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.

Stunning Completely Renovated 5 Bedroom 5.5 Bathroom Spanish Hacienda Architecture Home with Breathtaking Views. Formal Entry. Elegant Living Room with Fireplace. Formal Dining Room. Chef's Eat-in Kitchen with Center Island with Sink, Bay Window, Skylight, New Subzero Refrigerator, New Appliances, and Pantry. Spacious Family Room with Vaulted Ceilings, Built-Ins, and Fireplace. 5 Spacious Bedrooms. 5.5 Bathrooms. Separate Office with Built-in Cabinets and Shelves. Spacious Loft Area with Skylights. Laundry Room with Sink and Built-in Cabinets. Primary Suite Retreat Features High Ceilings, Two Spacious Walk-in Closets, Double Sinks, Standalone Tub, and Stall Shower. Interior Features Include Ample Natural Light, High Ceilings, Central Heating and Air Conditioning, New Skylights, Refinished Fireplaces, New Additional Bathroom, and High-end Finishes Throughout. New Roof. Complete Privacy on 1.65+/- Acres. Sparkling Pool and Spa. Award Winning Portola Valley Schools.

Premier Equestrian Estate in the Heart of Portola Valley Horse Country. 6 Bedrooms, 6 Baths, 2 half baths. Dramatic Foyer with 19' ceils, LIbrary with gas fireplace, Gallery, Living Room with Vaulted Ceilings, Formal DR. Great Room/Family Room with vaulted ceilings, wood burning fireplace and skylights.. Guest House with gas fireplace, kitchen,full bath. and w/d. Covered Gas BBQ and cabinets. Large Patio with gas firepit. Mature gardens, majestic redwoods and oaks. Commune with nature on over 2.5 acres of level, usable land. Direct access to Portola Valley's lovely horse and hiking trails. 2 entrances with security gates. Handsome, natural and full of understated elegance, this contemporary craftsman home was built in 2006 and finished in 2007 by CJW Architecture and Peninsula Custom Homes Contractors. Newer Barnmaster stable complete with full bathroom, office, tack room, laundry room, utility sink and large, matted stalls with individual paddocks. 75x130 state-of-the art arena with GGT footing and underground irrigation provides the ultimate riding experience. Large sun/shaded turn outs. Truly one of the finest private equestrian facilities in the area. Additional, adjoining acreage is available for sale with a separate driveway on Mapache Road.

Serene bay views welcome you to 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 small 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 open floor plan with smaller bedrooms was the original Usonian design of renowned Frank Lloyd Wright Taliesin West architect, Aaron Green. The remodeled home now includes an updated kitchen with marble counters, a larger master bedroom / bathroom and another large room that can function as a dining room / living room next to a tranquil Zen garden outside. Vaulted ceilings, floor-to-ceiling windows, and multiple skylights capture abundant natural light. In the master bath, relax in the jetted tub while gazing at heritage oaks. Custom features integrate the stunning views into the living spaces. The expansive deck, spanning the length of the house, is ideal for entertaining or viewing nighttime city lights around the Bay.

Spectacular! Private! One of a Kind!...are the best descriptions 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!

This exquisite property, in Santa Clara County w/Palo Alto schools captures the essence of Portola Valley on a spectacular 1.28 +/- acre lot. Boasting scenic beauty of Stanford hills and Felt Lake this home features a 1695 +/-sf single-level guest house w/ground-level access. With 3 beds, 3 bas, office and bonus room in the 4146 +/- sf main residence and 3 beds, 2 bas in guest house, plus 2-stall horse stable, this home provides versatile living options. Remodeled by RJ Dailey in 1983, the main homes exquisite structural beamed ceilings and custom windows perfectly frame the view of the surrounding open space and glorious sunsets. Cool tile and warm wood floors enhance the open floor plan and newly carpeted bedrooms provide comfort. Kitchen is large and bright w/luscious views. A separate guest house, accessible via its own driveway, offers independent living. High ceilings and large great room are complemented w/updated eat-in chefs kitchen and granite counters. The primary suite features, spa bath, luxurious soaking tub, 2 walk-in closets and storage loft. Each home features a 2-car garage and the guest house also includes a workout room/office and workshop.This property offers a tranquil sanctuary near hiking and biking trails, Rossottis Alpine Inn and Ladera Country Shopper.

Beautiful 3 Bedroom Home in Award Winning Portola Valley School District. Elegant Living Room with Fireplace. Formal Dining Area. Stunning Kitchen with Quartz Countertops and Skylight. 3 Bedrooms. Updated Bathroom with Double Sinks, Separate Shower, and Skylight. Spacious Patio with Outdoor TV and Trellis. Lovely Landscaped Yard. Award Winning Portola Valley School District. Best Value for Central Portola Valley

Stunning contemporary on 3 FLAT acres, minutes from Rossotti's Alpine Inn & Roberts Market. 1/2 mile up from Alpine Rd. This incredible CUSTOM home was built in 2016 by the current owners sparing no detail nor expense. Entirely SINGLE level with high ceilings and oversized Fleetwood windows & doors throughout, this home epitomizes California indoor/outdoor living. Gorgeous private setting abuts open space and is steps from hiking trails. Features include: Dramatic vaulted ceiling Living Room* Chef's Kitchen with huge island + Prep Kitchen* spacious Formal & Informal Dining Areas* Family Room* Office* Separate Guest Suite w/living area *Yoga Room* Huge Laundry/Mud Room* Wine Cellar* 3 Car Garage*3 EV Chargers* separate Solar Systems for Pool & House*16K Back-up Battery. Outside: Incredible 25 YARD, 2 lane LAP POOL with integrated SPA and COLD PLUNGE* Covered Trellis with custom louvered doors & built-in Heaters* Sound System ***CALGreen Tier 1 Rated Passive Home*** Property is on SEWER * PALO ALTO School District

Portola Valleys Finest! On the top of the hill at the end of a quiet cul-de-sac, this very private home offers spectacular 300 degree views. Take in downtown San Francisco from the kitchen window and enjoy fabulous Western Hill sunsets from the living room. Completely new rebuild in 2008 by the SF Peninsulas premier custom home builder, the craftsmanship and natural materials are second to none. The Main Home with its mostly one-level floor plan, promotes a wonderful entertaining flow from the kitchen, dining and living room, to the expansive outdoor Ipe-wood deck, perfect for indoor / outdoor living. On the lower level, an even larger stone patio with outdoor BBQ leads you past the 50 ft swimming pool to a one-bedroom Guest House with full kitchen and bath, a perfect venue for visiting guests, pool enjoyment or hosting large events. A third 3,015 sq ft Studio building provides the opportunity for a remote office, home gym, kids creativity area or maker space for the hobbyist in the family! Come see this exquisite one-of-a-kind estate.

Perched above the street and enveloped by nature, this country home offers a serene retreat with a distinctive Spanish flair. The two-story design exudes classic country living, featuring Saltillo tile, hardwood floors, and vaulted all-wood ceilings throughout. A bank of clerestory windows and multiple sliding glass doors fill the interiors with natural light and provide views from the upstairs balcony hallway, which spans the length of the home and overlooks the living and dining areas. Expansive sliding doors open to decks on three sides, plus there is an elevated level rear terrace. Three bedrooms and an office are located upstairs, including a primary suite, plus there is a bonus office on the front deck ideal for today's work-from-home needs. Conveniently located just minutes from Roberts Market, beautifully appointed, and with easy access to top-rated schools and miles of hiking and biking trails, this home provides a perfect blend of comfort and convenience.

Architecturally stunning home w/vaulted ceilings, skylights & oversized windows convey the feeling of living among nature. The rustic stacked stone fireplace, hardwood floors & heavy cross-beamed ceilings blend effortlessly w/sophistication of modern life demands: wide open floor plan, lofty ceilings, recessed lighting, built-in speakers, beautiful wall of windows & wide open connection to outdoor decks. Spacious kitchen features top appliances, generous skylight, picture window over the sink, peninsula breakfast bar, framed glass cabinetry & day desk. Very private primary bedroom suite has vaulted ceilings & is large enough to accommodate a desk area. Second bedroom & full bath are located on the main level. The lower level boasts yet another large bedroom w/ample room for desk area, adjacent full bath, & private access to an outdoor deck (could be a perfect au pair suite or home office). Lush landscaping surrounds the home w/multiple sitting, dining, & play areas. Woodside Highlands neighborhood is a place you will enjoy calling home gaining access to the Town's wonderful trail network is just a few doors away! Close by: Portola Valley's Town Center tennis courts, playing fields, library, & weekly farmers' market, Windmill preschool, Parkside Grill, and just 6 min to why 280.

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.

This stunning Zen retreat, two-story residence features contemporary elegance with serene living on a large level lot. Enjoy bright living and dining rooms, each featuring its own fireplace. The family room equipped with custom built-ins, seamlessly opens to a sparkling pool and spa patio with ceiling-mounted heaters, a built-in BBQ, and an ambiance tailored for alfresco dining. The chef's kitchen fitted with top-of-the-line appliances. A private office, complete with a humidor, sits adjacent to a bespoke bar room. A 4,000-bottle wine cellar adds to the luxury of the first level. Upstairs, a den area leads to six spacious bedrooms and five bathrooms, including three en-suites, each with walk-in closets. The expansive master suite featuring a fireplace, tranquil balconies, a two-story walk-in closet, and a jetted tub. The gated and fenced property is a private haven, protecting abundant fruit trees, vibrant roses, and a mini vineyard nourished by well water. Bali-imported statues, symbolizing peace, protection, and prosperity, alongside a large-scale 3 Faces sculpture by Gregory Hawthorne, add to the distinctiveness of this home. Near award-winning Portola Valley Schools, markets, hiking trails, and I-280, this Zen retreat offers a unique blend of luxury and tranquility.

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 Agent related to seller.

Designed to embrace the sweeping views of the western hills, this sophisticated home exemplifies contemporary elegance with signature floor-to-ceiling corner walls of glass in many rooms, plus towering ceilings, some with solarium glass. The result is tremendous natural light and volume with views at every turn. The dramatic open floor plan is unified with a Versailles pattern of travertine, marble, and granite on the floors, plush carpet in some rooms, and a soft neutral palette throughout. Designed also with entertaining in mind, there is a full bar opening to the pool, a temperature-controlled wine cellar, and a tremendous chefs kitchen. Personal accommodations include a lavish primary suite with a customized office, sitting/fitness room, and sauna. Two additional suites are found on the main level, a suite on the lower level is wired for an optional media room, plus there is a project room/art studio. Every room in the home opens to the outdoors, where the 2.26-acre grounds feature a stunning pool and spa and a vast cantilevered deck that takes full advantage of the views. With a premier location in the heart of central Portola Valley, this home also has a private gate to renowned hiking trails and access to excellent local schools.

Only 7 minute drive from Hwy 280 this brand new ultra high end construction (2024) Modern/Contemporary home (Certificate of Occupancy issued May 2024) boasting 6 bedrooms (5 ensuite) inc 2 primary suites w/soaking tubs, 7 bathrooms, fully equipped ADU unit with separate entrance, 24' high ceilings & 10 ft doors throughout, glass elevator w/3 stops, chef's kitchen with upgraded appliances flowing to grand family room w/double indoor/outdoor fireplaces, 500 bottle wine cellar, office, expansive sky deck view terrace. Radiant heat + A/C, and up to 10 car parking, Adjacent 8,000 sq ft lot also available for purchase. Rare to find a newly constructed home of this caliber in Portola Valley. Highly sought after Portola Valley School District. Ultra high-end construction.

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.

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.

SUBSTANTIAL PRICE IMPROVEMENT FOR THIS WONDERFUL SINGLE STORY HOME WITH WESTERN HILL VIEWS! Tucked away in privacy in sought after Portola Valley with direct views of Windy Hill. The classic traditional home features a colorful palette, fine hardwood floors, and traditional millwork, presenting a blend of timeless appeal and potential to infuse contemporary elegance into its classic structure. Spanning one level, each room flows easily from one to the other with formal living spaces, a tremendous eat-in kitchen, and a step-down family room opening to a spacious deck capturing exquisite Windy Hill views. Separate wing with 3 bedrooms, each with en suite bath, plus there is an additional full bath. The primary suite, kitchen, and dining room open to the level rear grounds with ample room for play and entertaining as well as a possible potential site for a pool or ADU. Excellent Portola Valley schools.

Step in to your own private wooded wonderland, located in the idyllic Santa Maria/Russell area... Enter the light filled living room with fireplace, high ceilings and built in bookcase; then flow to the open air kitchen, with large island & adjacent dining area. The front yard has an expansive lawn and majestic oak with rope swing, and includes a decked in area for cozy outdoor dining with built in overhead gas heater. The side yard is perfect for BBQ's or sipping sunset wine, with plenty of room for a steaming hot tub. Very nice indoor/outdoor house with French doors or sliders to the exterior on both levels. Open space on two sides, and with front door access to the extensive trail network including a path to the skyline & Alice's Restaurant....113 Tynan Way situated in the heart of Portola Valley but still close-in to freeway access...come live in magical Portola Valley and close to shopping, dining and freeway access.

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.

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.