-120 are being offered for sale together.