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

20 Meadow LN, Portola Valley

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

Sold listing courtesy of Leslie Bauer from CTYRE
479 Westridge DR, Portola Valley
$20,500,000
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
155 Grove DR, Portola Valley
$14,850,000
6 Beds ⋅ 6 Baths ⋅ ML82062830 MLS
Situated on 1.25 acres in central Portola Valley and comprised of four distinct structures, this property captures the essence of refined California living. The main residence is designed for effortless single-level living, characterized by vaulted ceilings, European white oak floors, honed marble, and custom designer lighting. The chef's kitchen is equipped with custom cabinetry, Moroccan tilework, and premium appliances. The primary suite offers a secluded sanctuary complete with vaulted ceilings, a fireplace sitting area, and French doors leading to a private garden terrace. Its ensuite bath is finished with radiant-heated Belgian Bluestone floors, a deep soaking tub, and a marble walk-in shower. Beyond the primary residence, two well-equipped, fully independent structures, a one-bedroom ADU and a detached studio/guest house provide exceptional flexibility. A heavy timber-built car barn with an upper-level recreation lounge adds further functionality to the compound. Private spaces for entertaining, dining and relaxation are set among mature redwoods, heritage oaks, and perennial gardens. Positioned minutes from Interstate 280, top-rated schools, open space preserves, and athletic clubs, this property offers a peaceful rural lifestyle with convenient access to Silicon Valley.

155 Grove DR, Portola Valley

Listed by The Dreyfus Group, 650-485-3476 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Renee Daskalakis from TODAY
241 Georgia LN, Portola Valley
$14,500,000
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

Sold listing courtesy of Sean Spanek from DEN
5660 Alpine RD, Portola Valley
$11,040,000
6 Beds ⋅ 11 Baths ⋅ ML81803721 MLS
Completed in 2006, this magnificent vineyard estate is the perfect place to escape from the fast daily pace of Silicon Valley. The approximately 41 acres are as peaceful as they are beautiful, with spectacular top-of-the-world San Francisco Bay views. Arriving on the front terrace is as if stepping into the Italian countryside. The scale of the home is destined for grand entertaining spilling out to exceptional front and rear terraces. The kitchen is a culinary retreat with commercial-quality appliances, and the wine cellar awaits a sizable collection. Multiple rooms for everyday living, a theatre, plus a well-being center with spa, steam, and sauna add luxurious touches. Both 5660 Alpine Road and APN 080-040-120 are being offered for sale together.

5660 Alpine RD, Portola Valley

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

Sold listing courtesy of Un Represented from NOBUY
3510 Alpine RD, Portola Valley
$10,850,000
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
56 Hillbrook DR, Portola Valley
$9,495,000
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
160 Fawn LN, Portola Valley
$8,500,000
5 Beds ⋅ 6 Baths ⋅ ML82061161 MLS
Built in 2021, this single-level main residence just-over-one-acre in central Portola Valley. Generous gathering spaces include formal living & dining rooms plus an impressive chefs kitchen & extra-large family room. Gas-log fireplaces in living & family rooms, while oversized media screens, distributed sound speakers, surround sound with automated window blinds on clerestory windows & in bedrooms. Privately accessed studio with full bath above the garage offer exceptional flexibility. Spacious primary suite with private terrace, oversized customized closet, & luxurious bath with freestanding tub & large shower. Outdoor living unfolds across a vast rear deck with gas fire pit & built-in barbecue center, large spa, & an expansive synthetic lawn with volleyball net. Terraced grounds extend up the hillside with steps to a sitting area with sweeping views. Extensive amenities include recently added 8.1 kW Tesla solar system with two Powerwall batteries for backup power, Lutron programmable lighting system, dual-zone air conditioning, & Nest thermostats. Survey & architectural renderings are also available for a 650-square-foot ADU. This central Portola Valley setting is just minutes from renowned hiking, biking, & equestrian trails and has access to excellent Portola Valley schools.

160 Fawn LN, Portola Valley

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

Sold listing courtesy of Glen Mitchell Group from KWPEN
120 Deer Meadow LN, Portola Valley
$8,400,000
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
1390 Westridge DR, Portola Valley
$8,100,000
5 Beds ⋅ 5 Baths ⋅ ML82033403 MLS
Contemporary single-level main residence with attached two-story ADU on 1.1+ private acres finished in 2021, offering direct Windy Hill views and walking distance to Portola Valley Town Center, library, restaurants, farmers market, and trailheads. Striking modern architecture features walls of glass, soaring ceilings, skylights, and white oak floors throughout. The dramatic great room opens to covered and open terraces and a level lawn just off the living room patio, with rear grounds anchored by a heritage oak. The designer kitchen showcases Calacatta marble surfaces, a waterfall island, and high-end appliances. The main residence includes a dedicated office, four bedrooms, and three and a half baths, highlighted by a serene primary suite with Windy Hill views and a Zen-inspired bath with private garden. A privately located bedroom suite is ideal for guests or an au pair. The attached ADU offers one bedroom, one bath, a full kitchen, and a living room with fireplace, with finishes matching the main home. Gated entry, custom pavers, cedar entry door, fountains, mature landscaping, level synthetic lawn, raised garden beds, and fully fenced grounds complete this desirable property. Total Finished square footage: 4,390 sq. ft. (main house: 3,520 sq. ft. and ADU: 870 sq. ft.)

1390 Westridge DR, Portola Valley

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

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

600 Westridge DR, Portola Valley

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

Sold listing courtesy of Hugh Cornish from CBR
2 Buck Meadow DR, Portola Valley
$7,250,000
5 Beds ⋅ 5 Baths ⋅ ML82061086 MLS ⋅ Blue Oaks BLDG.
Custom-designed & built in 2013 to harmoniously blend into the quintessential California landscape, this extraordinary residence seamlessly connects living spaces with the natural beauty outside. Positioned on 3 serene acres, every corner of the home has been masterfully crafted to offer distinct, functional living zones with high-end finishes & thoughtful details, creating an effortless balance of luxury & daily comfort. The main house features a primary suite with abundant storage, private deck & hot tub. The junior bedroom suite has fun living/sleeping spaces, a large 4th bedroom is currently used as a work out room.The 470 SF 1 bedroom cottage provides flexible guest accommodations. A chefs kitchen is equipped with Viking & Miele appliances, a separate clean-up room & walk in pantry. Floor to ceiling windows with gorgeous views of the meadow & oak trees from the living areas connect to paved patios. Dedicated executive office & media room. Other high-end features incl steel framed construction, radiant heat in polished concrete floors, emergency generator plumbed to gas utility with back up propane tank, Lutron smart lighting, owned solar panels, water filtration system, EV hook up, AC to be installed, storage room & walk in wine storage, 2 car garage & cyclist station.

2 Buck Meadow DR, Portola Valley

Listed by Michael Huang, 650-248-0006 from Compass
(If provided) CoList: from

Sold listing courtesy of Penelope Huang from THP
40 Hillbrook DR, Portola Valley
$7,000,000
5 Beds ⋅ 5 Baths ⋅ ML82059349 MLS
Set on a beautifully landscaped acre in Portola Valley, this expansive home offers nearly 5,300 square feet of living space beneath soaring ceilings and walls of glass, filling the home with natural light while bringing the verdant landscape into view. The main living spaces include a dramatic living room with statement fireplace, dining room with wet bar, chef's kitchen with top-brand appliances, and inviting family room. Five bedrooms include a retreat-like primary suite with fireplace and spa-inspired bathroom, while the lower level provides its own kitchen, living area, and separate garages. Outside, multi-level grounds feature a deck, hot tub, patios, and trellis-covered dining area. Close to Portola Valley's renowned trails, scenic preserves, Alpine Inn, and Ladera Country Shopper.

40 Hillbrook DR, Portola Valley

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(If provided) CoList: from

Sold listing courtesy of Kimberly Hansen from GGSIR
578 CRESTA VISTA LN, Portola Valley
$6,130,000
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
350 Willowbrook RD, Portola Valley
$6,100,000
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
747 Westridge DR, Portola Valley
$5,950,000
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
340 Willowbrook DR, Portola Valley
$5,900,000
6 Beds ⋅ 4 Baths ⋅ ML82039381 MLS
This masterwork of "ultimate bungalow" design evokes the spirit of the iconic Gamble and Gamble, honoring the Arts and Crafts movement's devotion to natural materials and visible joinery. This hand-crafted sanctuary offers a seamless transition from the wild creek-side environment to a sheltered interior. Clad in traditional cedar shingles with overhanging eaves, the home sits in organic harmony with its acre lot. An 18-foot ceiling anchors the Great Hall, its massive scale made intimate by hand-finished built-ins and intricate millwork. From the elegant dining room wainscoting to custom cabinetry, every detail celebrates "honesty of construction." The expansive canopy deck preserves two ancient redwoods that rise through the decking to create a living ceiling, a direct nod to building around nature. The architecture is a dialogue between forest and floor plan. The open-concept kitchen, with Wolf, Viking, and Sub-Zero appliances, integrates into a timeless space illuminated by lighting that highlights natural textures. True to the Craftsman ideal, French doors in the living room, primary suite, and massive upstairs loft dissolve the boundary between shelter and garden. Modern necessities, a Tesla charger, and turf lawn are implemented with a focus on environmental stewardship.

340 Willowbrook DR, Portola Valley

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

Sold listing courtesy of Dorothy Coulter from EXT
135 Meadowood DR, Portola Valley
$5,850,000
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
50 Bear Gulch DR, Portola Valley
$5,712,500
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
365 Alamos RD, Portola Valley
$5,600,000
3 Beds ⋅ 2 Baths ⋅ ML82047359 MLS ⋅ Westridge Arch. Supervis. Comm. BLDG.
Nestled along coveted Alamos Road in the prestigious Westridge area, this extraordinary property was refurbished top to bottom; presenting a rare opportunity to own a private retreat in one of the Peninsula's most exclusive neighborhoods. Set on nearly 2.75 acres of serene, country-like grounds, this exceptional estate offers unmatched privacy, tranquility, & breathtaking panoramic bay views; all just minutes from Highway 280 & Stanford Shopping Center & Campus. Beautifully & fully renovated, this move-in ready home features 3 bedrooms & 2 bathrooms, thoughtfully designed to capture stunning vistas from nearly every room. Expansive windows & outdoor spaces invite the natural beauty indoors, creating a peaceful sanctuary surrounded by lush greenery & rolling landscapes. Whether you choose to enjoy the home exactly as it is or envision expanding it into a larger custom estate, the possibilities are endless. Add a second story, subterranean garage, ADU, tennis court, lap pool, tranquil pond, an RV or other personalized amenities to create your dream compound. Opportunities like this are exceptionally rare - a timeless setting w/ forever views, exclusive privacy, & unlimited potential. Experience your own private piece of heaven & make this remarkable property yours before its gone!

365 Alamos RD, Portola Valley

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

Sold listing courtesy of Ken Glidewell from COMP29
147 Mapache DR, Portola Valley
$5,300,000
5 Beds ⋅ 3 Baths ⋅ ML82052353 MLS ⋅ Westridge BLDG.
Defined by the clean lines, soaring ceilings, and abundant natural light that characterize classic mid-century design, this circa 1957 home presents a compelling opportunity in Portola Valley's highly desirable Westridge neighborhood. Unlike many homes of the era, the interiors are bright and inviting, with painted finishes, expansive walls of glass, and a series of eight skylights that fill the home with natural light throughout the day. Vaulted ceilings, versatile gathering spaces, and a thoughtful floor plan create a comfortable environment ready for immediate enjoyment. Equally significant is the setting. Spanning approximately 2.51 acres, the property offers exceptional privacy, expansive mostly level grounds, and a premier location surrounded by some of Portola Valley's most desirable estate properties. Whether enjoyed as it stands today, remodeled, expanded, or reimagined entirely, the combination of land, location, and architectural character creates an opportunity that is becoming increasingly difficult to find in today's market. Further enhancing the appeal is the home's location within the highly regarded Portola Valley school system and its convenient access to Stanford University and many of Silicon Valley's leading technology centers.

147 Mapache DR, Portola Valley

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

Sold listing courtesy of John Chao from JCHAO
415 Golden Oak DR, Portola Valley
$5,300,000
4 Beds ⋅ 4 Baths ⋅ ML82006455 MLS
You wake up one morning on the deck of 415 Golden Oak Drive, coffee in hand, gazing at a view that makes time stand still. From this elevated perch in central Portola Valley, the South Bay unfolds rolling hills, morning mist, and the quiet promise of a perfect day. This beautifully updated 4-bedroom, 3.5-bath home offers approximately ~4,300 sq. ft. of refined living space, blending clean architectural lines, natural light, and sweeping sightlines. Set on just under two acres with lawn, pool, mature trees, and expansive decks the property is both functional and breathtaking. Inside, vaulted ceilings and large windows frame the views. The open living and dining areas flow into a thoughtfully designed kitchen with high-end appliances, custom cabinetry, and a spacious island ideal for entertaining or quiet mornings. The ~600 sq. ft. primary suite is a private retreat with a spa-like bath, walk-in closet, and a balcony perfect for stargazing or late-night talks. A separate bonus room with full bath offers flexible space for guests, work, or play. Located in the heart of Portola Valley, minutes from top-rated schools, scenic trails, and local shops, this isn't just a home its a vantage point. A place where space, calm, and style come together.

415 Golden Oak DR, Portola Valley

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS
880 La Mesa DR, Portola Valley
$5,150,000
5 Beds ⋅ 5 Baths ⋅ ML82024481 MLS

880 La Mesa DR, Portola Valley

Listed by Janie Barman, 650-759-1182 from Compass
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA
2 Horseshoe BND, Portola Valley
$5,100,000
4 Beds ⋅ 4 Baths ⋅ ML82031504 MLS ⋅ Portola Ranch Association BLDG.
Set in the tranquil Portola Valley Ranch with breathtaking views, this magnificent home blends architectural elegance with stunning natural surroundings. An open floor plan and walls of glass frame sweeping vistas of rolling hills and the Bay, with sightlines reaching San Francisco and Oakland. Multiple expansive decks, two spanning the full width of the home offer exceptional spaces for entertaining or relaxation. The main level features a grand entry illuminated by a dramatic skylight, leading to a striking LR/DR w/ soaring vaulted ceilings, skylights, FP, and a hidden bar. The light-filled eat-in kit, centered around an oversized oval island and SS appliances, opens directly to an al fresco dining deck. Also on the main level is a spacious bedroom w/ skylight and glass slider to a private deck, along with an elegant bath. The luxurious primary suite provides a serene retreat with its own FP, balcony, and WIC. An open staircase leads to the lower level, where a gorgeous FR w/ FP opens to a covered deck w/ expansive views. This level also includes a dedicated office, two full baths, laundry rm, and generous storage. With its thoughtful design and awe-inspiring setting, this home offers a rare opportunity for refined living in one of the Bay Areas most coveted communities.

2 Horseshoe BND, Portola Valley

Listed by Brian Chancellor, 650-303-5511 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Shena Hurley from DP
8 Hawkview ST, Portola Valley
$5,005,000
4 Beds ⋅ 4 Baths ⋅ ML82039665 MLS
Completely remodeled in 2020, this exceptional Portola Valley Ranch home showcases stunning western views framed by a majestic oak overlooking rolling, verdant open space, creating a picturesque, tranquil setting. The dramatic living room is anchored by a stone fireplace wall and bathed in natural light, seamlessly connecting to the adjacent dining area with oversized glass doors that showcase the views and open to an expansive entertainment deck for indoor-outdoor living. The chefs kitchen features Quartzite countertops, a waterfall island with prep sink, wine cooler, bar seating, Thermador appliances, sleek cabinetry, and a full pantry, flowing effortlessly into the main living spaces. The main level also includes a luxurious primary suite with fireplace, breathtaking vistas, spa-like bath, a stylish den with fireplace, designer powder room and a well-appointed laundry room. The lower level offers a spacious family room, a private ensuite bedroom, two additional bedrooms, a hall bath, and a second laundry room, providing flexible living and guest space. Enjoy resort-style amenities exclusive to the Ranch community, including 2 pools, 3 tennis courts, fitness center, Ranch House, community garden, vineyard, orchard, duck pond, dog park, miles of scenic trails, top-rated schools.

8 Hawkview ST, Portola Valley

Listed by Shelly Roberson, 650-464-3797 from Compass
(If provided) CoList: from

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

5 Oak Forest CT, Portola Valley

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

Sold listing courtesy of Loren Dakin from PARCA
2 Franciscan RDG, Portola Valley
$4,950,000
4 Beds ⋅ 4 Baths ⋅ ML82056839 MLS ⋅ Portola Valley Ranch BLDG.
Sweeping southeastern views create a spectacular backdrop for this beautifully refreshed 4 bdm 4 bath home, ideally perched atop one of the best locations in Portola Valley Ranch. Offering nearly 4,000 SF (see floorplan!) 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

Sold listing courtesy of Caitlin Darke from COMPS
200 Cherokee WAY, Portola Valley
$4,750,000
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
25 Cordova CT, Portola Valley
$4,625,000
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

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