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Portola Valley
$11,500,000
ML82062842 MLS ⋅ Active Status
Spanning an exceptionally rare 5.239 flat acres, this remarkable property offers an unrivaled combination of privacy & convenience in one of the Peninsula's most desirable locations. Large, level parcels of this scale are virtually impossible to find, particularly in such a central setting with effortless access to Palo Alto, Menlo Park, Stanford & leading tech campuses. The property enjoys a breathtaking pastoral setting framed by gently rolling hills & bordered by the tranquil waters of Los Trancos Creek. Unlike many large estates on the Peninsula, this exceptional property is reached without navigating winding hillside roads. Comprising two APNs of approximately 4 & 1.239 acres, the estate presents unparalleled flexibility for creating a legacy family compound. Preliminary design concepts by a renowned architect envision a spectacular estate 20,000+ sqft. Geographically located in Portola Valley, the property falls under Santa Clara County planning & building jurisdiction & benefits from acclaimed Palo Alto schools. Offering unmatched scale, a rare flat topography, extraordinary privacy, pastoral beauty & one of the Peninsula's most coveted locations, this is a remarkable canvas upon which to create a world-class estate that will be enjoyed for generations to come.

Portola Valley
5759 Los Trancos Woods Road, Portola Valley
$11,500,000
ML82062838 MLS ⋅ Active Status
Spanning an exceptionally rare 5.239 flat acres, this remarkable property offers an unrivaled combination of privacy & convenience in one of the Peninsula's most desirable locations. Large, level parcels of this scale are virtually impossible to find, particularly in such a central setting with effortless access to Palo Alto, Menlo Park, Stanford & leading tech campuses. The property enjoys a breathtaking pastoral setting framed by gently rolling hills & bordered by the tranquil waters of Los Trancos Creek. Unlike many large estates on the Peninsula, this exceptional property is reached without navigating winding hillside roads. Comprising two APNs of approximately 4 & 1.239 acres, the estate presents unparalleled flexibility for creating a legacy family compound. Preliminary design concepts by a renowned architect envision a spectacular estate 20,000+ sqft. Geographically located in Portola Valley, the property falls under Santa Clara County planning & building jurisdiction & benefits from acclaimed Palo Alto schools. Offering unmatched scale, a rare flat topography, extraordinary privacy, pastoral beauty & one of the Peninsula's most coveted locations, this is a remarkable canvas upon which to create a world-class estate that will be enjoyed for generations to come.

5759 Los Trancos Woods Road, Portola Valley
7 Redberry, Portola Valley
$8,748,000
5 Beds ⋅ 8 Baths ⋅ ML82034238 MLS ⋅ Active Status ⋅ 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, Portola Valley
1080 Westridge Drive, Portola Valley
$7,995,000
5 Beds ⋅ 4 Baths ⋅ ML82060701 MLS ⋅ Active Status
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
1 Redberry, Portola Valley
$7,495,000
5 Beds ⋅ 8 Baths ⋅ ML82036782 MLS ⋅ Active Status ⋅ 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, Portola Valley
670 La Mesa Drive, Portola Valley
$6,895,000
5 Beds ⋅ 5 Baths ⋅ ML82063753 MLS ⋅ Active Status
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
15 Naranja Way, Portola Valley
$6,750,000
4 Beds ⋅ 3 Baths ⋅ ML82058982 MLS ⋅ Active Status
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
285 Escobar Road, Portola Valley
$5,488,000
5 Beds ⋅ 4 Baths ⋅ ML82052826 MLS ⋅ Active Status
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
10 Joaquin Road, Portola Valley
$4,999,999
5 Beds ⋅ 4 Baths ⋅ ML82060764 MLS ⋅ Active Status
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
3343 Alpine Road, Portola Valley
$4,999,000
ML81973676 MLS ⋅ Active Status
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
3343 Alpine Road, Portola Valley
$4,999,000
6 Beds ⋅ 6 Baths ⋅ ML81981087 MLS ⋅ Active Status
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
12 Hawkview Street, Portola Valley
$4,995,000
4 Beds ⋅ 3 Baths ⋅ ML82064258 MLS ⋅ Active Status ⋅ 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 Street, Portola Valley
220 Canyon Drive, Portola Valley
$3,648,000
4 Beds ⋅ 3 Baths ⋅ ML82061674 MLS ⋅ Active Status
Almost a year in the making, this whole-house renovation in Portola Valley's Corte Madera neighborhood is now complete, a 4-bedroom, 3-bath home rebuilt to the studs and finished with real craft. New roof, new plumbing, new HVAC with added air conditioning, new windows, and new interior and exterior doors resolve everything you can't see; wide-plank white oak floors, vaulted tray ceilings and new trim throughout address everything you can. The open, two-tone kitchen pairs crisp white upper cabinetry and floating oak shelving with light oak lower cabinets, all overlooking serene forest views. A full stainless steel appliance suite, anchored by a 36-inch range, completes the space. The primary suite pairs a walk-in closet with a freestanding soaking tub and a glass-enclosed rainfall shower; the two secondary baths both carry sage green tile and floating vanities. New landscaping paths, terracing and deck vantage points surround a flagstone patio that steps into a private, wooded lot of approximately 16,000 square feet with mature tree privacy. Nestled in nature yet moments from the neighborhood shopping center, top-rated Corte Madera Middle School and Ormondale Elementary, and Windy Hill Open Space Preserve, with Alpine Road providing a direct connection to Palo Alto and Stanford.

220 Canyon Drive, Portola Valley
176 Los Trancos Circle, Portola Valley
$3,500,000
ML82056611 MLS ⋅ Active Status
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 Circle, Portola Valley
176 Los Trancos Circle, Portola Valley
$3,500,000
4 Beds ⋅ 4 Baths ⋅ ML82056610 MLS ⋅ Active Status
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 Circle, Portola Valley
133 Russell Avenue, Portola Valley
$3,495,000
3 Beds ⋅ 3 Baths ⋅ ML82056981 MLS ⋅ Active Status
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
45 Bear Paw, Portola Valley
$3,398,000
3 Beds ⋅ 2 Baths ⋅ ML82060118 MLS ⋅ Active Status ⋅ 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
251 Dedalera Drive, Portola Valley
$2,950,000
3 Beds ⋅ 2 Baths ⋅ ML82064337 MLS ⋅ Active Status ⋅ 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 Drive, Portola Valley
245 Bonita Road, Portola Valley
$2,595,000
2 Beds ⋅ 1 Baths ⋅ ML82052857 MLS ⋅ Active Status
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 Road, Portola Valley
Alpine Road, Portola Valley
$1,988,000
5 Beds ⋅ 5 Baths ⋅ ML81936165 MLS ⋅ Active Status
Exceptional opportunity for a developer or end user to build on this flat .77 acre lot, out of the flood zone (LOMA issued) with preliminary plans, land survey, geotechnical report, contractor bids and etc in a tranquil setting assigned to award-winning Palo Alto schools. Property is on a quiet lane off of Alpine Road so there is no traffic (punch in 4133 Alpine Road in GPS, property is next door). Plans are for a 5 bed, 4.5 bath modern two-story residence, designed by renowned M Design Architects. Though it feels removed, this one of a kind property is moments away from the Alpine Hills Swim and Tennis Club, Ladera Country Shopper, Stanford University & Shopping Center and vibrant Menlo Park and Palo Alto, while children may attend top-ranked Palo Alto schools, including Nixon Elementary (#6 Elementary School in California), Fletcher Middle (#8 Middle School in California), and Gunn High (#1 High School in California).

Alpine Road, Portola Valley
76 Old Spanish Trail, Portola Valley
$1,649,000
2 Beds ⋅ 2 Baths ⋅ ML82063275 MLS ⋅ Active Status
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
145 Foxwood Road Road, Portola Valley
$499,000
ML82037840 MLS ⋅ Active Status
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 Road, Portola Valley

Based on information from California Regional Multiple Listing Service, Inc. as of . This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.

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