Alpine / Uplands (Los Trancos) Real Estate

Welcome to the enchanting neighborhood of Alpine/Uplands, nestled within the serene beauty of Portola Valley, California. This hidden gem in San Mateo County offers a harmonious blend of natural splendor and a close-knit community, making it an ideal place for families, professionals, and nature enthusiasts alike.

Alpine/Uplands is characterized by its picturesque landscapes, featuring rolling hills, lush greenery, and an abundance of mature trees that create a tranquil atmosphere. Residents enjoy breathtaking views of the surrounding Santa Cruz Mountains, with ample opportunities for outdoor activities such as hiking, biking, and horseback riding. The nearby Los Trancos Open Space Preserve provides expansive trails and scenic vistas, inviting you to explore the great outdoors right at your doorstep.

The neighborhood is renowned for its luxurious homes, many of which are custom-built to take full advantage of the stunning surroundings. With spacious lots and a variety of architectural styles, Alpine/Uplands offers a unique blend of privacy and elegance. Families appreciate the top-rated Portola Valley School District, known for its commitment to academic excellence and nurturing environment.

Community spirit thrives here, with regular neighborhood events and gatherings that foster connections among residents. Whether you’re enjoying a leisurely afternoon at one of the local parks or participating in community activities, you’ll find that Alpine/Uplands is not just a place to live but a place to belong.

Experience the charm and tranquility of Alpine/Uplands, where nature meets community, and make it your new home in Portola Valley. Your dream lifestyle awaits!

Newest Listings in Alpine / Uplands (Los Trancos)

$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

$3,888,000

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

$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

$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

$499,888

BE41121971 MLS

A RARE FINDING VACANT LAND IN BEAUTIFUL OLD SPANISH TRAIL OF PORTOLA VALLEY!

00 Vista Verde, Portola

Listed by Jenny Yang, (510) 585-7009 from Compass
(If provided) CoList: from

$1,800,000

3 Beds ⋅ 2 Baths ⋅ ML82024365 MLS

Discover the perfect blend of nature and modern convenience at 1019 Los Trancos Road in the peaceful Los Trancos Woods neighborhood. This charming home, built in 1930, offers 1,770 SF of versatile living space (per the Seller) in two buildings with freshly painted exteriors. The 1,225 SF main house features three bedrooms and two baths, with vaulted ceilings and skylights that invite abundant natural light. The airy living room, featuring exposed beams, seamlessly transitions to a large deck and patio, ideal for indoor-outdoor entertainment. The galley kitchen is a chef's delight, featuring stainless steel appliances and ample cabinetry that overlooks the garden. A 545 SF studio is situated behind the one-car garage. While not reflected in the County records, the studio is a flexible space with a kitchen, stacked washer/dryer, full bathroom, new wall-to-wall carpeting, and a private deck - ideal for multi-generational living, working from home, or generating rental income. Positioned on a generous 9,360 SF parcel, you'll enjoy peaceful views and easy access to Portola Valley's lively Town Center and Highway 280 for easy commuting.

1019 Los Trancos RD, Portola Valley

Listed by Robert Parish, 650-400-1011 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 COMPASS 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.