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View All Portola Valley CA Home Listings - With Guest House

$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

$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

$7,485,000
3 Beds 3 Baths ML81998853 MLS Westridge HOA BLDG.
Contemporary masterpiece with spectacular Windy Hill views designed by architect Ana Williamson. Featuring steel I-beams, soaring ceilings create openness & strategically placed windows fill the space with light highlighting the natural setting. The modern open floor plan includes chef's kitchen with high-end appliances, custom Italian cabinetry & Dekton ceramic countertops. Floor to ceiling sliding Fleetwood glass doors make for easy indoor/outdoor entertaining, extending on to the covered patio with heated floors, fireplace, & Italian pizza oven. The primary suite upstairs has expansive views, walk-in closet & large chic bathroom. Built with fire safety in mind with a metal roof, no exposed eaves, fire sprinklers, owned solar & backup generator. Detached 770 sq ft guest house with full kitchen, 1.5 bathrooms & large bedroom. Bonus detached 350 sq ft workshop w/ extra storage provides a multitude of possibilities. Over 1 acre fully fenced with drought resistant Mediterranean native landscaping, mini orchard, ipe trellis with mature wisteria, 100 sq ft garden shed & raised garden beds. This thoughtfully designed luxury home offers privacy, stunning views, proximity to town, access to commute routes in Silicon Valley & serene hiking trails in the rolling hills of Portola Valley.

140 Pinon DR, Portola Valley

Listed by Julia Laquer, 650-434-2755 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Peter Cowperthwaite from DP

$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

$9,200,000
4 Beds 6 Baths ML81981281 MLS
Set on two acres of picturesque rolling hills dotted with California oaks, this country manor is architecturally designed to evoke the beauty & appeal of a French country estate. Inside & out, the home embodies elegance & charm with rustic sophistication. The exterior is a harmonious blend of natural stone & stucco siding, complemented by a high-pitched Vermont slate roof. Large arched windows & handcrafted oak timber doors enhance the sense of history & authenticity. The design features a masterfully constructed covered bridge, made from reclaimed barn wood & bluestone flooring, connecting the round turret of the main home to the upper-level guest quarters above one of two garages. Handcrafted wrought iron railings, skillfully forged by a blacksmith, adorn the bridge, the front porch, & stairways from the motor court, adding artistic detail at every corner. Home exudes rustic grandeur with lofty ceilings constructed from hand-hewn century-old beam timbers. Located just minutes from the heart of Silicon Valley, this country manor harmoniously blends architectural splendor, natural beauty, & modern conveniences. It stands as a testament to refined living, where the allure of the past meets the dynamism of the present, creating a sanctuary that is both timeless and contemporary.

220 Golden Hills DR, Portola Valley

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

Sold listing courtesy of Kavanaugh Group from CBR

$5,741,000
6 Beds 5 Baths ML81979643 MLS
This exquisite property, in Santa Clara County w/Palo Alto schools captures the essence of Portola Valley on a spectacular 1.28 +/- acre lot. Boasting scenic beauty of Stanford hills and Felt Lake this home features a 1695 +/-sf single-level guest house w/ground-level access. With 3 beds, 3 bas, office and bonus room in the 4146 +/- sf main residence and 3 beds, 2 bas in guest house, plus 2-stall horse stable, this home provides versatile living options. Remodeled by RJ Dailey in 1983, the main homes exquisite structural beamed ceilings and custom windows perfectly frame the view of the surrounding open space and glorious sunsets. Cool tile and warm wood floors enhance the open floor plan and newly carpeted bedrooms provide comfort. Kitchen is large and bright w/luscious views. A separate guest house, accessible via its own driveway, offers independent living. High ceilings and large great room are complemented w/updated eat-in chefs kitchen and granite counters. The primary suite features, spa bath, luxurious soaking tub, 2 walk-in closets and storage loft. Each home features a 2-car garage and the guest house also includes a workout room/office and workshop.This property offers a tranquil sanctuary near hiking and biking trails, Rossottis Alpine Inn and Ladera Country Shopper.

5 Arastradero RD, Portola Valley

Listed by Bogard-Tanigami Team, 650-924-8365 from The Agency
(If provided) CoList: from

Sold listing courtesy of RECIP from RCIP

$10,000,000
5 Beds 7 Baths ML81972934 MLS
Located in the prestigious Westridge area, this striking contemporary home stands as a testament to architectural brilliance by well-known architect Bob Stecker & construction by RJ Dailey. Home's signature aesthetic is unveiled with cathedral ceilings by Kalwall, with dispersed light intersecting at angles supported by open beams & trusses in clear heart redwood. This designs floods the home with diffused natural light, minimizing solar heat gain & maximizing thermal performance. The chorus of natural materials continues throughout, with vaulted ceilings in clear heart redwood, floors in oak, marble, or tile, & custom built-in wood cabinetry at every turn. Detached guest house with a full kitchen, bedroom, & bath. Set on approximately 2.5 acres, the outdoor experience is equally impressive. The grounds feature a newly remodeled pool & spa, a built-in barbecue center, & freshly designed & installed landscaping with expansive lawn for recreation. The Westridge Trail borders the property leading to miles of hiking & biking renowned throughout the town. Located within the highly acclaimed Portola Valley school district, this property is truly a special offering that combines architectural excellence with luxurious amenities & a remarkable setting with Bay views.

550 Westridge DR, Portola Valley

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

Sold listing courtesy of Mary & Brent Gullixson from COMPS

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