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$3,455,000
3 Beds ⋅ 3 Baths ⋅ ML82022989 MLS
Discover the potential at 475 Cervantes Rd, nestled in the heart of Portola Valley, where opportunity meets prime location. Situated on a lovely 1 acre lot, this property presents a remarkable canvas for those looking to build or remodel in order to create their optimal living space. The home boasts 2,550 feet of living space, featuring 3 bedrooms, 2.5 bathrooms. The primary bedroom is a retreat in itself, complete with an ensuite bathroom that includes a separate tub and shower. The additional two bedrooms share a convenient and spacious hall bath. The heart of this home is its open-concept kitchen and family room, perfect for gatherings and entertaining. The kitchen comes equipped with a center island and a cozy eating area, while the family room offers built-in bookcases and fireplace. For more formal occasions, enjoy the separate dining room and large living room. To enhance the thoughtful flow of the home, all common areas lead to the serene backyard. Additional amenities include a dedicated laundry room, a detached 2-car garage, a screened patio and a deck overlooking the private yard while offering a peaceful retreat and space for outdoor enjoyment. This home already offers fabulous spaces and a thoughtful floor plan; it just needs the creativity of its next owner.

475 Cervantes RD, Portola Valley

Listed by Jennifer Alfaro, 650-888-8338 from Compass
(If provided) CoList: Kimm Terpening from Compass

Sold listing courtesy of Eric Ruxton from TERA
$4,025,000
4 Beds ⋅ 4 Baths ⋅ ML82021580 MLS ⋅ Portola Valley Ranch BLDG.
This is a home that's all about light, views, and easy living. Whether you're gathering with friends, finding a quiet corner to unwind, or just enjoying the beauty of nature right outside your door, this home has it all. As you arrive, a soothing water feature sets a calming tone. Step inside to a dramatic living room with soaring open-beam ceiling and a sliding skylight that fills the space with natural light and fresh air. The open kitchen and dining areas make gatherings effortless, flowing easily for everyday living or entertaining. The primary suite is a true retreat, with a fireplace, a spa-like bathroom, and a generous walk-in closet. With four bedrooms and four bathrooms in total, plus a private-entry studio perfect for guests, work, or creative pursuits. Multiple decks and patio offer sweeping views of the hillsides and valley beyond. This home includes a tropical-themed spa room with a hot tub and sauna, a wellness escape right at home. Portola Valley Ranch amenities include a vineyard, two swimming pools, tennis, a fitness facility, community garden, community room, access to hiking trails, a dog park, and so much more. Located near shops and restaurants, Stanford, Silicon Valley, commute routes, and midway between San Francisco & San Jose international airports.

11 Hawk View, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Jim Tierney from NTE
$5,500,000
4 Beds ⋅ 3 Baths ⋅ ML82011438 MLS
Fabulous views at this 3800 sf home plus 1200 sf ADU , greenhouse and pool on nearly 2 acres in prime Portola Valley. Gorgeous property with sublime views on nearly 2 acres in the prime Westridge neighborhood of Portola Valley. The gorgeous updated ranch-style home has sublime views of the hills and 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.

1175 Westridge DR, Portola Valley

Listed by Monica & Mandy Group, 650-823-8212 from Compass
(If provided) CoList: from

Sold listing courtesy of Cindy Hung from NTERO
$4,250,000
4 Beds ⋅ 3 Baths ⋅ ML82019049 MLS
Welcome to this beautiful home located in central Portola Valley. This spacious 4-bedroom, 3-bathroom residence offers comfortable living with generous amenities. A secluded fourth bedroom and full bath provide a comfortable solution for guests or extended family. The kitchen is well-positioned with an electric cooktop, double oven, refrigerator, and opens to the rear patio. The living room boasts vaulted ceilings, providing an open and airy feel enhanced by a wall of windows overlooking the patio area. The bedrooms are well-sized with ample closet space. Recently painted in a neutral tone with complementary carpets, this home is turn-key and one can move right in and enjoy the holidays! Ideally positioned on 1.6 acres. with two level tiers and a downslope, the oak studded lot is both private and accessible. The property features a solar-heated in-ground pool, and a convenient pool house complete with a full bath - perfect for relaxation and entertaining. The Portola Valley Elementary School District serves the area. With additional structures like a lighted pergola, and large storage shed, this home is a perfect blend of comfort and functionality.

20 Bear Gulch DR, Portola Valley

Listed by Denise Welsh, 415-999-0727 from Compass
(If provided) CoList: from

Sold listing courtesy of Ashu Chadha from COMPS
$7,257,000
4 Beds ⋅ 4 Baths ⋅ ML82019615 MLS
Nearly every room of this ±1-acre property captures sweeping views of nature, gardens, a sparkling pool, and the iconic Windy Hill backdrop. Completely and thoughtfully remodeled, the home blends modern comfort with exceptional attention to detail. The single -level floor plan features 4 bedrooms (one currently used as an office) and 3.5 beautifully updated baths. The layout includes both a living room and a separate family room, while the kitchen shines with high-end appliances, a large island with seating, and a coffee/serving bar with sink and storageperfect for entertaining. The kitchen and dining areas flow together seamlessly, easily accommodating large gatherings. The primary suite opens directly to the pool and spa, with a spa-inspired bath that includes a free-standing tub, oversized shower, dual vanities with designer cabinetry, custom tile and hardware, and a walk-in custom closet. A private ADU provides an additional bedroom and bath, along with its own entrance, soaring ceilings, oversized windows, and a full kitchenideal for guests, extended family, or flexible use. In the heart of Portola Valley, close proximity Alpine Hills Swim & Tennis Club, the historic Alpine Inn, and top-rated PV schools minutes to Highway 280 for easy access to Silicon Valley and SF.

415 Cervantes RD, Portola Valley

Listed by Peter Cowperthwaite, 650-207-4101 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Erika Demma from APR
$6,950,000
4 Beds ⋅ 3 Baths ⋅ ML82019602 MLS
Located in the desirable WESTRIDGE Neighborhood, this impressive 2.62+/- ac. property offers views, room for expansion, a vineyard, separate ADU, and a freshly updated home with 4 bedrooms & 3 remodeled baths. The kitchen has new appliances, & flows into a family living space. The large dining area sets the stage for entertaining. The Primary Suite has tall beamed ceiling, 3 closets, & deck that overlooks the property & Windy Hill views. Additional bedrooms enjoy a private wing that centers around a flexible space This space is served by a separate entrance for flexibility. A lower level is a blank slate. Finishedit has a work-shop, lots of storage, 2 rooms with sliding glass doors, a large well-lit space thats ideal as a game room or exercise center. Potential for a wine cellar. And there is a full bath. The ADU is 1 bed. 1 bath & has an open living/dining/kitchenette space, + private deck & entrance. There is a small upper pasture or a large area at the front of the property that could be used for horses or pool, possibly a tennis court or just let nature share its beauty with you. Central Portola Valley location, convenient to shopping, Alpine Hills Swim & Tennis club, The Alpine Inn, excellent PV schools, & just 5+/- min. to Hwy. 280.

15 Naranja WAY, Portola Valley

Listed by Peter Cowperthwaite, 650-544-8968 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Peter Cowperthwaite from DP
$4,600,000
4 Beds ⋅ 3 Baths ⋅ ML82017822 MLS
Single-level ranch home set on a private acre in a forest-like oasis with majestic redwoods. This renovated 4-bedroom, 2.5-bath residence features a cozy family room and a spacious living room with cathedral ceilings and a wall of windows that fill the home with natural light while showcasing the serene yard. A half-moon driveway provides a welcoming approach, complemented by a separate driveway leading to a large garage. The kitchen is designed for both beauty and function, with custom cabinetry, interior lighting, double sinks, built-in Thermador refrigerator, La CornuFe' range with an elegant exhaust. The bathrooms are thoughtfully updated, offering a soaking tub and walk-in shower. Portola Valley Trails are right outside your door!

240 Willowbrook DR, Portola Valley

Listed by Roberto Ruiz, 408-234-7249 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Samira Amid-Hozour from SGP
$4,400,000
5 Beds ⋅ 3 Baths ⋅ ML82018200 MLS
Set against the stunning backdrop of Portola Valleys rolling hills, 369 La Cuesta Drive offers a rare blend of natural beauty and modern convenience. This coveted location is known for its peaceful atmosphere, scenic trails, highly regarded schools, and proximity to the tech and business hubs of Silicon Valleyideal for those seeking both tranquility and connectivity. This brand-new Aro Home is a showcase of sophisticated design and thoughtful functionality. The architecture features clean, modern lines and expansive glass that brings the outdoors in. Open living and dining areas flow into a chefs kitchen with premium appliances, a large island, and high-end finishes. Bedrooms offer comfort and privacy, and the primary suite includes a walk-in closet and spa-inspired bath with a walk-in shower. Pioneering sustainable living, this carbon-negative home features solar power, energy-efficient systems, water-saving fixtures, and precision-engineered construction. Built off-site and assembled on location, it reflects Aro Homes commitment to environmental responsibility. Smart home integration allows seamless control of lighting, climate, and security offering a truly modern living experience.

369 La Cuesta DR, Portola Valley

Listed by Josh Rubin, 650-575-5981 from Compass
(If provided) CoList: from

Sold listing courtesy of RECIP from RCIP
$3,700,000
3 Beds ⋅ 4 Baths ⋅ ML82017999 MLS ⋅ Portola Valley Ranch BLDG.
Surrounded by a sea of oak trees and level open spaces, this wonderfully bright home is located on a corner lot of nearly one-half acre in sought-after Portola Valley Ranch. Soaring ceilings with exposed beams, numerous sliding glass doors, and multiple skylights fill the interiors with natural light. Recently completed updates include fresh exterior paint, refinished Brazilian teak floors, and a luxurious primary suite bath on the main level with heated floors and a curbless shower. The open living and dining room combination is served by a sleek modern kitchen with granite finishes, premium appliances, and a casual dining area. The lower level offers a flexible recreation/media room with potential for a fourth bedroom complementing two additional bedrooms and two baths on this level. Expansive decks on both levels invite outdoor living. Rounding out the home are the Ranch amenities that include pools, tennis courts, hiking trails, and a community vineyard, along with access to top-rated Portola Valley schools - the perfect place to call home midway between San Francisco and Silicon Valley.

2 Thistle ST, Portola Valley

Listed by Michael Warren, 650-315-0224 from Compass
(If provided) CoList: from

Sold listing courtesy of Omar M. Kinaan from DP
$3,850,000
5 Beds ⋅ 3 Baths ⋅ ML82016762 MLS ⋅ Ladera BLDG.
Nestled in the highly sought-after Ladera neighborhood, this spacious home is the perfect blend of serenity, functionality, & comfort. With breathtaking views of the San Francisco Bay & surrounding treetops, this property is a private retreat that effortlessly accommodates both everyday living & vibrant entertaining. Step into the expansive living room, where a vaulted ceiling, hardwood floors, & a cozy fireplace create a warm & inviting ambiance. A wraparound deck offers seamless indoor-outdoor flow & stunning panoramic views. Adjacent to the living space is a light-filled dining room with a direct line of sight to San Francisco. Chef's eat-in kitchen has a large center island and breakfast bar. Primary suite offers stunning vistas and a peaceful haven at the end of the day. Downstairs, three bedrooms share a full bath with an adjoining family room, offering flexibility for family, guests, or a home office. A fully independent 1-bedroom, 1-bath attached unit with its own entrance, kitchenette, & access to the backyard presents an exceptional opportunity for guest accommodations, au pair quarters. The private backyard is a level space perfect for play, gardening, or relaxing in the shade. Optional membership is available to the Ladera Rec Center with swim & tennis.

760 La Mesa DR, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Fred Glick from GLICK
$3,200,000
3 Beds ⋅ 2 Baths ⋅ ML82010192 MLS
Discover this mid-century modern-style gem in the sought-after Corte Madera neighborhood. Positioned on a desirable street and flat lot at the top of Canyon Drive and Crescent Road, this 3-bed, 2-bath home features vaulted ceilings, an open floor plan, fireplace, hardwood floors, floating staircase and abundant natural light through glass doors, picture windows and skylights. The versatile bedroom or possible media room on the first-floor opens to an inviting outdoor space with a fenced backyard and garden. Additional highlights include a 2-car garage with side yard access, washer/dryer hookup, and a storage shed for extra workspace. Enjoy a pet-friendly, active community walking distance to top rated public and private schools, Roberts Market, biking routes, and network of local hiking trails, just minutes from Stanford University and Palo Alto without ever having to get on the highway.

340 Canyon DR, Portola Valley

Listed by Karen Gunn, 650-888-9457 from Compass
(If provided) CoList: from

Sold listing courtesy of Isabella Esguerra from APR
$3,229,000
4 Beds ⋅ 3 Baths ⋅ ML82012992 MLS
Ideally located in the heart of Silicon Valleys most exclusive corridor, this Portola Valley estate offers effortless access to Highway 280, Stanford University, Stanford Hospital, Sand Hill Road venture capital firms, and leading technology campuses including Meta, Google, Apple, NVIDIA, and Tesla. Perched on an elevated approx 2 acre private hillside lot, the property showcases dramatic 180-degree panoramic Bay views across the Peninsula skyline and western mountain ranges, a rare vantage point that must be experienced in person. This is a premier opportunity to build a custom modern estate or reimagine the existing residence into a luxury Silicon Valley retreat. Nearly every window frames sweeping natural vistas and seamless indoor outdoor living.Experience executive-level living with privacy, scale, and proximity, minutes to Palo Alto, Menlo Park, Los Altos, top-rated schools, elite dining, and major innovation hubs, while enjoying the tranquility of one of the Peninsulas most prestigious residential enclaves.A rare opportunity to secure a legacy view property in Silicon Valley, ideal for those seeking privacy, convenience, and world-class panoramic views.

30 Pine Ridge WAY, Portola Valley

Listed by Angie Wolff, 650-704-0475 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Angie Wolff from NTERO
$2,500,000
4 Beds ⋅ 2 Baths ⋅ ML82016089 MLS ⋅ Ladera BLDG.
Mid-century modern diamond in the rough. Unlock the full potential of this 4-bedroom, 2-bath mid-century modern gem nestled in the desirable Ladera neighborhood. Set on a private and spacious corner lot with mature landscaping, this home is brimming with opportunity for the savvy buyer to renovate and restore its original charm or build your dream home from the ground up. Convenient to the Ladera Shopper, Ladera Rec, school bus stop, Stanford 3.5 miles, easy access to Silicon Valley, commute routes & mid-way between SFO & SJC International airports. This is your chance to create your dream home in one of the Peninsula's most sought-after communities.

291 La Mesa DR, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Sonia Maiello from NTERO
$3,380,000
3 Beds ⋅ 2 Baths ⋅ ML82014861 MLS
VALUE VALUE VALUE! Nestled in the heart of one of Silicon Valleys most sought-after communities, 10 Bear Gulch Drive in Portola Valley presents a rare and exciting opportunity. This timeless Craftsman-style home sits on a sprawling 1.25-acre parcel and offers a 3-bedroom, 2-bath main residence plus a detached guest cottageideal for extended family, home office, or rental potential. Priced to sell due to its current condition, this property is the ultimate blank canvas for those seeking to remodel, rebuild, or even explore lot-split potential (buyer to verify with city). Whether youre dreaming of a serene family retreat or a visionary development project, the possibilities are endless. Living in Portola Valley means being surrounded by nature while remaining remarkably close to everything. Just moments from local favorites like Rossottis Alpine Inn and the Portola Valley Town Center, you'll also enjoy access to the scenic Windy Hill Open Space Preserve, miles of biking and hiking trails, and beloved community events like the summer concert series and farmers market. With top-rated schools, a welcoming small-town atmosphere, and a laid-back commute to Stanford, Sand Hill Road, and Highway 280, this location blends peaceful living with everyday convenience. Make this yours!

10 Bear Gulch DR, Portola Valley

Listed by Danny Burgess, 650-665-0922 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Heidi Tang from VINE
$6,020,000
3 Beds ⋅ 3 Baths ⋅ ML82012718 MLS
Modern Luxury on 2+ Acres with Windy Hill Views || Striking modern design, total privacy, and chic designer interiors define this exceptional property in the heart of central Portola Valley. Gated at the end of a long driveway and spanning over 2 acres, the setting offers expansive grounds with views toward Windy Hill and a layout designed for effortless indoor/outdoor living. Every detail of the home has been meticulously curated, with radiant-heated concrete and white oak floors, soaring ceilings, and floor-to-ceiling walls of glass stretching the entire length of the home. The sleek white kitchen is finished with Carrara marble and anchored by two large islands part of a dramatic great room that includes formal and casual living spaces, dining area, and seamless access to the outdoors, pool, and views. The multi-level floor plan features a luxurious primary suite with spa-inspired bath and an enormous skylit dressing room, two additional bedrooms with a shared luxe bath, and a striking hallway bath. Outdoor amenities include a solar-heated pool, spa, fire pits, crushed stone walking paths, an elevated pavilion, and expansive Ipe deck. All just minutes from trails, town conveniences, and top-rated Portola Valley schools.

22 Grove DR, Portola Valley

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Judy Citron from COMPS
$5,205,000
6 Beds ⋅ 6 Baths ⋅ ML82012664 MLS
Positioned behind electronic gates at the end of a cul-de-sac with just four other homes, this architecturally significant home offers privacy, scale, & thoughtfully considered living on 1.354 acres. Spanning approximately 5,970 square feet of living space offering ample accommodations. Main level offers beautifully scaled rooms designed for entertaining & everyday comfort, flexible layout for formal living & dining areas, lounge, & a connoisseur's wine cellar with adjoining tasting room. Kitchen is appointed with granite finishes, high-end appliances, & space for casual dining, plus an expansive open family room in the center of the design. Primary suite positioned for optimal light & privacy, dual terraces, sitting area with fireplace, couture closet room, & luxurious en suite bath. An adjoining bedroom provides the ideal space for a nursery/office. Outdoor amenities are equally impressive with a large pool, separate spa, built-in barbecue, prolific rose garden, a protected vegetable garden, fruit trees, & a small vineyard. With two attached 2-car garages, extensive storage, & access to acclaimed Portola Valley schools, this home presents a rare opportunity to own a one-of-a-kind property in an exceptional location.

3 Oak Forest CT, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Val Vandervort from VERIT
$8,750,000
6 Beds ⋅ 9 Baths ⋅ ML82011147 MLS ⋅ Blue Oaks BLDG.
Prominently perched on the Portola Valley hillside, this contemporary home has been upgraded with the finest materials and craftsmanship providing glorious panoramic views of rolling hills with Silicon Valley and the Bay in the distance. This home is elegant, sophisticated and secluded and just a short drive to Silicon Valley with easy freeway access. The flexible floor plan includes six bedroom suites, dedicated office/den with fireplace, living room with soaring ceilings, fireplace, adjacent balcony and forever views, great room with access to the outdoor kitchen and spa plus a gathering spot and an in-home theater on the lower level. The kitchen is appointed with high-end appliances, butlers pantry, island and breakfast bar, all open to the casual dining/family room--perfect for intimate gatherings and sufficient for hosting formal dinner parties or large events. The garden boasts wrap around balconies and patios, views, beautiful plantings in front and sunny, enclosed fruit/vegetable beds below. Solar power system with robust Tesla battery support, 5 zone heat & A/C, full property security system, two laundry facilities, two two-car garages and community pool/spa complete this move-in ready home. Top rated Portola Valley schools. Close by hiking/biking/equestrian trails.

5 Redberry RDG, Portola Valley

Listed by Omar M. Kinaan, 650-776-2828 from Golden Gate Sotheby's International Realty
(If provided) CoList: Ellen Ashley from Golden Gate Sotheby's International Realty

Sold listing courtesy of Kavanaugh Group from CBR
$2,950,000
3 Beds ⋅ 2 Baths ⋅ ML82009816 MLS
On the market for the first time in nearly 50 years, this classic ranch home is set on a lushly planted corner lot of approximately one-third acre. Gardens are the soul of this property - loving tended & richly layered with heritage roses, wisetria, towering redwoods, & a soothing water feature. Brick walkway winds through the front gardens, while the private rear grounds invite outdoor living with a large patio, an arbor-covered lounge, a deck built around a majestic oak tree, & a seasonal creek along the edge of the property. This home offers timeless comfort with three bedrooms & two full baths, including a spacious primary suite with French doors to the gardens. Cathedral wood-paneled ceiling in the living room, numerous skylights throughout the home, & generously sized windows bring natural light into every space. Kitchen & casual dining area open directly to the rear yard, as well as to the family room with fireplace. Located close to Portola Valley's town center & Windy Hill trailhead, & with access to top-rated schools, this cherished home offers a wonderful opportunity to enjoy peaceful surroundings & exceptional gardens in a close-in location.

3 Wyndham DR, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Lynn Roberts from COMP52
$6,700,000
3 Beds ⋅ 3 Baths ⋅ ML82008992 MLS
Welcome to this stunning home in Portola Valley, offering a perfect blend of comfort and elegance. With a generous living space of 4,088 sq ft situated on a 47,517 sq ft lot, this property provides ample room for relaxation and entertainment. The home features three spacious bedrooms, including a primary bedroom conveniently located on the ground floor, and two full bathrooms equipped with double sinks. Separate structure perfect for office or large gym. Sunroom for relaxing and views. PV Schools The kitchen is a culinary delight with its sleek granite countertops, ideal for preparing gourmet meals. Enjoy dining in the formal dining room or the eat-in kitchen, catering to both casual and formal occasions. The family room offers a separate retreat for gatherings and relaxation. This beautiful residence boasts exquisite hardwood and wood flooring throughout, adding warmth and charm to the interior. Cozy up by the fireplace on cooler evenings, creating a perfect ambiance. Laundry is convenient with an inside washer and dryer setup. The home is part of the Portola Valley Elementary School District. Additional amenities include central AC, a whole house/attic fan, central forced air heating, and a two-car garage, ensuring comfort and practicality all year round.

165 Golden Oak DR, Portola Valley

Listed by Dana Cappiello, 415-264-5464 from Sotheby's Intl Rlty
(If provided) CoList: Derek Cappiello from Sotheby's Intl Rlty

Sold listing courtesy of Keyko Pintz from AGNC
$3,566,750
5 Beds ⋅ 4 Baths ⋅ ML82007268 MLS
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.

1005 Portola RD, Portola Valley

Listed by Kavanaugh Group, 650-400-5312 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Lena Gustafsson from COMPS
$2,550,000
3 Beds ⋅ 3 Baths ⋅ ML82007263 MLS
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.

40 Deer Path DR, Portola Valley

Listed by Kavanaugh Group, 650-400-5312 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Andy Pham from FIHI
$3,925,000
3 Beds ⋅ 3 Baths ⋅ ML82006466 MLS
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.

300 Cervantes RD, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Daniel Flores from COMP
$5,300,000
4 Beds ⋅ 4 Baths ⋅ ML82006455 MLS
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 approximately ~4,300 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.

415 Golden Oak DR, Portola Valley

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS
$4,412,000
3 Beds ⋅ 3 Baths ⋅ ML82005872 MLS
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 !

1036 Los Trancos RD, Portola Valley

Listed by Liz Daschbach, 650-207-0781 from Compass
(If provided) CoList: from

Sold listing courtesy of Angie Wolff from NTERO
$4,250,000
3 Beds ⋅ 3 Baths ⋅ ML82005491 MLS ⋅ Ladera BLDG.
Nestled in one of Ladera's most sought-after cul-de-sac locations, this updated split-level home offers the perfect blend of comfort, style, and functionality. This residence is ideal for modern living with three spacious bedrooms and three full bathrooms. A large living room features a lighted coffered ceiling, designer color palette, and custom-built-ins. Cooking is a snap in the chef's kitchen with a breakfast bar and open floor plan to the dining and living rooms. A split-level bonus room has a vaulted ceiling, a full bath, and a home office with serene views of the Stanford Hills. The primary suite has two walk-in closets and an elegantly updated bathroom. Enjoy the California indoor-outdoor lifestyle in the beautifully landscaped backyard, where two French doors lead to a covered patio. A brick terrace framed by a low-maintenance succulent garden surrounds a fire table, ideal for entertaining or relaxing with friends and family under the stars. Direct access to the main Ladera walking path puts you minutes from the Ladera Shopper, school bus stop, and just a short distance to the Ladera Rec Center. Perfectly positioned just 4 miles to Stanford, with quick access to major Silicon Valley tech campuses, and midway between San Francisco and San Jose International airports.

161 E Floresta WAY, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS
$8,000,000
5 Beds ⋅ 4 Baths ⋅ ML82004802 MLS
On the top of the hill at the end of a long private driveway and nestled on 3.5 mostly usable acres sits this very private home. Offering spectacular 270 degree views this 5 bedroom, 3 bath home sits on one of the finest sites in Portola Valley. The well-appointed private home features bright and light interiors with wonderful views throughout its effortless multi level design. The main level offers a living room, office, dining room, family room kitchen and primary suite all with western hill views. The lower level offers 4 additional bedroom, a laundry room and additional Office of Exercise room. There is also a barn and a large fenced in garden area.

909 Westridge DR, Portola Valley

Listed by Peter Cowperthwaite, 650-207-4101 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA
$3,800,000
3 Beds ⋅ 2 Baths ⋅ ML81999778 MLS
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.

90 Bear Gulch DR, Portola Valley

Listed by Kavanaugh Group, 650-400-5312 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Camille Eder from CBR
$3,460,000
3 Beds ⋅ 5 Baths ⋅ ML82004013 MLS
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!

846 Portola RD, Portola Valley

Listed by Elena Licari, 650-868-0069 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Anne King from KWPA
$9,000,000
4 Beds ⋅ 4 Baths ⋅ ML82003847 MLS
In Portola Valleys most coveted Westridge corridor, this striking property captures iconic Windy Hill views from its setting on more than 2 acres. The grounds unfold with California splendor sweeping level lawns, meandering garden paths amid native plantings, and a resort-style pool and spa perfectly oriented to Windy Hill. Inside, the home stuns with cathedral ceilings richly paneled in wood and white oak floors that span the open, multi-level floor plan designed for flow and functionality. Expanses of glass at every turn bring in the light, the landscape, and the views, creating a seamless connection to the outdoors. The living, dining, and family rooms flow off the chefs kitchen, which is highlighted by a commercial-quality AGA range. The primary suite is privately located, three bedrooms and two baths are in a separate wing, plus there is a gym with outside sauna. A rare and captivating retreat in one of Portola Valleys most exclusive locations.

130 Deer Meadow LN, Portola Valley

Listed by Peter Cowperthwaite, 650-207-4101 from Golden Gate Sotheby's International Realty
(If provided) CoList: Helen Miller from Compass

Sold listing courtesy of Vincent O'Shea, from ALREB
$5,000,000
3 Beds ⋅ 4 Baths ⋅ ML82003366 MLS ⋅ Ladera BLDG.
Step into this stunning single-level remodeled modern home nestled in the desirable Ladera neighborhood. Blending contemporary design with everyday comfort, this thoughtfully renovated home is the ultimate expression of California living. Dream chef's kitchen featuring a large center island, high-end appliances, custom cabinetry, & a walk-in pantry. This home has radiant heating, custom concrete floors, & large picture windows that flood the space with natural light, seamlessly blending indoor & outdoor living. Two spacious bedrooms share a Jack & Jill bathroom. A versatile bonus room perfect for a media room, home office, or even a fourth bedroom. Your own private resort awaits outside. Relax or entertain in the lush backyard, complete with a sparkling pool, mature landscaping, and multiple outdoor living areas. Convenienty located to the Ladera Rec Center, 5 miles to Stanford, near Silicon Valley, commute routes, and midway between San Francisco & San Jose international airports.

831 La Mesa DR, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Mark Cohan from COMPS

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