Portola Valley Real Estate

Nestled in the heart of San Mateo County, Portola Valley is a picturesque town that embodies the essence of California living. Known for its stunning natural beauty and serene atmosphere, this charming community is a haven for those seeking a peaceful retreat from the hustle and bustle of urban life. With rolling hills, lush landscapes, and an abundance of open space, Portola Valley is a nature lover's paradise, offering miles of hiking and biking trails that wind through the stunning surroundings.

Portola Valley boasts an impressive array of outdoor activities, including the nearby Windy Hill Open Space Preserve, where residents can enjoy panoramic views of the Bay Area while immersing themselves in the tranquility of nature. The town's commitment to preserving its natural beauty is evident in its well-maintained parks and recreational facilities, making it a perfect place for families and outdoor enthusiasts alike.

In addition to its stunning landscapes, Portola Valley is renowned for its strong sense of community. The town hosts a variety of events throughout the year, fostering connections among residents and creating a warm, welcoming atmosphere. With highly-rated schools and a focus on sustainability, families are drawn to the area for its excellent educational opportunities and commitment to environmental stewardship.

Centrally located, Portola Valley offers easy access to the vibrant tech hubs of Silicon Valley while maintaining a quaint, small-town charm. Whether you’re looking for a serene retreat or a community-oriented lifestyle, Portola Valley is a perfect place to call home. Discover the allure of this hidden gem in California, where nature and community come together harmoniously.

Newest Listings in Portola Valley

$20,000,000

5 Beds ⋅ 10 Baths ⋅ ML82054797 MLS

Extraordinary custom estate built by RJ Dailey Construction in 2018 and designed by CJW Architecture on more than 4 acres 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 built in 2021 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

$5,988,000

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

$15,495,000

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

$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

$3,750,000

4 Beds ⋅ 4 Baths ⋅ ML82051067 MLS

Perched on an elevated corner lot, this spacious contemporary residence is filled with natural light and showcases marvelous Bay views. Skylights and oversized windows illuminate the dramatic two-story entry foyer, creating a bright and airy atmosphere that enhances the home's open-concept design. Expansive views serve as a stunning backdrop to the living room, primary suite, and wraparound outdoor decks, seamlessly blending indoor and outdoor living. The thoughtfully designed kitchen, complete with an informal eating area, opens to both the family room and formal dining room, offering an ideal layout for everyday living and effortless entertaining. The flexible floor plan provides excellent separation of space. Two bedrooms on the main level share a hall bathroom, while upstairs, the luxurious primary suite serves as a private sanctuary. Connected by an elevated walkway, it is thoughtfully separated from the guest suite and dedicated office area. Move-in ready and located in a highly sought-after community with access to the excellent Las Lomitas School District, the Ladera Recreation Center, the Ladera Country Shopping Center, and Stanford University all in close proximity this home presents an outstanding lifestyle opportunity!

918 La Mesa DR, Portola Valley

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

$6,850,000

5 Beds ⋅ 5 Baths ⋅ ML82050920 MLS

Stunning new construction Craftsman residence in the sought-after Ladera neighborhood of Portola Valley. This home features a bright, open-concept floor plan with expansive living spaces that flow to the backyard through large stacking glass sliders and a covered patio for indoor-outdoor living. The chefs kitchen includes Wolf and Sub-Zero appliances, ceiling-height cabinetry, quartz countertops with full-height backsplash, a large waterfall-edge island, walk-in pantry, and butlers pantry with additional counter space, storage, sink, and second dishwasher. A private first-floor ADU offers flexibility for guests or multigenerational living. Upstairs, a loft provides additional living space alongside three secondary bedrooms and a laundry room with sink and storage. The primary suite features a large walk-in closet and spa-like bath with soaking tub and oversized walk-in shower. Located in the Ladera community near open space, parks, hiking and biking trails, and convenient access to Stanford, Sand Hill Road, and Highway 280. Buy early to enjoy preferred pricing and the opportunity to personalize finishes. Estimated completion is Q2 2027. *All imagery is illustrative and subject to change and does not depict the subject property.

670 La Mesa DR, Portola Valley

Listed by Nadine Masarweh, 925-270-6807 from Thomas James Real Estate Services, Inc,
(If provided) CoList: from

$3,888,000

4 Beds ⋅ 3 Baths ⋅ ML82049530 MLS

Welcome to 310 Old Spanish Trail in Portola Valley, a beautifully maintained custom home built in 2006 and lovingly cared for by its original owner. With gleaming floors, soaring ceilings, and expansive windows framing the natural landscape, the home feels remarkably fresh and almost brand new. Set in one of the Bay Area's most desirable communities, this property offers a rare combination of privacy, tranquility, and value. The scenic drive through Portola Valley's rolling hills leads to a setting that feels secluded, yet is minutes from restaurants, shops, and conveniences. Designed for modern living, every room is generously sized with high ceilings and abundant natural light. Expansive decks stretch across the rear of the home, creating seamless indoor/outdoor living with peaceful tree views. The decks connect directly to a high-end gourmet kitchen, making the home ideal for entertaining. The living, family, and dining rooms are stunning, featuring dramatic windows, beautiful finishes, and an exceptional open layout. In addition to four bedrooms, including a spacious primary suite, the home offers a dedicated office and a huge unfinished bonus room not included in the stated square footage (450 sq ft), providing excellent potential for expansion, recreation, or storage.

310 Old Spanish TRL, Portola Valley

Listed by Costantini Team, 650-430-8425 from Compass
(If provided) CoList: from

$4,288,000

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

$3,850,000

4 Beds ⋅ 5 Baths ⋅ ML82043726 MLS

Bay views and cutting-edge smart house design come together in this newly built retreat by the lake. Surrounded by nature, the contemporary home is on a quiet cul-de-sac, leading to acres of open space and hiking trails, The home is designed to embrace its setting with expansive windows, skylights, multiple outdoor spaces, and views stretching to the Bay. At the heart of the home is a light-filled, open-concept living space anchored by a striking chef's kitchen, complete with an oversized island, wet bar, wine fridge, and high-tech appliances. The kitchen flows seamlessly into generous living and entertaining areas, a potential home office, and out to expansive decks, creating an effortless connection between indoors and the surrounding landscape. The multi-level design offers flexibility, including a permitted attached ADU that could alternatively function as an auxiliary family room with second kitchen for guests, a media room or fitness space. Privately situated bedrooms provide peaceful retreats, while the primary suite and rooftop deck offer elevated views of the surrounding greenery to the Bay. State-of-the-art technology is integrated throughout, including Wi-Fi-enabled appliances, solar, Tesla Powerwall, and a dumbwaiter connecting the garage to the main level.

141 Lake RD, Portola Valley

Listed by Kavanaugh Group, 415-377-2924 from Coldwell Banker Realty
(If provided) CoList: from

$7,998,000

6 Beds ⋅ 6 Baths ⋅ ML82042439 MLS ⋅ Westridge Subdivision BLDG.

Rarely available estate, located in the highly sought-after Westridge neighborhood of Portola Valley. This lovely home is set on 3.86 serene acres w/ majestic oaks and offers a panoramic view of the SF Bay from Stanford to Mount Diablo. Enjoy a picturesque vista from the main home and newly built, stunning ADU. A gated driveway escorts you to a light-filled home highlighted by an open concept floorplan with high beamed ceilings and a wall of sliding doors to an expansive deck for al fresco dining and entertaining. Enjoy peaceful days and quiet nights filled with sparkling lights from the bay. The main home, containing 5bd/ 5ba, private office, family room and den one primarily one-story. The 1bd/1ba ADU has a spectacular deck with views too! Adding to the appeal is the sprawling grounds including a resort-like pool, hot tub, fire pit, gazebo, greenhouse, chicken coop and 2 fenced dog runs. Family/friends can gather throughout the exquisite property at numerous quaint outposts. This home is ideal for entertaining. Easy access to 280, Stanford University, Westridge hiking trails, shops and restaurants. Just 1.5 miles to the Ladera Shopping center, a 5-minute drive to Interstate 280, and access to top-ranked Portola Valley schools (buyer to verify eligibility)

138 Bolivar LN, Portola Valley

Listed by Stephanie Elkins, 650-400-2933 from Coldwell Banker Realty
(If provided) CoList: from

$499,000

ML82037840 MLS

Create your dream home on this spacious 25,878 sq/ft lot in Los Trancos Woods, Portola Valley. Slightly sloped lot with room to build a 4000+ sq/ft home. All utilities are available on the street as well as soil and engineering reports. Located just short drive to Alpine Hills Tennis and Swimming Club, Alpine Inn, Roberts Market, and award-winning Portola Valley schools. Views of Foothills Park and easy access to endless hiking, biking, and running trails.

145 Foxwood Road RD, Portola Valley

Listed by Josh Felder, 650-400-7142 from Redfin
(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 Fine Group Real Estate 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.