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$3,495,000

This move-in-ready Portola Valley retreat perfectly balances mid-century character with modern updates. The main level features an open, light-filled layout centered around a fireplace, with large windows framing views of the surrounding greenery. The new kitchen and living areas flow directly onto a private deck, overlooking a fenced backyard, mature gardens & relaxing setting perfect for morning coffee & a dining place for intimate gatherings. A stylish modern handrail leads you to the versatile lower level, which includes a third bedroom, a full bathroom, a dedicated office area, and a secondary living space with its own fireplace and sliding glass doors to the garden patio & curated pathways leading to a gathering space atop the hillside. The lower level offers a unique opportunity for buyers to potentially add a fourth bedroom and additional bath, or potentially a JADU to the existing footprint of the walk in utility space. Ideally located for enjoying the Peninsulas outdoor lifestyle, this home is minutes from local dining, shopping, and extensive trail & bike networks. With easy access to Silicon Valley hubs and Stanford University, this is a prime opportunity to own a renovated, nature-connected home in a sought-after location.

3 Beds ⋅ 2 Baths ⋅ ML82047795 MLS

This move-in-ready Portola Valley retreat perfectly balances mid-century character with modern updates. The main level features an open, light-filled layout centered around a fireplace, with large windows framing views of the surrounding greenery. The new kitchen and living areas flow directly onto a private deck, overlooking a fenced backyard, mature gardens & relaxing setting perfect for morning coffee & a dining place for intimate gatherings. A stylish modern handrail leads you to the versatile lower level, which includes a third bedroom, a full bathroom, a dedicated office area, and a secondary living space with its own fireplace and sliding glass doors to the garden patio & curated pathways leading to a gathering space atop the hillside. The lower level offers a unique opportunity for buyers to potentially add a fourth bedroom and additional bath, or potentially a JADU to the existing footprint of the walk in utility space. Ideally located for enjoying the Peninsulas outdoor lifestyle, this home is minutes from local dining, shopping, and extensive trail & bike networks. With easy access to Silicon Valley hubs and Stanford University, this is a prime opportunity to own a renovated, nature-connected home in a sought-after location.

163 Crescent AVE, Portola Valley

Listed by Karen Gunn, 650-888-9457 from Compass
(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

$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

$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

$4,625,000

Sweeping, unobstructed views define this mid-century modern home, set on more than two acres in central Portola Valley - just minutes from interstate 280, Stanford University, & grocery stores. Entire walls of glass frame the hills from nearly every room, while beamed & paneled ceilings & classic design elements like the fireplace & redwood-paneled walls reflect the home's architectural roots & connection to its natural surroundings. The home offers a light-filled environment that is ready to move right in. The expansive setting & generous lot-size present exceptional potential to further transform, expand or even build new to fully capitalize on the extraordinary views. The predominantly one-level floor plan offers comfortable living with a combination of open gathering spaces, private bedrooms, plus a flexible-use lower level that includes a possible office & fourth bedroom. Outdoor spaces are highlighted by a large screened-in porch & deck, providing effortless indoor-outdoor living, all oriented toward the breathtaking Portola Valley views. Rarely does a property offer such a compelling combination of immediate livability & long-term potential, all centered around some of the most iconic, sweeping views of Portola Valley.

3 Beds ⋅ 3 Baths ⋅ ML82042701 MLS

Sweeping, unobstructed views define this mid-century modern home, set on more than two acres in central Portola Valley - just minutes from interstate 280, Stanford University, & grocery stores. Entire walls of glass frame the hills from nearly every room, while beamed & paneled ceilings & classic design elements like the fireplace & redwood-paneled walls reflect the home's architectural roots & connection to its natural surroundings. The home offers a light-filled environment that is ready to move right in. The expansive setting & generous lot-size present exceptional potential to further transform, expand or even build new to fully capitalize on the extraordinary views. The predominantly one-level floor plan offers comfortable living with a combination of open gathering spaces, private bedrooms, plus a flexible-use lower level that includes a possible office & fourth bedroom. Outdoor spaces are highlighted by a large screened-in porch & deck, providing effortless indoor-outdoor living, all oriented toward the breathtaking Portola Valley views. Rarely does a property offer such a compelling combination of immediate livability & long-term potential, all centered around some of the most iconic, sweeping views of Portola Valley.

25 Cordova CT, Portola Valley

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

Sold listing courtesy of Loren Dakin from PARCA

$1,760,000

Vintage home, circa 1956, situated on a 1/3 acre parcel in a quiet corner of Portola Valley. This cozy, uncomplicated home could become your haven away from the hustle and bustle of Silicon Valley life -- or, it could become the site of your dream home. Reimage this cottage or create something completely new! Nearby is Robert's Market (groceries,etc.) a hardware store, the fire department, a full-service (gas and repairs) station. This area is favored by cyclists and hikers. And it's a quick distance to Freeway 280 for commutes north and south.

2 Beds ⋅ 1 Baths ⋅ ML82042381 MLS

Vintage home, circa 1956, situated on a 1/3 acre parcel in a quiet corner of Portola Valley. This cozy, uncomplicated home could become your haven away from the hustle and bustle of Silicon Valley life -- or, it could become the site of your dream home. Reimage this cottage or create something completely new! Nearby is Robert's Market (groceries,etc.) a hardware store, the fire department, a full-service (gas and repairs) station. This area is favored by cyclists and hikers. And it's a quick distance to Freeway 280 for commutes north and south.

208 Canyon DR, Portola Valley

Listed by Nancy Goldcamp, 650-400-5800 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Samie Goodman from CBR

$9,495,000

A Hilltop Home Shaped by Light, Landscape and Contemporary Architecture-Designed as a sanctuary for the senses, this 4885 sq ft, 2007 contemporary masterpiece rises from the crest of central Portola Valley. the custom architecture was crafted to invite tranquility, framing soft, filtered views of the surrounding landscape . Here, the rare luxury of expansive, level grounds that breathes in rhythm with its hilltop surroundingsa true haven of quiet elegance. This home is a gem! On the main level, the 11-foot-ceilinged public rooms include a formal entry, a large living room that doubles as a media room with 3 walls of glass sliding doors opening to the gardens, a formal dining room designed to seat 12, a chefs kitchen that faces a secret garden, and a family room facing the rear gardens. An open-tread staircase lined with clear glass panels connects the upper, main, and lower levels of the home. On the lower level, there is a recreation room, a wine cellar, full bath and, across a stone patio, a fitness studio with walk-out access to the rear grounds. 2 bedrooms and 1.5 baths on the main level and an upper level devoted to the primary suite with a large private balcony and a spacious office, perfect for todays work-from-home needs. Detached studio guest house with full bath.

3 Beds ⋅ 4 Baths ⋅ ML82042340 MLS

A Hilltop Home Shaped by Light, Landscape and Contemporary Architecture-Designed as a sanctuary for the senses, this 4885 sq ft, 2007 contemporary masterpiece rises from the crest of central Portola Valley. the custom architecture was crafted to invite tranquility, framing soft, filtered views of the surrounding landscape . Here, the rare luxury of expansive, level grounds that breathes in rhythm with its hilltop surroundingsa true haven of quiet elegance. This home is a gem! On the main level, the 11-foot-ceilinged public rooms include a formal entry, a large living room that doubles as a media room with 3 walls of glass sliding doors opening to the gardens, a formal dining room designed to seat 12, a chefs kitchen that faces a secret garden, and a family room facing the rear gardens. An open-tread staircase lined with clear glass panels connects the upper, main, and lower levels of the home. On the lower level, there is a recreation room, a wine cellar, full bath and, across a stone patio, a fitness studio with walk-out access to the rear grounds. 2 bedrooms and 1.5 baths on the main level and an upper level devoted to the primary suite with a large private balcony and a spacious office, perfect for todays work-from-home needs. Detached studio guest house with full bath.

56 Hillbrook DR, Portola Valley

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

Sold listing courtesy of Nancy Goldcamp from CBR

$5,712,500

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

5 Beds ⋅ 4 Baths ⋅ ML82039321 MLS

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

50 Bear Gulch DR, Portola Valley

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

Sold listing courtesy of Jennifer Alfaro from COMPS

$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

$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

$3,000,000

Escape the ordinary at 435 Golden Oak Drive, an architecturally distinct 4-bedroom, 3.5-bath retreat in one of Portola Valleys most coveted enclaves. Set on nearly 1.5 acres at the end of a private drive, this residence offers rare privacy while still being minutes from Silicon Valley conveniences. Expansive windows fill the home with natural light and frame the surrounding landscape. Multiple decks across different levels create seamless indoor-outdoor living and provide inviting spaces for morning coffee, evening wine, or entertaining. The interior has been refreshed with new flooring and paint throughout, creating a clean, modern backdrop. The layout offers flexibility for family living, hosting, or working from home, with generous bedrooms and well-placed common areas. Located in an exclusive neighborhood known for its beauty, privacy, and top-rated schools, the property is also walking distance to the iconic Alpine Inn. Nearby are some of the Peninsulas most prestigious country clubs offering golf, tennis, dining, and social amenities. A rare opportunity to own a true retreat in the heart of the Peninsula.

4 Beds ⋅ 4 Baths ⋅ ML82025132 MLS

Escape the ordinary at 435 Golden Oak Drive, an architecturally distinct 4-bedroom, 3.5-bath retreat in one of Portola Valleys most coveted enclaves. Set on nearly 1.5 acres at the end of a private drive, this residence offers rare privacy while still being minutes from Silicon Valley conveniences. Expansive windows fill the home with natural light and frame the surrounding landscape. Multiple decks across different levels create seamless indoor-outdoor living and provide inviting spaces for morning coffee, evening wine, or entertaining. The interior has been refreshed with new flooring and paint throughout, creating a clean, modern backdrop. The layout offers flexibility for family living, hosting, or working from home, with generous bedrooms and well-placed common areas. Located in an exclusive neighborhood known for its beauty, privacy, and top-rated schools, the property is also walking distance to the iconic Alpine Inn. Nearby are some of the Peninsulas most prestigious country clubs offering golf, tennis, dining, and social amenities. A rare opportunity to own a true retreat in the heart of the Peninsula.

435 Golden Oak DR, Portola Valley

Listed by Joe Polyak, 415-595-2647 from Rise Homes
(If provided) CoList: Valerie Mattei from Rise Homes

Sold listing courtesy of Sergey Yusupov from RISEHOME

$6,200,000

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

5 Beds ⋅ 4 Baths ⋅ ML82022890 MLS

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

70 Stonegate RD, Portola Valley

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

Sold listing courtesy of Erika Demma from APR

$3,455,000

Discover the potential at 475 Cervantes Rd, nestled in the heart of Portola Valley, where opportunity meets prime location. Situated on a lovely 1 acre lot, this property presents a remarkable canvas for those looking to build or remodel in order to create their optimal living space. The home boasts 2,550 feet of living space, featuring 3 bedrooms, 2.5 bathrooms. The primary bedroom is a retreat in itself, complete with an ensuite bathroom that includes a separate tub and shower. The additional two bedrooms share a convenient and spacious hall bath. The heart of this home is its open-concept kitchen and family room, perfect for gatherings and entertaining. The kitchen comes equipped with a center island and a cozy eating area, while the family room offers built-in bookcases and fireplace. For more formal occasions, enjoy the separate dining room and large living room. To enhance the thoughtful flow of the home, all common areas lead to the serene backyard. Additional amenities include a dedicated laundry room, a detached 2-car garage, a screened patio and a deck overlooking the private yard while offering a peaceful retreat and space for outdoor enjoyment. This home already offers fabulous spaces and a thoughtful floor plan; it just needs the creativity of its next owner.

3 Beds ⋅ 3 Baths ⋅ ML82022989 MLS

Discover the potential at 475 Cervantes Rd, nestled in the heart of Portola Valley, where opportunity meets prime location. Situated on a lovely 1 acre lot, this property presents a remarkable canvas for those looking to build or remodel in order to create their optimal living space. The home boasts 2,550 feet of living space, featuring 3 bedrooms, 2.5 bathrooms. The primary bedroom is a retreat in itself, complete with an ensuite bathroom that includes a separate tub and shower. The additional two bedrooms share a convenient and spacious hall bath. The heart of this home is its open-concept kitchen and family room, perfect for gatherings and entertaining. The kitchen comes equipped with a center island and a cozy eating area, while the family room offers built-in bookcases and fireplace. For more formal occasions, enjoy the separate dining room and large living room. To enhance the thoughtful flow of the home, all common areas lead to the serene backyard. Additional amenities include a dedicated laundry room, a detached 2-car garage, a screened patio and a deck overlooking the private yard while offering a peaceful retreat and space for outdoor enjoyment. This home already offers fabulous spaces and a thoughtful floor plan; it just needs the creativity of its next owner.

475 Cervantes RD, Portola Valley

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

Sold listing courtesy of Eric Ruxton from TERA

$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

$3,200,000

Discover this mid-century modern-style gem in the sought-after Corte Madera neighborhood. Positioned on a desirable street and flat lot at the top of Canyon Drive and Crescent Road, this 3-bed, 2-bath home features vaulted ceilings, an open floor plan, fireplace, hardwood floors, floating staircase and abundant natural light through glass doors, picture windows and skylights. The versatile bedroom or possible media room on the first-floor opens to an inviting outdoor space with a fenced backyard and garden. Additional highlights include a 2-car garage with side yard access, washer/dryer hookup, and a storage shed for extra workspace. Enjoy a pet-friendly, active community walking distance to top rated public and private schools, Roberts Market, biking routes, and network of local hiking trails, just minutes from Stanford University and Palo Alto without ever having to get on the highway.

3 Beds ⋅ 2 Baths ⋅ ML82010192 MLS

Discover this mid-century modern-style gem in the sought-after Corte Madera neighborhood. Positioned on a desirable street and flat lot at the top of Canyon Drive and Crescent Road, this 3-bed, 2-bath home features vaulted ceilings, an open floor plan, fireplace, hardwood floors, floating staircase and abundant natural light through glass doors, picture windows and skylights. The versatile bedroom or possible media room on the first-floor opens to an inviting outdoor space with a fenced backyard and garden. Additional highlights include a 2-car garage with side yard access, washer/dryer hookup, and a storage shed for extra workspace. Enjoy a pet-friendly, active community walking distance to top rated public and private schools, Roberts Market, biking routes, and network of local hiking trails, just minutes from Stanford University and Palo Alto without ever having to get on the highway.

340 Canyon DR, Portola Valley

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

Sold listing courtesy of Isabella Esguerra from APR

$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

$6,700,000

Welcome to this stunning home in Portola Valley, offering a perfect blend of comfort and elegance. With a generous living space of 4,088 sq ft situated on a 47,517 sq ft lot, this property provides ample room for relaxation and entertainment. The home features three spacious bedrooms, including a primary bedroom conveniently located on the ground floor, and two full bathrooms equipped with double sinks. Separate structure perfect for office or large gym. Sunroom for relaxing and views. PV Schools The kitchen is a culinary delight with its sleek granite countertops, ideal for preparing gourmet meals. Enjoy dining in the formal dining room or the eat-in kitchen, catering to both casual and formal occasions. The family room offers a separate retreat for gatherings and relaxation. This beautiful residence boasts exquisite hardwood and wood flooring throughout, adding warmth and charm to the interior. Cozy up by the fireplace on cooler evenings, creating a perfect ambiance. Laundry is convenient with an inside washer and dryer setup. The home is part of the Portola Valley Elementary School District. Additional amenities include central AC, a whole house/attic fan, central forced air heating, and a two-car garage, ensuring comfort and practicality all year round.

3 Beds ⋅ 3 Baths ⋅ ML82008992 MLS

Welcome to this stunning home in Portola Valley, offering a perfect blend of comfort and elegance. With a generous living space of 4,088 sq ft situated on a 47,517 sq ft lot, this property provides ample room for relaxation and entertainment. The home features three spacious bedrooms, including a primary bedroom conveniently located on the ground floor, and two full bathrooms equipped with double sinks. Separate structure perfect for office or large gym. Sunroom for relaxing and views. PV Schools The kitchen is a culinary delight with its sleek granite countertops, ideal for preparing gourmet meals. Enjoy dining in the formal dining room or the eat-in kitchen, catering to both casual and formal occasions. The family room offers a separate retreat for gatherings and relaxation. This beautiful residence boasts exquisite hardwood and wood flooring throughout, adding warmth and charm to the interior. Cozy up by the fireplace on cooler evenings, creating a perfect ambiance. Laundry is convenient with an inside washer and dryer setup. The home is part of the Portola Valley Elementary School District. Additional amenities include central AC, a whole house/attic fan, central forced air heating, and a two-car garage, ensuring comfort and practicality all year round.

165 Golden Oak DR, Portola Valley

Listed by Dana Cappiello, 415-264-5464 from Sotheby's Intl Rlty
(If provided) CoList: Derek Cappiello from Sotheby's Intl Rlty

Sold listing courtesy of Keyko Pintz from AGNC

$3,925,000

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

$8,000,000

On the top of the hill at the end of a long private driveway and nestled on 3.5 mostly usable acres sits this very private home. Offering spectacular 270 degree views this 5 bedroom, 3 bath home sits on one of the finest sites in Portola Valley. The well-appointed private home features bright and light interiors with wonderful views throughout its effortless multi level design. The main level offers a living room, office, dining room, family room kitchen and primary suite all with western hill views. The lower level offers 4 additional bedroom, a laundry room and additional Office of Exercise room. There is also a barn and a large fenced in garden area.

5 Beds ⋅ 4 Baths ⋅ ML82004802 MLS

On the top of the hill at the end of a long private driveway and nestled on 3.5 mostly usable acres sits this very private home. Offering spectacular 270 degree views this 5 bedroom, 3 bath home sits on one of the finest sites in Portola Valley. The well-appointed private home features bright and light interiors with wonderful views throughout its effortless multi level design. The main level offers a living room, office, dining room, family room kitchen and primary suite all with western hill views. The lower level offers 4 additional bedroom, a laundry room and additional Office of Exercise room. There is also a barn and a large fenced in garden area.

909 Westridge DR, Portola Valley

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

Sold listing courtesy of Keri Nicholas from PARCA

$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