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Tucked away on one of Laderas most desirable cul-de-sacs, this delightful classic ranch home offers timeless charm, comfortable living, and a wonderful connection to the outdoors. Filled with natural light, the inviting interior features gleaming hardwood floors, a spacious living room with a wall of windows, and filtered views of the Stanford Hills. The updated eat-in kitchen combines style and functionality with custom cabinetry, and abundant storage. Three generously sized bedrooms provide comfortable retreats, including a spacious primary suite with an updated bathroom featuring a contemporary design and walk-in shower. Set on a private, sunny 8,800-square-foot tiered lot, the grounds feature fruit trees and inviting outdoor spaces with plenty of room for entertaining, gardening, or play. Whether enjoying a quiet morning in the sunshine or gathering with family and friends, this special property offers a relaxed California lifestyle. Ideally located near the Ladera Shopper and Ladera Rec. It's also close to Stanford University, major commute routes, and many Silicon Valley employers. Situated between San Francisco and San Jose International Airports, this charming home combines a peaceful neighborhood setting with everyday convenience.

3 Beds ⋅ 2 Baths ⋅ ML82064337 MLS ⋅ Ladera BLDG.

Tucked away on one of Laderas most desirable cul-de-sacs, this delightful classic ranch home offers timeless charm, comfortable living, and a wonderful connection to the outdoors. Filled with natural light, the inviting interior features gleaming hardwood floors, a spacious living room with a wall of windows, and filtered views of the Stanford Hills. The updated eat-in kitchen combines style and functionality with custom cabinetry, and abundant storage. Three generously sized bedrooms provide comfortable retreats, including a spacious primary suite with an updated bathroom featuring a contemporary design and walk-in shower. Set on a private, sunny 8,800-square-foot tiered lot, the grounds feature fruit trees and inviting outdoor spaces with plenty of room for entertaining, gardening, or play. Whether enjoying a quiet morning in the sunshine or gathering with family and friends, this special property offers a relaxed California lifestyle. Ideally located near the Ladera Shopper and Ladera Rec. It's also close to Stanford University, major commute routes, and many Silicon Valley employers. Situated between San Francisco and San Jose International Airports, this charming home combines a peaceful neighborhood setting with everyday convenience.

251 Dedalera DR, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

$4,995,000

Perched along the western ridge of prestigious Portola Valley Ranch, this exceptional residence captures breathtaking views of Windy Hill, rolling hillsides, and spectacular sunsets. Soaring ceilings, dramatic walls of glass, abundant skylights, and expansive view decks create a seamless connection between indoor and outdoor living. The thoughtfully designed main level features gracious living and dining rooms opening to view decks, a skylit kitchen with granite island, and a spacious primary suite showcasing panoramic ridge views. A dedicated office and second bedroom with private deck and adjacent full bath complete the main level. Downstairs, a generous family/media room with custom built-ins, two additional bedrooms, guest bath, and access to the lower deck provide exceptional versatility. Set amid 453 acres of natural beauty, the Portola Valley Ranch offers miles of scenic trails, swimming pools, tennis courts, fitness center, clubhouse, community garden, orchard, vineyard and dog park. Ideally located near top Portola Valley schools, Woodside Priory, Robert's Market, Ladera Shopping Center, Alpine Hills and Ladera Oaks swim and tennis clubs, and Stanford. An extraordinary opportunity to enjoy spectacular views, natural tranquility, and the coveted Portola Valley lifestyle.

4 Beds ⋅ 3 Baths ⋅ ML82064258 MLS ⋅ Portola Valley Ranch BLDG.

Perched along the western ridge of prestigious Portola Valley Ranch, this exceptional residence captures breathtaking views of Windy Hill, rolling hillsides, and spectacular sunsets. Soaring ceilings, dramatic walls of glass, abundant skylights, and expansive view decks create a seamless connection between indoor and outdoor living. The thoughtfully designed main level features gracious living and dining rooms opening to view decks, a skylit kitchen with granite island, and a spacious primary suite showcasing panoramic ridge views. A dedicated office and second bedroom with private deck and adjacent full bath complete the main level. Downstairs, a generous family/media room with custom built-ins, two additional bedrooms, guest bath, and access to the lower deck provide exceptional versatility. Set amid 453 acres of natural beauty, the Portola Valley Ranch offers miles of scenic trails, swimming pools, tennis courts, fitness center, clubhouse, community garden, orchard, vineyard and dog park. Ideally located near top Portola Valley schools, Woodside Priory, Robert's Market, Ladera Shopping Center, Alpine Hills and Ladera Oaks swim and tennis clubs, and Stanford. An extraordinary opportunity to enjoy spectacular views, natural tranquility, and the coveted Portola Valley lifestyle.

12 Hawkview ST, Portola Valley

Listed by Shelly Roberson, 650-464-3797 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

$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 DR, Portola Valley

Listed by Nadine Masarweh, 925-270-6807 from Thomas James Real Estate Services, Inc,
(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

$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 DR, Portola Valley

Listed by Josh Rubin, 650-575-5981 from Compass
(If provided) CoList: from

$3,398,000

45 Bear Paw offers a rare opportunity to own an updated, single-level home just steps from the entry to Portola Valley Ranch. A 2 car garage with ample storage connects to the main level via interior elevator for easy, step-free access. Large windows frame the gracious living room, where soaring ceilings, designer chandeliers, and an attractive marble fireplace surround create a serene, light-filled space. Striking bar with custom glass shelving, wine fridge and floral wallpaper. Spacious kitchen offers handsome wood cabinetry, and recently updated counters and backsplash. Three generous bedrooms and two beautifully updated bathrooms are grouped together in bedroom wing. The primary suite enjoys its own peaceful views of Windy Hill, updated bath with roll-in shower, walk-in closet, and its own 100-sq.-ft. deck. Living space extends outdoors with a substantial patio and a 216-sq.-ft. attached sunroom. The Ranch is an extraordinary place to call home-- a 6 minute drive to the Ladera County Shopper and 8 minutes to Highway 280, yet offering a remote, resort-like feel with exceptional community amenities including heated pools, tennis courts, a fitness center, a community vineyard, gardens, and miles of hiking trails. Excellent Portola Valley schools. Roof recently replaced.

3 Beds ⋅ 2 Baths ⋅ ML82060118 MLS ⋅ Portola Valley Ranch BLDG.

45 Bear Paw offers a rare opportunity to own an updated, single-level home just steps from the entry to Portola Valley Ranch. A 2 car garage with ample storage connects to the main level via interior elevator for easy, step-free access. Large windows frame the gracious living room, where soaring ceilings, designer chandeliers, and an attractive marble fireplace surround create a serene, light-filled space. Striking bar with custom glass shelving, wine fridge and floral wallpaper. Spacious kitchen offers handsome wood cabinetry, and recently updated counters and backsplash. Three generous bedrooms and two beautifully updated bathrooms are grouped together in bedroom wing. The primary suite enjoys its own peaceful views of Windy Hill, updated bath with roll-in shower, walk-in closet, and its own 100-sq.-ft. deck. Living space extends outdoors with a substantial patio and a 216-sq.-ft. attached sunroom. The Ranch is an extraordinary place to call home-- a 6 minute drive to the Ladera County Shopper and 8 minutes to Highway 280, yet offering a remote, resort-like feel with exceptional community amenities including heated pools, tennis courts, a fitness center, a community vineyard, gardens, and miles of hiking trails. Excellent Portola Valley schools. Roof recently replaced.

45 Bear Paw, Portola Valley

Listed by Lynn Wilson Roberts, 650-255-6987 from Compass
(If provided) CoList: Annie Roberts from Compass

$6,750,000

Located in the highly desirable Westridge neighborhood, this impressive 2.62+/- acre property offers views, room for expansion, a vineyard, a separate ADU, and a freshly updated home with 4 bedrooms and 3 remodeled baths. The kitchen has new appliances and flows into a family living space. The large dining area sets the stage for entertaining. The Primary Suite has a tall, beamed ceiling, 3 closets and a deck that overlooks the property and Windy Hill views. Additional bedrooms enjoy a private wing that centers around a flexible space. This space is served by a separate entrance for flexibility. A lower level is a blank slate. It has a workshop, lots of storage, 2 rooms with sliding glass doors, a large well-lit space thats ideal as a game room or exercise center and a full bath. Potential for a wine cellar. The ADU is 1 bed, 1 bath and has an open living/dining/kitchenette space, as well as a private deck and entrance. There is a small upper pasture and a large area at the front of the property that could be used for horses, a pool, or possibly a tennis court. Central Portola Valley location, convenient to shopping, Alpine Hills Tennis and Swim Club, The Alpine Inn, excellent PV schools and easy commute routes.

4 Beds ⋅ 3 Baths ⋅ ML82058982 MLS

Located in the highly desirable Westridge neighborhood, this impressive 2.62+/- acre property offers views, room for expansion, a vineyard, a separate ADU, and a freshly updated home with 4 bedrooms and 3 remodeled baths. The kitchen has new appliances and flows into a family living space. The large dining area sets the stage for entertaining. The Primary Suite has a tall, beamed ceiling, 3 closets and a deck that overlooks the property and Windy Hill views. Additional bedrooms enjoy a private wing that centers around a flexible space. This space is served by a separate entrance for flexibility. A lower level is a blank slate. It has a workshop, lots of storage, 2 rooms with sliding glass doors, a large well-lit space thats ideal as a game room or exercise center and a full bath. Potential for a wine cellar. The ADU is 1 bed, 1 bath and has an open living/dining/kitchenette space, as well as a private deck and entrance. There is a small upper pasture and a large area at the front of the property that could be used for horses, a pool, or possibly a tennis court. Central Portola Valley location, convenient to shopping, Alpine Hills Tennis and Swim Club, The Alpine Inn, excellent PV schools and easy commute routes.

15 Naranja WAY, Portola Valley

Listed by Peter Cowperthwaite, 650-207-4101 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$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 AVE, Portola Valley

Listed by Carrie Davis, 650-269-4768 from Coldwell Banker Realty
(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

$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 RD, Portola Valley

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(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

$3,850,000

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.

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

$7,495,000

On the market for the first time, this exceptional Craftsman home is located in prestigious Blue Oaks, an enclave of estate homes surrounded by 285 acres of open space & trails. Built by Chessler Construction in 2003, the home showcases timeless architecture, exquisite woodwork, & a flexible multi-level floor plan designed for today's lifestyle. Set on approx. 1.29 acres, the property enjoys a backdrop of natural beauty with miles of nearby hiking trails, plus sweeping views out to the San Francisco Bay & East Bay hills from the top level. Main level is ideal for both grand entertaining & comfortable everyday living, offering formal venues, professional office, & seamless connection to expansive outdoor spaces that include front & rear terraces, loggia with fireplace, plus an in-ground spa & outdoor shower. Primary suite has Bay views & each bedroom has private balconies & elegantly appointed bathrooms. Finishing touches include an attached 4-car garage, backup generator, & a community pool & clubhouse. Blue Oaks location offers quick access to Portola Valley's charming town center & excellent public & privates schools, with Stanford University just 15 minutes away. Acreage & open space provide unmatched lifestyle in one of the area's most sought-after neighborhoods.

5 Beds ⋅ 8 Baths ⋅ ML82036782 MLS ⋅ Blue Oaks BLDG.

On the market for the first time, this exceptional Craftsman home is located in prestigious Blue Oaks, an enclave of estate homes surrounded by 285 acres of open space & trails. Built by Chessler Construction in 2003, the home showcases timeless architecture, exquisite woodwork, & a flexible multi-level floor plan designed for today's lifestyle. Set on approx. 1.29 acres, the property enjoys a backdrop of natural beauty with miles of nearby hiking trails, plus sweeping views out to the San Francisco Bay & East Bay hills from the top level. Main level is ideal for both grand entertaining & comfortable everyday living, offering formal venues, professional office, & seamless connection to expansive outdoor spaces that include front & rear terraces, loggia with fireplace, plus an in-ground spa & outdoor shower. Primary suite has Bay views & each bedroom has private balconies & elegantly appointed bathrooms. Finishing touches include an attached 4-car garage, backup generator, & a community pool & clubhouse. Blue Oaks location offers quick access to Portola Valley's charming town center & excellent public & privates schools, with Stanford University just 15 minutes away. Acreage & open space provide unmatched lifestyle in one of the area's most sought-after neighborhoods.

1 Redberry RDG, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

$8,748,000

Perched on a knolltop within prestigious Blue Oaks, this luxurious estate epitomizes elegance and exclusivity. Set on 2.53 acres of naturally organic beauty, this residence offers unparalleled privacy and breathtaking views of the San Francisco Bay. A true sanctuary, the home seamlessly blends sophisticated design with the tranquility of its natural surroundings. The expansive living room, bathed in natural light from floor-to-ceiling windows, provides a stunning backdrop of the sweeping Bay views. The heart of the home is the gourmet kitchen, a culinary enthusiast's dream, that opens to a spacious family room, creating a true great room that is ideal for both everyday living and entertaining. Multiple adjacent terraces offer 360-degree views. Each of the 5 bedrooms is an en suite retreat. The primary suite offers a luxurious spa-like bath, walk-in closet, fireplace and picture windows that capture the serene vistas. In addition to an executive home office, the estate boasts a home gym, media/rec room, wine cellar, expansive swimming pool and 4-car garage. This estate in Blue Oaks is more than a home; it is a lifestyle. With its unmatched privacy, luxurious amenities and awe-inspiring views, it offers a unique opportunity to experience the pinnacle of Silicon Valley living.

5 Beds ⋅ 8 Baths ⋅ ML82034238 MLS ⋅ Blue Oaks BLDG.

Perched on a knolltop within prestigious Blue Oaks, this luxurious estate epitomizes elegance and exclusivity. Set on 2.53 acres of naturally organic beauty, this residence offers unparalleled privacy and breathtaking views of the San Francisco Bay. A true sanctuary, the home seamlessly blends sophisticated design with the tranquility of its natural surroundings. The expansive living room, bathed in natural light from floor-to-ceiling windows, provides a stunning backdrop of the sweeping Bay views. The heart of the home is the gourmet kitchen, a culinary enthusiast's dream, that opens to a spacious family room, creating a true great room that is ideal for both everyday living and entertaining. Multiple adjacent terraces offer 360-degree views. Each of the 5 bedrooms is an en suite retreat. The primary suite offers a luxurious spa-like bath, walk-in closet, fireplace and picture windows that capture the serene vistas. In addition to an executive home office, the estate boasts a home gym, media/rec room, wine cellar, expansive swimming pool and 4-car garage. This estate in Blue Oaks is more than a home; it is a lifestyle. With its unmatched privacy, luxurious amenities and awe-inspiring views, it offers a unique opportunity to experience the pinnacle of Silicon Valley living.

7 Redberry RDG, Portola Valley

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: from

$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 RD, Portola Valley

Listed by David Cauchi, 415-203-5726 from Compass
(If provided) CoList: from

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