Portola Valley CA Real Estate & Homes for Sale

Originally the 1912 gatehouse to Willowbrook Farm, this iconic compound was expanded and totally rebuilt in 2012. This "Home of the Future" is within a storied stone envelope, set on 1.13 flat, gated acres. The over 5,000sf compound features soaring ceilings, Venetian plaster walls, individually climate-controlled rooms, including the wine/library lower level, and a finished attic retreat. The culinary kitchen is a masterpiece with Carrara marble counters, a massive island, and chef-quality appliances. Designed for a "live-work-play" lifestyle, the estate includes a detached guest Cottage and a huge studio that can serve as the ultimate tech HQ, yoga sanctuary, or artist retreat (virtually staged). 10 Tesla Powerwalls (135kWh) for 48-hour grid independence + 80amp EV charging. Direct $50k fiber line; 12 Wi-Fi 7/6 access points for full-acre coverage. 10-zone smart HVAC (9 new units in 2024) with simultaneous heat/cool capability and 24/7 Unifi AI security. Water: Whole-home filtration, leak-detection shut-off, and smart Rachio irrigation. The Grounds: A resort-style sanctuary featuring a crushed granite drive, double electronic gates, a meandering creek, and an expansive pool decks with a dedicated bath. Updated for the next century of living.

Imagine life at this exceptional Portola Valley residence: an elevated lifestyle in one of the areas most coveted settings. Close-in to Alpine Rd and Hwy 280, this private sanctuary is surrounded by natural beauty while close to every convenience. A dramatic arrival begins with a sculptural stone waterfall and a grand entry flanked by flexible living spaces: a private office or fifth bedroom with1/2 bath on one side, and a guest retreat with kitchenette & full bath on the other. This sets the tone for the homes sleek design and exceptional craftsmanship. Upstairs, soaring ceilings define the expansive living area, where walls of glass invite the outdoors in. Designed for entertaining and everyday living, the great room with modern fireplace opens through telescoping glass doors to an expansive terrace and resort-inspired grounds with a spa. The adjoining kitchen features bespoke counters, rich walnut cabinetry, generous pantry, and top-tier appliances. The luxurious primary suite offers a private terrace, walk-in wardrobe, and serene bath with skylit shower and rainfall fixture. Addt'l spaces include two more bedrooms, a library with fireplace, wine room, and mudroom. Owned solar and EV charging (240V) add efficiency. 12,400 sq. ft. lot within the Portola Valley Sch. District.

Nestled on one of Ladera's most sought-after streets, this delightful ranch-style home blends timeless charm with everyday comfort. A cozy living room with a fireplace and an expansive picture window invites natural light and serene views of the lush, private backyard. The eat-in kitchen features granite countertops, stainless steel appliances, and seamless access to the patio, perfect for indoor-outdoor living. The thoughtfully designed bedroom wing includes four bedrooms, two of which are connected by a Jack-and-Jill pocket door, ideal for shared living or added privacy. The primary suite offers its own en-suite bath and direct patio access. Enjoy a prime location near the Ladera Recreation Center, school bus stop, and Ladera walking paths, with easy access to Stanford, major commute routes, and top Silicon Valley employers. This charming home provides the perfect canvas to add your personal touch and make it your own!

This home personifies tranquility. Nestled in a serene country setting just minutes from I-280 and top-rated Portola Valley schools, this beautifully updated 6-bedroom, 2- Office 3+-bathroom custom designed home perfectly balances rural privacy with modern convenience. The interior boasts an expansive, light-filled atmosphere defined by cathedral ceilings and large windows that frame the surrounding natural beauty. High-end functional upgrades include a spacious center island kitchen with adjacent family area & fireplace. A formal dining room overlooking the pond and into the Redwoods. A spacious living room with soaring ceilings and fireplace. A large primary bedroom with a spacious walk in master bathroom and a nice private deck with a hot tub. 2 artist studios / offices. One was used a pottery studio the other was a photographic studio. Outside, the property serves as a private retreat with direct access to local hiking and biking trails. An additional magical feature is the adjacent pond. This provides a magical setting and helps the home create an oasis of peace and tranquility.

Newly built and tucked into the serene landscape of Portola Valley, this exquisitely designed contemporary residence offers a rare blend of privacy, scale, smart-home features, and flexible living spaces. The multi-level home is designed to embrace its Bay views and natural surroundings. Situated by a lake, the home is on a cul-de-sac leading to acres of open space and hiking trails. The main level features generous living and entertaining areas, including a spacious living room with fireplace, seamlessly connected to an outdoor deck ideal for indoor-outdoor living. Expansive windows and skylights invite in abundant light and peaceful views. The open and functional layout includes a high-tech chefs kitchen and dining area complete with wet bar and wine fridge. A dumb waiter connects the garage to the main level. Wi-Fi-enabled appliances, a Tesla PowerWall, and solar system fuel the multiple smart home features. An auxiliary family room and kitchen combination offers flexible living spaces for a home office, fitness area, guest suite, or attached ADU. Bedrooms are privately situated, offering quiet retreats. Step outside to experience Bay views from the master bedroom and rooftop deck that provide multiple vantage points to relax and take in the surrounding greenery.

Expansive grounds and sweeping Windy Hill Views define this extraordinary property in a premier and private Golden Hills setting. Spanning approximately 2.6 acres the property unfolds with open meadows, magnificent oaks, a prolific orchard, and a newly resurfaced pool and spa. The home is spacious, flexible, bright and welcoming--one that is immediately comfortable and highly livable. The predominantly single-level floor plan, fully oriented to the spectacular views, with an upstairs primary suite, offers generous scale, abundant natural light, and a seamless connection to the surrounding landscape. The garden and the home create a magical place for exploration, imagination and outdoor play. At the same time, the property presents an exceptional long-term opportunity. The expansive acreage, extraordinary views, and quiet, coveted location provide an ideal foundation for further transformation whether through renovation or the creation of a dream home. The result is a property that offers both immediate enjoyment and significant potential in one of Portola Valley's most sought-after settings.

Far-reaching views of Coal Mine Ridge define this beautifully remodeled home at Portola Valley Ranch, set on nearly one-half acre. Expanses of glass, soaring ceilings, and dramatic skylights fill the interiors with light and volume, while fine hardwood floors underscore a cohesive, modern aesthetic throughout the open main level. Indoor-outdoor living extends across both levels with expansive decks positioned to take full advantage of the natural surroundings. The primary suite with a spa-inspired remodeled bath is conveniently located on the main level and the lower level provides a family room, flexible-use room, and two additional bedrooms and a bath. Adding to the appeal is a full complement of amenities at The Ranch, including pools, tennis courts, a fitness center, vineyard and garden areas, a playground, and miles of scenic trails. A wonderful opportunity to enjoy a close connection to nature with convenient access to both San Francisco and Silicon Valley.

Rarely available estate, located in the highly sought-after Westridge neighborhood of Portola Valley. This lovely home is set on 3.86 serene acres w/ majestic oaks and offers a panoramic view of the SF Bay from Stanford to Mount Diablo. Enjoy a picturesque vista from the main home and newly built, stunning ADU. A gated driveway escorts you to a light-filled home highlighted by an open concept floorplan with high beamed ceilings and a wall of sliding doors to an expansive deck for al fresco dining and entertaining. Enjoy peaceful days and quiet nights filled with sparkling lights from the bay. The main home, containing 5bd/ 5ba, private office, family room and den one primarily one-story. The 1bd/1ba ADU has a spectacular deck with views too! Adding to the appeal is the sprawling grounds including a resort-like pool, hot tub, fire pit, gazebo, greenhouse, chicken coop and 2 fenced dog runs. Family/friends can gather throughout the exquisite property at numerous quaint outposts. This home is ideal for entertaining. Easy access to 280, Stanford University, Westridge hiking trails, shops and restaurants. Just 1.5 miles to the Ladera Shopping center, a 5-minute drive to Interstate 280, and access to top-ranked Portola Valley schools (buyer to verify eligibility)

Set on a rare, relatively flat .28-acre cul-de-sac lot in the heart of Ladera, this 4BD/3BA home offers an ideal blend of location, layout, and everyday livability. Quiet, safe, and incredibly convenient, it's just a short stroll to the Recreation Center with pool, tennis, and more, as well as the Ladera Shopping Centers restaurants, caf s, and grocery, with easy access to Highway 280. The home features a well-designed, highly functional floor plan with great flow between living spaces and bedrooms. The main level includes a sunken sunroom with skylights, an eat-in kitchen with floor-to-ceiling storage, and a living room with a wood-burning fireplace. Three bedrooms are on the main level, including one ensuite, plus a private den or home office. Upstairs, the oversized primary suite is a true retreat with private deck, walk-in cedar closet, and separate double vanity. The expansive lot creates a true outdoor oasis with terraced planters, generous activity space, and room to relax, play, and entertain. Modern essentials include an ADT alarm, centralized Ethernet/coax wiring, an oversized two-car garage, and laundry. Located within the highly regarded Las Lomitas School District, this is a rare opportunity to own a move-in ready home in one of Laderas most desirable neighborhoods.

TRI-LEVEL ESTATE OFFERS POOL HOUSE, 3+ ACRES | Transport yourself to the East Coast in this incomparable custom estate. Gated acreage framed by California oaks reveals an exquisite Shingle-style home surrounded by bridges, enchanting gardens, a three-car garage, and fully functional pool house with pool and spa. Faced by a circular gravel drive, the tri-level main residence built in 2010 has been wonderfully maintained, boasting all ensuite bedrooms, a study, gym, and media lounge with full bar. Enjoy a sensational master chefs kitchen, ultra-luxurious primary suite, multiple fireplaces, surround sound, and ground-level guest/au pair quarters. Superb details include graceful turrets, round windows, soaring ceilings, gorgeous hardwood floors, and extensive millwork throughout. Outdoor retreats abound with amenities like a barbecue island, fireplace, paver terraces, wisteria-laden pergola, raised beds, and more. Moments from shopping, dining, trails, and breathtaking scenery, this piece of bucolic paradise is nestled near tech and venture capital centers, and only ~ 30 minutes from SFO and SJC. Excellent Portola Valley Schools. Property is on sewer giving a buyer full use of the lot. Main residence 5861 sq ft, guest house 732 sq ft=6593 sq ft Plus 888 sq ft garage.

Spectacular VIEWS are the backdrop for this outstanding remodeled mid-century home located on a quiet, close in cul-de-sac in prime Westridge. Expand this lovely home or BUILD NEW on this spectacular 2.57 acre property featuring incredible views, peaceful gardens & gorgeous Oak studded knolls. Dramatic vaulted ceiling living room features built-in bar & floor to ceiling windows showcasing the views. Separate formal dining room overlooks the courtyard garden. Gourmet kitchen features custom cabinetry, slab stone countertops and quality appliances. 3 large bedrooms and 3.5 bathrooms include 2 primary suites, one upstairs & one downstairs. All bedrooms are suites & feature walk-in closets, views and marble bathrooms. Magnificent gardens include a charming, fenced courtyard entry with specimen trees & shrubs, colorful flowering annuals & perennials. The fenced rear garden showcases the VIEWS from the sparkling POOL surrounded by a patio/deck with roses, and flower beds, and features a waterfall and stream. Much of the property is usable/level and scattered w/ native trees, shrubs & well-kept Oaks. This is truly one of the prettiest, most serene settings in PV. Move into this turnkey home, or rent it while you make plans to build your dream home on this amazing view property!

On the market for the first time, this exceptional Craftsman home is located in prestigious Blue Oaks, an enclave of estate homes surrounded by 285 acres of open space & trails. Built by Chessler Construction in 2003, the home showcases timeless architecture, exquisite woodwork, & a flexible multi-level floor plan designed for today's lifestyle. Set on approx. 1.29 acres, the property enjoys a backdrop of natural beauty with miles of nearby hiking trails, plus sweeping views out to the San Francisco Bay & East Bay hills from the top level. Main level is ideal for both grand entertaining & comfortable everyday living, offering formal venues, professional office, & seamless connection to expansive outdoor spaces that include front & rear terraces, loggia with fireplace, plus an in-ground spa & outdoor shower. Primary suite has Bay views & each bedroom has private balconies & elegantly appointed bathrooms. Finishing touches include an attached 4-car garage, backup generator, & a community pool & clubhouse. Blue Oaks location offers quick access to Portola Valley's charming town center & excellent public & privates schools, with Stanford University just 15 minutes away. Acreage & open space provide unmatched lifestyle in one of the area's most sought-after neighborhoods.

Sunlit Gem on Nearly One-Half Acre with Plans to Expand. Fresh, inviting, and completely sophisticated, this retreat has been transformed into a light-filled setting. Easily accessed via wide streets, the property spans nearly one-half acre of predominantly level grounds and includes approved plans for a future expansion. The current home, with 2 bedrooms and 2 baths, offers a streamlined scale yet the open concept design lends an unexpected sense of expansiveness. A crisp palette of whites defines the interiors, from the all-white kitchen with quartz countertops and subway tile backsplashes to the remodeled baths finished in marble and tile. Vaulted ceilings with skylights and exposed beams enhance the airy atmosphere, while wood-like luxury vinyl floors provide continuity throughout. Multiple sets of glass doors open to wraparound flagstone patios and expansive land, where limited tree canopies allow brilliant sunlight to fill both the interiors and outdoor gathering spaces. Finishing touches include a separate laundry room, an outdoor storage shed, and a two-car carport. Portola Valleys acclaimed schools and miles of scenic trails are just moments away, making this a remarkable opportunity to enjoy contemporary style and comfort today with the option to expand in the future.

Perched on a knolltop within prestigious Blue Oaks, this luxurious estate epitomizes elegance and exclusivity. Set on 2.53 acres of naturally organic beauty, this residence offers unparalleled privacy and breathtaking views of the San Francisco Bay. A true sanctuary, the home seamlessly blends sophisticated design with the tranquility of its natural surroundings. The expansive living room, bathed in natural light from floor-to-ceiling windows, provides a stunning backdrop of the sweeping Bay views. The heart of the home is the gourmet kitchen, a culinary enthusiast's dream, that opens to a spacious family room, creating a true great room that is ideal for both everyday living and entertaining. Multiple adjacent terraces offer 360-degree views. Each of the 5 bedrooms is an en suite retreat. The primary suite offers a luxurious spa-like bath, walk-in closet, fireplace and picture windows that capture the serene vistas. In addition to an executive home office, the estate boasts a home gym, media/rec room, wine cellar, expansive swimming pool and 4-car garage. This estate in Blue Oaks is more than a home; it is a lifestyle. With its unmatched privacy, luxurious amenities and awe-inspiring views, it offers a unique opportunity to experience the pinnacle of Silicon Valley living.

Discover the perfect blend of nature and modern convenience at 1019 Los Trancos Road in the peaceful Los Trancos Woods neighborhood. This charming home, built in 1930, offers 1,770 SF of versatile living space (per the Seller) in two buildings with freshly painted exteriors. The 1,225 SF main house features three bedrooms and two baths, with vaulted ceilings and skylights that invite abundant natural light. The airy living room, featuring exposed beams, seamlessly transitions to a large deck and patio, ideal for indoor-outdoor entertainment. The galley kitchen is a chef's delight, featuring stainless steel appliances and ample cabinetry that overlooks the garden. A 545 SF studio is situated behind the one-car garage. While not reflected in the County records, the studio is a flexible space with a kitchen, stacked washer/dryer, full bathroom, new wall-to-wall carpeting, and a private deck - ideal for multi-generational living, working from home, or generating rental income. Positioned on a generous 9,360 SF parcel, you'll enjoy peaceful views and easy access to Portola Valley's lively Town Center and Highway 280 for easy commuting.

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.