Portola Valley CA Real Estate & Homes for Sale

Stunning Hacienda Compound with Separate Guest House, Pool House, and Greenhouse Amidst Beautifully Landscaped Courtyards. Formal Entry Elegant Living Room. Separate Office with Built-ins. Formal Dining Room. Chef's Kitchen with Center Island, Wolf Appliances, and Breakfast Room Opens to Spacious Family Room with Fireplace and Built-ins. Primary Suite Retreat Features Double Sinks, Stall Shower, Stone Soaking Tub, and Two Walk-in Closets. 4 Spacious Bedrooms. 4.5 Bathrooms. Upper Level Features Spacious Loft and Full Bathroom. Lower Level Features Expansive Wine Cellar. Interior Features Include High Ceilings, Multi-Zone Heating and Airconditioning, Laundry Room, and Vaulted Ceilings. Separate Guest House Includes Kitchen, Fireplace, and Full Bathroom. Separate Pool House Includes Full Bathroom. Lovely Landscaped 2.86 +/- Acre Lot with Sparkling Pool, Enclosed Courtyards, Mature Cactus Gardens and Landscaping, and Hand Laid Stonework. Award Winning Portola Valley Schools.

Located on one of Ladera's most desirable streets, this home offers the perfect blend of style, functionality, and comfort. Experience classic mid-century aesthetic with vaulted ceilings and expansive walls of windows that seamlessly connect the indoors with the outdoors. The family room has a cozy gas fireplace and lots of built-ins that include two pull-down tables perfect for work, study or hobby. Light and bright, the primary suite includes a walk-in closet and tucked-away bonus home office, providing a quiet space for work or study, plus stunning views of the backyard. Two bedrooms share a bathroom equipped with a Sauna. Formal dining room, built for hosting large gatherings, has a vaulted ceiling & ample built-in storage. Eat-in chef's kitchen has high-end app, lots of custom cabinetry, and granite counters, making cooking a snap. Enjoy your private backyard oasis featuring a stunning black-bottom pool and spa, ideal for hosting summer gatherings and relaxing with family and friends. A bonus 1 bedroom, 1 bath ADU is perfect for visiting guests or family members, offering them a private and comfortable space with private entry. Convenient to the Ladera Recreation Center, school bus stop, Stanford, easy access to Silicon Valley, commute routes & mid-way between SFO & SJC

Resting on over 3 acres, this spectacular estate, completed in 2024, presents an unparalleled living experience. Sleek exteriors, characterized by clean lines and minimalist design, evoke the precision of modern art. Step inside to experience interiors thoughtfully crafted to cater to a contemporary lifestyle, with walls of glass that seamlessly integrate indoor and outdoor spaces while showcasing awe-inspiring views spanning the San Francisco Bay and beyond. Generous gathering areas, a chef's kitchen, office, and more provide captivating venues, complemented by grounds featuring a pool. And this incredible location offers all-encompassing feelings of seclusion while still being close to everything Silicon Valley has to offer - San Francisco and San Jose are ~40 minutes way, two international airports are easily accessible, and Palo Alto, Stanford University, Sand Hill Road, and the area's premier public and private schools are all within easy reach.

Custom built in 2014, this organic contemporary home showcases architectural excellence by Simpson Design Group and meticulous construction by Portola Valley Builders. Situated on a beautiful 1.04-acre lot with sweeping views from the western hills at the front to Mount Hamilton at the rear, the property features a secluded pool and spa, plus a chicken coop and vegetable garden for a farm-to-table lifestyle. An inviting front courtyard offers incredible space for outdoor living, leading to the secluded pool area. The one-level, open-concept floor plan boasts towering ceilings, clerestory windows, extensive glass, and white oak floors throughout. Every room opens to the outdoors, including each of the four bedrooms, and skylights illuminate each of the three and a half baths. A spacious office caters to remote work needs or can serve as a fitness or media room. Modern conveniences include EV charging, remote-controlled blinds in the primary suite, surround sound in the great room, and a comprehensive security and surveillance system. Located near Roberts Market, Ladera Shopping Center, and renowned hiking and biking trails, this home is also within the excellent Portola Valley school district. This property offers the perfect blend of luxury, comfort, and convenience.

Secluded on a lush 1.5-acre lot, this tranquil Portola Valley home features 4 bedrooms, 5.5 bathrooms, and over 4,200 square feet of welcoming living space. The moment you step inside, you'll feel connected to the natural beauty surrounding the home, thanks to abundant light from picture windows, skylights, and transom windows, which highlight the serene grounds. High ceilings create a fresh, airy atmosphere throughout. No expense was spared in this stunning remodeled contemporary home. Key features include three stunning fireplaces, a chef's kitchen, with top of the line Hestan appliances, that opens to a spacious family room, and a home office ideal for remote work. Enjoy the comfort of a large primary suite and the convenience of an additional bedroom suite for guests or family. The property boasts ample patio space and a peaceful deck shaded by majestic trees. This prime location is just moments from nature trails and preserves, a short trip to Roberts Market, and close to both public and private renowned schools.

Magnificent! You will not believe the spectacular views of the Western Hills from this stunning contemporary move-in-ready compound. Located in the sought after Westridge Corridor of Central Portola Valley at the end of an elevated cul-de-sac, this estate offers the perfect blend of privacy and entertainment options. The current owners completely rebuilt the main home, upgraded the guest house and built a new two story detached studio to create an indoor/outdoor experience beyond comparison. The main home has an enviable mostly one level floor plan which not only captures the dramatic views from nearly every room but was also designed to promote an easy entertaining flow from the connecting kitchen, dining and living rooms to the expansive outdoor Ipe-wood deck. On the lower level, an even larger entertaining patio of custom Buckskin stone with outdoor barbeque surrounds a 50 foot pool and one bedroom detached guesthouse with full kitchen, a perfect venue for private lounging, providing a stay to visiting guests or hosting a large event. A third detached building incorporates a large two-level studio providing the opportunity for a remote office, workout gym, additional living unit or hobby workshop. Come see this amazing estate!

From the wall of windows that spans the entire width of the home to the multiple expansive and private front and back decks, 116 Foxwood Road captures and celebrates the inspiring sounds and views of nature that Portola Valley is so famous for. The grand open concept great room shares the glorious views with the generous kitchen featuring stainless steel Bosch and Wolf appliances making for amazing indoor relaxing and entertaining space. Just a few steps and you are on the first of 3 back decks, the uppermost of which offers views over the treetops of Foothills Nature Preserve and the possibility of spotting hawks or even eagles soaring in the vast open skies. A quick 7-minute drive (per Google Maps) and you are at Roberts Market and Jaliscos Grill, and 3 minutes more and you are at I-280. And of course Ormondale School serving TK-3rd grades and Corte Madera School serving 4-8th grades offer town kids excellent education opportunities.

Vacation and work peacefully at home in this single-level, 3-bedroom, office/bonus room, 2 bath private retreat in Portola Valleys best kept secret, Los Trancos Woods. Set among mature oaks, enjoy sweeping bay views of three bridges, San Francisco, Stanford University, and the East Bay. The secluded property is on a cul-de-sac just steps across the road from a serene lake and acres of open space with walking trails. Live in a private world apart, yet minutes from Stanford University, 280, Menlo Park, Palo Alto and all Silicon Valley has to offer. The extensively remodeled and updated open floor plan enhances the original Usonian design of renowned Frank Lloyd Wright Taliesin West architect, Aaron Green. Custom features integrate the stunning views into the living spaces. The expansive deck, spanning the length of the house and overlooking Foothill Park, is ideal for entertaining, relaxing, and watching fireworks around the Bay. High vaulted ceilings, floor-to-ceiling windows, and multiple skylights capture abundant natural light. A magnificent family room addition is bathed in sun from four skylights and looks out to the serene fire pit seating area and heritage oaks. Awaken in the enlarged master bedroom to view spectacular sunrises over the bay, heritage oaks, and Foothill Park. Fall asleep looking out over Silicon Valley's city lights. Look through skylights framing soaring hawks and glittering stars. Alpine Hills Swim and Tennis Club and Portola Vineyards are just down the hill. High-quality Portola Valley schools, Ormondale Elementary (K-3) and Corte Madera School (4-8), make a compelling reason to purchase in PV!

Nestled in serene Portola Valley, this property offers stunning western hill views and three separate parcels totaling almost half an acre of mostly level yard space. In addition to the main residence, a thoughtfully designed guest house awaits, complete with its own address and separate access, offering the perfect opportunity for rental income or accommodating guests in comfort and style. Both the main house and guest house have been recently renovated, ensuring modern amenities and tasteful finishes at every turn. With over 1,000 square feet of deck space, the outdoor areas offer an ideal setting for hosting gatherings while enjoying a California sunset over the Western Hills. The allure continues outside with a thriving garden including vegetables, fruit and citrus trees, providing a serene retreat for gardening enthusiasts or those seeking a connection to nature. Conveniently close to Highway 280, Stanford, and local amenities, this private oasis presents a rare opportunity for tranquil and private living in a wonderful neighborhood. Top rated Portola Valley schools.

Located in central Westridge, the most sought-after area in all of Portola Valley, this property offers an exceptional setting with myriad possibilities & the opportunity to transform it into a dream vision. Home exudes an organic contemporary style with a Spanish flair, characterized by signature details like decorative tile stair rises & wrought-iron lighting. Home retains its original charm with all-wood cathedral ceilings, tiled floors in most public rooms, & in the primary suite, & naturally finished wood cabinetry topped with tile. Expansive windows & sliding glass doors open to spacious deck built around mature trees, offering views of the East Bay Hills & the surrounding natural beauty of Portola Valley. Main living area is open & especially spacious featuring a sunken conversation pit - a distinctive-of-the-era design element perfect for entertaining. There are 3 bedrooms & 3.5 baths plus a bonus room which possibly be a 4th bedroom. Set on approximately 3.2 acres, the grounds offer exceptional privacy & ample space for future pursuits. The nearby Westridge Trail provides access to miles of hiking, biking, & equestrian trails, renowned throughout Portola Valley. This property presents an unparalleled opportunity to create a personalized dream home in an idyllic setting.

Experience the epitome of Portola Valley living in this 3-bedroom, 2-bathroom home at the end of a quiet cul-de-sac. Nestled on 2.52 acres of serenity with views of Windy Hill, this property offers 1913 sq. ft. - buyer to verify - of elegant living space. The foyer leads to a spacious living room with vaulted ceilings and a fireplace. Almost-approved plans from the town of Portola Valley will expand the livable square footage with an attached JADU. Additional building opportunities have been explored, and plans to build a new home are available for review with our architect. The beautifully landscaped yard boasts a pool, perfect for entertaining. Located in the top-rated Portola Valley school district, close to hiking trails, and a short drive to town, this home combines tranquility with convenience. Dont miss out on this exceptional opportunity to own in Portola Valley.

This property presents an unparalleled opportunity for renovation, expansion or new construction in the esteemed Westridge corridor of central Portola Valley with direct stunning views of the Windy Hill Preserve and the western hills. Situated on approximately 2.55 acres, the property boasts magnificent natural surroundings and views on one of the best streets in all of Portola Valley - truly a magical setting with the utmost in privacy. While feeling miles away from everything, world-class hiking, biking, and equestrian trails are just outside the front door. Shops, restaurants, and Portola Valley Town Center are just minutes away. The existing home has a unique radial design where three central core structural points anchor the open rafter ceilings that radiate like a starburst across the rooms. The home is in the acclaimed Portola Valley School District, walkable to the schools. Come see this beautiful property!

This home is exceptionally well located on a quiet cul-de-sac walking distance to highly acclaimed schools, local market, and Alpine Hills tennis/swim club. With direct access to hiking and biking routes, the quintessential Portola Valley experience awaits. Step onto the stunning decks to enjoy sunset views of the rolling hills, or starry nights by the fire pit, or year-round alfresco dining on the covered patio for the best of California outdoor living. The 3 car garage offers 770 square feet organized with walls of cabinets, abundant storage, and a "mud room" cubby area for all your athletic gear and toys, plus a secondary washer and dryer so the dirtiest of hobbies never leave the garage. The newly remodeled kitchen is a chefs delight with stunning tile and quartzite counters. Coved ceilings, transom windows, and panoramic doors are just a few of the distinct architectural elements. Striking an elegant balance between formal entertaining and cozy causal spaces, this home is more than a house; its a lifestyle.

Spectacular!...is the best description with its 270-degree unparalleled views of the Western Hills and enhanced by a host of thoughtful upgrades, this stunning contemporary masterpiece by Tobin Dougherty seamlessly blends bold architectural design with the natural landscaping of the knoll top site and is absolutely move-in-ready. Located in sought-after central Portola Valley on a quiet cul-de-sac, this architectural gem is not only perfectly set up for indoor/outdoor private entertaining, but is also surrounded by nature and trails, offering a lifestyle where outdoor activities, excellent schools, and local conveniences are all within easy reach, making it an epitome of sophisticated Silicon Valley living; features floor to ceiling windows, advanced iPad-based home automation, upgraded state-of-the-art digital theater, a gourmet chefs kitchen, outdoor patios off each bedroom, sauna, a recently added private office/4th bedroom. Plans previously drawn for additional 750 sf guest house. Come see this amazing home!

Rare 3.3 level acres-perfect for a family compound with multiple structures for the ultimate in flexibility of use and all in a fabulous close-in-location. Comprised of several buildings with the opportunity to create a family compound, conference center, or both, the entire estate blends Spanish Revival architecture, with signature red-tiled roofs, and sleek modern interiors. Espresso-hued hardwood floors, towering sky-lit ceilings, and entire walls of glass imbue the home with sophisticated style and brilliant natural light and all on an exceptional setting. Main home with 4 bedrooms and 5.5 baths, including a 2-bath primary suite. Impressive open concept kitchen with vaulted ceiling opening seamlessly to the family room with multiple doors to the impressive grounds. Detached office/conference center/recreation structure with 1 bedroom and 1.5 baths. Attached fitness center/recreation room with 1 bath and sauna. Detached guest house,1-bedroom, 1-bath with full kitchen. Two three car garages for a total of 6 garage spaces. All inclusive approximately 10,066 square feet-buyer to verify. Incredible value and opportunity with excellent Portola Valley Schools, perimeter trees, sparkling pool, gated estate-a must see.

This meticulously designed property offers luxurious living spaces and breathtaking views, featuring sleek lines, large windows, and natural gardens for an inviting atmosphere. Step inside to discover a spacious interior flooded with natural light, seamlessly connecting the living, dining, and professional kitchen areas. Additional living spaces include a 500+ sq ft basement with two external doors and windows, a 120 sq ft finished office, and a 900+ sq ft patio adjoining the living room, featuring Folding Glass WallsSuperior Design & Performance, expanding the total living area beyond 3500 sq ft. The kitchen boasts top-of-the-line appliances, ample counter space, and custom cabinetry for gourmet meals and gatherings. Bedrooms are tranquil retreats, while bathrooms offer spa-like amenities. Enjoy outdoor living with multiple patios, landscaped gardens, and stunning views. Don't miss the chance to make this extraordinary residence your own! Welcome to the extraordinary lifestyle of Portola Valley w/this COMPLETELY REBUILT in 2021 and ready for your enjoyment

New engineering & architectural masterpiece on 6.6 acres of complete privacy for those seeking absolute discretion. Architecture by award-winning Swatt Miers & top-end construction. 360-degee views of the Bay, East Bay hills, Windy Hill, and western mountains. Over 11,000sf of total space with 3 levels with elevator and seamless indoor/outdoor transitions with disappearing glass walls. 6 bedrooms, 2 lounges, office, family room/kitchen, recreation room with bar, theatre & wine cellar, plus detached ADU also ideal for fitness center or remote office. Detached 4-car garage and significant off-street parking. A world-class destination for luxurious living as well as corporate and/or professional events with vast level grounds, infinity edge pool, and amazing rooftop deck with breathtaking vistas. Midway between San Francisco and Silicon Valley. Minutes to shops, restaurants and Hwy 280. Excellent Portola Valley schools.

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.