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$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
$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
$1,650,000
2 Beds ⋅ 2 Baths ⋅ ML82002420 MLS
Come see this modern marvel. With a variety of recent updates, this spacious two bedroom bungalow is a wonderful country living retreat. Views of open space hills and near to Coal Mine Open Space Preserve and a host of scenic hiking trails. Situated on a 7,440 sf lot with ample off street parking on newly paved driveway, the home features a new roof, a main floor living room with high ceilings, hardwood floors, large wood white-washed beams, large glass picture windows and a scenic deck for having your morning coffee. The recently updated kitchen is conveniently located near a sunny series of rear decks, framed with gardens, mature oak trees and a sloping backyard, making a picturesque setting for outdoor entertaining. The primary suite is on the main level and includes space for a small office set up and an updated bathroom with dual sinks and a spa tub. A second bedroom upstairs has views of the nearby open space hills and features another recently updated bathroom. Los Trancos Woods neighborhood is only minutes from a host of amenities which include Roberts Market, Windy Hill Open Space Preserve, Rossottis Alpine Inn, Stanford University and Hospital and Silicon Valley business activities. It is in the acclaimed Portola Valley School District. This is your next home!

128 Los Trancos CIR, Portola Valley

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

Sold listing courtesy of RECIP from RCIP
$6,550,000
4 Beds ⋅ 4 Baths ⋅ ML82001354 MLS
Transformed with a whole-home renovation, this exquisite home offers luxurious designer style and wellness-focused amenities in a prime Central Portola Valley location. Every detail has been elevated, with stunning interiors featuring heated tiled floors in every room. Expansive retractable glass doors create a seamless indoor/outdoor connection in the living and dining room plus there is a spacious kitchen and family room combination with built-in casual dining area. A spa-like ambiance defines this 4-bedroom, 3.5-bath home, anchored by a sumptuous primary suite with steam shower. A private wellness retreat continues outside on the tremendous rear deck which feels like living space, including a recessed spa, cold plunge tub, and cedar-lined sauna. A lower deck with linear gas fireplace invites gatherings, sanded walking paths encourage quiet reflection beside the creek, and a vast synthetic lawn awaits recreation. Designed for effortless living and exceptional comfort, this home also has a wonderfully converted garage bay with the perfect space for a remote office.

30 Cheyenne PT, Portola Valley

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

Sold listing courtesy of Bryan Jacobs from RWH
$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
$1,600,000
2 Beds ⋅ 3 Baths ⋅ ML82001310 MLS
Welcome to a remaining piece of Portola Valley history, full of possibilities! The charming and rustic original structure, with its tall brick fireplace, high ceiling, and exposed rafters, rests on a sunny, gently sloped, half acre lot. Later additions include a very large primary bedroom and bath. A wide veranda wraps around two sides of the house, perfect for relaxing while taking in the expansive view over Portola Valley and on to the East Bay hills. Colorful sunrises, full moons, and an occasional complete rainbow are yours to enjoy. An additional deck provides another viewing spot, with access from both the primary bedroom and the dining room. Nestled in the Woodside Highlands neighborhood, this location offers Portola Valley's excellent schools and provides nearby access to Portola Valley's hiking trails and to the popular Town Center with its library, children's playground, tennis and pickle ball courts, playing field, a redwood grove, and farmers' market. The half acre lot is all usable. Old stonework lines paths and a pond, and off street parking is plentiful. Bring your imagination and make this lovely space your own!

102 Santa Maria AVE, Portola Valley

Listed by Jean Isaacson, 650-387-8427 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Jean Isaacson from GGSIR
$2,925,000
3 Beds ⋅ 3 Baths ⋅ ML82001168 MLS
Sweeping views of the San Francisco Bay, this beautifully appointed home borders the 235-acre Coal Mine Ridge Open Space Preserve & has access to its 10+ miles of scenic hiking trails. Approximately 0.75 acre comprising a 7,585 square-foot lot plus a permanent, exclusive-use easement of 25,015 square feet. Nearly every room enjoys breathtaking Bay views. Dramatic living room flows seamlessly into the elegant dining room. Open kitchen & large breakfast area are well-appointed with custom cherry cabinetry & premium appliances. Primary bedroom suite is a luxurious retreat that spans one end of the main level, with significant customized wardrobe space off a foyer entrance with walk in closet. A private balcony with Bay Views, a signature wood-paneled & vaulted ceiling, & a spa-like bath with a jetted tub and shower, each for two. Lower level with a spacious family room & large deck with Bay views. There are two bedrooms on this level including one that opens to the Bay view deck shared with the family room & one with large walk-in closet, plus there is a well-appointed bath. Lot size is approximately 7,585 sq. ft. plus a permanent exclusive-use easement of 25,015 square feet. Excellent Portola Valley schools and close proximity to Stanford.

1144 Los Trancos RD, Portola Valley

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

Sold listing courtesy of Lyn jason Cobb from CBR
$3,550,000
4 Beds ⋅ 4 Baths ⋅ ML81999222 MLS
Located in desirable Portola Valley, this 4-bedroom, 4-bath approximately 2930 square foot home offers a tranquil setting for everyday living and entertaining. Situated on an acre lot (per county), the property provides ample outdoor space including a tiered deck, stable and paddock. High ceilings in the spacious foyer and living room create a dramatic, light-filled entry to the home. The formal dining room with wet bar overlooks the living room, creating an ideal setting for entertaining. The kitchen is conveniently located between the dining and family rooms and includes a spacious area for casual dining as well as a separate built-in cabinet unit providing added prep space. The primary suite and two additional bedrooms are clustered at one end of the house. The primary bedroom includes deck access and a spacious en-suite bath with a walk-in closet. One of the additional bedrooms includes en-suite bath and the remaining bedroom is adjacent to a third full bath. The fourth bedroom and full bath are located just off the family room an ideal setting for house guests. Photos are virtually staged.

4760 Alpine RD, Portola Valley

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

Sold listing courtesy of Rachel Sudano from CBR
$3,350,000
3 Beds ⋅ 2 Baths ⋅ ML81998188 MLS
Location is everything in real estate, & this charmer on an expansive lot could not be more ideal in the highly desirable Ladera neighborhood! Featuring 3 bedrooms, 2 full bathrooms, & a bonus room all on one level. Recent interior paint, updated floors & kitchen w/ granite countertops, double pane windows & custom sliders, & fresh landscaping. Expansive wrap around yard w/ potential & ideal for entertaining & gatherings. Close proximity to an award winning school district, Stanford University, Ladera Shopping Center, Ladera Recreation Center, horseback riding at Webb Ranch, Highway 280, hiking & biking trails, & so much more!

240 Dedalera DR, Portola Valley

Listed by Chris A. Sabido, 650-922-8888 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Camilo Perez from RWH
$1,850,000
2 Beds ⋅ 1 Baths ⋅ ML81988410 MLS
Luxury Silicon Valley Getaway in Portola Valley with Views, updated single family /rustic modern interior, move-in ready and personal retreat on a large 11,500 square foot lot, surrounded by natural beauty, a network of trails. Open floor plan with natural light throughout, skylights, hardwood floors, built in bookshelves, new kitchen and appliances, eat-in kitchen and sliding glass doors to the expansive deck from living room and primary bedroom, outdoor Jacuzzi, bonus room below can be used for guests, entertainment, media room, hobbies, workshop or possible JDU, Room to expand on large lot. Less than 5 miles without getting on the freeway to Stanford University. Enjoy the Sunrise trail steps away from your private sanctuary with access to 650+ acres open space and trails. Also, direct access to Arastradero Preserve and Los Trancos Open Space with over 1500 acres of more hiking trails.

1023 Los Trancos RD, Portola Valley

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

Sold listing courtesy of JJ Team:Jones/Cassel from NTERO
$2,450,000
3 Beds ⋅ 1 Baths ⋅ ML81997941 MLS
Welcome to this charming single-story home ideally located in central Portola Valley. Scenic trails, open space preserves, and popular biking routes are right outside the door. Town Center's library, tennis courts, playing fields, and weekly Farmers Market are just a short stroll away. Coveted preschools in addition to Portola Valley's highly acclaimed elementary and middle schools provide exceptional educational opportunities. Expansive windows fill the house with sunlight and create inviting interior space. Three large bedrooms, beautiful oak hardwood floors, and a newly updated kitchen and bathroom make this home move-in ready. Enjoy it as is or plan for expansion - renderings from 2016 for a proposed expansion are available for review. The sunny backyard is lightly shaded by Redwood trees and provides exceptional space for entertaining or to unwind and enjoy the outdoors. Wyndham Drive, a circular street of approximately 29 homes, hosts annual block parties and provides a multigenerational neighborhood reminiscent of days gone by. With so much to offer, this home is not to be missed. Come see the best of Portola Valley living.

319 Wyndham DR, Portola Valley

Listed by Carrie Davis, 650-269-4768 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Leslie Woods from SGP
$7,575,000
4 Beds ⋅ 4 Baths ⋅ ML81997192 MLS
Just over 1 acre in central Portola Valley, this modernist masterpiece was designed by award- winning architect Arthur Dyson who worked with Frank Lloyd Wright. The Zen-inspired lifestyle has resort-like grounds and breathtaking Windy Hill views. A striking glass walkway continues inside, where a 2-story wall of falling water and all-glass staircase set a tone of modern panache. The organic ambiance continues with barrel-vaulted ceilings with glass at each end, copper wall accents, and floors in slate and maple. Living room, dining room, and family room offer seamless sightlines to a central cantilevered fireplace, entire walls of glass present the views, and the kitchen is equipped with top-tier appliances. A private office plus main-level primary suite with additional office space cater to remote work needs. Second bedroom and bath on main level plus 2 bedrooms and bath on lower level. Pool, separate spa, plus vast open and covered decks. Excellent Portola Valley schools.

65 Cheyenne PT, Portola Valley

Listed by Kimm Terpening, 650-867-4880 from Compass
(If provided) CoList: Jessica Edwards from Compass

Sold listing courtesy of Billy McNair from CBR
$2,325,000
3 Beds ⋅ 1 Baths ⋅ ML81996192 MLS
Beautiful 3 Bedroom Home in Award Winning Portola Valley School District. Elegant Living Room with Fireplace. Formal Dining Area. Stunning Kitchen with Quartz Countertops and Skylight. 3 Bedrooms. Updated Bathroom with Double Sinks, Separate Shower, and Skylight. Spacious Patio with Outdoor TV and Trellis. Lovely Landscaped Yard. Award Winning Portola Valley School District. Best Value for Central Portola Valley

322 Wyndham DR, Portola Valley

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

Sold listing courtesy of Denise Crosetti Schaul from DCBR
$4,995,000
4 Beds ⋅ 3 Baths ⋅ ML81996063 MLS
Freshly Updated on a Beautiful 1+ Acre Level Lot. This stunning level one-acre property offers a rare opportunity to embrace the essence of Portola Valley living, whether enjoying today with its fresh updates or transforming for the future. Just blocks from Town Center and Windy Hill trails, the location is ideal. The main residence features random plank hardwood floors in the living areas, an updated kitchen and baths, and numerous glass doors opening to the wraparound grounds with privacy afforded from its set-back location. With 4 bedrooms and 3 baths, there is also ample space for the addition of an ADU, plus there is a 2-stall vintage barn with tack room and hay room, and large storage shed. Completing the appeal is access to top-rated Portola Valley schools, with the elementary school just minutes away. A rare opportunity to create your dream lifestyle in a premier location.

1365 Westridge DR, Portola Valley

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

Sold listing courtesy of Erika Demma from APR
$3,025,000
4 Beds ⋅ 3 Baths ⋅ ML81995172 MLS
A rare gem in the heart of Portola Valley! Nestled on a serene 1/3-acre lot, this beautifully maintained property offers two charming homesperfect for multi-generational living, guests, or rental income. The main residence boasts 3 beds, 2 baths, a formal living and dining area, an inviting family room, and a luxurious primary suite. High ceilings, abundant natural light, and thoughtful updates enhance the warm, welcoming ambiance. The detached 1-bed, 1-bath guest cottage (approx. 600 sq. ft.) has a private entrance, ideal for extended stays or potential rental income. Outside, enjoy the asphalted sports court, lush landscaping, and ample parking, including a spacious oversized garage. Connected to the sewer, this home is move-in ready with top-rated Portola Valley schools nearby. Access to hiking trails. Located minutes from Alpine Rd., this peaceful retreat offers both tranquility and convenience. Don't miss this exceptional opportunity!

111 Carmel WAY, Portola Valley

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

Sold listing courtesy of Kimm Terpening from COMPS
$4,350,000
3 Beds ⋅ 3 Baths ⋅ ML81994941 MLS
Formal entry. Elegant living room with fireplace. Chefs kitchen with center island and dining area. Open family room with fireplace. Spacious yard with pool and spa. 3 bedrooms, 3 bathrooms, 2-car garage and extras off-street parking. Over 19,300 square foot lot. A must see!

441 La Mesa DR, Portola Valley

Listed by Loren Dakin, 650-714-8662 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA
$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
$6,900,000
4 Beds ⋅ 2 Baths ⋅ ML81993203 MLS
Tucked away in a serene, private enclave bordering the picturesque Pearson-Arastradero Preserve, this remarkable 2.8-acre estate offers an unparalleled views and usable land. With breathtaking panoramic views of the western hills, direct access to an extensive network of scenic trails, and a charming residence spanning 3,225 square feet, this property is a true haven for those seeking tranquility and sophistication. The thoughtful layout ensures both comfort and functionality, featuring designated office spaces for productivity, as well as inviting restful areas throughout the home. A striking spiral staircase elegantly connects the expansive living room to a private office, epitomizing the seamless fusion of style and practicality.

6 Arastradero RD, Portola Valley

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

Sold listing courtesy of Christina Hengehold from CBR
$56,000,000
6 Beds ⋅ 13 Baths ⋅ ML81978361 MLS
Villa del Prato is a singular gem among Silicon Valley estates. Nestled in the woodlands of Portola Valley on nearly 12 acres of tranquil, private, flat land, the estate comprises three structures: a main house (12,000 sf); an entertainment or business building (6,500 sf); and a pool house (2,000 sf). Inspired by classic Palladian Italian architecture, each structure is reminiscent of a Tuscan villa, featuring soaring arches, 20-foot ceilings, dramatic skylights, solid stone columns direct from Italy, and the finest-quality finishes. The main home, built on two levels, features a one-of-a-kind 900-square-foot dressing suite that doubles as a safe room. Unseen are advanced systems for the comfort and security of residents and guests. The entertainment/business building provides an opportunity for customization. With its towering columns, airy loggia, and spacious ballroom, it could be utilized for entertaining, as a home office, conference center, staff housing, or a home for your next startup. Electrical, plumbing, HVAC, and other key systems are fully fitted out. This grand estate is centrally located close to Hwy 280 mid-way between San Francisco and San Jose, with easy access to major airports and technology and business centers. (All sf info per plans).

20 Meadow LN, Portola Valley

Listed by Chris Iverson, 650-450-0450 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Leslie Bauer from CTYRE
$4,990,000
4 Beds ⋅ 6 Baths ⋅ ML81990000 MLS
Nestled on more than 1.5 acres, this exquisite home has been thoughtfully transformed to deliver an unparalleled living experience. With more than 4,200 sf, the home exudes luxury, from its soaring ceilings and impeccable finishes to the dramatic use of glass. Expansive living areas, multiple fireplaces, a gourmet kitchen, and an executive office offer both comfort and style. Four bedrooms are highlighted by a private, retreat-like primary suite, complete with a spa-inspired bathroom. Outside, multi-level grounds provide the perfect venues for enjoying the idyllic setting, and this home also includes air conditioning, and a 3-car garage. Located just moments from trails, nature preserves, and Roberts Market, this home offers tranquility and convenience, while easy access to Interstate 280 ensures the entirety of the Bay Area is within easy reach. Plus, children may attend acclaimed schools such as Ormondale Elementary and Corte Madera Middle (buyer to verify eligibility).

5 Oak Forest CT, Portola Valley

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

Sold listing courtesy of Loren Dakin from PARCA
$1,250,000
ML81990224 MLS
Fully PERMITTED & APPROVED plans! Ready to go to build your dream home. Large vacant approximately 1.586 acre parcel in a pastoral setting. Private and secluded gentle sloped building site with lush mature trees. Enjoy this central Portola Valley location immediately close to the PV Town Center recreational facilities, library, weekly farmer's market, Windmill Pre-school and Parkside Restaurant. Hiking and biking trails also immediately accessible. All this and only a 10-minute drive to Highway 280. Disclosures include: PV Issued permit, Architectural plans, Lot & Topo Survey, Arborist reports, GEO study, PERC, Septic development and other related documents. Utilities: electric, telecom and water available at lot line.

501 Wayside RD, Portola Valley

Listed by Dulcy Freeman, 650-804-8884 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of RECIP from RCIP

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