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Tucked away in the heart of the Vista Verde neighborhood, 205 Old Spanish Trail offers a rare sense of scale and connection to the landscape. Set on approximately 1.6 acres, this property feels like a private retreat, where the architecture serves as a front-row seat to the rolling hills and lush, wooded surroundings that make Portola Valley so iconic. The main residence features 4 bedrooms and 2 bathrooms designed with an emphasis on flow and natural light. High ceilings and large windows frame stunning bay views and greenery outside, while the expansive decks act as a true extension of the living space. Whether youre hosting a sunset dinner or enjoying a quiet morning above the treeline, these outdoor areas provide a breathtaking backdrop for everyday life. Complementing the main home is a separate 1-bedroom, 1-bathroom guest house. This versatile space is ideal for visitors, a quiet home office, or a creative studio, offering a level of flexibility that is hard to find. Surrounded by mature trees and crisp air, the property feels worlds away while remaining deeply connected to the Peninsulas most sought-after amenities. It is a home that celebrates its environment, offering a lifestyle defined by space, serenity, and the timeless beauty of the California woods.

4 Beds ⋅ 2 Baths ⋅ ML82065541 MLS

Tucked away in the heart of the Vista Verde neighborhood, 205 Old Spanish Trail offers a rare sense of scale and connection to the landscape. Set on approximately 1.6 acres, this property feels like a private retreat, where the architecture serves as a front-row seat to the rolling hills and lush, wooded surroundings that make Portola Valley so iconic. The main residence features 4 bedrooms and 2 bathrooms designed with an emphasis on flow and natural light. High ceilings and large windows frame stunning bay views and greenery outside, while the expansive decks act as a true extension of the living space. Whether youre hosting a sunset dinner or enjoying a quiet morning above the treeline, these outdoor areas provide a breathtaking backdrop for everyday life. Complementing the main home is a separate 1-bedroom, 1-bathroom guest house. This versatile space is ideal for visitors, a quiet home office, or a creative studio, offering a level of flexibility that is hard to find. Surrounded by mature trees and crisp air, the property feels worlds away while remaining deeply connected to the Peninsulas most sought-after amenities. It is a home that celebrates its environment, offering a lifestyle defined by space, serenity, and the timeless beauty of the California woods.

205 Old Spanish TRL, Portola Valley

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

$799,000

Discover a rare opportunity in Portola Valleys highly sought-after Los Trancos neighborhood. Spanning a picturesque one-acre lot, this premier property offers sweeping views of the surrounding greenbelt, canyon, valley, and, on a clear day, the iconic San Francisco skyline. As one of the few remaining parcels in the area, the listing includes seller-provided plans for a sleek, contemporary modular home designed by renowned architect Daniel Piechota, recently featured in the Wall Street Journal. Echoing design elements from Piechotas celebrated $9 million Carmel residence, the architectural vision showcases expansive walls of glass that seamlessly frame the surrounding natural beauty. According to the seller, the modular plans have already received approval from the State of California, with site and foundation plans fully complete and ready for submission to the county. Whether you choose to capitalize on these stunning, high-end plans to save significant design and planning time, or decide to craft a custom vision from the ground up, this extraordinary property provides the ultimate foundation for your dream California retreat.

ML82065204 MLS

Discover a rare opportunity in Portola Valleys highly sought-after Los Trancos neighborhood. Spanning a picturesque one-acre lot, this premier property offers sweeping views of the surrounding greenbelt, canyon, valley, and, on a clear day, the iconic San Francisco skyline. As one of the few remaining parcels in the area, the listing includes seller-provided plans for a sleek, contemporary modular home designed by renowned architect Daniel Piechota, recently featured in the Wall Street Journal. Echoing design elements from Piechotas celebrated $9 million Carmel residence, the architectural vision showcases expansive walls of glass that seamlessly frame the surrounding natural beauty. According to the seller, the modular plans have already received approval from the State of California, with site and foundation plans fully complete and ready for submission to the county. Whether you choose to capitalize on these stunning, high-end plans to save significant design and planning time, or decide to craft a custom vision from the ground up, this extraordinary property provides the ultimate foundation for your dream California retreat.

Vista Verde WAY, Portola Valley

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

$4,999,999

A rare expression of Old World Spanish architecture awaits on approximately 3.13 private acres in Portola Valley. Built in 1963, this distinctive adobe residence offers approximately 5,040 square feet, five bedrooms, and three-and-a-half baths, with a sense of character seldom encountered in Silicon Valley. Original architectural details, richly textured adobe and brickwork, and a Spanish tile roof evoke the warmth of a secluded Mediterranean retreat. Generous living and gathering spaces, a formal dining room, fireplaces, and an expansive upper-level wraparound deck create opportunities to enjoy the homes remarkable setting. Multiple patios overlook natural surroundings, while mature landscaping and generous grounds offer privacy, tranquility, and room to envision the next chapter. Preserved in largely original condition, the home invites a discerning buyer to celebrate its authentic craftsmanship or undertake a considered restoration. Located in the Portola Valley school district, this is a compelling opportunity to own a substantial estate property where land, architecture, and peaceful surroundings take center stage.

5 Beds ⋅ 4 Baths ⋅ ML82060764 MLS

A rare expression of Old World Spanish architecture awaits on approximately 3.13 private acres in Portola Valley. Built in 1963, this distinctive adobe residence offers approximately 5,040 square feet, five bedrooms, and three-and-a-half baths, with a sense of character seldom encountered in Silicon Valley. Original architectural details, richly textured adobe and brickwork, and a Spanish tile roof evoke the warmth of a secluded Mediterranean retreat. Generous living and gathering spaces, a formal dining room, fireplaces, and an expansive upper-level wraparound deck create opportunities to enjoy the homes remarkable setting. Multiple patios overlook natural surroundings, while mature landscaping and generous grounds offer privacy, tranquility, and room to envision the next chapter. Preserved in largely original condition, the home invites a discerning buyer to celebrate its authentic craftsmanship or undertake a considered restoration. Located in the Portola Valley school district, this is a compelling opportunity to own a substantial estate property where land, architecture, and peaceful surroundings take center stage.

10 Joaquin RD, Portola Valley

Listed by Wen Guo RE Group, 650-776-4085 from KW Advisors
(If provided) CoList: from

$1,649,000

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. Easy access to Sand Hill Road, Stanford, HWY 280 & more

2 Beds ⋅ 2 Baths ⋅ ML82063275 MLS

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. Easy access to Sand Hill Road, Stanford, HWY 280 & more

76 Old Spanish TRL, Portola Valley

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

$3,500,000

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.

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

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.

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

$2,595,000

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.

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

$499,000

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.

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

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

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

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