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$8,750,000

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

6 Beds ⋅ 9 Baths ⋅ ML82011147 MLS ⋅ Blue Oaks BLDG.

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

5 Redberry RDG, Portola Valley

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

Sold listing courtesy of Kavanaugh Group from CBR

$2,950,000

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

3 Beds ⋅ 2 Baths ⋅ ML82009816 MLS

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

3 Wyndham DR, Portola Valley

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

Sold listing courtesy of Lynn Roberts from COMP52

$5,300,000

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.

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

$3,800,000

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.

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

$9,000,000

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.

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

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.

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

$6,550,000

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.

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

$1,600,000

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!

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

$3,350,000

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!

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

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.

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

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.

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

$2,325,000

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

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

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.

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

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!

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

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!

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

$56,000,000

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).

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

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).

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

$2,900,000

Welcome to 1 Hayfields Road! Motivated Seller - best price on the flats of Portola Valley!!! Nestled in a serene and peaceful country setting, this inviting rancher offers the perfect balance of privacy and convenience. With stunning access to nearby trails, you can enjoy the natural beauty right outside your doorstep, whether you're hiking, biking, or simply soaking in the outdoors. Inside, this lovely, updated home are multiple living areas, including 4 bedrooms and 2 bathrooms. Featuring soaring cathedral ceilings, skylights, and expansive windows, the home is filled with natural light, creating a bright, open atmosphere. Updated kitchen with stainless appliances. Separate laundry with top of the line LG washer and dryer. Solar panels and 240 outlet in garage for EV charging. The yard offers a natural retreat with seating and dining areas, and is partially fenced for either a dog run or a child's playground. Located just 3 miles from 280, and close to the Portola Valley Schools, and local amenities, you won't have to sacrifice accessibility for country living.

4 Beds ⋅ 2 Baths ⋅ ML81990121 MLS

Welcome to 1 Hayfields Road! Motivated Seller - best price on the flats of Portola Valley!!! Nestled in a serene and peaceful country setting, this inviting rancher offers the perfect balance of privacy and convenience. With stunning access to nearby trails, you can enjoy the natural beauty right outside your doorstep, whether you're hiking, biking, or simply soaking in the outdoors. Inside, this lovely, updated home are multiple living areas, including 4 bedrooms and 2 bathrooms. Featuring soaring cathedral ceilings, skylights, and expansive windows, the home is filled with natural light, creating a bright, open atmosphere. Updated kitchen with stainless appliances. Separate laundry with top of the line LG washer and dryer. Solar panels and 240 outlet in garage for EV charging. The yard offers a natural retreat with seating and dining areas, and is partially fenced for either a dog run or a child's playground. Located just 3 miles from 280, and close to the Portola Valley Schools, and local amenities, you won't have to sacrifice accessibility for country living.

1 Hayfields RD, Portola Valley

Listed by Debora Smith, 650-580-8286 from Sotheby's Intl Rlty
(If provided) CoList: from

Sold listing courtesy of Chris Iverson from GGSIR

$7,998,000

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.

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

$2,500,000

Nestled in a serene location, this beautifully maintained 3 bedroom, 2 bath home offers the perfect blend of comfort and functionality. Step inside to discover the welcoming formal entry way. Charming stairs lead you to the main living space which showcases dramatic high ceilings and an open-concept floor plan that creates a bright & airy ambiance. The living room perfectly opens up to a front balcony while also seamlessly opening up to a large flat backyard creating a space that is perfect for everyday living & entertaining. The updated kitchen features a center island, lots of cabinet space and peaceful views to the surrounding nature. In addition, this home boasts 3 bedrooms on the main level plus a cozy loft ideal for a home office, playroom or additional living space. A few additional features include beautiful hardwood floors throughout, views, lots of natural light, a wonderful landscaped flat yard featuring a rose garden and a darling functional playhouse. The very large attached garage/basement area provides a huge amount of bonus space and additional storage offering plenty of room for all your needs. With top rated PV schools, being minutes from town center, 280 and hiking trails this unique property presents an incredible opportunity for a lucky buyer.

3 Beds ⋅ 2 Baths ⋅ ML81989993 MLS

Nestled in a serene location, this beautifully maintained 3 bedroom, 2 bath home offers the perfect blend of comfort and functionality. Step inside to discover the welcoming formal entry way. Charming stairs lead you to the main living space which showcases dramatic high ceilings and an open-concept floor plan that creates a bright & airy ambiance. The living room perfectly opens up to a front balcony while also seamlessly opening up to a large flat backyard creating a space that is perfect for everyday living & entertaining. The updated kitchen features a center island, lots of cabinet space and peaceful views to the surrounding nature. In addition, this home boasts 3 bedrooms on the main level plus a cozy loft ideal for a home office, playroom or additional living space. A few additional features include beautiful hardwood floors throughout, views, lots of natural light, a wonderful landscaped flat yard featuring a rose garden and a darling functional playhouse. The very large attached garage/basement area provides a huge amount of bonus space and additional storage offering plenty of room for all your needs. With top rated PV schools, being minutes from town center, 280 and hiking trails this unique property presents an incredible opportunity for a lucky buyer.

16 Tynan WAY, Portola Valley

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

Sold listing courtesy of Susan Nystrom-Walsh from COMPS

$4,050,000

Welcome to 130 Escanyo Way, a newly remodeled gem nestled in the desirable Ladera neighborhood of Portola Valley. This elegant 4 bedroom 3 bathroom home is designed for comfort and style. Step inside to discover a spacious living room adorned with soaring ceilings, built-in bookcases and a cozy fireplace. Walls of windows and multiple skylights bathe the home in natural light. The heart of the home is the open-concept family room, kitchen and dining area which seamlessly opens to the private backyard. The kitchen boasts a center island, beautiful cabinetry and brand-new appliances. The spa-like primary suite is a true sanctuary featuring two walk-in closets, a luxurious soaking tub and separate shower. Two additional bedrooms share an ensuite bathroom and the 4th bedroom provides comfort and convenience for family or guests. The attached garage and driveway space allow for extra storage and convenient parking. Located on a cul-de-sac this home offers a serene retreat while only being a short stroll to Ladera Recreation Center, shopping and 280. Don't miss this rare opportunity to own a home that perfectly blends tranquility and modern living.

4 Beds ⋅ 3 Baths ⋅ ML81989990 MLS

Welcome to 130 Escanyo Way, a newly remodeled gem nestled in the desirable Ladera neighborhood of Portola Valley. This elegant 4 bedroom 3 bathroom home is designed for comfort and style. Step inside to discover a spacious living room adorned with soaring ceilings, built-in bookcases and a cozy fireplace. Walls of windows and multiple skylights bathe the home in natural light. The heart of the home is the open-concept family room, kitchen and dining area which seamlessly opens to the private backyard. The kitchen boasts a center island, beautiful cabinetry and brand-new appliances. The spa-like primary suite is a true sanctuary featuring two walk-in closets, a luxurious soaking tub and separate shower. Two additional bedrooms share an ensuite bathroom and the 4th bedroom provides comfort and convenience for family or guests. The attached garage and driveway space allow for extra storage and convenient parking. Located on a cul-de-sac this home offers a serene retreat while only being a short stroll to Ladera Recreation Center, shopping and 280. Don't miss this rare opportunity to own a home that perfectly blends tranquility and modern living.

130 Escanyo WAY, Portola Valley

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

Sold listing courtesy of Josh Rubin from COMPS

$3,180,000

3 Beds ⋅ 2 Baths ⋅ ML81989690 MLS

369 La Cuesta DR, Portola Valley

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

Sold listing courtesy of Josh Rubin from COMPS

$4,230,000

Welcome to this beautifully remodeled residence in the heart of Portola Valley. This phenomenal home boasts an inviting open floor plan that seamlessly blends modern elegance with cozy comfort. The kitchen is a chef's delight featuring a brand new 6 burner range, two sinks, lots of counter space, ample storage, island counter seating and two wine refrigerators. Opening perfectly into the dining area and family room, you will find this to be the heart of the home. Warmed with natural light, skylights and a gas fireplace, the living area provides a bright and airy space with a great indoor/outdoor flow. With 3 spacious bedrooms and 2.5 spa-like bathrooms, this home offers plenty of room for every day relaxation and entertaining. The laundry area is thoughtfully located near the bedrooms. The hardwood floors add a touch of warmth and sophistication. Attached 2 car garage. Situated on a flat 1.2 acre lot, this property offers endless possibilities. Whether you're dreaming of a lush garden, a play area, or even an ADU there's ample space to make it your own or enjoy as-is. Located in prime Central Portola Valley, you're just a short walk from the scenic trails, local amenities & top-rated PV schools. This move-in ready home provides a perfect blend of style, comfort and opportunity.

3 Beds ⋅ 3 Baths ⋅ ML81987552 MLS

Welcome to this beautifully remodeled residence in the heart of Portola Valley. This phenomenal home boasts an inviting open floor plan that seamlessly blends modern elegance with cozy comfort. The kitchen is a chef's delight featuring a brand new 6 burner range, two sinks, lots of counter space, ample storage, island counter seating and two wine refrigerators. Opening perfectly into the dining area and family room, you will find this to be the heart of the home. Warmed with natural light, skylights and a gas fireplace, the living area provides a bright and airy space with a great indoor/outdoor flow. With 3 spacious bedrooms and 2.5 spa-like bathrooms, this home offers plenty of room for every day relaxation and entertaining. The laundry area is thoughtfully located near the bedrooms. The hardwood floors add a touch of warmth and sophistication. Attached 2 car garage. Situated on a flat 1.2 acre lot, this property offers endless possibilities. Whether you're dreaming of a lush garden, a play area, or even an ADU there's ample space to make it your own or enjoy as-is. Located in prime Central Portola Valley, you're just a short walk from the scenic trails, local amenities & top-rated PV schools. This move-in ready home provides a perfect blend of style, comfort and opportunity.

115 Sausal DR, Portola Valley

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

Sold listing courtesy of DeLeon Team from DLRPA

$4,200,000

Prime location on a tranquil cul-de-sac in central Portola Valley. This beautifully updated ranch-style home offers a harmonious blend of modern elegance and warm charm. Inside, you'll find 4 bedrooms plus a dedicated office, all set within a thoughtfully designed interior featuring high vaulted ceilings, exposed wooden beams, and expansive floor-to-ceiling windows. The open-concept layout creates a light-filled, airy ambiance, ideal for both entertaining and relaxing. Step outside to a private backyard retreat, complete with a sparkling in-ground pool surrounded by lush, mature landscaping. Located just a short walk from Ormondale Elementary and the prestigious Priory School, this home combines convenience with serenity, making it a true gem in the heart of Portola Valley.

4 Beds ⋅ 3 Baths ⋅ ML81987626 MLS

Prime location on a tranquil cul-de-sac in central Portola Valley. This beautifully updated ranch-style home offers a harmonious blend of modern elegance and warm charm. Inside, you'll find 4 bedrooms plus a dedicated office, all set within a thoughtfully designed interior featuring high vaulted ceilings, exposed wooden beams, and expansive floor-to-ceiling windows. The open-concept layout creates a light-filled, airy ambiance, ideal for both entertaining and relaxing. Step outside to a private backyard retreat, complete with a sparkling in-ground pool surrounded by lush, mature landscaping. Located just a short walk from Ormondale Elementary and the prestigious Priory School, this home combines convenience with serenity, making it a true gem in the heart of Portola Valley.

150 Grove DR, Portola Valley

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

Sold listing courtesy of Francesca Lampert from CBR