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$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

$5,600,000
3 Beds ⋅ 2 Baths ⋅ ML82047359 MLS ⋅ Westridge Arch. Supervis. Comm. BLDG.
Nestled along coveted Alamos Road in the prestigious Westridge area, this extraordinary property was refurbished top to bottom; presenting a rare opportunity to own a private retreat in one of the Peninsula's most exclusive neighborhoods. Set on nearly 2.75 acres of serene, country-like grounds, this exceptional estate offers unmatched privacy, tranquility, & breathtaking panoramic bay views; all just minutes from Highway 280 & Stanford Shopping Center & Campus. Beautifully & fully renovated, this move-in ready home features 3 bedrooms & 2 bathrooms, thoughtfully designed to capture stunning vistas from nearly every room. Expansive windows & outdoor spaces invite the natural beauty indoors, creating a peaceful sanctuary surrounded by lush greenery & rolling landscapes. Whether you choose to enjoy the home exactly as it is or envision expanding it into a larger custom estate, the possibilities are endless. Add a second story, subterranean garage, ADU, tennis court, lap pool, tranquil pond, an RV or other personalized amenities to create your dream compound. Opportunities like this are exceptionally rare - a timeless setting w/ forever views, exclusive privacy, & unlimited potential. Experience your own private piece of heaven & make this remarkable property yours before its gone!

365 Alamos RD, Portola Valley

Listed by Jeanette Cook, 650-344-3447 from Cook Properties
(If provided) CoList: from

Sold listing courtesy of Ken Glidewell from COMP29
$7,998,000
6 Beds ⋅ 6 Baths ⋅ ML82042439 MLS ⋅ Westridge Subdivision BLDG.
Rarely available estate, located in the highly sought-after Westridge neighborhood of Portola Valley. This lovely home is set on 3.86 serene acres w/ majestic oaks and offers a panoramic view of the SF Bay from Stanford to Mount Diablo. Enjoy a picturesque vista from the main home and newly built, stunning ADU. A gated driveway escorts you to a light-filled home highlighted by an open concept floorplan with high beamed ceilings and a wall of sliding doors to an expansive deck for al fresco dining and entertaining. Enjoy peaceful days and quiet nights filled with sparkling lights from the bay. The main home, containing 5bd/ 5ba, private office, family room and den one primarily one-story. The 1bd/1ba ADU has a spectacular deck with views too! Adding to the appeal is the sprawling grounds including a resort-like pool, hot tub, fire pit, gazebo, greenhouse, chicken coop and 2 fenced dog runs. Family/friends can gather throughout the exquisite property at numerous quaint outposts. This home is ideal for entertaining. Easy access to 280, Stanford University, Westridge hiking trails, shops and restaurants. Just 1.5 miles to the Ladera Shopping center, a 5-minute drive to Interstate 280, and access to top-ranked Portola Valley schools (buyer to verify eligibility)

138 Bolivar LN, Portola Valley

Listed by Stephanie Elkins, 650-400-2933 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
$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
$7,485,000
3 Beds ⋅ 3 Baths ⋅ ML81998853 MLS ⋅ Westridge HOA BLDG.
Contemporary masterpiece with spectacular Windy Hill views designed by architect Ana Williamson. Featuring steel I-beams, soaring ceilings create openness & strategically placed windows fill the space with light highlighting the natural setting. The modern open floor plan includes chef's kitchen with high-end appliances, custom Italian cabinetry & Dekton ceramic countertops. Floor to ceiling sliding Fleetwood glass doors make for easy indoor/outdoor entertaining, extending on to the covered patio with heated floors, fireplace, & Italian pizza oven. The primary suite upstairs has expansive views, walk-in closet & large chic bathroom. Built with fire safety in mind with a metal roof, no exposed eaves, fire sprinklers, owned solar & backup generator. Detached 770 sq ft guest house with full kitchen, 1.5 bathrooms & large bedroom. Bonus detached 350 sq ft workshop w/ extra storage provides a multitude of possibilities. Over 1 acre fully fenced with drought resistant Mediterranean native landscaping, mini orchard, ipe trellis with mature wisteria, 100 sq ft garden shed & raised garden beds. This thoughtfully designed luxury home offers privacy, stunning views, proximity to town, access to commute routes in Silicon Valley & serene hiking trails in the rolling hills of Portola Valley.

140 Pinon DR, Portola Valley

Listed by Julia Laquer, 650-434-2755 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Peter Cowperthwaite from DP
$7,998,000
4 Beds ⋅ 4 Baths ⋅ ML81990081 MLS
This rare offering truly has it all 2.5 acres in the prestigious Westridge area with complete privacy set back from the street, San Francisco and foothill views, a regulation-size tennis court, resort-style pool with elevated spa and waterfall, and a poolside sauna with an outdoor shower. The well-appointed classic ranch home features bright and light interiors with fine hardwood floors throughout its effortless single-level design. Recent updates, including crisp white paint, refinished floors, new lighting, and newer appliances, make this home move-in ready while also presenting an excellent opportunity to further transform it into your dream vision. Four spacious bedrooms, each with an en suite bath, include one that is privately located and perfect for guests or a home office. In a premier location, with 2.5-acre minimum parcels, and access to top-rated Portola Valley schools, this property offers an unparalleled lifestyle of sophistication, serenity, and endless potential.

600 Westridge DR, Portola Valley

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

Sold listing courtesy of Hugh Cornish from CBR
$10,625,000
4 Beds ⋅ 5 Baths ⋅ ML81980491 MLS
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.

178 Pinon DR, Portola Valley

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

Sold listing courtesy of Tim Kerns from CBR
$10,000,000
6 Beds ⋅ 8 Baths ⋅ ML81976258 MLS ⋅ Westridge BLDG.
Premier Westridge Estate in the Heart of Portola Valley. 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.

1240 Westridge DR, Portola Valley

Listed by Don DeFranco, 415-722-7259 from Compass
(If provided) CoList: from

Sold listing courtesy of Kavanaugh Group from CBR
$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
$18,800,000
7 Beds ⋅ 8 Baths ⋅ ML81969904 MLS
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.

138 Goya RD, Portola Valley

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

Sold listing courtesy of Mary & Brent Gullixson from COMPS
$5,300,000
3 Beds ⋅ 4 Baths ⋅ ML81968110 MLS
Located in central Westridge, the most sought-after area in all of Portola Valley, this property offers an exceptional setting with myriad possibilities & the opportunity to transform it into a dream vision. Home exudes an organic contemporary style with a Spanish flair, characterized by signature details like decorative tile stair rises & wrought-iron lighting. Home retains its original charm with all-wood cathedral ceilings, tiled floors in most public rooms, & in the primary suite, & naturally finished wood cabinetry topped with tile. Expansive windows & sliding glass doors open to spacious deck built around mature trees, offering views of the East Bay Hills & the surrounding natural beauty of Portola Valley. Main living area is open & especially spacious featuring a sunken conversation pit - a distinctive-of-the-era design element perfect for entertaining. There are 3 bedrooms & 3.5 baths plus a bonus room which possibly be a 4th bedroom. Set on approximately 3.2 acres, the grounds offer exceptional privacy & ample space for future pursuits. The nearby Westridge Trail provides access to miles of hiking, biking, & equestrian trails, renowned throughout Portola Valley. This property presents an unparalleled opportunity to create a personalized dream home in an idyllic setting.

298 Escobar RD, Portola Valley

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

Sold listing courtesy of Jason Sewald from CTCH
$6,500,000
4 Beds ⋅ 3 Baths ⋅ ML81964145 MLS
This property presents an unparalleled opportunity for renovation, expansion or new construction in the esteemed Westridge corridor of central Portola Valley with direct stunning views of the Windy Hill Preserve and the western hills. Situated on approximately 2.55 acres, the property boasts magnificent natural surroundings and views on one of the best streets in all of Portola Valley - truly a magical setting with the utmost in privacy. While feeling miles away from everything, world-class hiking, biking, and equestrian trails are just outside the front door. Shops, restaurants, and Portola Valley Town Center are just minutes away. The existing home has a unique radial design where three central core structural points anchor the open rafter ceilings that radiate like a starburst across the rooms. The home is in the acclaimed Portola Valley School District, walkable to the schools. Come see this beautiful property!

297 Mapache DR, Portola Valley

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Helen Miller from APR
$4,153,000
4 Beds ⋅ 3 Baths ⋅ ML81965016 MLS
Embrace breathtaking views from this mid-century modern rustic home in prime Westridge location of Portola Valley. Set on ~2.5 private acres, this gem is a blank canvas for the creative buyer. Great layout with good-sized rooms ready for personalized improvements. Ideal location with top-rated Portola Valley Schools. Incredible value!

137 Pinon DR, Portola Valley

Listed by Terri Kerwin, 650-868-0272 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Christopher Fling from CBR
$6,800,000
4 Beds ⋅ 6 Baths ⋅ ML81962402 MLS
Rare 3.3 level acres-perfect for a family compound with multiple structures for the ultimate in flexibility of use and all in a fabulous close-in-location. Comprised of several buildings with the opportunity to create a family compound, conference center, or both, the entire estate blends Spanish Revival architecture, with signature red-tiled roofs, and sleek modern interiors. Espresso-hued hardwood floors, towering sky-lit ceilings, and entire walls of glass imbue the home with sophisticated style and brilliant natural light and all on an exceptional setting. Main home with 4 bedrooms and 5.5 baths, including a 2-bath primary suite. Impressive open concept kitchen with vaulted ceiling opening seamlessly to the family room with multiple doors to the impressive grounds. Detached office/conference center/recreation structure with 1 bedroom and 1.5 baths. Attached fitness center/recreation room with 1 bath and sauna. Detached guest house,1-bedroom, 1-bath with full kitchen. Two three car garages for a total of 6 garage spaces. All inclusive approximately 10,066 square feet-buyer to verify. Incredible value and opportunity with excellent Portola Valley Schools, perimeter trees, sparkling pool, gated estate-a must see.

237 Mapache DR, Portola Valley

Listed by Judy Citron, 650-400-8424 from Compass
(If provided) CoList: Talia Citron from Compass

Sold listing courtesy of Debora Smith from SIR
$4,500,000
4 Beds ⋅ 3 Baths ⋅ ML81957969 MLS
An incredible lot of over 2.5 acres offers tremendous possibilities and plays host to this spacious home with spectacular views towards Felt Lake and the Western Hills. Highlights include 2 fireplaces, large gathering spaces, the kitchen with appliances from brands including Viking, a flexible-use room perfect for a gym or office, and numerous glass doors opening to the grounds for a true indoor/outdoor lifestyle. A guest house offers comfortable, modern living space for friends or extended family, while sweeping grounds take full advantage of Portola Valley's verdant beauty and provide peaceful venues for entertaining or play. Adding the finishing touch is a great location close to numerous nature preserves, a 5-minute drive from the shops and restaurants of Ladera Country Shopper, within 1.5 miles of Interstate 280, and with access to highly sought-after Portola Valley schools (buyer to verify eligibility).

100 Alamos RD, Portola Valley

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

Sold listing courtesy of Karen Fryling from NTERO
$10,500,000
4 Beds ⋅ 5 Baths ⋅ ML81954802 MLS
Spectacular Bay and hill VIEWS are the backdrop for this impeccably remodeled classic Westridge rancher. Located down a private driveway off the road, the home is nestled on 2.57 serene acres of largely usable land. Features include a sparkling pool and separate spa, two firepits, an outdoor kitchen, a putting green, bocce ball court, gorgeous gardens, a state of the art chicken coop, raised beds, and beautiful Oak covered knolls. Meticulously remodeled with no expense spared, quality features and finishes include Fleetwood sliders, custom Blomberg metal windows, custom cabinetry & built-ins, natural stone & concrete countertops, Oak hardwood floors, barn doors and custom fittings throughout. In addition to the Main House -- *POOL HOUSE: Large Studio/w/2 office areas, Full Bathroom, Kitchenette, a full wall Nano-Door, built-in storage, barn doors, radiant heat and an additional shower outside *Spacious ADU: 1BD/1BA, Living Room, Full kitchen, Laundry, Dressing Room, Custom Barn doors to separate the space, a built-in desk *3 car semi-attached Garage * Property is connected to the SEWER not on septic

332 Westridge DR, Portola Valley

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

Sold listing courtesy of Robert Godar from NTERO
$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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