Portola Valley CA 5 Bedroom Real Estate, Homes, Condos for Sale

5 Beds ⋅ 10 Baths ⋅ ML82054797 MLS

Extraordinary custom estate built by RJ Dailey Construction and designed by CJW Architecture in the desirable Westridge neighborhood. Designed to embrace western hill views with disappearing walls of glass, expansive terraces, and seamless indoor/outdoor living. The predominantly single-level floor plan features 5 bedroom suites, executive and day offices, spacious public rooms for formal and everyday gatherings, a gourmet kitchen, tremendous recreation and wellness level, plus craft/study room. A separate 2-bedroom, 1.5-bath guest house is also perfect for extended family. Resort-inspired grounds include a 50-foot pool, vegetable garden, orchard, barn, 4-car garage, oversized carport, and direct access to scenic trails. Exceptional privacy, remarkable views, and a premier location close to Stanford University, Silicon Valley, and acclaimed public and private schools complete this one-of-a-kind offering.

479 Westridge DR, Portola Valley

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Scott Dancer from APR

$5,988,000

5 Beds ⋅ 4 Baths ⋅ ML82052826 MLS

Set on 2.8 AC, this home offers a peaceful retreat in a coveted setting. Warm, welcoming interiors span more than 3,700 SF across a multi-level floorplan, blending rustic character with an easy livability that harmonizes with the surrounding landscape. A soaring vaulted ceiling elevates the living room anchored by a fireplace and expansive windows framing views that reach toward the Stanford Dish, while the main living spaces also include a formal dining room, granite kitchen with Thermador appliances, a comfortable family room with a fireplace, and a lower-level recreation room. Five bedrooms plus an office provide flexibility and comfort. With nearby access to scenic nature preserves and trailheads, a short drive to the Ladera Country Shopper shopping center and local favorites such as Alpine Inn, this home offers a rare balance of seclusion and convenience, all with access to acclaimed schools including Ormondale and Corte Madera (buyer to verify eligibility).

285 Escobar RD, Portola Valley

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(If provided) CoList: from

$5,495,000

5 Beds ⋅ 3 Baths ⋅ ML82052353 MLS ⋅ Westridge BLDG.

Defined by the clean lines, soaring ceilings, and abundant natural light that characterize classic mid-century design, this circa 1957 home presents a compelling opportunity in Portola Valley's highly desirable Westridge neighborhood. Unlike many homes of the era, the interiors are bright and inviting, with painted finishes, expansive walls of glass, and a series of eight skylights that fill the home with natural light throughout the day. Vaulted ceilings, versatile gathering spaces, and a thoughtful floor plan create a comfortable environment ready for immediate enjoyment. Equally significant is the setting. Spanning approximately 2.51 acres, the property offers exceptional privacy, expansive mostly level grounds, and a premier location surrounded by some of Portola Valley's most desirable estate properties. Whether enjoyed as it stands today, remodeled, expanded, or reimagined entirely, the combination of land, location, and architectural character creates an opportunity that is becoming increasingly difficult to find in today's market. Further enhancing the appeal is the home's location within the highly regarded Portola Valley school system and its convenient access to Stanford University and many of Silicon Valley's leading technology centers.

147 Mapache DR, Portola Valley

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

$6,850,000

5 Beds ⋅ 5 Baths ⋅ ML82050920 MLS

Stunning new construction Craftsman residence in the sought-after Ladera neighborhood of Portola Valley. This home features a bright, open-concept floor plan with expansive living spaces that flow to the backyard through large stacking glass sliders and a covered patio for indoor-outdoor living. The chefs kitchen includes Wolf and Sub-Zero appliances, ceiling-height cabinetry, quartz countertops with full-height backsplash, a large waterfall-edge island, walk-in pantry, and butlers pantry with additional counter space, storage, sink, and second dishwasher. A private first-floor ADU offers flexibility for guests or multigenerational living. Upstairs, a loft provides additional living space alongside three secondary bedrooms and a laundry room with sink and storage. The primary suite features a large walk-in closet and spa-like bath with soaking tub and oversized walk-in shower. Located in the Ladera community near open space, parks, hiking and biking trails, and convenient access to Stanford, Sand Hill Road, and Highway 280. Buy early to enjoy preferred pricing and the opportunity to personalize finishes. Estimated completion is Q2 2027. *All imagery is illustrative and subject to change and does not depict the subject property.

670 La Mesa DR, Portola Valley

Listed by Nadine Masarweh, 925-270-6807 from Thomas James Real Estate Services, Inc,
(If provided) CoList: from

$4,288,000

5 Beds ⋅ 4 Baths ⋅ ML82049073 MLS

Mid-Century Modern enthusiasts will delight in this one of a kind architectural gem. This home boasts blissful views reaching from San Francisco to Santa Clara. An entertainers dream! Tucked away from the flats, this stunning retreat is quiet and private. The home boasts three large decks, a hot tub, two gas fireplaces, two Tesla chargers in the garage, five bedrooms, three and a half bathrooms, an office upstairs, two living areas, generous 2,940 SqFt of living space plus an expansive remodeled finished basement of 1,280 SqFt. The dining room contains Herman Miller light fixtures and high ceilings meet walls of expansive glass to thrill and entertain guests. Come claim this magical home that some have said has the best views in the Silicon Valley.

410 Conil WAY, Portola Valley

Listed by Monique Anton, 650-380-5512 from Modern Homes Realty
(If provided) CoList: from

$8,400,000

5 Beds ⋅ 4 Baths ⋅ ML82042620 MLS

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

120 Deer Meadow LN, Portola Valley

Listed by Colleen Foraker, 650-380-0085 from Compass
(If provided) CoList: Carolyn Keddington from Compass

Sold listing courtesy of The reSolve Group from COMPS

$5,712,500

5 Beds ⋅ 4 Baths ⋅ ML82039321 MLS

With 5 bed /4 baths, this home has space & options. The 1.14+/- ac. gated prop. enjoys level lawn, pool & mature privacy trees. The home is welcomingthey say the kitchen is the heart of the home & this space embodies that. Amenities include quality appliances & extras: 6-burner Wolf range, 2 ovens, microwave & warming drawers, 2 dishwashers-one for dishes/one for pots & pans. Exceptional storage with pull out shelving, custom corner cabinets & and an appliance lift. The island provides workspace & seating. An adjacent family room has light, a fireplace, & access to the large deck. French doors open to incorporate the formal dining/living rooms into this space. Beamed ceilings, a fireplace, hardwood floors, a wall of windows & doors allow you to access the deck, to enjoy the view & host large gatherings. With a private entry a flexible, bookshelf-lined space could be an office, au pair or guest suite. There are 2 primary suites: 3 additional bedrooms + an office. The upper-level has the second primary & includes a bonus room for an office/nursery/or workout space. There is a bedroom off the family room (ideal for guests). Great Portola Valley location: close to local shopping, Alpine Hills Swim & Tennis club, The Alpine Inn, excellent PV schools, & just 4 min. to Hwy. 280.

50 Bear Gulch 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 Jennifer Alfaro from COMPS

$7,495,000

5 Beds ⋅ 8 Baths ⋅ ML82036782 MLS ⋅ Blue Oaks BLDG.

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

1 Redberry RDG, Portola Valley

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

$8,748,000

5 Beds ⋅ 8 Baths ⋅ ML82034238 MLS ⋅ Blue Oaks BLDG.

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.

7 Redberry RDG, Portola Valley

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: from

$8,100,000

5 Beds ⋅ 5 Baths ⋅ ML82033403 MLS

Contemporary single-level main residence with attached two-story ADU on 1.1+ private acres finished in 2021, offering direct Windy Hill views and walking distance to Portola Valley Town Center, library, restaurants, farmers market, and trailheads. Striking modern architecture features walls of glass, soaring ceilings, skylights, and white oak floors throughout. The dramatic great room opens to covered and open terraces and a level lawn just off the living room patio, with rear grounds anchored by a heritage oak. The designer kitchen showcases Calacatta marble surfaces, a waterfall island, and high-end appliances. The main residence includes a dedicated office, four bedrooms, and three and a half baths, highlighted by a serene primary suite with Windy Hill views and a Zen-inspired bath with private garden. A privately located bedroom suite is ideal for guests or an au pair. The attached ADU offers one bedroom, one bath, a full kitchen, and a living room with fireplace, with finishes matching the main home. Gated entry, custom pavers, cedar entry door, fountains, mature landscaping, level synthetic lawn, raised garden beds, and fully fenced grounds complete this desirable property. Total Finished square footage: 4,390 sq. ft. (main house: 3,520 sq. ft. and ADU: 870 sq. ft.)

1390 Westridge DR, Portola Valley

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

Sold listing courtesy of John Kavanaugh from CBR

$4,000,000

5 Beds ⋅ 6 Baths ⋅ ML82025339 MLS

Come right in. Enjoy the view. This stunning remodel completed in 2025 offers space, views, and peace of mind. With completely new high-end finishes throughout, this Mid-Century Modern masterpiece sits atop a private, lush acre, seamlessly blending modern luxury with nature's tranquility. Designed for those who appreciate both serenity and grand entertaining, a true retreat where hawks glide above. The expansive open-concept living space flows into a gourmet kitchen, featuring Bertazzoni five-burner gas stove, refrigerator and dishwasher plus gorgeous brass fixtures. Floor-to-ceiling windows showcase panoramic views of rolling hills & twinkling city lights, creating an awe-inspiring backdrop. A grand two-story entryway leads to an elegant dining area, warmed by a glass-enclosed gas fireplace. Step onto the rooftop deck, where alfresco dining meets unparalleled stargazing & sunset views. The primary suite is a private sanctuary, complete with a spa-like soaking tub and a bed perfectly positioned for breathtaking sunset views. Four additional bedrooms offer luxury & privacy for all, each has its own full bath. This is more than a home. It's an experience of modern elegance, timeless design, & natures embrace.

76 Vista Verde WAY, Portola Valley

Listed by Deniece Watkins Smith, 650-744-0888 from Compass
(If provided) CoList: from

Sold listing courtesy of Ruth Mistry from CBR

$5,150,000

5 Beds ⋅ 5 Baths ⋅ ML82024481 MLS

880 La Mesa DR, Portola Valley

Listed by Janie Barman, 650-759-1182 from Compass
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA

$6,200,000

5 Beds ⋅ 4 Baths ⋅ ML82022890 MLS

Remodeled and expanded on 1.3 level acres with tennis court, views, and beautiful grounds in central Portola Valley. Custom craftsmanship and artistic detail showcase cathedral ceilings with industrial lighting and windmill-style fans, numerous skylights, and reclaimed wood accents creating rustic sophistication. Two dramatic works by a Post Ranch Inn artist a sculptural stainless-steel fireplace surround and a custom steel hot tub on the elevated deck merge art and function. Gourmet kitchen with French Lacanche range and rolling ladder to upper storage. Primary suite couture closet designed for nearly 500 pairs of shoes also has a rolling ladder plus a spa like bath with open shower. Natural landscaping, pollinator gardens, and impressive variety of fruit trees. Private tennis court enhances the rear grounds. Moments from the town center and Windy Hill trails for the ultimate Portola Valley lifestyle. Excellent Portola Valley schools.

70 Stonegate RD, Portola Valley

Listed by Ciana Megan Tierney, 650-954-8642 from Compass
(If provided) CoList: from

Sold listing courtesy of Erika Demma from APR

$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

$3,850,000

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

$3,566,750

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

$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

$8,000,000

5 Beds ⋅ 4 Baths ⋅ ML81996632 MLS

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.

45 Bear Gulch Drive, Portola Valley

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

Sold listing courtesy of Donald Knight from CBR

$4,625,000

5 Beds ⋅ 4 Baths ⋅ ML81995488 MLS ⋅ Portola Valley Ranch BLDG.

Portola Valley Ranch, the hidden gem of the Bay Area embodying the perfect combination of convenience and serenity. Located on 450 acres with 350 of those dedicated to open space with miles of hiking trails. Experience luxury living in this spacious 5-bedroom, 3.5 bath home with breathtaking views of the hills. Expansive windows, large skylights and multiple sliding doors create multi-directional light. The large kitchen with custom island and quartz countertops includes a fireplace and big eat-in area with soaring windows. This home has hardwood floors throughout and many upgrades including custom touches of Italian plaster walls in updated bathrooms, wet bar, temperature-controlled wine cellar, sauna, EV Level 1 chargers. Residents enjoy the pools, tennis courts, vineyard, fitness center, community garden, dog park and childrens play area with easy access to Stanford University, Hospital and shopping. Acclaimed Portola Valley Schools.

4 Franciscan RDG, Portola Valley

Listed by Scott Chase, 650-947-4685 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Brad K. Le from ELEV

$5,027,000

5 Beds ⋅ 4 Baths ⋅ ML81993243 MLS ⋅ Ladera BLDG.

Remodeled & expanded modern rustic home in the heart of Ladera blends timeless style & sophistication & offers the perfect balance of luxury & comfort. An elevated patio provides a great welcoming space to greet your guests & take in the view. The chefs kitchen will have you cooking like a pro, featuring casual dining, a large island with sink, high-end appliances, custom walnut cabinets, & sleek design details like kickboard lighting. Wide plank white oak floors flow seamlessly through the home, creating a warm & inviting atmosphere. Open up the living space with a moveable wall or create effortless indoor-outdoor living with a foldable window wall. Integrated smart home systems give you added control at your fingertips. Light-filled primary suite has a luxurious bathroom with soaking tub, picture window, & stunning views of the Stanford Hills & Portola Valley from your private balcony. A finished bonus room is perfect for a home gym with ample storage. Gorgeous mature landscaping surrounds the home, offering a serene & private retreat with hot tub, wood-burning pizza oven, & gas firepit ideal for year-round enjoyment. Conveniently located to Ladera Rec, 4.5 mi. to Stanford, easy access to Silicon Valley, commute routes & mid-way between SFO & SJC International airports.

171 Gabarda WAY, Portola Valley

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

Sold listing courtesy of Michael Galli from APR

$6,700,000

5 Beds ⋅ 6 Baths ⋅ ML81980494 MLS

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.

155 Bear Gulch DR, Portola Valley

Listed by Keri Nicholas, 650-533-7373 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Loren Dakin from PARCA

$9,350,000

5 Beds ⋅ 5 Baths ⋅ ML81979365 MLS

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

805 Los Trancos RD, Portola Valley

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

Sold listing courtesy of RECIP from RCIP

$3,995,000

5 Beds ⋅ 4 Baths ⋅ ML81970104 MLS

Price Improvement! Estate home situated in a quiet & serene park like setting tucked away from the street. This gated property is located in the heart of Portola Valley, a short stroll to Town center, Famers market, Summer concerts, Just a few minutes drive to 280 & Sand Hill Venture Row. 5 bedrooms/3.5 fully remodeled baths with a unique welcoming feeling. Primary suite with a freshly remodeled bathroom & walk-in closet. Located on a wooded yet sunny 1.3 acre's. The 3,600 s.f. Home has a gourmet Chef's kitchen, Calcutta marble, custom cabinets, commercial grade appliances, gas range/oven, Liebherr refrigerator, breakfast bar, and bench seat storage. Large formal living room with high ceilings and slider to outdoor entertaining area. Separate family room/library with high ceilings. hardwood floors throughout. Double pane windows throughout. Inside laundry and abundance of storage cabinets. Two outdoor living rooms for entertaining. Raised planters for a vegetable & herb garden, Space ideal for a chicken coop, Tons of usable lawn space, On cooler nights, there is a spacious theater that insures many hours of entertainment. Wonderfully high ceilings & high end custom finishes throughout. No detail was ignored This home speaks of quality Come home to style and comfortable elegance.

1077 Portola RD, Portola Valley

Listed by William Lister, 408-892-9300 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jennifer Alfaro from COMPS

$10,000,000

5 Beds ⋅ 7 Baths ⋅ ML81972934 MLS

Located in the prestigious Westridge area, this striking contemporary home stands as a testament to architectural brilliance by well-known architect Bob Stecker & construction by RJ Dailey. Home's signature aesthetic is unveiled with cathedral ceilings by Kalwall, with dispersed light intersecting at angles supported by open beams & trusses in clear heart redwood. This designs floods the home with diffused natural light, minimizing solar heat gain & maximizing thermal performance. The chorus of natural materials continues throughout, with vaulted ceilings in clear heart redwood, floors in oak, marble, or tile, & custom built-in wood cabinetry at every turn. Detached guest house with a full kitchen, bedroom, & bath. Set on approximately 2.5 acres, the outdoor experience is equally impressive. The grounds feature a newly remodeled pool & spa, a built-in barbecue center, & freshly designed & installed landscaping with expansive lawn for recreation. The Westridge Trail borders the property leading to miles of hiking & biking renowned throughout the town. Located within the highly acclaimed Portola Valley school district, this property is truly a special offering that combines architectural excellence with luxurious amenities & a remarkable setting with Bay views.

550 Westridge DR, Portola Valley

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

Sold listing courtesy of Mary & Brent Gullixson from COMPS

$6,150,000

5 Beds ⋅ 5 Baths ⋅ ML81968096 MLS

Gorgeous Portola Valley Estate with Level Lot and Views in Prime Location. Formal entry, spacious living room with western hill views, separate dining room opens to terrace. Gourmet chef's kitchen with center island, built-in nook, Viking cooktop, double ovens and Thermador refrigerator. Expansive family room with threes sets of doors opens to stunning yard. Custom office, 5 spacious bedrooms, 4.5 remodeled custom baths, main level bedroom and bath with separate entrance. Indoor laundry room with ample storage, custom mud room, exquisite primary suite with views of western hills and walk in closet. Primary bath includes dual vanities, steam shower, and jetted tub. Ring doorbell, Nest thermostats, gated driveway. Outdoor area includes pool, spa, two fire pits, and heated cabana. Close to Alpine Swim and Tennis. Award winning Portola Valley Schools.

25 Bear Gulch DR, Portola Valley

Listed by Keri Nicholas, 650-533-7373 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Rayyan Fani from COMPS

$3,450,000

5 Beds ⋅ 6 Baths ⋅ ML81961409 MLS

Over an acre plays host to this spectacular Mediterranean-style home with breathtaking views of the San Francisco Bay. Step inside to discover 4,400 sf of interiors adorned with high-end finishes and appointments, with two fireplaces, expansive formal rooms, a gym, office, and a gourmet kitchen equipped with premium appliances. 5 bedrooms, each with its own en suite, are highlighted by the primary suite featuring a spa-inspired bathroom. French doors throughout the home beckon you to breezy outdoor spaces, where panoramic views await amidst lush surroundings, and the sprawling front yard provides ample space for recreation and relaxation. Though you will feel a wonderful sense of privacy here, you will still be within reach of all the area has to offer, with easy access to nearby amenities such as nature preserves, trails, downtown Los Altos, and Interstate 280. Additionally, children may attend acclaimed schools Ormondale Elementary and Corte Madera (buyer to verify eligibility).

190 Vista Verde WAY, Portola Valley

Listed by DeLeon Team, 650-900-7000 from Deleon Realty
(If provided) CoList: from

Sold listing courtesy of DeLeon Team from DLRPA

$8,500,000

5 Beds ⋅ 6 Baths ⋅ ML81957088 MLS

Timeless design aligns w/ contemporary details in this fabulous 5br/4.5ba home. This private 1.23-acre property provides mature landscaping, wrap-around views, & an incredible space for everyday living. Floor-to-ceiling windows fill the home w/ abundant natural light. The main level offers a welcoming entry leading to a designer kitchen w/ endless cabinets, an island w/ bar seating & large windows that frame the outdoor landscape. Off the kitchen is a family room w/ vaulted ceilings, a stone fireplace & direct access to the backyard. Gather in the formal DR or open glass doors in the adjoining LR to enjoy a large deck w/ views overlooking the peaceful pool & spa area. Completing the lower level are 2 bdrms joined by a full bthrm + an ensuite bdrm, laundry room, & versatile bonus room. Upstairs is an ensuite bdrm next to the primary retreat, which features dual walk-in closets, lovely views & a spa-like bthrm. Every room leads to an outdoor space, further showcasing the phenomenal floor plan. A detached bonus space can be used for a gym/office or hobby room. This home also offers an outdoor shower, 1/2 bath by the pool, & storage room that doubles as a wine room. Relish in trails & outdoor recreation throughout Central Portola Valley. A home like this doesn't come around often.

161 Sausal DR, Portola Valley

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

Sold listing courtesy of Terri Kerwin from DP

$2,610,816

5 Beds ⋅ 3 Baths ⋅ ML81946329 MLS

This oak studded approximately 1.05-acre property with striking views of the bay is located in the quiet Los Trancos neighborhood of Portola Valley. The inspired use of clerestory and roof windows and sliding glass doors fills the two-level, 5-bedroom, 3-bath home with an abundance of natural light and views of the tranquil surroundings. The two-story foyer creates a dramatic entry and flows directly into the living room and dining room, both with views to the East bay hills. The updated kitchen with new appliances includes a casual dining area and conveniently connects to both the dining room and large family room with an office space. Enjoy the peaceful, serene setting of Los Trancos while being just minutes to local shopping and restaurants, open space preserves, commute routes, Stanford and the excellent Portola Valley schools.

371 Old Spanish TRL, Portola Valley

Listed by Kavanaugh Group, 415-377-2924 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Rowene Hood from ROWH

$4,550,000

5 Beds ⋅ 3 Baths ⋅ ML81945139 MLS

With its modern design and open floor plan, you'll delight in spacious sun-filled rooms, as you explore this 5-bedroom, 3-bathroom home which has been exquisitely updated and remodeled. Beautiful European oak flooring in living area & bedrooms. Kitchen features Carrera marble counters, custom cabinetry, Thermador appliances, & a walk-in pantry. 3 downstairs bedrooms, including an ensuite. Hall bathroom with marble counters & beautiful tile floors. Don't miss the stunning wine room, with space for nearly 200 bottles. Beautiful cast link open staircase imported from Italy. Upstairs has 2 bedrooms including a large primary suite with walk-in closets & spa-like bathroom. Offering the best of California living, the interior flows seamlessly to the outdoors through the La Cantina 5-panel folding door. The backyard is an oasis-like retreat with a kitchen, fire pit table, & multiple seating or dining areas. An attached two-car garage includes a car charger. Don't miss this rare opportunity.

230 S Balsamina WAY, Portola Valley

Listed by Janeen Poutre, 408-209-6640 from Coldwell Banker Realty
(If provided) CoList: Colleen Cooley from Coldwell Banker Realty

Sold listing courtesy of The Laugesen Team from KWPEN

$4,500,000

5 Beds ⋅ 3 Baths ⋅ ML81943643 MLS

From its central Portola Valley location, this newly remodeled home is set far back from the street on a corner lot of nearly one acre. Expansive meadows envelop the property, leading to a backyard oasis with sparkling pool and ample space for outdoor gatherings. Updates abound, including elegant white oak floors on the main level, new carpet upstairs, plus remodeled kitchen and bathrooms, all complemented by a fresh contemporary color palette inside and out. The living and formal dining rooms are perfect for refined entertaining, yet the true focal point is the kitchen and adjoining family room, which open to the pool area through sliding glass doors. With 5 bedrooms and 3 baths, including one on the main level, as well as the primary suite upstairs and three additional bedrooms, this home is both spacious and versatile for remote work needs. With Its convenient location to nearby hiking and riding trails as well as top-rated schools... This an excellent place to call home.

8 Hillbrook DR, Portola Valley

Listed by Dean Asborno, 650-255-2147 from Compass
(If provided) CoList: from

Sold listing courtesy of Judy Byrnes from CBR

$6,505,000

5 Beds ⋅ 5 Baths ⋅ ML81942694 MLS

Unique opportunity to buy and build your dream home with Thomas James Homes in the idyllic Ladera neighborhood. Head inside to an open concept floorplan thats perfect for entertaining with a gourmet kitchen that features an eat-at island, top-of-the-line appliances, quartz countertops, walk-in pantry, dining area, and spacious great room. Adjacent is an office, flex room, and ADU with a private entrance, kitchenette, and en suite bath. Ascend the stairs to discover a loft, laundry room with sink, 3 secondary bedrooms, and 2 full baths. The grand suite features a luxurious grand bath with a dual-sink vanity, walk-in shower, freestanding soaking tub, and walk-in closet. Closing out the home is a roof deck where you catch the scenic view of Portola Valley. Estimated home completion date is Spring 2024. This home is part of our escalated pricing program. Please inquire to learn more. *Illustrative landscaping shown is generic and does not represent the landscaping proposed for this site.

264 La Cuesta DR, Portola Valley

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

Sold listing courtesy of Jodi Campion from APR

$6,500,000

5 Beds ⋅ 5 Baths ⋅ ML81937485 MLS

Nestled away from the street in premier central Portola Valley, this exquisite home boasts an elevated position that affords sweeping views of the San Francisco Bay and vistas across Silicon Valley. The Spanish hacienda architecture is evident from the moment you arrive, with decorative tile work, scrolled iron railings, and graceful arches creating an aura of elegance and charm. The front of the home is designed to maximize the views, with a vast terrace surrounding a sparkling pool and spa that beckons for outdoor entertainment. The grand living room, formal dining room, family room, and upstairs primary suite all offer access to the outdoor spaces with sweeping views. Surrounded in complete privacy on more than 1.6 acres, this architectural tour de force is a true masterpiece of design, with captivating gardens that create a romantic setting. Indulge in the beauty and luxury of this remarkable property and experience the ultimate in California living. Premier location + Top Schools!

155 Bear Gulch DR, Portola Valley

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

Sold listing courtesy of Keri Nicholas from PARCA

$7,800,000

5 Beds ⋅ 7 Baths ⋅ ML81924892 MLS

Stunning home in rarely available Blue Oaks neighborhood surrounded by 217 acres of open space. Best Windy Hill views from many rooms. Extra-spacious floor plan with bamboo floors, towering ceilings, entire walls of windows, and sleek maple cabinetry. Gently stepped levels on the first floor with grand living room, formal dining room, office/library, open kitchen and family room, plus separate wing with 5 bedrooms and 4 baths including luxe primary suite with private nook and outdoor spa, second suite, and 3 bedrooms served by 2 baths. Entire lower level for recreation, media, fitness, study, wine cellar, and amazing storage. 3 half-baths. Outdoor fireplace terrace and barbecue center, fully fenced vegetable garden. Attached approximately 800 square foot, 3-car garage. Community pool, spa, clubhouse, and miles of trails. Excellent Portola Valley schools.

10 Redberry RDG, Portola Valley

Listed by Kavanaugh Group, 650-400-8076 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Hugh Cornish from CBR

$3,753,750

5 Beds ⋅ 5 Baths ⋅ ML81924088 MLS

Outstanding opportunity in Westridge area on 2.5 acres with San Francisco Bay and East Bay hill views, vineyard potential, and absolute privacy. Vintage home ready to renovate or build new for your own dream vision. Of-the-era style includes towering beamed ceilings, floor-to-ceiling windows, and tile and lava rock finishes. Two levels with primary living spaces on the main level, including primary suite and 3 additional bedrooms plus lower-level recreation room, bar, wine cellar, and multi-room bedroom suite with outside entrance. Almost every room opens to a deck that spans the home or to a huge entertainment deck on lower level. Sun-swept open space and terraced hillsides dotted with mature trees. Excellent Portola Valley schools; just 2 miles from shops and restaurants.

111 Escobar RD, Portola Valley

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

Sold listing courtesy of RECIP from RCIP

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