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This thoughtfully reimagined Corte Madera gem in Portola Valley offers 4 bedrooms and 3 baths, is the result of a yearlong top-to-bottom transformation, including the roof, plumbing, windows, doors and HVAC system. Upon entry, the white oak floors lead into an open concept design centered on a two-tone kitchen of white and light oak cabinetry, fitted with Bosch and Zline appliances and a Samsung Smart Refrigerator adjoined by a separate family area. A new LG washer and dryer add everyday convenience. Two en-suite bedrooms include the primary suite, distinguished by an oversized walk-in closet and an expansive, spa-inspired bath with a soaking tub, dual vanity and glass enclosed rainfall walk-in shower. The beautifully landscaped, terraced grounds offer an upper-tier deck with wooded hillside views and a stone patio on a private expansive large lot. Just moments from the neighborhood Roberts Market, the home sits within a top-rated school district including Ormondale & Corte Madera and is close to Windy Hill Open Space Preserve. With easy access to Alpine Road and Highway 280, this private and nature-filled retreat offers a prime central location in the heart of Silicon Valley, while keeping Palo Alto and Stanford effortlessly within reach.

4 Beds ⋅ 3 Baths ⋅ ML82066310 MLS

This thoughtfully reimagined Corte Madera gem in Portola Valley offers 4 bedrooms and 3 baths, is the result of a yearlong top-to-bottom transformation, including the roof, plumbing, windows, doors and HVAC system. Upon entry, the white oak floors lead into an open concept design centered on a two-tone kitchen of white and light oak cabinetry, fitted with Bosch and Zline appliances and a Samsung Smart Refrigerator adjoined by a separate family area. A new LG washer and dryer add everyday convenience. Two en-suite bedrooms include the primary suite, distinguished by an oversized walk-in closet and an expansive, spa-inspired bath with a soaking tub, dual vanity and glass enclosed rainfall walk-in shower. The beautifully landscaped, terraced grounds offer an upper-tier deck with wooded hillside views and a stone patio on a private expansive large lot. Just moments from the neighborhood Roberts Market, the home sits within a top-rated school district including Ormondale & Corte Madera and is close to Windy Hill Open Space Preserve. With easy access to Alpine Road and Highway 280, this private and nature-filled retreat offers a prime central location in the heart of Silicon Valley, while keeping Palo Alto and Stanford effortlessly within reach.

220 Canyon Drive, Portola Valley

Listing courtesy of Greg Stange from Compass. 650-208-5196

$3,150,000

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 Trail, Portola Valley

Listing courtesy of from Coldwell Banker Realty. 415-377-2924

$3,999,999

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 Road, Portola Valley

Listing courtesy of from KW Advisors. 650-627-3700

$6,895,000

Stunning new construction 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 Q3 2027. *All imagery is illustrative and subject to change and does not depict the subject property."

5 Beds ⋅ 5 Baths ⋅ ML82063753 MLS

Stunning new construction 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 Q3 2027. *All imagery is illustrative and subject to change and does not depict the subject property."

670 La Mesa Drive, Portola Valley

Listing courtesy of Nadine Masarweh from Thomas James Real Estate Services, Inc,. 925-270-6807

$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 Trail, Portola Valley

Listing courtesy of Erika Demma from Compass. 650-740-2970

$7,995,000

Set across more than 2.5 mostly level acres, this exceptional Portola Valley estate offers a rare sense of scale, privacy, and versatility. At the heart of the property is a beautifully designed single-level residence, complemented by a 600 sq. ft. one-bedroom guest house that creates an ideal setting for extended family, visitors, work-from-home living, or a private retreat. Western views, expansive grounds, and glowing sunsets give the property an unmistakable sense of place. The property includes approximately 4,765 total sq. ft., comprised of: Main Residence: 3,425 sq. ft. Guest House: 600 sq. ft. Detached Three-Car Garage: 740 sq. ft. The four-bedroom, three-bath main residence is designed entirely on one level, with bright, inviting interiors and an effortless connection between everyday living and entertaining. An elegant foyer opens to a generous living room and well-equipped kitchen, while abundant natural light creates a calm, welcoming atmosphere throughout. With 4,025 sq. ft. of combined living space, a separate guest house, extensive parking and storage, and a coveted setting near acclaimed Portola Valley schools, the property offers a distinctive combination of privacy, flexibility, and refined indoor-outdoor living.

5 Beds ⋅ 4 Baths ⋅ ML82060701 MLS

Set across more than 2.5 mostly level acres, this exceptional Portola Valley estate offers a rare sense of scale, privacy, and versatility. At the heart of the property is a beautifully designed single-level residence, complemented by a 600 sq. ft. one-bedroom guest house that creates an ideal setting for extended family, visitors, work-from-home living, or a private retreat. Western views, expansive grounds, and glowing sunsets give the property an unmistakable sense of place. The property includes approximately 4,765 total sq. ft., comprised of: Main Residence: 3,425 sq. ft. Guest House: 600 sq. ft. Detached Three-Car Garage: 740 sq. ft. The four-bedroom, three-bath main residence is designed entirely on one level, with bright, inviting interiors and an effortless connection between everyday living and entertaining. An elegant foyer opens to a generous living room and well-equipped kitchen, while abundant natural light creates a calm, welcoming atmosphere throughout. With 4,025 sq. ft. of combined living space, a separate guest house, extensive parking and storage, and a coveted setting near acclaimed Portola Valley schools, the property offers a distinctive combination of privacy, flexibility, and refined indoor-outdoor living.

1080 Westridge Drive, Portola Valley

Listing courtesy of Josh Rubin from Compass. 650-575-5981

$3,495,000

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.

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 Avenue, Portola Valley

Listing courtesy of Carrie Davis from Coldwell Banker Realty. 650-269-4768

$5,488,000

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).

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 Road, Portola Valley

Listing courtesy of from Deleon Realty. 650-543-8500

$4,999,000

Build your dream home on this approx. 4.2-acre undeveloped country parcel situated adjacent to Portola Valley on Santa Clara County land just up from the Ladera Shopping Center shops and restaurants. The lot is surrounded by open space, Stanford lands and the gently flowing Los Trancos Creek and is in the Palo Alto Unified School District.

6 Beds ⋅ 6 Baths ⋅ ML81981087 MLS

Build your dream home on this approx. 4.2-acre undeveloped country parcel situated adjacent to Portola Valley on Santa Clara County land just up from the Ladera Shopping Center shops and restaurants. The lot is surrounded by open space, Stanford lands and the gently flowing Los Trancos Creek and is in the Palo Alto Unified School District.

3343 Alpine Road, Portola Valley

Listing courtesy of David Cauchi from Compass. 415-203-5726

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