Alpine / Uplands (Los Trancos) Homes for Sale

Welcome to the enchanting neighborhood of Alpine/Uplands in Portola Valley, California, where nature meets luxury living. Nestled in the heart of San Mateo County, this picturesque area is known for its stunning landscapes, serene ambiance, and a strong sense of community. With its lush hillsides and sprawling oak trees, Alpine/Uplands offers an idyllic retreat just a stone's throw from the bustling energy of the Bay Area.

Residents here enjoy a tranquil lifestyle, surrounded by miles of hiking and biking trails, perfect for outdoor enthusiasts and families alike. The neighborhood boasts a rich tapestry of architectural styles, from charming cottages to sprawling estates, each home echoing the beauty of its natural surroundings. With homes for sale in this coveted area, you have the opportunity to become part of this vibrant community.

Alpine/Uplands is not just about stunning views and beautiful homes; it’s also about connection and convenience. The area is served by top-rated schools, ensuring that education is a priority for families. Additionally, the nearby Portola Valley Town Center offers a selection of local shops, cafes, and community events, fostering a warm and inviting atmosphere.

Whether you’re looking for a peaceful retreat or a place to raise a family, Alpine/Uplands has something to offer everyone. With homes for sale in this desirable neighborhood, now is the perfect time to discover your dream home in this enchanting corner of Portola Valley. Embrace the lifestyle you’ve always envisioned in Alpine/Uplands, where every day feels like a getaway.

Newest Alpine / Uplands (Los Trancos) Homes for Sale

$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

$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 Christie's International Real Estate Sereno 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.