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$4,595,000

Sweeping southeastern views create a spectacular backdrop for this beautifully refreshed four-bedroom, four-bath residence, ideally perched atop one of the best locations in Portola Valley Ranch. Offering nearly 4,000 SF of thoughtfully designed living space, this move-in ready home blends timeless elegance with the relaxed sophistication of Portola Valley living. The expansive main level is designed to capture breathtaking vistas from nearly every room. A spacious open kitchen flows seamlessly into the dining room and gracious living room, where soaring ceilings, walls of glass, fireplace, and a wraparound deck create an exceptional setting for everyday living and entertaining. The large main-level primary suite features an oversized bath and dressing area, while a second bedroom offers flexibility as a guest suite, home office, or additional bedroom. The lower level features a spacious family room separating two private ensuite bedrooms, creating an ideal retreat for family or guests. A second fireplace, secondary laundry, storage room, and wine room complete this level. Expansive decks on both floors provide spaces to relax and enjoy the views. Residents enjoy the two swimming pools, tennis courts, a community center, scenic walking trails, and an active, welcoming community.

4 Beds ⋅ 4 Baths ⋅ ML82056839 MLS ⋅ Portola Valley Ranch BLDG.

Sweeping southeastern views create a spectacular backdrop for this beautifully refreshed four-bedroom, four-bath residence, ideally perched atop one of the best locations in Portola Valley Ranch. Offering nearly 4,000 SF of thoughtfully designed living space, this move-in ready home blends timeless elegance with the relaxed sophistication of Portola Valley living. The expansive main level is designed to capture breathtaking vistas from nearly every room. A spacious open kitchen flows seamlessly into the dining room and gracious living room, where soaring ceilings, walls of glass, fireplace, and a wraparound deck create an exceptional setting for everyday living and entertaining. The large main-level primary suite features an oversized bath and dressing area, while a second bedroom offers flexibility as a guest suite, home office, or additional bedroom. The lower level features a spacious family room separating two private ensuite bedrooms, creating an ideal retreat for family or guests. A second fireplace, secondary laundry, storage room, and wine room complete this level. Expansive decks on both floors provide spaces to relax and enjoy the views. Residents enjoy the two swimming pools, tennis courts, a community center, scenic walking trails, and an active, welcoming community.

2 Franciscan RDG, Portola Valley

Listed by Lisa Keith, 650-703-8644 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$20,500,000

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

5 Beds ⋅ 10 Baths ⋅ ML82054797 MLS

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

479 Westridge DR, Portola Valley

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

Sold listing courtesy of Scott Dancer from APR

$5,988,000

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).

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

$15,495,000

Nearly one acre of level grounds sets the stage for this exceptional new home, defined by clean lines, sophisticated materials, and seamless indoor-outdoor living. White oak floors, soaring ceilings, and walls of glass enhance the light-filled interiors that open to the rear grounds where an infinity-edge pool and spa invite entertaining and recreational enjoyment. A tremendous great room anchors the design, complemented by a stunning kitchen, a separate caterers kitchen, and a temperature-controlled wine cellar. A lower-level recreation room with full bar adds flexibility for gatherings and leisure. The main home offers five en suite bedrooms and a half-bath across two levels, including a luxurious primary suite with fireplace and spa-inspired bath. A separate guest house provides additional living space with its own kitchen and private accommodations. Solar power, Tesla Powerwalls, and Lutron home automation enhance comfort and efficiency, all within the highly regarded Portola Valley school district and just minutes from the town center and miles of hiking and biking trails. Square Footage: Main Residence 5,686 | Guest House 800 | Garage 756 | Total 7,242

6 Beds ⋅ 7 Baths ⋅ ML82053175 MLS

Nearly one acre of level grounds sets the stage for this exceptional new home, defined by clean lines, sophisticated materials, and seamless indoor-outdoor living. White oak floors, soaring ceilings, and walls of glass enhance the light-filled interiors that open to the rear grounds where an infinity-edge pool and spa invite entertaining and recreational enjoyment. A tremendous great room anchors the design, complemented by a stunning kitchen, a separate caterers kitchen, and a temperature-controlled wine cellar. A lower-level recreation room with full bar adds flexibility for gatherings and leisure. The main home offers five en suite bedrooms and a half-bath across two levels, including a luxurious primary suite with fireplace and spa-inspired bath. A separate guest house provides additional living space with its own kitchen and private accommodations. Solar power, Tesla Powerwalls, and Lutron home automation enhance comfort and efficiency, all within the highly regarded Portola Valley school district and just minutes from the town center and miles of hiking and biking trails. Square Footage: Main Residence 5,686 | Guest House 800 | Garage 756 | Total 7,242

241 Georgia LN, Portola Valley

Listed by Brent & Mary Gullixson, 650-888-0860 from Compass
(If provided) CoList: from

$6,130,000

Spectacular VIEWS are the backdrop of this outstanding remodeled mid-century home located on a quiet, close in cul-de-sac in prime Westridge. Expand, build new or enjoy this lovely home as is, on this spectacular 2.57 acre property featuring incredible views, peaceful gardens & gorgeous Oak studded knolls. Dramatic vaulted ceiling living room w/ full length custom skylight features floor to ceiling windows showcasing the views. Separate formal dining room overlooks the courtyard garden. Gourmet kitchen has custom cabinetry, slab stone countertops and quality appliances. 3 large bedrooms and 3.5 bathrooms include 2 primary suites, one upstairs & one on the main level, all w/ walk-in closets, views & marble bathrooms. Magnificent gardens include a charming, fenced courtyard entry with specimen trees & shrubs, flowering annuals & perennials. The deer fenced rear garden showcases views from the sparkling POOL surrounded by a patio/deck with roses, flower beds and a water feature. Much of the property is usable/level and scattered w/ native trees & well-kept Oaks. This is truly one of the prettiest, most serene settings in PV. Move into this turnkey home, or rent it while you make plans to build your dream home on this amazing, quiet view property!

3 Beds ⋅ 4 Baths ⋅ ML82052876 MLS

Spectacular VIEWS are the backdrop of this outstanding remodeled mid-century home located on a quiet, close in cul-de-sac in prime Westridge. Expand, build new or enjoy this lovely home as is, on this spectacular 2.57 acre property featuring incredible views, peaceful gardens & gorgeous Oak studded knolls. Dramatic vaulted ceiling living room w/ full length custom skylight features floor to ceiling windows showcasing the views. Separate formal dining room overlooks the courtyard garden. Gourmet kitchen has custom cabinetry, slab stone countertops and quality appliances. 3 large bedrooms and 3.5 bathrooms include 2 primary suites, one upstairs & one on the main level, all w/ walk-in closets, views & marble bathrooms. Magnificent gardens include a charming, fenced courtyard entry with specimen trees & shrubs, flowering annuals & perennials. The deer fenced rear garden showcases views from the sparkling POOL surrounded by a patio/deck with roses, flower beds and a water feature. Much of the property is usable/level and scattered w/ native trees & well-kept Oaks. This is truly one of the prettiest, most serene settings in PV. Move into this turnkey home, or rent it while you make plans to build your dream home on this amazing, quiet view property!

578 CRESTA VISTA LN, Portola Valley

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

Sold listing courtesy of Mandana Simai from SGP

$6,100,000

Iconic compound expanded and totally rebuilt in 2012. This home with a storied stone envelope is set on 1.13 flat, gated acres. The over 5,000sf compound features soaring ceilings, Venetian plaster walls, individually climate-controlled rooms, including the wine/library lower level, and a finished attic retreat. The culinary kitchen is a masterpiece with Carrara marble counters, a massive island, and chef-quality appliances. Designed for a "live-work-play" lifestyle, the estate includes a detached guest Cottage and a huge studio that can serve as the ultimate tech HQ, yoga sanctuary, or artist retreat (virtually staged). 10 Tesla Powerwalls (135kWh) for 48-hour grid independence + 80amp EV charging. Direct $50k fiber line; 12 Wi-Fi 7/6 access points for full-acre coverage. 10-zone smart HVAC (9 new units in 2024) with simultaneous heat/cool capability and 24/7 Unifi AI security. Water: Whole-home filtration, leak-detection shut-off, and smart Rachio irrigation. The Grounds: A resort-style sanctuary featuring a crushed granite drive, double electronic gates, a meandering creek, and an expansive pool deck with a dedicated bath. Updated for the next century of living.

4 Beds ⋅ 6 Baths ⋅ ML82044823 MLS

Iconic compound expanded and totally rebuilt in 2012. This home with a storied stone envelope is set on 1.13 flat, gated acres. The over 5,000sf compound features soaring ceilings, Venetian plaster walls, individually climate-controlled rooms, including the wine/library lower level, and a finished attic retreat. The culinary kitchen is a masterpiece with Carrara marble counters, a massive island, and chef-quality appliances. Designed for a "live-work-play" lifestyle, the estate includes a detached guest Cottage and a huge studio that can serve as the ultimate tech HQ, yoga sanctuary, or artist retreat (virtually staged). 10 Tesla Powerwalls (135kWh) for 48-hour grid independence + 80amp EV charging. Direct $50k fiber line; 12 Wi-Fi 7/6 access points for full-acre coverage. 10-zone smart HVAC (9 new units in 2024) with simultaneous heat/cool capability and 24/7 Unifi AI security. Water: Whole-home filtration, leak-detection shut-off, and smart Rachio irrigation. The Grounds: A resort-style sanctuary featuring a crushed granite drive, double electronic gates, a meandering creek, and an expansive pool deck with a dedicated bath. Updated for the next century of living.

350 Willowbrook RD, Portola Valley

Listed by Art Sharif, 650-804-4770 from Sotheby's Intl Rlty
(If provided) CoList: from

Sold listing courtesy of Omar Pina from COMPS

$5,950,000

Located in the highly desirable Westridge subdivision of Portola Valley, this approximately 3.9-acre property presents an exceptional opportunity to remodel or create a new legacy estate. The superb setting is defined by privacy and sweeping western hill views, including Windy Hill. The expansive parcel offers broad open space, mature oaks, and gently terraced grounds providing a remarkable canvas for a future vision. The existing circa 1967 single-level Ranch style home spans approximately 3,300 square feet with 4 bedrooms, an office, and 3 full baths. Freshly painted interiors and exterior enhance its character, which includes walls in fine wood paneling, floors in terra cotta tile and hardwood, cathedral ceilings, and numerous sliding glass doors oriented to the western hill views. Located within the highly regarded Portola Valley school system and moments from Stanford University and key Silicon Valley tech centers, this property offers rare scale, views, and opportunity in a premier location.

4 Beds ⋅ 3 Baths ⋅ ML82045714 MLS

Located in the highly desirable Westridge subdivision of Portola Valley, this approximately 3.9-acre property presents an exceptional opportunity to remodel or create a new legacy estate. The superb setting is defined by privacy and sweeping western hill views, including Windy Hill. The expansive parcel offers broad open space, mature oaks, and gently terraced grounds providing a remarkable canvas for a future vision. The existing circa 1967 single-level Ranch style home spans approximately 3,300 square feet with 4 bedrooms, an office, and 3 full baths. Freshly painted interiors and exterior enhance its character, which includes walls in fine wood paneling, floors in terra cotta tile and hardwood, cathedral ceilings, and numerous sliding glass doors oriented to the western hill views. Located within the highly regarded Portola Valley school system and moments from Stanford University and key Silicon Valley tech centers, this property offers rare scale, views, and opportunity in a premier location.

747 Westridge DR, Portola Valley

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

Sold listing courtesy of Keri Nicholas from PARCA

$8,400,000

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

5 Beds ⋅ 4 Baths ⋅ ML82042620 MLS

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

120 Deer Meadow LN, Portola Valley

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

Sold listing courtesy of The reSolve Group from COMPS

$3,600,000

Far-reaching views of Coal Mine Ridge define this beautifully remodeled home at Portola Valley Ranch, set on nearly one-half acre. Expanses of glass, soaring ceilings, and dramatic skylights fill the interiors with light and volume, while fine hardwood floors underscore a cohesive, modern aesthetic throughout the open main level. Indoor-outdoor living extends across both levels with expansive decks positioned to take full advantage of the natural surroundings. The primary suite with a spa-inspired remodeled bath is conveniently located on the main level and the lower level provides a family room, flexible-use room, and two additional bedrooms and a bath. Adding to the appeal is a full complement of amenities at The Ranch, including pools, tennis courts, a fitness center, vineyard and garden areas, a playground, and miles of scenic trails. A wonderful opportunity to enjoy a close connection to nature with convenient access to both San Francisco and Silicon Valley.

3 Beds ⋅ 3 Baths ⋅ ML82042677 MLS ⋅ Portola Valley Ranch BLDG.

Far-reaching views of Coal Mine Ridge define this beautifully remodeled home at Portola Valley Ranch, set on nearly one-half acre. Expanses of glass, soaring ceilings, and dramatic skylights fill the interiors with light and volume, while fine hardwood floors underscore a cohesive, modern aesthetic throughout the open main level. Indoor-outdoor living extends across both levels with expansive decks positioned to take full advantage of the natural surroundings. The primary suite with a spa-inspired remodeled bath is conveniently located on the main level and the lower level provides a family room, flexible-use room, and two additional bedrooms and a bath. Adding to the appeal is a full complement of amenities at The Ranch, including pools, tennis courts, a fitness center, vineyard and garden areas, a playground, and miles of scenic trails. A wonderful opportunity to enjoy a close connection to nature with convenient access to both San Francisco and Silicon Valley.

5 Sandstone ST, Portola Valley

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

Sold listing courtesy of Shelly Roberson from APR

$1,750,000

Tucked among mature oaks in the coveted Woodside Highlands, 9 Russell Avenue offers a rare blend of privacy, character, and opportunity on nearly one-third of an acre in prestigious Portola Valley. The main level features a generous living room anchored by a remarkable stone fireplace crafted from historic ship ballast, along with a separate family room, two bedrooms, and a full bath. Downstairs, bonus room, second bath, and laundry/storage area provide flexibility for guests, a home office, or future customization, with direct access to the 2 car garage. The main level is approximately 1440 sq. ft, with another 900 sq. of finished basement. The private grounds include a pool and multiple outdoor shaded gathering spaces beneath the oaks to relax or reimagine. Portola Valley is known for its top-rated schools, including Ormondale and Corte Madera, its vibrant Town Center, and miles of scenic trails at Windy Hill Preserve. Whether you envision a thoughtful renovation or a custom rebuild, this property delivers exceptional upside in a premier location.

2 Beds ⋅ 2 Baths ⋅ ML82042559 MLS

Tucked among mature oaks in the coveted Woodside Highlands, 9 Russell Avenue offers a rare blend of privacy, character, and opportunity on nearly one-third of an acre in prestigious Portola Valley. The main level features a generous living room anchored by a remarkable stone fireplace crafted from historic ship ballast, along with a separate family room, two bedrooms, and a full bath. Downstairs, bonus room, second bath, and laundry/storage area provide flexibility for guests, a home office, or future customization, with direct access to the 2 car garage. The main level is approximately 1440 sq. ft, with another 900 sq. of finished basement. The private grounds include a pool and multiple outdoor shaded gathering spaces beneath the oaks to relax or reimagine. Portola Valley is known for its top-rated schools, including Ormondale and Corte Madera, its vibrant Town Center, and miles of scenic trails at Windy Hill Preserve. Whether you envision a thoughtful renovation or a custom rebuild, this property delivers exceptional upside in a premier location.

9 Russell AVE, Portola Valley

Listed by James Gardner, 408-202-9602 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Esther Wang from ASPR

$7,998,000

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)

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

$10,850,000

TRI-LEVEL ESTATE OFFERS POOL HOUSE, 3+ ACRES | Transport yourself to the East Coast in this incomparable custom estate. Gated acreage framed by California oaks reveals an exquisite Shingle-style home surrounded by bridges, enchanting gardens, a three-car garage, and fully functional pool house with pool and spa. Faced by a circular gravel drive, the tri-level main residence built in 2010 has been wonderfully maintained, boasting all ensuite bedrooms, a study, gym, and media lounge with full bar. Enjoy a sensational master chefs kitchen, ultra-luxurious primary suite, multiple fireplaces, surround sound, and ground-level guest/au pair quarters. Superb details include graceful turrets, round windows, soaring ceilings, gorgeous hardwood floors, and extensive millwork throughout. Outdoor retreats abound with amenities like a barbecue island, fireplace, paver terraces, wisteria-laden pergola, raised beds, and more. Moments from shopping, dining, trails, and breathtaking scenery, this piece of bucolic paradise is nestled near tech and venture capital centers, and only ~ 30 minutes from SFO and SJC. Excellent Portola Valley Schools. Property is on sewer giving a buyer full use of the lot. Main residence 5861 sq ft, guest house 732 sq ft=6593 sq ft Plus 888 sq ft garage.

4 Beds ⋅ 7 Baths ⋅ ML82038785 MLS ⋅ Westridge BLDG.

TRI-LEVEL ESTATE OFFERS POOL HOUSE, 3+ ACRES | Transport yourself to the East Coast in this incomparable custom estate. Gated acreage framed by California oaks reveals an exquisite Shingle-style home surrounded by bridges, enchanting gardens, a three-car garage, and fully functional pool house with pool and spa. Faced by a circular gravel drive, the tri-level main residence built in 2010 has been wonderfully maintained, boasting all ensuite bedrooms, a study, gym, and media lounge with full bar. Enjoy a sensational master chefs kitchen, ultra-luxurious primary suite, multiple fireplaces, surround sound, and ground-level guest/au pair quarters. Superb details include graceful turrets, round windows, soaring ceilings, gorgeous hardwood floors, and extensive millwork throughout. Outdoor retreats abound with amenities like a barbecue island, fireplace, paver terraces, wisteria-laden pergola, raised beds, and more. Moments from shopping, dining, trails, and breathtaking scenery, this piece of bucolic paradise is nestled near tech and venture capital centers, and only ~ 30 minutes from SFO and SJC. Excellent Portola Valley Schools. Property is on sewer giving a buyer full use of the lot. Main residence 5861 sq ft, guest house 732 sq ft=6593 sq ft Plus 888 sq ft garage.

3510 Alpine RD, Portola Valley

Listed by Sue Crawford, 650-207-8444 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Hope Pilch from HPPRO

$3,800,000

Located in prime central Portola Valley, discover the potential of this single-level home & spectacular property. With 3 bdrms, 2 bthrms, & 2,210 sq. ft. of living space on an expansive 42,575 sq. ft. lot, this home offers a rare opportunity to create your dream lifestyle. The front door leads you into a spacious living room w/ a cozy fireplace, stunning floor-to-ceiling windows & a dining area. The kitchen & adjoining family room flow seamlessly to the private backyardfeaturing a large deck and sparkling pool. On clear days, enjoy stunning views of the South Bay both while inside the home and from the backyard. The freshly painted interior and brand-new carpet provide a clean slate, ready for your personal touch. The primary suite includes two walk-in closets and a private bathroom, while the two additional bedrooms share a convenient hall bath. Functional amenities like a dedicated laundry room and attached 2-car garage add to the home's overall comfort and practicality. Ideally situated for easy access to PV schools, Stanford, Highway 280, local shopping, and scenic hiking trails, this property combines convenience and natural beauty. First time on the market, this home presents a unique opportunity to customize and enjoy a peaceful retreat in a very desirable location.

3 Beds ⋅ 2 Baths ⋅ ML82037272 MLS

Located in prime central Portola Valley, discover the potential of this single-level home & spectacular property. With 3 bdrms, 2 bthrms, & 2,210 sq. ft. of living space on an expansive 42,575 sq. ft. lot, this home offers a rare opportunity to create your dream lifestyle. The front door leads you into a spacious living room w/ a cozy fireplace, stunning floor-to-ceiling windows & a dining area. The kitchen & adjoining family room flow seamlessly to the private backyardfeaturing a large deck and sparkling pool. On clear days, enjoy stunning views of the South Bay both while inside the home and from the backyard. The freshly painted interior and brand-new carpet provide a clean slate, ready for your personal touch. The primary suite includes two walk-in closets and a private bathroom, while the two additional bedrooms share a convenient hall bath. Functional amenities like a dedicated laundry room and attached 2-car garage add to the home's overall comfort and practicality. Ideally situated for easy access to PV schools, Stanford, Highway 280, local shopping, and scenic hiking trails, this property combines convenience and natural beauty. First time on the market, this home presents a unique opportunity to customize and enjoy a peaceful retreat in a very desirable location.

285 Golden Oak DR, Portola Valley

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

Sold listing courtesy of Lisa Dippel from NTERO

$8,748,000

Perched on a knolltop within prestigious Blue Oaks, this luxurious estate epitomizes elegance and exclusivity. Set on 2.53 acres of naturally organic beauty, this residence offers unparalleled privacy and breathtaking views of the San Francisco Bay. A true sanctuary, the home seamlessly blends sophisticated design with the tranquility of its natural surroundings. The expansive living room, bathed in natural light from floor-to-ceiling windows, provides a stunning backdrop of the sweeping Bay views. The heart of the home is the gourmet kitchen, a culinary enthusiast's dream, that opens to a spacious family room, creating a true great room that is ideal for both everyday living and entertaining. Multiple adjacent terraces offer 360-degree views. Each of the 5 bedrooms is an en suite retreat. The primary suite offers a luxurious spa-like bath, walk-in closet, fireplace and picture windows that capture the serene vistas. In addition to an executive home office, the estate boasts a home gym, media/rec room, wine cellar, expansive swimming pool and 4-car garage. This estate in Blue Oaks is more than a home; it is a lifestyle. With its unmatched privacy, luxurious amenities and awe-inspiring views, it offers a unique opportunity to experience the pinnacle of Silicon Valley living.

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

Perched on a knolltop within prestigious Blue Oaks, this luxurious estate epitomizes elegance and exclusivity. Set on 2.53 acres of naturally organic beauty, this residence offers unparalleled privacy and breathtaking views of the San Francisco Bay. A true sanctuary, the home seamlessly blends sophisticated design with the tranquility of its natural surroundings. The expansive living room, bathed in natural light from floor-to-ceiling windows, provides a stunning backdrop of the sweeping Bay views. The heart of the home is the gourmet kitchen, a culinary enthusiast's dream, that opens to a spacious family room, creating a true great room that is ideal for both everyday living and entertaining. Multiple adjacent terraces offer 360-degree views. Each of the 5 bedrooms is an en suite retreat. The primary suite offers a luxurious spa-like bath, walk-in closet, fireplace and picture windows that capture the serene vistas. In addition to an executive home office, the estate boasts a home gym, media/rec room, wine cellar, expansive swimming pool and 4-car garage. This estate in Blue Oaks is more than a home; it is a lifestyle. With its unmatched privacy, luxurious amenities and awe-inspiring views, it offers a unique opportunity to experience the pinnacle of Silicon Valley living.

7 Redberry RDG, Portola Valley

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

$7,998,000

Set on an acre at the end of a quiet cul-de-sac in central Portola Valley, this striking contemporary residence captures unobstructed panoramic views of the western hills & Windy Hill. Designed by award-winning architect Arthur Dyson, a Frank Lloyd Wright protégé, the home is a refined modernist retreat where architecture & landscape exist in seamless harmony. A dramatic glass entry walkway leads to a foyer highlighted by a two-story cascading water feature & sculptural staircase. The living room features a barrel-vaulted ceiling & wall of folding glass doors opening to an expansive view deck, creating an effortless indoor-outdoor connection. Walls of glass throughout the living, dining & family rooms frame sweeping vistas, while a fireplace anchors the open living spaces. The chef's kitchen features top-tier appliances, slab counters & generous workspace, all oriented toward the views. The main level living space features an executive office, secondary bedroom & primary suite with sitting room & fireplace. Two additional bedrooms & a rec room are located at the lower level. The stunning grounds include a pool, spa, waterfall & expansive decks for entertaining. With dramatic design, breathtaking views, privacy & PV schools, this is a rare modern retreat in a coveted setting.

4 Beds ⋅ 4 Baths ⋅ ML82032104 MLS

Set on an acre at the end of a quiet cul-de-sac in central Portola Valley, this striking contemporary residence captures unobstructed panoramic views of the western hills & Windy Hill. Designed by award-winning architect Arthur Dyson, a Frank Lloyd Wright protégé, the home is a refined modernist retreat where architecture & landscape exist in seamless harmony. A dramatic glass entry walkway leads to a foyer highlighted by a two-story cascading water feature & sculptural staircase. The living room features a barrel-vaulted ceiling & wall of folding glass doors opening to an expansive view deck, creating an effortless indoor-outdoor connection. Walls of glass throughout the living, dining & family rooms frame sweeping vistas, while a fireplace anchors the open living spaces. The chef's kitchen features top-tier appliances, slab counters & generous workspace, all oriented toward the views. The main level living space features an executive office, secondary bedroom & primary suite with sitting room & fireplace. Two additional bedrooms & a rec room are located at the lower level. The stunning grounds include a pool, spa, waterfall & expansive decks for entertaining. With dramatic design, breathtaking views, privacy & PV schools, this is a rare modern retreat in a coveted setting.

65 Cheyenne PT, Portola Valley

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

Sold listing courtesy of Marc Roos from SGP

$4,750,000

Welcome to 200 Cherokee Way, a spacious and private Portola Valley residence offering exceptional indoor and outdoor living. Tucked away at the end of a quiet cul-de-sac, the 1+ acre retreat with pool and spa features unparalleled Windy Hill views. Spanning approximately 4,825 square feet, the 4-bedroom, 3.5 bath home with separate office provides flexibility for family living, entertaining, and work-from-home needs.

4 Beds ⋅ 4 Baths ⋅ ML82028480 MLS

Welcome to 200 Cherokee Way, a spacious and private Portola Valley residence offering exceptional indoor and outdoor living. Tucked away at the end of a quiet cul-de-sac, the 1+ acre retreat with pool and spa features unparalleled Windy Hill views. Spanning approximately 4,825 square feet, the 4-bedroom, 3.5 bath home with separate office provides flexibility for family living, entertaining, and work-from-home needs.

200 Cherokee WAY, Portola Valley

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

Sold listing courtesy of Peter Cowperthwaite from DP

$5,850,000

On an expansive, level acre, this single-level residence captures the essence of relaxed California living where indoor and outdoor spaces flow effortlessly and every detail invites connection with nature. A welcoming front patio opens to the home's bright and spacious interiors, where generous living and dining areas are anchored by broad windows and warm hardwood floors. The open-concept kitchen and breakfast area overlook the pool and gardens, blending casual comfort with an easy elegance that defines the homes spirit. Three bedrooms, three baths, and two dedicated offices create flexibility for family life, guests, and work-from-home needs. The expansive primary suite enjoys garden views, large walk-in closet, and a spa-like bath. Outside, the property unfolds like a private oasis, complete with a sparkling pool and spa, multiple entertaining terraces, lush lawn, and a dedicated pickleball court. Additional features include a large recreation room, laundry/mud room, carport, and three storage sheds. Perfectly located within one of Portola Valleys most desirable neighborhoods, this home is moments from scenic hiking trails, top-rated schools, and the conveniences of nearby Sand Hill Road, Menlo Park, and Stanford University.

3 Beds ⋅ 3 Baths ⋅ ML82025817 MLS

On an expansive, level acre, this single-level residence captures the essence of relaxed California living where indoor and outdoor spaces flow effortlessly and every detail invites connection with nature. A welcoming front patio opens to the home's bright and spacious interiors, where generous living and dining areas are anchored by broad windows and warm hardwood floors. The open-concept kitchen and breakfast area overlook the pool and gardens, blending casual comfort with an easy elegance that defines the homes spirit. Three bedrooms, three baths, and two dedicated offices create flexibility for family life, guests, and work-from-home needs. The expansive primary suite enjoys garden views, large walk-in closet, and a spa-like bath. Outside, the property unfolds like a private oasis, complete with a sparkling pool and spa, multiple entertaining terraces, lush lawn, and a dedicated pickleball court. Additional features include a large recreation room, laundry/mud room, carport, and three storage sheds. Perfectly located within one of Portola Valleys most desirable neighborhoods, this home is moments from scenic hiking trails, top-rated schools, and the conveniences of nearby Sand Hill Road, Menlo Park, and Stanford University.

135 Meadowood DR, Portola Valley

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

Sold listing courtesy of Evan Kohen from APR

$3,300,000

Experience serene, modern living in this beautifully updated 3-bedroom, 2-bath ranch home infused with Japanese-inspired design, with a harmonious connection to the outdoors, creating an atmosphere of calm and balance throughout. Light-filled living spaces flow seamlessly to a private backyard oasis, creating the perfect setting for both relaxation and entertaining. Spacious living room featuring a built-in bookcase and gas fireplace. Modern kitchen with granite and stainless steel counters, breakfast bar, and updated cabinetry. Separate family room with easy access to the backyard. Private backyard retreat with black-bottom pool, pergola, with space for gatherings. Close to the Ladera Shopper and Ladera Recreation Center, near the bus stop and Woodland School, just 3.5 miles to Stanford University, easy access to commute routes, Silicon Valley, and mid-way between San Francisco and San Jose International Airports. Optional membership to the Ladera Recreation Center provides year-round tennis, pickleball & fitness programs, a seasonal aquatics program, and a variety of community events and activities.

3 Beds ⋅ 2 Baths ⋅ ML82025326 MLS ⋅ Ladera BLDG.

Experience serene, modern living in this beautifully updated 3-bedroom, 2-bath ranch home infused with Japanese-inspired design, with a harmonious connection to the outdoors, creating an atmosphere of calm and balance throughout. Light-filled living spaces flow seamlessly to a private backyard oasis, creating the perfect setting for both relaxation and entertaining. Spacious living room featuring a built-in bookcase and gas fireplace. Modern kitchen with granite and stainless steel counters, breakfast bar, and updated cabinetry. Separate family room with easy access to the backyard. Private backyard retreat with black-bottom pool, pergola, with space for gatherings. Close to the Ladera Shopper and Ladera Recreation Center, near the bus stop and Woodland School, just 3.5 miles to Stanford University, easy access to commute routes, Silicon Valley, and mid-way between San Francisco and San Jose International Airports. Optional membership to the Ladera Recreation Center provides year-round tennis, pickleball & fitness programs, a seasonal aquatics program, and a variety of community events and activities.

375 La Cuesta DR, 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

$3,595,000

Located in one of Silicon Valleys most desirable residential enclaves, Portola Valley Ranch, amid 350 acres of private open space preserve, this refined contemporary home fully embraces its natural surroundings. Clean architectural lines, sliding glass doors and clerestory windows define the expansive living / dining great room and suffuse it with light. Beautiful Australian eucalyptus flooring throughout the home unifies it with a warm, welcoming aesthetic. Custom cherry cabinetry accentuated by walnut trim in the chef's kitchen and adjacent family room create an inviting setting for cooking while gathering with family and friends. The oversized primary bedroom with a front balcony that extends the length of the room has a marvelous view of mature trees framing the western hills. Two additional bedrooms, both opening to the outdoors, share the bright hall bath. The oversized two car garage includes an EV charger and a storage closet ideal for wine collectors. Tucked away on a quiet cul-de-sac in this special community offering a clubhouse, tennis courts, pools, exercise facilities, a vineyard, a playground and hiking trails, this serene retreat feels miles away but is conveniently located just minutes from highway 280 and Stanford University. Dont miss it!

3 Beds ⋅ 3 Baths ⋅ ML82024569 MLS ⋅ Portola Valley Ranch Association BLDG.

Located in one of Silicon Valleys most desirable residential enclaves, Portola Valley Ranch, amid 350 acres of private open space preserve, this refined contemporary home fully embraces its natural surroundings. Clean architectural lines, sliding glass doors and clerestory windows define the expansive living / dining great room and suffuse it with light. Beautiful Australian eucalyptus flooring throughout the home unifies it with a warm, welcoming aesthetic. Custom cherry cabinetry accentuated by walnut trim in the chef's kitchen and adjacent family room create an inviting setting for cooking while gathering with family and friends. The oversized primary bedroom with a front balcony that extends the length of the room has a marvelous view of mature trees framing the western hills. Two additional bedrooms, both opening to the outdoors, share the bright hall bath. The oversized two car garage includes an EV charger and a storage closet ideal for wine collectors. Tucked away on a quiet cul-de-sac in this special community offering a clubhouse, tennis courts, pools, exercise facilities, a vineyard, a playground and hiking trails, this serene retreat feels miles away but is conveniently located just minutes from highway 280 and Stanford University. Dont miss it!

35 Bear Paw, Portola Valley

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

Sold listing courtesy of Wen Guo RE Group from KWPEN

$5,500,000

Fabulous views at this 3800 sf home plus 1200 sf ADU , greenhouse and pool on nearly 2 acres in prime Portola Valley. Gorgeous property with sublime views on nearly 2 acres in the prime Westridge neighborhood of Portola Valley. The gorgeous updated ranch-style home has sublime views of the hills and a formal entry, living room with fireplace and built-ins, large eat-in kitchen with Viking range, and two subzero refrigerators, bright pantry with skylight; full bath off kitchen, large office with built-in file drawers and fireplace. The 1,000-sf sunroom accommodates living, dining and work areas and has Bosch dishwasher, Thermador grill and a wine cooler. Four distinct bedrooms; primary has doors to patio, walk-in closet, bathroom with steam shower and heated floors. Large office in main home + in converted garage bay. Outside there is a gorgeous garden in full bloom, pool, hot tub, greenhouse, ample extra storage and beautiful views to the coastal mountains. Separate private well-appointed two+ bedroom ADU. Loads of built-in bookcases, and cabinets. You won't want to miss this distinctive property on almost two acres. Solar panels provide electricity throughout the property.

4 Beds ⋅ 3 Baths ⋅ ML82011438 MLS

Fabulous views at this 3800 sf home plus 1200 sf ADU , greenhouse and pool on nearly 2 acres in prime Portola Valley. Gorgeous property with sublime views on nearly 2 acres in the prime Westridge neighborhood of Portola Valley. The gorgeous updated ranch-style home has sublime views of the hills and a formal entry, living room with fireplace and built-ins, large eat-in kitchen with Viking range, and two subzero refrigerators, bright pantry with skylight; full bath off kitchen, large office with built-in file drawers and fireplace. The 1,000-sf sunroom accommodates living, dining and work areas and has Bosch dishwasher, Thermador grill and a wine cooler. Four distinct bedrooms; primary has doors to patio, walk-in closet, bathroom with steam shower and heated floors. Large office in main home + in converted garage bay. Outside there is a gorgeous garden in full bloom, pool, hot tub, greenhouse, ample extra storage and beautiful views to the coastal mountains. Separate private well-appointed two+ bedroom ADU. Loads of built-in bookcases, and cabinets. You won't want to miss this distinctive property on almost two acres. Solar panels provide electricity throughout the property.

1175 Westridge DR, Portola Valley

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

Sold listing courtesy of Cindy Hung from NTERO

$4,250,000

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

4 Beds ⋅ 3 Baths ⋅ ML82019049 MLS

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

20 Bear Gulch DR, Portola Valley

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

Sold listing courtesy of Ashu Chadha from COMPS

$7,257,000

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

4 Beds ⋅ 4 Baths ⋅ ML82019615 MLS

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

415 Cervantes RD, Portola Valley

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

Sold listing courtesy of Erika Demma from APR

$3,700,000

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

3 Beds ⋅ 4 Baths ⋅ ML82017999 MLS ⋅ Portola Valley Ranch BLDG.

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

2 Thistle ST, Portola Valley

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

Sold listing courtesy of Omar M. Kinaan from DP

$3,229,000

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

4 Beds ⋅ 3 Baths ⋅ ML82012992 MLS

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

30 Pine Ridge WAY, Portola Valley

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

Sold listing courtesy of Angie Wolff from NTERO

$3,380,000

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

3 Beds ⋅ 2 Baths ⋅ ML82014861 MLS

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

10 Bear Gulch DR, Portola Valley

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

Sold listing courtesy of Heidi Tang from VINE

$6,020,000

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

3 Beds ⋅ 3 Baths ⋅ ML82012718 MLS

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

22 Grove DR, Portola Valley

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

Sold listing courtesy of Judy Citron from COMPS

$5,205,000

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

6 Beds ⋅ 6 Baths ⋅ ML82012664 MLS

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

3 Oak Forest CT, Portola Valley

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

Sold listing courtesy of Val Vandervort from VERIT

$3,925,000

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.

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

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

$4,412,000

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 !

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