Portola Valley CA Real Estate & Homes for Sale

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 living/ dining with 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 windows/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, fam room and den, is largely 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, and greenhouse and 2 fenced dog runs. Family/friends can gather throughout the exquisite property at numerous quaint outposts.. This home is ideal for entertainment,. 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)

This extraordinary Portola Valley Ranch property combines rare level land, breathtaking Windy Hill views from every floor, and a comprehensive whole-home remodel all on just over one-half acre. The homes thoughtful expansion and renovation, along with just completed interior and exterior painting and completely redone bamboo and hickory floors throughout, present a beautiful ambiance. With large windows enhanced by skylights in almost every room, the house is filled with natural light. Formal living and dining rooms extend to expansive decks at both the front and rear, perfect for fresh air entertaining AND outdoor play hard to find features in the Ranch. At the heart of it all is a beautifully remodeled kitchen appointed with custom cabinetry and high-end appliances.

Secluded in complete privacy above the street, this contemporary home embodies a true connection to nature through its vast expanses of glass and warm, organic finishes. Designed with a modernist spirit, and award-winning for green design, the home showcases soaring vaulted ceilings, open concept living spaces, and entire walls of glass that frame the surrounding greenery. Bamboo floors, cherry cabinetry, slate accents, and terrazzo countertops combine to create a sophisticated yet welcoming ambiance that harmonizes beautifully with the natural setting. Sustainable living unfolds behind the scenes with four Powerwall's, two EV charging stations, tankless hot water, and 11-zone radiant heat. The home's versatile layout offers ideal flexibility for recreation, entertaining, or even private living quarters, plus a separate office with half-bath. Indoor-outdoor flow is seamless with multiple decks, an atrium-style entry, and numerous sliding glass doors opening to fresh-air living spaces. Set on an expansive lot of approximately 30,040 square feet, comprised of three separate parcels, the property offers rare space and serenity while still being close to everything. Access is easy from a convenient driveway on Wayside Road, leading to carport parking with EV charging.

Nestled at the end of a private drive, this 3,320 square foot sits on almost 1.5 acres (per county) in tranquil Los Trancos Woods. Floor-to-ceiling and clerestory windows as well as skylights and sliding doors fill the 2-story home with natural light and provide views to the surrounding natural environment from every room. The top level includes an open-concept layout creating a seamless flow between the living room, dining area and kitchen. The expansive living room includes a wood burning fireplace surrounded by a sunken, built-in circular sofa, a wet bar and an additional large area ideal for a game table. The dining area flows seamlessly to the large kitchen, complete with island and walk in pantry. Access to the connecting deck from all three areas creates a large space ideal for indoor/outdoor entertaining. Completing the level is a spacious bedroom, a full bath. The lower level accommodates the primary suite and the third spacious bedroom, both with en suite baths, walk-in closets and outside access. The conveniently placed large laundry room includes ample cabinetry, a sink and an attached large storage room.

Discover the perfect blend of nature and modern convenience in this beautifully designed home in peaceful Los Trancos Woods. This 9360-foot lot is surrounded by scenic hiking trails and just minutes from downtown shopping, Stanford University, and major commute routes, this spacious residence offers the best of both worlds. Originally built in 1930, the 1750 Square feet of total living space features a custom multi-generational layout ideal for families or extended living. Vaulted ceilings with exposed beams, large windows, and skylights fill the space with natural light and architectural charm. The galley kitchen includes stainless steel appliances, ample cabinetry, and a garden view. Two bedrooms offer vaulted ceilings, double closets, and built-in storage. The third includes an ensuite half bath. The open-concept living room flows to a large deck and patio perfect for indoor/outdoor entertaining. A detached 550 square foot turnkey guesthouse adds a bonus bedroom and bath, with its own kitchen, laundry, and private deck ideal for guests or rental income. Located in the highly regarded Portola Valley school district, this move-in-ready home is a rare find in one of the area s most serene and sought-after neighborhoods.

Tucked away on nearly 2 acres at the end of a quiet cul-de-sac in lush Portola Valley, this updated contemporary home offers the perfect blend of privacy and natural beauty. Bright, airy interiors feature high ceilings and a mix of travertine and oak floors, creating a warm and inviting atmosphere. The spacious living areas, including a large great room and chef's kitchen with top-tier appliances, flow seamlessly for easy entertaining. Expansive glass doors open to an outdoor kitchen with BBQ and pizza oven, infinity-edge pool, and stunning views of Windy Hill Preserve. The single-level layout wraps around a peaceful open-air courtyard with fire pit. Four bedrooms-one currently used as an office-offer versatility. Solar panels, central A/C, and an ideal location near Stanford, top-rated schools, and scenic trails complete this exceptional home.

Located in the sought-after Westridge area of Portola Valley, this well-appointed home is embraced by forested surroundings & a pool on an expansive 2.37-acre lot. Classic Craftsman exterior clad in shingles gives way to bright, contemporary interiors filled with incredible natural light. Vaulted ceilings rise above the rooms, complemented by numerous skylights & an extraordinary use of picture windows & sliding glass doors that frame the breathtaking scenery at every turn. Thoughtfully designed layout spans two levels with 3 bedrooms & 2.5 baths, a recreation room with an office center & built-in Murphy bed, plus a flexible-use room for office, fitness, or play. Designed for both everyday living & effortless entertaining, the home features grand gathering spaces that flow seamlessly to expansive outdoor venues, including two separate decks, one with built-in barbecue & adjoining covered dining lounge. Adding a rare & unexpected highlight, a separately fenced & sunswept pool is positioned at one end of the grounds surrounded by lawn & wooded views. Completing the appeal are a detached two-car garage, abundant off-street parking, & access to excellent Portola Valley schools. A truly special opportunity in one of the Peninsula's most desirable neighborhoods.

You wake up one morning on the deck of 415 Golden Oak Drive, coffee in hand, gazing at a view that makes time stand still. From this elevated perch in central Portola Valley, the South Bay unfolds rolling hills, morning mist, and the quiet promise of a perfect day. This beautifully updated 4-bedroom, 3.5-bath home offers ~3,700 sq. ft. of refined living space, blending clean architectural lines, natural light, and sweeping sightlines. Set on just under two acres with lawn, pool, mature trees, and expansive decks the property is both functional and breathtaking. Inside, vaulted ceilings and large windows frame the views. The open living and dining areas flow into a thoughtfully designed kitchen with high-end appliances, custom cabinetry, and a spacious island ideal for entertaining or quiet mornings. The ~600 sq. ft. primary suite is a private retreat with a spa-like bath, walk-in closet, and a balcony perfect for stargazing or late-night talks. A separate bonus room with full bath offers flexible space for guests, work, or play. Located in the heart of Portola Valley, minutes from top-rated schools, scenic trails, and local shops, this isn't just a home its a vantage point. A place where space, calm, and style come together. Come for the view. Stay for everything else.

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.

Tucked away on approximately 2.77 acres in the Vista Verde community with easy access to the amenities of Portola Valley, this remarkable property offers a peaceful retreat from the fast-paced life of Silicon Valley. A sweeping tiled stairway descends through lushly planted gardens to the main entrance, where the home opens to grand yet understated interiors that echo the serenity and refinement of the grounds. Enter the expansive main level with its 10 and 12 foot ceilings, including a spacious kitchen and family room combination with a large pantry for entertaining; adjoining dining and living rooms with arch-top windows that capture the stunning wooded views; and an elegant primary suite with dual exterior balconies, sitting area with fireplace, spacious walk-in closet, and a luxurious marble bath all enhanced by fine millwork, solid oak hardwood floors, and recessed lighting. The multi-functional lower level features two additional bedrooms one en suite a home office, an artist studio or home gym, and a large recreation room that opens to a massive, multi-level deck and pergola with a linear natural gas fire pit and a built-in kitchen barbecue area, creating an adjoining indoor-outdoor entertainment space that overlooks the private rear grounds.

Nestled on a gorgeous virtually flat half acre this stunning Mediterranean style home is surrounded by the pristine beauty of the adjacent Blue Oaks open space, with VIEWS stretching across the East Bay to the glittering Oakland skyline. Masterfully built in 2011 the homes thoughtful design marries a spacious, versatile floor plan with exquisite details: soaring reclaimed wood beams, graceful arched plaster doorways, a classic clay tile roof, and vibrant tile accents, including handcrafted stair risers that add a touch of old-world charm. Expansive custom windows and doors frame the idyllic setting flooding the interior with natural light and seamlessly connecting to the rear deck open and sparkling newly built POOL (2023). This property truly offers the best of everything ! A tranquil retreat in a great neighborhood, just minutes to local shopping, commute routes, Stanford and the award winning Portola Valley schools !

Gorgeous property with sublime views on nearly 2 acres in the prime Westridge neighborhood of Portola Valley. The beautifully updated ranch-style home has a formal entry, living room with fireplace and built-ins, large eat-in kitchen with Viking range, and two subzero refrigerators, bright pantry with skylight; full bath off kitchen, large office with built-in file drawers and fireplace. The 1,000-sf sunroom accommodates living, dining and work areas and has Bosch dishwasher, Thermador grill and a wine cooler. Four distinct bedrooms; primary has doors to patio, walk-in closet, bathroom with steam shower and heated floors. Large office in main home + in converted garage bay. Outside there is a gorgeous garden in full bloom, pool, hot tub, greenhouse, ample extra storage and beautiful views to the coastal mountains. Separate private well-appointed two+ bedroom ADU. Loads of built-in bookcases, and cabinets. You won't want to miss this distinctive property on almost two acres. Solar panels provide electricity throughout the property.

Located in tranquil Portola Valley, this single-level, 3-bedroom, 2-bath home with pool and spa sits on an oak tree studded 1.2-acre lot (per county). Ample skylights, sliding doors and picture windows create rooms filled with natural light and peaceful views of the surrounding landscape. The spacious living room and dining area flow seamlessly into the large, modern kitchen and family room. Easy access to the rear yard from these spaces make them ideal for indoor and outdoor entertaining. The bedroom wing includes the primary suite with remodeled ensuite bath, two additional bedrooms, a second remodeled full bath with new LG washer/dryer, and a hall linen closet. A two-story structure adjacent to the main house offers a range of possibilities. The upper level includes new flooring, a closet and remodeled 1/2 bath, ideal for use as a guest room, office, artist studio or game room. The lower level includes a wine cellar, workshop and storage space. This convenient location is just minutes to local hiking trails, shopping and restaurants, major commute routes, Stanford University and the excellent Portola Valley schools.

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!

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.

Extensively remodeled and move in ready. This 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 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 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.

Stunning vistas of the hills and bay in this once in a lifetime opportunity to own 12.55 acres in Palo Alto Open Space with a Portola Valley mailing address located on an exclusive private road. Build a new estate or remodel the existing mid-century style home with expansive hill views. Large living room with high ceilings and separate dining room have breathtaking views. Family room/solarium is off the eat-in kitchen with island. Two bedroom suites one being the large primary bedroom and two bedrooms with Jack and Jill bathroom. Garage converted refinished into a studio plus large workshop and storage. Separate two bedroom guest cottage with living room with fireplace and sunny deck with views. Sunny Pool surrounded by gardens. Tennis court was built before land was subdivided and is partially on neighbor's property. Property has Greenhouses and sheds for storage, a walking trail on the property, and is very private but close to shopping, Menlo Park and 280 corridor to Silicon Valley. The bay view photos were from the trail on the back part of the property.

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 sliding Fleetwood glass doors make for easy indoor/outdoor entertaining, extending on to the covered patio with heated floors, fireplace, & Italian pizza oven. The 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 770 sq ft guest house with full kitchen, 1.5 bathrooms & large bedroom. Bonus detached 350 sq ft workshop w/ 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 with Views, updated single family /rustic modern interior, move-in ready and personal retreat on a large 11,500 square foot lot, surrounded by natural beauty, a 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, Room to expand on large lot. Less than 5 miles without getting on the freeway to Stanford University. Enjoy the Sunrise trail steps away from your private sanctuary 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.

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).