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56 Hillbrook DR, Portola Valley
$9,495,000
3 Beds ⋅ 4 Baths ⋅ ML82042340 MLS
A Hilltop Home Shaped by Light, Landscape and Contemporary Architecture-Designed as a sanctuary for the senses, this 4885 sq ft, 2007 contemporary masterpiece rises from the crest of central Portola Valley. the custom architecture was crafted to invite tranquility, framing soft, filtered views of the surrounding landscape . Here, the rare luxury of expansive, level grounds that breathes in rhythm with its hilltop surroundingsa true haven of quiet elegance. This home is a gem! On the main level, the 11-foot-ceilinged public rooms include a formal entry, a large living room that doubles as a media room with 3 walls of glass sliding doors opening to the gardens, a formal dining room designed to seat 12, a chefs kitchen that faces a secret garden, and a family room facing the rear gardens. An open-tread staircase lined with clear glass panels connects the upper, main, and lower levels of the home. On the lower level, there is a recreation room, a wine cellar, full bath and, across a stone patio, a fitness studio with walk-out access to the rear grounds. 2 bedrooms and 1.5 baths on the main level and an upper level devoted to the primary suite with a large private balcony and a spacious office, perfect for todays work-from-home needs. Detached studio guest house with full bath.

56 Hillbrook DR, Portola Valley

2316 Loma Prieta LN, Menlo Park
$8,950,000
6 Beds ⋅ 6 Baths ⋅ ML82040554 MLS
A newly built estate that represents the pinnacle of luxury craftsmanship, thoughtfully designed to capture modern living through expansive open spaces, panoramic outdoor views, and custom finishes throughout. Set on a 13,123 sq ft lot, this property offers 4,680 sq ft of total living space, including a 3,876 sq ft 4BD/4.5BA main residence and an 804 sq ft 2BD/1BA attached guest unit. A dramatic 20-foot entry creates a striking first impression, leading into a residence of monumental scale, characterized by soaring verticality and a floor plan that prioritizes sophisticated spatial harmony. The chef's kitchen anchors the main level, connecting to the family and dining areas for seamless entertaining. A main-level guest suite adds flexibility for visitors or a refined home office, while the attached guest unit provides added living space with its own laundry. Upstairs, the primary suite features a private balcony, spa-like bath, and walk-in closet. The upper level is completed by an additional en-suite bedroom, a third bedroom with nearby full bath, and a laundry room. Ideally situated in the prestigious Sharon Heights enclave of Menlo Park, offering effortless access to upscale shopping, Stanford, premier VC hubs, global tech HQs, and major international airports.

2316 Loma Prieta LN, Menlo Park

3215 Woodside RD, Woodside
$8,900,000
4 Beds ⋅ 3 Baths ⋅ ML82037417 MLS
First time on the market in generations, this rare Woodside property offers a unique opportunity to own a piece of local history. The Victorian home, originally built in 1901 and remodeled in 2010, has remained in the same family for decades and sits on a private 3.4 acre lot, offering potential to split the lot and build your dream home. The home features 4 bedrooms and 2.5 bathrooms, blending classic architectural character with thoughtful updates for comfortable living. The size and location of the property create a distinctive setting that is increasingly rare in Woodside. Ideally located next to Woodside Elementary and just minutes from Woodside Village, with convenient access to Roberts Market, The Village Bakery, Bucks Restaurant, and the Woodside Village Church. A special opportunity offering space, privacy, and historic charm in a highly desirable location.

3215 Woodside RD, Woodside

150 Brookwood RD, Woodside
$8,700,000
4 Beds ⋅ 5 Baths ⋅ ML82044880 MLS ⋅ Woodside Hills BLDG.
A rare opportunity to own an earthy modern estate set in the esteemed Woodside Hills with breathtaking sweeping Bay views. The residence was reimagined with uncompromising attention to detail, offering a truly like-new experience that has never been lived in. Situated on 0.98 acres, the 6,809 sq ft home blends dramatic scale with warm, livable sophistication for true California Living. The thoughtfully designed floor plan includes 4 well-appointed bedrooms, 4 designer bathrooms, 1 powder room, dedicated office, flex studio, media room, laundry/mud room, and luxurious rec room. The designer kitchen serves as both a functional showpiece and an entertainers dream, featuring open steel & beam vaulted ceiling, natural light, custom white oak cabinetry, top-of-the-line appliances, wet bar, pantry, temperature controlled wine cellar, and designer finishes. The grounds include a stunning chefs kitchen, fire pit lounge, abundance of areas to entertain, view decks, and a refreshing pool. Surrounded by other distinguished estates, 150 Brookwood Rd is an iconic offering, combining design-forward architecture, extraordinary views, exceptional outdoor living, and an unparalleled Woodside setting to create a one-of-a-kind luxury retreat. Buyer to verify.

150 Brookwood RD, Woodside

15 Boroughwood PL, Hillsborough
$8,700,000
6 Beds ⋅ 9 Baths ⋅ ML82039853 MLS
Perched on nearly two acres at the end of a quiet cul-de-sac in Hillsborough's sought-after Carolands neighborhood, this gated Mediterranean contemporary estate offers privacy, scale, and sweeping hill views. Remodeled in 1996 by a principal architect of Frank Lloyd Wright's company, the home showcases refined contemporary living with timeless architectural influence. Walls of glass, skylights, and French doors fill the interiors with natural light. A grand foyer with spiral staircase and chandelier sets the tone, opening to elegant living and dining rooms with fireplaces, hardwood floors, and view balconies. The showpiece is the expansive chef's kitchen, thoughtfully designed with COMMERCIAL-GRADE stainless steel appliances, custom cabinetry, and generous workspace. A striking breakfast bar with Wolf gas griddle anchors the space, while French doors open to a balcony, creating seamless indoor outdoor flow ideal for entertaining. The upper level features four en-suite bedrooms including a luxurious primary suite with fireplace, private balcony, dual walk-in closets, and spa-like bath. Lower level amenities include a wine cellar, bar, media area, indoor pool, and guest suite. Experience this exceptional estate in person and schedule your private tour today.

15 Boroughwood PL, Hillsborough

1 Larch DR, Atherton
$8,600,000
5 Beds ⋅ 4 Baths ⋅ ML82039652 MLS
Nestled on a private Lindenwood cul-de-sac, this ~0.92-acre Atherton estate offers an exceptional opportunity in one of the Peninsulas most coveted neighborhoods. The main residence offers 5 bedrooms and 4 bathrooms, including two versatile rooms ideal for offices, plus a spacious family room. Interiors feature soaring ceilings, expansive windows, and bright living areas. A permitted ~740 sq ft detached ADU provides a private 1-bedroom, 1-bath layout, ideal for guests or multigenerational living. Recently refreshed with crisp paint and refined flooring, the home is move-in ready while retaining timeless character. Whether for renovation or a bespoke luxury estate, the property is a rare blank canvas. The seller has engaged a designer for plans of a grand residence. Buyers may collaborate on a 6-bedroom, 6.5-bath main house with a 1-bedroom, 1-bath ADU, totaling over 11,600 sq ft. Concept highlights include a basement theater, golf simulator, wine cellar, open living spaces, a spa-inspired primary suite, and renderings showcasing pool and outdoor living. Minutes from downtown Menlo Park and Palo Alto, with top schools and easy access to 101 and 280, this is a rare chance to secure a premier Atherton estate.

1 Larch DR, Atherton

1780 Bay Laurel DR, Menlo Park
$8,557,000
4 Beds ⋅ 4 Baths ⋅ ML82060104 MLS
Rare single-level home on one of Menlo Park's most coveted tree-lined streets. Beautifully remodeled and expanded home. Four generous bedrooms, two full baths and two powder baths thoughtfully appointed throughout the home with an excellent floor plan. Great room with vaulted wood-beamed ceiling, brick fireplace, opens to patio through expansive sliders. Chef's kitchen includes Sub-Zero, Wolf, Cove appliances, Neolith counters, walnut bar, walk-in pantry. Custom cabinetry throughout. Office/craft room plus large, separate entertainment room with wet bar, dual wine fridges, French doors to garden. Primary suite with walk-in closet, Carrera marble bath, glass steam shower, standalone tub. High-end finishes throughout, including French oak floors, plantation shutters, Lutron lighting and blind controls, skylights, multi-zone radiant plus forced air heat. Outdoor kitchen with Wolf BBQ and bar seating, Connecticut bluestone patio, turf lawn, fire pit, mature landscaping. Owned solar, Tesla and Autel chargers, dual AC. Two Car Garage with epoxy floor, extensive shelving, cabinetry with stainless Steel countertop and barn wood ceiling, and shop sink. Walk to top-rated Menlo Park public schools and local private schools. Easy access to Stanford, Silicon Valley, downtown MP. A+ location!

1780 Bay Laurel DR, Menlo Park

160 Fawn LN, Portola Valley
$8,500,000
5 Beds ⋅ 6 Baths ⋅ ML82061161 MLS
Built in 2021, this single-level main residence just-over-one-acre in central Portola Valley. Generous gathering spaces include formal living & dining rooms plus an impressive chefs kitchen & extra-large family room. Gas-log fireplaces in living & family rooms, while oversized media screens, distributed sound speakers, surround sound with automated window blinds on clerestory windows & in bedrooms. Privately accessed studio with full bath above the garage offer exceptional flexibility. Spacious primary suite with private terrace, oversized customized closet, & luxurious bath with freestanding tub & large shower. Outdoor living unfolds across a vast rear deck with gas fire pit & built-in barbecue center, large spa, & an expansive synthetic lawn with volleyball net. Terraced grounds extend up the hillside with steps to a sitting area with sweeping views. Extensive amenities include recently added 8.1 kW Tesla solar system with two Powerwall batteries for backup power, Lutron programmable lighting system, dual-zone air conditioning, & Nest thermostats. Survey & architectural renderings are also available for a 650-square-foot ADU. This central Portola Valley setting is just minutes from renowned hiking, biking, & equestrian trails and has access to excellent Portola Valley schools.

160 Fawn LN, Portola Valley

120 Deer Meadow LN, Portola Valley
$8,400,000
5 Beds ⋅ 4 Baths ⋅ ML82042620 MLS
Expansive grounds and sweeping Windy Hill Views define this extraordinary property in a premier and private Golden Hills setting. Spanning approximately 2.6 acres the property unfolds with open meadows, magnificent oaks, a prolific orchard, and a newly resurfaced pool and spa. The home is spacious, flexible, bright and welcoming--one that is immediately comfortable and highly livable. The predominantly single-level floor plan, fully oriented to the spectacular views, with an upstairs primary suite, offers generous scale, abundant natural light, and a seamless connection to the surrounding landscape. The garden and the home create a magical place for exploration, imagination and outdoor play. At the same time, the property presents an exceptional long-term opportunity. The expansive acreage, extraordinary views, and quiet, coveted location provide an ideal foundation for further transformation whether through renovation or the creation of a dream home. The result is a property that offers both immediate enjoyment and significant potential in one of Portola Valley's most sought-after settings.

120 Deer Meadow LN, Portola Valley

200 Tobin Clark DR, Hillsborough
$8,300,000
6 Beds ⋅ 7 Baths ⋅ ML82039635 MLS
Panoramic Bay views take center stage in this extraordinary estate, w/ sweeping vistas from the SF skyline to the San Mateo Bridge & across the East Bay hills. Set on ~3.4 acres in prestigious Tobin Clark Estate, this property offers rare privacy, scale & presence. Built in 1981 by the areas original developer as his personal residence, it sits on one of the communitys most desirable sites. Spanning ~7,000 sq.ft., the home features grand living spaces, soaring ceilings & expansive windows framing the views throughout. A dramatic foyer w/ curved staircase leads to elegant living & entertaining areas. Spacious family rm w/ bar opens seamlessly to the grounds, while the kitchen w/ breakfast area captures natural light & scenic outlooks. Multiple bedroom suites + dedicated office, incl. a luxurious primary suite w/ fireplace, dual baths, dual walk-in closets & private view balcony. Resort-style grounds feature pool, full-size tennis court, lawns & covered patios. Gated circular drive w/ porte cochère leads to a 3-car garage, completing this rare Hillsborough legacy estate near Silicon Valley & SF.

200 Tobin Clark DR, Hillsborough

40 Montana LN, Menlo Park
$8,250,250
4 Beds ⋅ 3 Baths ⋅ ML82055595 MLS
Situated at the crown of the cul-de-sac, a majestic, storybook estate bordering Atherton in the heart of West Menlo Park. Truly exquisite, is this timeless Craftsman built in 2007 w/ an abundance of period details. Opulence begins at the front door, leading to a grand living room w/ soaring ceilings, overlooked by a second floor landing w/ custom built-in book shelves. A gourmet chef's eat-in kitchen awaits w/ soapstone countertops, custom cabinetry, stainless steel appliances w/ a 5-burner gas stove, a large custom island, & even an office. Impressive attention to detail throughout including French doors, wainscoting, crown moldings, baseboards, hardwood floors, a secured wine cellar, plus a see-through fireplace. All upstairs bedrooms are complimented w/ vaulted ceilings, including a sumptuous primary bedroom w/ suite w/ walk-in closet & closet organizer. Enjoy the spacious porch w/ built-in heaters & 2 different seating areas overlooking the lush landscaping w/ mature trees, water feature, & fire pit w/ built-in seating. Incredible location on one of the larger sprawling lots in the neighborhood close to award winning Las Lomitas Elementary School, & conveniently located near parks along w/ shops & eateries on Santa Cruz Avenue. Truly a special home, & not one to miss.

40 Montana LN, Menlo Park

820 Eucalyptus AVE, Hillsborough
$8,038,000
6 Beds ⋅ 4 Baths ⋅ ML82053844 MLS
Located in lower Hillsborough, this custom-made mid-century modern home blends timeless architecture with the effortless California lifestyle. Set behind mature landscaping and surrounded by exceptional privacy, this home is filled with natural light thanks to dramatic walls of glass that blur the line between indoors and out. Every main living space looks onto the backyard landscaping and private pool. The living room, dining room and family room all feature dramatic vaulted ceilings and fireplaces in each room. The flexible floor plan offers six bedrooms and four bathrooms, including a primary suite and various options for an office or work-out space. Rich hardwood floors extend throughout the home. This home captures everything people love about mid-century modern design: open spaces, incredible natural light, seamless indoor-outdoor living and an unmistakable sense of style. All this plus award-winning public schools and perfectly situated between Silicon Valley and San Francisco.

820 Eucalyptus AVE, Hillsborough

55 Mission Trail RD, Woodside
$8,000,000
4 Beds ⋅ 6 Baths ⋅ ML82060993 MLS
Privately positioned at the end of a gated country lane, this elegant French Country estate combines sweeping Western Hills and sunset views with the convenience of a prime Central Woodside location. Set on approximately 1.11 acres, the grounds feature expansive terraces, mature landscaping, and inviting spaces for indoor-outdoor living and entertaining. The main residence features four bedrooms, five-and-a-half bathrooms, a dedicated office/library, a main-level primary suite with an adjoining flexible-use room, and a recently updated chefs kitchen with a sunny breakfast area. Patterned oak floors, high ceilings, and abundant natural light create a warm, sophisticated atmosphere throughout. A detached one-bedroom, one-bath guest house with a full kitchen, fireplace, and high ceilings provides an ideal setting for guests, extended stays, or a private workspace. Just moments from Woodside Town Center, Woodside School, Interstate 280, Sand Hill Road, and Stanford University, this exceptional property offers a rare combination of privacy, usable acreage, inspiring views, and close-in convenience.

55 Mission Trail RD, Woodside

730 Hillsborough BLVD, Hillsborough
$8,000,000
5 Beds ⋅ 5 Baths ⋅ ML82036808 MLS
Situated in Lower North Hillsborough, this gated property encompasses approximately 30,348 square feet flat lot and represents a rare estate-caliber parcel for the discerning buyer. Mature landscaping, privacy, and abundant sun exposure define the setting, just moments from downtown San Mateo, Burlingame Avenues shopping and dining, and top-rated Hillsborough schools. The expansive grounds feature broad lawn areas, a sparkling pool and cabana, detached guest house, greenhouse, two-car garage, enclosed carport, and circular drive, creating a substantial footprint across the site. The existing residence, including a 1997 addition, is approximately 5,533 square feet, offers generous scale and presents an opportunity for significant renovation, reconfiguration, or potential redevelopment. See floor plans for details. Large, flat lot of this size are increasingly scarce in Lower North Hillsborough, providing the opportunity to create a customized estate in one of the Peninsulas most desirable neighborhoods with enduring long-term value.

730 Hillsborough BLVD, Hillsborough

16351 Skyline BLVD, Woodside
$8,000,000
6 Beds ⋅ 9 Baths ⋅ ML82034677 MLS
One of the most extraordinary properties on the SF Peninsula on 17 acres. The property has endless potential and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. 17 minutes to Woodside town center.

16351 Skyline BLVD, Woodside

335 El Portal AVE, Hillsborough
$7,895,000
5 Beds ⋅ 4 Baths ⋅ ML82041699 MLS
Regally set back on a lush +/-0.41-acre corner lot in coveted Lower South Hillsborough, this timeless Mediterranean estate blends classic architectural elegance with expansive living spaces and private, resort-like grounds - ideal for both effortless daily living and grand-scale entertaining. Boasting +/-4,235sf, the 5-bedroom, 3.5-bath home welcomes you with an elegant foyer that leads to an impressive living room with rich hardwood floors, a grand fireplace, and French doors opening to a vast rear patio. The formal dining room flows seamlessly into a stunning gourmet kitchen/family room ensemble with French doors leading to the verdant grounds. The main level includes a private guest bedroom or office with ensuite bath, a well-appointed laundry room, and elegant powder room. Upstairs, 3 sizeable bedrooms are complemented by a marble hall bath, while the lavish primary suite with multiple closets and spa-inspired bath awaits you. The resort-like grounds feature lush, mature landscaping, pool, fire pit, and sun-drenched patio with pergola. The lower level offers an attached garage, gym, & abundant storage space. Located near top-rated schools, downtown, and major commute routes, this classic estate offers a rare opportunity in one of Hillsborough's most prestigious neighborhoods.

335 El Portal AVE, Hillsborough

725 Evergreen ST, Menlo Park
$7,850,000
5 Beds ⋅ 5 Baths ⋅ ML82054807 MLS
Set on nearly a quarter acre in Central Menlo, this striking contemporary home blends modern farmhouse influence with clean architectural lines. Completed in 2023, the3,400+ SF single-level residence features soaring ceilings, exceptional natural light, and refined finishes including Taj Mahal and Bardiglio marble, oak floors, Poliform cabinetry, Vola fixtures, and Bocci chandeliers. The chef's kitchen features Thermador and Miele appliances, a 48-inch refrigerator and freezer, oversized quartz counters, and butler's pantry. Five bedrooms offer flexibility, with four en suite bathrooms, including an attached ADU with its own entrance. Outdoor spaces include a courtyard, low-water garden, and mature redwoods. A sophisticated technology and infrastructure package includes Lutron Ketra lighting, Savant automation, enterprise-grade networking, solar panels, two Tesla PowerWalls, and EV charging. Minutes from downtown Menlo Park, Palo Alto, Stanford, Sand Hill Road, Meta, top schools.

725 Evergreen ST, Menlo Park

1955 Parkside AVE, Hillsborough
$7,825,000
4 Beds ⋅ 5 Baths ⋅ ML82046534 MLS
For the first time in over half a century, this remarkable family estate is opening its doors to a new chapter. Built in 1967 and held by the same family ever since, this is more than just a homeit is a rare opportunity to acquire a residence of incredible character and complete seclusion. The expansive floor plan is thoughtfully designed for both grand entertaining and intimate daily life, featuring four generous bedrooms along with three full and two half baths. Among its many refined living spaces is a sophisticated library, offering the perfect sanctuary for a home office or quiet reflection. Every room is bathed in natural light, creating a seamless connection between the interior and the breathtaking grounds outside. Set within a lush, private envelope, the property is defined by stunning curated gardens that create a verdant oasis. These meticulously maintained outdoor spaces provide a level of privacy that is increasingly rare, ensuring a serene retreat. Meticulously cared for and brimming with potential, this is a once-in-a-generation opportunity to acquire this remarkable estate and steward its beautiful legacy into a new era.

1955 Parkside AVE, Hillsborough

306 Walsh RD, Atherton
$7,755,000
5 Beds ⋅ 5 Baths ⋅ ML82051800 MLS
Set on more than 1.2 acres in prestigious Atherton, this exceptional California ranch offers timeless elegance, privacy, and beautiful grounds beneath a canopy of majestic redwoods. A gated entrance and charming bridge lead to more than 4,700 square feet filled with natural light, hardwood floors, marble finishes, chandeliers, and classic architectural character. Grand living spaces include a chef's kitchen with premium appliances, a welcoming family room with a fireplace, private office, and 5 bedrooms highlighted by a luxurious primary suite with a spa-inspired bath. Resort-like grounds with lush lawn, a pool, spa, fire pit, and deck create an incredible setting for entertaining, all close to downtown Menlo Park and Palo Alto, Stanford University, Sand Hill Road, and acclaimed Las Lomitas schools (buyer to verify).

306 Walsh RD, Atherton

2245 Oakdale RD, Hillsborough
$7,600,000
5 Beds ⋅ 5 Baths ⋅ ML82054472 MLS
Nestled on a nearly 19,255 square foot lot in coveted Lower North Hillsborough, this inviting residence offers exceptional privacy and an effortless Peninsula lifestyle. Fresh, comfortable, and move-in ready, the home is designed for primarily single-level living with four bedrooms, an office, and four full baths on the main level. Nearly every room opens to the spectacular backyard, while walls of glass fill the home with natural light and create a seamless connection to the resort-inspired grounds. The backyard is the heart of the home. Enjoy sunny afternoons by the sparkling pool, entertain on expansive patios, or watch children play on the sprawling level lawn below, reminiscent of a private playing field. A separate lower level with its own entrance includes a bedroom, full bath, and spacious family roomideal for an au pair, extended family, guests, a home gym, or a private retreat. Lovingly maintained, including an updated heating system, this is a rare opportunity to own a timeless Hillsborough home where privacy, comfort, and exceptional indoor-outdoor living come together.

2245 Oakdale RD, Hillsborough

1330 University DR 92, Menlo Park
$7,600,000
4 Beds ⋅ 4 Baths ⋅ ML82042104 MLS ⋅ Menlo Towers Condominium Assoc BLDG.
Positioned at the pinnacle of Menlo Towers in downtown Menlo Park, this rare penthouse is one of only two in the building, with neither trading in over 30 years. Offering approximately 4,880 square feet of single-level living plus more than 4,000 square feet of private exterior terraces, it delivers exceptional scale & privacy. Natural light fills the home through skylights & expansive windows, framing panoramic treetop & western hill views. A formal foyer opens to a grand living room with fireplace, elevated ceilings & sweeping outlooks. The dining room & main living spaces connect seamlessly to the terraces, creating effortless indoor-outdoor flow. The kitchen features a center island, casual dining area & walk-in pantry with wine refrigeration, while a separate media room adds flexibility. The private bedroom wing includes a spacious primary suite with remarkable views, a large bath & custom closets. Two additional en suite bedrooms, a den & office provide comfortable accommodations. Wraparound terraces define the residence, with turf lawn, putting green & multiple seating areas above the tree line. Menlo Towers is a secure environment with a staffed lobby, gym & pool. In the heart of downtown shops & restaurants, this is an exceptional residence of rare scale & distinction.

1330 University DR 92, Menlo Park

333 Raymundo DR, Woodside
$7,500,000
4 Beds ⋅ 5 Baths ⋅ ML82017471 MLS
Set on a 3.1-acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly-updated residence offers the perfect blend of refined luxury and modern comfort - just minutes from town. Flooded with natural light from expansive floor-to-ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public spaces in +/-5,555sf. The open-concept living room boasts 24-foot ceilings, massive curved windows, a striking fireplace, and flows seamlessly into the sun-filled dining room. The chef's kitchen opens to a huge family room with 10-foot ceilings, a dramatic fireplace, bar, and French doors opening to a patio-perfect for indoor/outdoor living. Designed for everyday comfort and entertainment, the home offers multiple terraces, temperature-controlled wine storage, and an expansive lower level replete with a gym, home theater, and full bath. Outdoor amenities include a pool with spa, tennis court, meandering paths that encircle the property, level lawns, and a vineyard. A detached 2BR/2BA, +/-1,135sf guest house is ideal for extended family or visitors. Access to the top-rated Woodside Elementary School completes this rare opportunity to experience a lifestyle of elegance, privacy, and convenience.

333 Raymundo DR, Woodside

55 Mission Trail RD, Woodside
$7,495,000
4 Beds ⋅ 6 Baths ⋅ ML82044344 MLS
New Price! Set at the end of a private, gated country lane on approximately 1.11 fully usable acres, this elegant estate with French country architecture offers an exceptional blend of refined living and natural beauty, with sweeping views of the Western Hills and stunning sunsets. The main residence features 4 BR and 5.5 BA and a dedicated office/library with inspiring views. A recently updated chefs kitchen with a sunny breakfast area, main-level primary suite with connecting recreation room, patterned oak hardwood floors, and dual-paned windows throughout create a warm yet sophisticated ambiance. Designed for indoor/outdoor entertaining with expansive terraces and beautifully landscaped gardens this is a one of a kind home. A detached 1 BR 1 BA guest house has a full kitchen, wood-burning fireplace, and high ceilings, perfect for guests, extended family, or independent work space. An additional 520 square feet of garage space and 795 square feet of basement storage provide functionality alongside luxury. Ideally located within walking distance to Woodside Town Centers shops and restaurants, and close to Woodside School (Pre-K8th), Interstate 280, Sand Hill Road, and Stanford University, this home exemplifies the best of serene, convenient, and elegant Woodside living

55 Mission Trail RD, Woodside

1215 Tournament DR, Hillsborough
$7,470,000
7 Beds ⋅ 9 Baths ⋅ ML82025914 MLS
https://1215TournamentDr.com/ Rare estate in the prestigious Tobin Clark area of Hillsborough.Set on a private,resort-like lot with mature trees, layered outdoor spaces,and a private walking trail.Surrounded by top private schools, the home is thoughtfully laid out with 7beds & 7.5baths, along with formal living and dining rooms that connect to a spacious family room and kitchen. A group of four bedrooms are located together in one area of the home, making it especially practical for families with multiple children.The primary suite itself feels like a quiet retreat,featuring a spa-like bath and an expansive walk-in closet.A wood-paneled office provides a dedicated workspace,while the au pair quarters offer additional privacy for guests or extended household needs. A large open area is designed for everyday enjoyment like watching movies,playing games,or hosting.With a wet bar,full kitchenette,nearby bedroom and bath,and direct access to the outdoors,this space can also function as a self-contained living area. Outside,the grounds unfold with lawns,terraces,and an outdoor fireplace.Creating places to sit,walk, and host.Additional highlights include a rare 5-car garage & dual laundry areas.A home where space,privacy, and everyday living come together in a way that simply works.

1215 Tournament DR, Hillsborough

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This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,