Portola Valley Real Estate

Welcome to Portola Valley, California—a hidden gem nestled in the heart of San Mateo County. This enchanting town, known for its stunning natural beauty and serene ambiance, offers a unique blend of rural charm and modern convenience. With a population of just over 4,500 residents, Portola Valley is celebrated for its tight-knit community and commitment to preserving its picturesque landscapes.

Surrounded by the majestic Santa Cruz Mountains, Portola Valley boasts an array of outdoor activities that cater to nature lovers and adventure seekers alike. Explore the miles of hiking and biking trails that weave through lush forests and open spaces, offering breathtaking views and a chance to connect with the region's diverse wildlife. The town’s dedication to preserving its natural environment is evident in its numerous parks, including the popular Windy Hill Open Space Preserve.

Portola Valley is not just about stunning scenery; it also features a highly esteemed school district, making it an ideal location for families seeking quality education for their children. The town’s vibrant community spirit is reflected in its various events and gatherings, fostering a sense of belonging among residents.

Culturally rich and conveniently located, Portola Valley is just a short drive from the bustling tech hub of Silicon Valley, providing residents with easy access to world-class amenities, dining, and entertainment. Whether you’re looking for a peaceful retreat or a place to raise a family, Portola Valley offers a harmonious blend of tranquility and opportunity. Come discover the charm of this extraordinary town, where every day feels like a breath of fresh air!

Newest Listings in Portola Valley

$6,250,000

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

$3,998,000

3 Beds ⋅ 5 Baths ⋅ ML82060715 MLS

Set within 2.77 acres, this remarkable residence is enveloped by gardens, mature trees, and the kind of natural stillness that feels increasingly rare in Silicon Valley. Though close to the amenities of Portola Valley, the property has the character of a private retreat. A long, tiled staircase moves through layers of lush planting, creating a sense of anticipation before the architecture comes into view. Inside, the house reveals soaring 10- and 12-foot ceilings, fine millwork, oak floors, and an abundance of natural light. The main level unfolds naturally. A generous kitchen and family room form the heart of the home, with a substantial pantry designed for effortless entertaining. Beyond, the dining and living rooms are framed by graceful arch-top windows, their wooded outlooks becoming an ever-changing part of the interior. The primary suite is conceived as a sanctuary of its own. Two private balconies open toward the surrounding landscape, while a fireside sitting area offers a quiet place to retreat. An expansive walk-in closet and beautifully appointed marble bath complete the suite with a sense of understated luxury. Two additional bedrooms, one is en-suite. Sweeping views, multi-level deck and pergola extend into the gardens, with a built-in outdoor kitchen and barbecue.

55 Vista Verde WAY, Portola Valley

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

$3,498,000

3 Beds ⋅ 2 Baths ⋅ ML82060118 MLS ⋅ Portola Valley Ranch BLDG.

45 Bear Paw offers a rare opportunity to own an updated, single-level home just steps from the entry to Portola Valley Ranch. A 2 car garage with ample storage connects to the main level via interior elevator for easy, step-free access. Large windows frame the gracious living room, where soaring ceilings, designer chandeliers, and an attractive marble fireplace surround create a serene, light-filled space. Striking bar with custom glass shelving, wine fridge and floral wallpaper. Spacious kitchen offers handsome wood cabinetry, and recently updated counters and backsplash. Three generous bedrooms and two beautifully updated bathrooms are grouped together in bedroom wing. The primary suite enjoys its own peaceful views of Windy Hill, updated bath with roll-in shower, walk-in closet, and its own 100-sq.-ft. deck. Living space extends outdoors with a substantial patio and a 216-sq.-ft. attached sunroom. The Ranch is an extraordinary place to call home-- a 6 minute drive to the Ladera County Shopper and 8 minutes to Highway 280, yet offering a remote, resort-like feel with exceptional community amenities including heated pools, tennis courts, a fitness center, a community vineyard, gardens, and miles of hiking trails. Excellent Portola Valley schools. Roof recently replaced.

45 Bear Paw, Portola Valley

Listed by Lynn Wilson Roberts, 650-255-6987 from Compass
(If provided) CoList: Annie Roberts from Compass

$7,495,000

4 Beds ⋅ 3 Baths ⋅ ML82058982 MLS

Located in the highly desirable Westridge neighborhood, this impressive 2.62+/- acre property offers views, room for expansion, a vineyard, a separate ADU, and a freshly updated home with 4 bedrooms and 3 remodeled baths. The kitchen has new appliances and flows into a family living space. The large dining area sets the stage for entertaining. The Primary Suite has a tall, beamed ceiling, 3 closets and a deck that overlooks the property and Windy Hill views. Additional bedrooms enjoy a private wing that centers around a flexible space. This space is served by a separate entrance for flexibility. A lower level is a blank slate. It has a workshop, lots of storage, 2 rooms with sliding glass doors, a large well-lit space thats ideal as a game room or exercise center and a full bath. Potential for a wine cellar. The ADU is 1 bed, 1 bath and has an open living/dining/kitchenette space, as well as a private deck and entrance. There is a small upper pasture and a large area at the front of the property that could be used for horses, a pool, or possibly a tennis court. Central Portola Valley location, convenient to shopping, Alpine Hills Tennis and Swim Club, The Alpine Inn, excellent PV schools and easy commute routes.

15 Naranja WAY, Portola Valley

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

$3,695,000

3 Beds ⋅ 3 Baths ⋅ ML82056981 MLS

Some homes are simply built. Others are cared for, collected, and shaped over time. Set among mature trees and thoughtfully designed gardens, this distinctive Portola Valley farmhouse reflects years of careful stewardship. Reclaimed wide-plank North Carolina pine floors, plaster walls and ceilings, painted millwork, marble, handmade tile, exposed beams and French doors give the home its character. The kitchen features a La Cornue range, original farmhouse sink, marble countertops, generous island, butler's pantry and cozy dining nook. The dining room is suited to everyday meals and larger gatherings, while the living room centers on a marble wood-burning fireplace and opens through two sets of French doors to a covered porch overlooking the gardens. The primary suite includes a walk-in closet and marble bath with mosaic tile and imported European brass fixtures. Upstairs are two additional bedrooms, a claw-foot bath and flexible spaces for study, work, hobbies or storage. A spacious family room is located downstairs. Originally designed by landscape artist Cevan Forristt, the grounds are rare for Portola Valley largely flat and usable, with mature trees, fruit trees, grapevines, water features and multiple areas for outdoor gathering.

133 Russell AVE, Portola Valley

Listed by Carrie Davis, 650-269-4768 from Coldwell Banker Realty
(If provided) CoList: from

$3,500,000

4 Beds ⋅ ML82056611 MLS

Located in Portola Valley, this spacious 2,960 sq. ft. home sits on a sizable 17,623 sq. ft. lot. The kitchen is equipped with modern amenities including a built-in gas oven range, microwave, island, hood over range, and garbage disposal, offering both functionality and convenience for everyday cooking. The home features central forced air gas heating and central air conditioning to maintain comfort year-round. This property does not include a garage. It is part of the Portola Valley Elementary School District. This residence combines ample living space with essential features in a desirable town setting.

176 Los Trancos CIR, Portola Valley

Listed by Tim Gilmartin, 650-348-2020 from Gilmartin Group
(If provided) CoList: from

$3,500,000

4 Beds ⋅ 4 Baths ⋅ ML82056610 MLS

Located in Portola Valley, this spacious 2,960 sq ft home features four bedrooms and four full bathrooms. The kitchen is equipped with built-in gas oven range, microwave, hood over range, island, and garbage disposal, opening to a combined kitchen and family room area. Enjoy two fireplaces, one in the living room and another in the primary bedroom, providing warmth and ambiance. The home includes a dining area with a breakfast bar, central forced air gas heating, and central AC for comfort. Laundry facilities are conveniently located inside the home. The property sits on a 17,623 sq ft lot and falls within the Portola Valley Elementary school district.

176 Los Trancos CIR, Portola Valley

Listed by Tim Gilmartin, 650-348-2020 from Gilmartin Group
(If provided) CoList: from

$3,395,000

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 & 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

$5,488,000

5 Beds ⋅ 4 Baths ⋅ ML82052826 MLS

Set on 2.8 AC, this home offers a peaceful retreat in a coveted setting. Warm, welcoming interiors span more than 3,700 SF across a multi-level floorplan, blending rustic character with an easy livability that harmonizes with the surrounding landscape. A soaring vaulted ceiling elevates the living room anchored by a fireplace and expansive windows framing views that reach toward the Stanford Dish, while the main living spaces also include a formal dining room, granite kitchen with Thermador appliances, a comfortable family room with a fireplace, and a lower-level recreation room. Five bedrooms plus an office provide flexibility and comfort. With nearby access to scenic nature preserves and trailheads, a short drive to the Ladera Country Shopper shopping center and local favorites such as Alpine Inn, this home offers a rare balance of seclusion and convenience, all with access to acclaimed schools including Ormondale and Corte Madera (buyer to verify eligibility).

285 Escobar RD, Portola Valley

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

$2,595,000

2 Beds ⋅ 1 Baths ⋅ ML82052857 MLS

Beautiful (Bonita!) very large property in upper Los Trancos Woods. Over 1.6 AC of mostly flat land with old, mostly not habitable House, Cottage, Garage and Carport, comfortably spread throughout the property. In Feb 2026, San Mateo County approved a 2 lot subdivision, and work is ongoing to complete the final map recording. The house is available prior to recording of the subdivision as a single lot for buyers who might want more flexibility in what they do with the property. Extensive geological, geotechnical, arborist, historical, biological and civil reports and plans come with the property.

245 Bonita RD, Portola Valley

Listed by Mike Sokolsky, 650-465-2573 from Coldwell Banker Realty
(If provided) CoList: from

$4,188,000

5 Beds ⋅ 4 Baths ⋅ ML82049073 MLS

Mid-Century Modern enthusiasts will delight in this one of a kind architectural gem. This home boasts blissful views reaching from San Francisco to Santa Clara. An entertainers dream! Tucked away from the flats, this stunning retreat is quiet and private. The home boasts three large decks, a hot tub, two gas fireplaces, two Tesla chargers in the garage, five bedrooms, three and a half bathrooms, an office upstairs, two living areas, generous 2,940 SqFt of living space plus an expansive remodeled finished basement of 1,280 SqFt. The dining room contains Herman Miller light fixtures and high ceilings meet walls of expansive glass to thrill and entertain guests. Come claim this magical home that some have said has the best views in the Silicon Valley.

410 Conil WAY, Portola Valley

Listed by Monique Anton, 650-380-5512 from Modern Homes Realty
(If provided) CoList: from

$1,749,000

2 Beds ⋅ 2 Baths ⋅ ML82047556 MLS

SUNLIT GEM ON NEARLY ONE-HALF ACRE WITH PLANS TO EXPAND! Fresh, inviting, and completely sophisticated, this retreat has been transformed into a light-filled setting. Easily accessed via wide streets, the property spans nearly one-half acre of predominantly level grounds and includes plans for a future expansion. The current home, with 2 bedrooms and 2 baths, offers a streamlined scale yet the open concept design lends an unexpected sense of expansiveness. A crisp palette of whites defines the interiors, from the all-white kitchen with quartz countertops and subway tile backsplashes to the remodeled baths finished in marble and tile. Vaulted ceilings with skylights and exposed beams enhance the airy atmosphere, while wood-like luxury vinyl floors provide continuity throughout. Multiple sets of glass doors open to wraparound flagstone patios and expansive land, where limited tree canopies allow brilliant sunlight to fill both the interiors and outdoor gathering spaces. Finishing touches include a separate laundry room, an outdoor storage shed, and a two-car carport. Portola Valleys acclaimed schools and miles of scenic trails are just moments away, making this a remarkable opportunity to enjoy contemporary style and comfort today with the option to expand in the future.

76 Old Spanish TRL, Portola Valley

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

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Intero Real Estate Services are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.