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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.

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

Listed by The Dwyer Group, (650) 931-2036 from Compass
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

$8,800,000

FOR COMP PURPOSES ONLY

6 Beds ⋅ 6 Baths ⋅ ML82053405 MLS

FOR COMP PURPOSES ONLY

30 Bayberry PL, Hillsborough

Listed by The Dwyer Group, (650) 931-2036 from Compass
(If provided) CoList: from

Sold listing courtesy of Jenn Gilson from MCGR

$10,500,000

Gracefully tucked behind private gates in Lower Hillsborough's premier location, this exceptional contemporary residence offers a rare blend of privacy, sophistication, and effortless indoor-outdoor living. Directly across from the lush fairways of Burlingame Country Club, the home enjoys expansive green views, a majestic redwood grove, and a serene connection to nature. Designed for both relaxed everyday living and elegant entertaining, the residence features five bedrooms, four-and-one-half bathrooms, and light-filled living spaces. Expansive glass doors create a seamless connection to the landscaped grounds, where mature gardens, multiple outdoor entertaining areas, and a sparkling pool create a resort-like retreat. The thoughtfully designed single-level floor plan includes formal and informal living spaces, a spacious family room, and a well-appointed chef's kitchen, all designed for comfort and seamless living. Located moments from Burlingame Avenue, top-rated Hillsborough schools, San Francisco International Airport, and Silicon Valley, this exceptional residence offers an extraordinary Peninsula lifestyle.

5 Beds ⋅ 5 Baths ⋅ ML82053151 MLS

Gracefully tucked behind private gates in Lower Hillsborough's premier location, this exceptional contemporary residence offers a rare blend of privacy, sophistication, and effortless indoor-outdoor living. Directly across from the lush fairways of Burlingame Country Club, the home enjoys expansive green views, a majestic redwood grove, and a serene connection to nature. Designed for both relaxed everyday living and elegant entertaining, the residence features five bedrooms, four-and-one-half bathrooms, and light-filled living spaces. Expansive glass doors create a seamless connection to the landscaped grounds, where mature gardens, multiple outdoor entertaining areas, and a sparkling pool create a resort-like retreat. The thoughtfully designed single-level floor plan includes formal and informal living spaces, a spacious family room, and a well-appointed chef's kitchen, all designed for comfort and seamless living. Located moments from Burlingame Avenue, top-rated Hillsborough schools, San Francisco International Airport, and Silicon Valley, this exceptional residence offers an extraordinary Peninsula lifestyle.

1850 Brookvale RD, Hillsborough

Listed by Phil Chen, 415-271-1920 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Raziel A. Ungar from APR

$5,280,000

An exquisite property located in the exclusive Skyfarm neighborhood of Hillsborough. Set on over 0.69 acres, this home offers breathtaking views of the Bay, the airport, and downtown San Francisco. It creates a perfect setting for indoor / outdoor living in Hillsborough. The formal dining room and living room open onto the back deck, while the chef's kitchen combines a family room and an eat-in formal dining area with a private patio. The primary bedroom features an ensuite bathroom and a walk-in closet. Top-rated West Elementary School and Crocker Middle School. County records show 3,500 SqFt. 4 Bedrooms, 3 Full Baths. Seller converted the home to 5 Bedrooms, 4 Full Baths, which are permitted.

5 Beds ⋅ 4 Baths ⋅ ML82053052 MLS

An exquisite property located in the exclusive Skyfarm neighborhood of Hillsborough. Set on over 0.69 acres, this home offers breathtaking views of the Bay, the airport, and downtown San Francisco. It creates a perfect setting for indoor / outdoor living in Hillsborough. The formal dining room and living room open onto the back deck, while the chef's kitchen combines a family room and an eat-in formal dining area with a private patio. The primary bedroom features an ensuite bathroom and a walk-in closet. Top-rated West Elementary School and Crocker Middle School. County records show 3,500 SqFt. 4 Bedrooms, 3 Full Baths. Seller converted the home to 5 Bedrooms, 4 Full Baths, which are permitted.

36 Eugenia WAY, Hillsborough

Listed by John Pang, 650-699-2838 from Realty One Group Extreme
(If provided) CoList: from

$15,190,000

-- COMP PURPOSES ONLY --

5 Beds ⋅ 6 Baths ⋅ ML82051492 MLS

-- COMP PURPOSES ONLY --

245 W Santa Inez AVE, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

$3,700,000

Don't Miss the latest updates. Located in a community renowned for exceptional schools, this is a compelling Hillsborough opportunity. Offered at the lowest price per sq. ft. in Hillsborough, it delivers outstanding value in the community & across the Peninsula. Sweeping Bay & San Mateo Bridge views define this home. It features newly painted interiors, hardwood floors & a dramatic great room w/walls of glass overlooking the pool, expansive deck & panoramic viewsan exceptional setting for everyday living & entertaining. Designed for multigenerational living , w/ADU potential, the home offers 2 kitchens, 2 laundry rooms, separate exterior access & living & work-from-home spaces. Main level includes 2 primary suites, powder rm & view kitchen w/stone countertops, generous island, eating area & fireplace. Nearby office offers potential for a 5th BR or primary suite expansion. Lower level includes 2 BRs, full BA, 2nd kit/dining area & flexible bonus room ideal as a 2nd office or craft room. Direct patio, pool & outdoor access makes this level ideal for extended family, guests, caregivers or independent living. Wine cellar, workshop, 2-car garage, oversized driveway & generous storage complete this rare offering w/exceptional views, impressive scale, versatility & unmatched value.

4 Beds ⋅ 4 Baths ⋅ ML82051481 MLS

Don't Miss the latest updates. Located in a community renowned for exceptional schools, this is a compelling Hillsborough opportunity. Offered at the lowest price per sq. ft. in Hillsborough, it delivers outstanding value in the community & across the Peninsula. Sweeping Bay & San Mateo Bridge views define this home. It features newly painted interiors, hardwood floors & a dramatic great room w/walls of glass overlooking the pool, expansive deck & panoramic viewsan exceptional setting for everyday living & entertaining. Designed for multigenerational living , w/ADU potential, the home offers 2 kitchens, 2 laundry rooms, separate exterior access & living & work-from-home spaces. Main level includes 2 primary suites, powder rm & view kitchen w/stone countertops, generous island, eating area & fireplace. Nearby office offers potential for a 5th BR or primary suite expansion. Lower level includes 2 BRs, full BA, 2nd kit/dining area & flexible bonus room ideal as a 2nd office or craft room. Direct patio, pool & outdoor access makes this level ideal for extended family, guests, caregivers or independent living. Wine cellar, workshop, 2-car garage, oversized driveway & generous storage complete this rare offering w/exceptional views, impressive scale, versatility & unmatched value.

1407 Carlton RD, Hillsborough

Listed by Samia Morgan, 650-678-3633 from eXp Realty of Northern California, Inc.
(If provided) CoList: from

Sold listing courtesy of Minh-Ngoc Nguyen from KINOKO

$6,300,000

Experience refined California living in this exceptional Spanish Revival estate in coveted Lower North Hillsborough. Designed for seamless indoor-outdoor living, the home blends timeless architecture with resort-style amenities in a private, beautifully landscaped setting. Light-filled interiors feature a sunken living room with beamed ceiling, an arched entry to the formal dining room, and a chefs kitchen with marble countertops and center island with breakfast bar. The adjoining family room opens to the grounds and features walls of windows, creating both abundant natural light and effortless flow. A desirable ground-floor bedroom suite offers flexibility for guests or extended living, while four additional bedrooms upstairs include a serene primary suite. The backyard is truly a retreat with a resort-style pool, spa, and waterfall, multiple seating areas, and lawn space for play. An outdoor kitchen with built-in grill and a pizza oven connects to a patio with heaters and adjacent al fresco dining area - both ideal for effortless entertaining. Moments from downtown Burlingame, Hillsborough's top-rated schools, and key commute routes, this is a rare offering that combines luxury, comfort, and an exceptional lifestyle in one of the Peninsulas most prestigious neighborhoods.

5 Beds ⋅ 4 Baths ⋅ ML82041280 MLS

Experience refined California living in this exceptional Spanish Revival estate in coveted Lower North Hillsborough. Designed for seamless indoor-outdoor living, the home blends timeless architecture with resort-style amenities in a private, beautifully landscaped setting. Light-filled interiors feature a sunken living room with beamed ceiling, an arched entry to the formal dining room, and a chefs kitchen with marble countertops and center island with breakfast bar. The adjoining family room opens to the grounds and features walls of windows, creating both abundant natural light and effortless flow. A desirable ground-floor bedroom suite offers flexibility for guests or extended living, while four additional bedrooms upstairs include a serene primary suite. The backyard is truly a retreat with a resort-style pool, spa, and waterfall, multiple seating areas, and lawn space for play. An outdoor kitchen with built-in grill and a pizza oven connects to a patio with heaters and adjacent al fresco dining area - both ideal for effortless entertaining. Moments from downtown Burlingame, Hillsborough's top-rated schools, and key commute routes, this is a rare offering that combines luxury, comfort, and an exceptional lifestyle in one of the Peninsulas most prestigious neighborhoods.

973 Baileyana RD, Hillsborough

Listed by The Dwyer Group, 650-759-4409 from Compass
(If provided) CoList: from

Sold listing courtesy of Rachel Sudano from CBR

$8,250,000

4 Beds ⋅ 6 Baths ⋅ ML82051234 MLS

15 Annescourt, Hillsborough

Listed by Jenny MacLeod, 650-678-4151 from Compass
(If provided) CoList: Gina Haggarty from Compass

Sold listing courtesy of Geoffrey Nelson from CBR

$10,500,000

Commanding one of Hillsborough's most coveted view settings, this magnificent French-inspired chateau is set on +/-1.05 acres with top-of-the-world sweeping, unobstructed views spanning San Francisco, the Bay, and the East Bay Hills. Designed and custom built by renowned architect Farro Essalat, the estate offers +/-8,145s.f. of impeccably crafted living space that blends timeless elegance with modern comfort. Behind a gated motor court, the home offers 7 bedrooms, 6 full baths, 2 half baths, a library, two family rooms, and a media room. The massive gourmet kitchen & adjoining family room create a warm and inviting hub for everyday living, while the grand formal rooms with soaring ceilings, elegant columns, and French doors open to expansive view-facing terraces. Upstairs, the enormous primary suite includes a lavish marble bath, jetted tub, steam shower, and breathtaking views. The resort-style grounds are equally impressive, with expansive terraces, manicured gardens, a pool & spa, and generous lawn area overlooking the Bay. A substantial lower portion of the property presents potential for a possible tennis or pickleball court and/or an ADU. Combining timeless architecture, unparalleled views, and exceptional privacy, this is one of Hillsborough's most distinguished offerings

7 Beds ⋅ 8 Baths ⋅ ML82050881 MLS

Commanding one of Hillsborough's most coveted view settings, this magnificent French-inspired chateau is set on +/-1.05 acres with top-of-the-world sweeping, unobstructed views spanning San Francisco, the Bay, and the East Bay Hills. Designed and custom built by renowned architect Farro Essalat, the estate offers +/-8,145s.f. of impeccably crafted living space that blends timeless elegance with modern comfort. Behind a gated motor court, the home offers 7 bedrooms, 6 full baths, 2 half baths, a library, two family rooms, and a media room. The massive gourmet kitchen & adjoining family room create a warm and inviting hub for everyday living, while the grand formal rooms with soaring ceilings, elegant columns, and French doors open to expansive view-facing terraces. Upstairs, the enormous primary suite includes a lavish marble bath, jetted tub, steam shower, and breathtaking views. The resort-style grounds are equally impressive, with expansive terraces, manicured gardens, a pool & spa, and generous lawn area overlooking the Bay. A substantial lower portion of the property presents potential for a possible tennis or pickleball court and/or an ADU. Combining timeless architecture, unparalleled views, and exceptional privacy, this is one of Hillsborough's most distinguished offerings

225 TOBIN CLARK DR, Hillsborough

Listed by Jim Arbeed, 650-558-4248 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Shaun Walter from CBR

$6,500,000

Lower South Hillsborough estate property on more than one-half acre with gated entrances from Roblar Ave and W Santa Inez Ave. Recently updated with fresh paint, select new hardwood floors, new kitchen counters, and new garage doors. There are grand public rooms, kitchen and family room combination, and 5 bedrooms arranged for privacy and flexibility including exceptional poolside cabana with living room, full kitchen, bath, and bedroom with bath - ideal for extended family, guests, or poolside entertaining. The upstairs primary suite, with sitting area, balcony, two dressing rooms, and two full baths, is next to two additional suites. A private wing upstairs also has a suite ideal for an au pair, guests, or an office. Sparkling pool, level lawn, raised garden bed, and seasonal creek enhance the private setting. Excellent Hillsborough schools and just over one mile to either downtown Burlingame or San Mateo. With regard to square footage (See Square Footage Advisory), Tax records and WFG Property Profile show: 4,281 Sq Ft. County Characteristics for the main residence shows: 4,555 Sq Ft and 1,055 Sq Ft for Pool Cabana. Paid Marketing Vendor (Floor Plans) measure: 5,645 Sq Ft. Prior MLS shows 5,283 Sq Ft.

5 Beds ⋅ 8 Baths ⋅ ML82050602 MLS

Lower South Hillsborough estate property on more than one-half acre with gated entrances from Roblar Ave and W Santa Inez Ave. Recently updated with fresh paint, select new hardwood floors, new kitchen counters, and new garage doors. There are grand public rooms, kitchen and family room combination, and 5 bedrooms arranged for privacy and flexibility including exceptional poolside cabana with living room, full kitchen, bath, and bedroom with bath - ideal for extended family, guests, or poolside entertaining. The upstairs primary suite, with sitting area, balcony, two dressing rooms, and two full baths, is next to two additional suites. A private wing upstairs also has a suite ideal for an au pair, guests, or an office. Sparkling pool, level lawn, raised garden bed, and seasonal creek enhance the private setting. Excellent Hillsborough schools and just over one mile to either downtown Burlingame or San Mateo. With regard to square footage (See Square Footage Advisory), Tax records and WFG Property Profile show: 4,281 Sq Ft. County Characteristics for the main residence shows: 4,555 Sq Ft and 1,055 Sq Ft for Pool Cabana. Paid Marketing Vendor (Floor Plans) measure: 5,645 Sq Ft. Prior MLS shows 5,283 Sq Ft.

452 Roblar AVE, Hillsborough

Listed by Andrew J. Klink, 650-222-9999 from Compass
(If provided) CoList: Sandra Comaroto from Compass

Sold listing courtesy of Serena Conti from APR

$11,800,000

Located in desirable lower South Hillsborough, 255 Brentwood offers modern design, vaulted ceilings, exceptional natural light throughout, and seamless indoor-outdoor living. A striking front entry opens to a bright, welcoming foyer, leading into thoughtfully designed living spaces filled with natural light. The open kitchen and dining area serves as the heart of the homeperfect for both everyday living and entertainingfeaturing Miele appliances, two dishwashers, a pantry, and seamless flow to a built-in bar with wine fridge. The main level includes a casual living room, two en-suite bedrooms, and a stunning formal living room wrapped in glass doors and windows with direct access to the backyard. A private elevator connects all levels, offering ease and convenience throughout the home. The lower level offers added flexibility with a bedroom, mudroom, and wine room. Upstairs, the private primary suite features its own balcony, creating a peaceful retreat, while two additional en-suite bedrooms with generous closets complete the level. Outdoor spaces are designed for true California living, featuring a sport court, putting green, outdoor kitchen, sound system, curated lighting, four fireplaces, and beautifully landscaped grounds with a blend of turf and grass.

6 Beds ⋅ 6 Baths ⋅ ML82047705 MLS

Located in desirable lower South Hillsborough, 255 Brentwood offers modern design, vaulted ceilings, exceptional natural light throughout, and seamless indoor-outdoor living. A striking front entry opens to a bright, welcoming foyer, leading into thoughtfully designed living spaces filled with natural light. The open kitchen and dining area serves as the heart of the homeperfect for both everyday living and entertainingfeaturing Miele appliances, two dishwashers, a pantry, and seamless flow to a built-in bar with wine fridge. The main level includes a casual living room, two en-suite bedrooms, and a stunning formal living room wrapped in glass doors and windows with direct access to the backyard. A private elevator connects all levels, offering ease and convenience throughout the home. The lower level offers added flexibility with a bedroom, mudroom, and wine room. Upstairs, the private primary suite features its own balcony, creating a peaceful retreat, while two additional en-suite bedrooms with generous closets complete the level. Outdoor spaces are designed for true California living, featuring a sport court, putting green, outdoor kitchen, sound system, curated lighting, four fireplaces, and beautifully landscaped grounds with a blend of turf and grass.

255 Brentwood RD, Hillsborough

Listed by The Sharp Group, 650-766-5333 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Phil Chen from SGP

$5,600,000

A rare and irreplaceable work of art. Designed by renowned architect James H. Mitchell in the dramatic Art Deco/Art Moderne tradition, this is one of the Peninsula's most architecturally significant residences. Bold, streamlined geometry and masterful craftsmanship define every elevation of this striking 5,050± sq ft estate, while expansive wraparound decks and architecturally designed terraces off the living room and office invite the outside in, capturing sweeping panoramic views of the Bay, hills, and valley from every room in the home. Situated on a lush 0.71± acre lot, the scale is magnificent and the soul is irreplaceable. A home of genuine artistic pedigree in the heart of Hillsborough's most coveted corridor, near top-ranked schools and effortless Peninsula commuting. Architecture this significant does not come to market twice.

6 Beds ⋅ 8 Baths ⋅ ML82046550 MLS

A rare and irreplaceable work of art. Designed by renowned architect James H. Mitchell in the dramatic Art Deco/Art Moderne tradition, this is one of the Peninsula's most architecturally significant residences. Bold, streamlined geometry and masterful craftsmanship define every elevation of this striking 5,050± sq ft estate, while expansive wraparound decks and architecturally designed terraces off the living room and office invite the outside in, capturing sweeping panoramic views of the Bay, hills, and valley from every room in the home. Situated on a lush 0.71± acre lot, the scale is magnificent and the soul is irreplaceable. A home of genuine artistic pedigree in the heart of Hillsborough's most coveted corridor, near top-ranked schools and effortless Peninsula commuting. Architecture this significant does not come to market twice.

1325 Marlborough RD, Hillsborough

Listed by Jenn Gilson, 650-642-6957 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Yvonne Yang from APR

$6,500,000

Evoking the romance and timeless elegance of classic Spanish Colonial Revival architecture, this enchanting residence welcomes with a sun-drenched brick courtyard framed by lush gardens and climbing bougainvillea. Rich in character, the home showcases exposed wood beams, hand-laid terracotta tile, and artisan-inspired finishes that create a warm yet sophisticated ambiance throughout. Designed for effortless indoor-outdoor living, the expansive courtyard terrace offers multiple gathering spaces ideal for entertaining, quiet mornings, or alfresco dining beneath the canopy of mature landscaping. A sprawling lawn with a grand fountain frame the rear of the property. Charming balconies, arched passageways, and architectural detailing lend an old-world European feel while abundant natural light enhances the homes inviting atmosphere. Inside, the home boasts nearly 6,000 square feet of living space, including multiple separate living quarters perfect for large families, live-in help or guests. Exquisite woodwork and details are abundant throughout the household, with hand-carved fireplaces, curved leaded glass windows, and hand-painted murals. Private, serene, and full of architectural distinction, this is a rare offering that captures the beauty and craftsmanship of a bygone era.

6 Beds ⋅ 6 Baths ⋅ ML82046653 MLS

Evoking the romance and timeless elegance of classic Spanish Colonial Revival architecture, this enchanting residence welcomes with a sun-drenched brick courtyard framed by lush gardens and climbing bougainvillea. Rich in character, the home showcases exposed wood beams, hand-laid terracotta tile, and artisan-inspired finishes that create a warm yet sophisticated ambiance throughout. Designed for effortless indoor-outdoor living, the expansive courtyard terrace offers multiple gathering spaces ideal for entertaining, quiet mornings, or alfresco dining beneath the canopy of mature landscaping. A sprawling lawn with a grand fountain frame the rear of the property. Charming balconies, arched passageways, and architectural detailing lend an old-world European feel while abundant natural light enhances the homes inviting atmosphere. Inside, the home boasts nearly 6,000 square feet of living space, including multiple separate living quarters perfect for large families, live-in help or guests. Exquisite woodwork and details are abundant throughout the household, with hand-carved fireplaces, curved leaded glass windows, and hand-painted murals. Private, serene, and full of architectural distinction, this is a rare offering that captures the beauty and craftsmanship of a bygone era.

420 El Arroyo RD, Hillsborough

Listed by Pierre & Alex Buljan, 650-400-1188 from Compass
(If provided) CoList: from

Sold listing courtesy of Charles Griffith from MCGR

$7,825,000

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.

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

Listed by Gina Haggarty, 650-207-5192 from Compass
(If provided) CoList: from

Sold listing courtesy of Jenny MacLeod from APR

$7,300,000

Beyond the gates, perched atop a knoll w/ westerly hill views, a remarkable estate in the heart of Hillsborough. Fine luxury living is a timeless Craftsman built in 2009. Opulence begins at the front door to a grand foyer w/ soaring ceilings including a living room, a formal dining room, breakfast room, separate family room, & a gourmet chefs eat-in kitchen w/ custom cabinetry, Viking stainless steel appliances, a large custom island w/ prep sink & wine cooler, a 6-burner gas stove, & walk-in pantry plus office. Five en-suite bedrooms w/ a sumptuous primary bedroom suite complete w/ dual walk-in closets w/ closet organizers, & a spa-like bathroom w/ dual sinks w/ separate shower & tub. Impressive attention to detail throughout including French doors, wainscoting, crown moldings, baseboards, refinished hardwood floors, iron railings, & 2 mantled fireplaces plus central heating & air conditioning for added comfort. Additional library w/ coffered ceilings welcomes you to a garden oasis w/ mature landscaping, spacious faux grass area, dual patios, & your very own custom koi pond. Welcome home, to The Crown of Jewell Place.

5 Beds ⋅ 6 Baths ⋅ ML82046420 MLS

Beyond the gates, perched atop a knoll w/ westerly hill views, a remarkable estate in the heart of Hillsborough. Fine luxury living is a timeless Craftsman built in 2009. Opulence begins at the front door to a grand foyer w/ soaring ceilings including a living room, a formal dining room, breakfast room, separate family room, & a gourmet chefs eat-in kitchen w/ custom cabinetry, Viking stainless steel appliances, a large custom island w/ prep sink & wine cooler, a 6-burner gas stove, & walk-in pantry plus office. Five en-suite bedrooms w/ a sumptuous primary bedroom suite complete w/ dual walk-in closets w/ closet organizers, & a spa-like bathroom w/ dual sinks w/ separate shower & tub. Impressive attention to detail throughout including French doors, wainscoting, crown moldings, baseboards, refinished hardwood floors, iron railings, & 2 mantled fireplaces plus central heating & air conditioning for added comfort. Additional library w/ coffered ceilings welcomes you to a garden oasis w/ mature landscaping, spacious faux grass area, dual patios, & your very own custom koi pond. Welcome home, to The Crown of Jewell Place.

15 Jewell PL, Hillsborough

Listed by Chris A. Sabido, 650-922-8888 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Max Lo from GRBA

$5,200,000

This stunning Chateau-style residence is gracefully situated on coveted Chateau Drive in the prestigious Carolands area of Hillsborough. Set on approximately .77 acres of gated grounds with Bay views, a circular driveway, and lush mature landscaping, this private estate is offered for the first time since its original construction. Spanning over 4,200 square feet, the home reflects timeless architecture, grand proportions, and light-filled interiors. A gracious entry opens to an expansive living room anchored by a marble fireplace, an adjoining library, and dramatic arched windows framing serene views. The elegant dining room with coffered ceilings and intricate hardwood floors is ideal for entertaining, while multiple covered verandas create seamless indoor-outdoor living. The home offers 4 bedrooms and 3.5 bathrooms, including a lower-level retreat with closet, fireplace, and patio access, well suited for guests, a private office, or extended living. Featuring a spacious family room, dry sauna, 3 fireplaces, dual laundry areas, and a 3-car garage w/ additional driveway parking. Mostly level grounds enhanced with fruit trees offer potential for a pool or ADU, creating a private estate-like setting. A rare offering in a premier sought after location.

4 Beds ⋅ 4 Baths ⋅ ML82046360 MLS

This stunning Chateau-style residence is gracefully situated on coveted Chateau Drive in the prestigious Carolands area of Hillsborough. Set on approximately .77 acres of gated grounds with Bay views, a circular driveway, and lush mature landscaping, this private estate is offered for the first time since its original construction. Spanning over 4,200 square feet, the home reflects timeless architecture, grand proportions, and light-filled interiors. A gracious entry opens to an expansive living room anchored by a marble fireplace, an adjoining library, and dramatic arched windows framing serene views. The elegant dining room with coffered ceilings and intricate hardwood floors is ideal for entertaining, while multiple covered verandas create seamless indoor-outdoor living. The home offers 4 bedrooms and 3.5 bathrooms, including a lower-level retreat with closet, fireplace, and patio access, well suited for guests, a private office, or extended living. Featuring a spacious family room, dry sauna, 3 fireplaces, dual laundry areas, and a 3-car garage w/ additional driveway parking. Mostly level grounds enhanced with fruit trees offer potential for a pool or ADU, creating a private estate-like setting. A rare offering in a premier sought after location.

555 Chateau DR, Hillsborough

Listed by Tim Allen Alevizos, 650-255-7635 from Remax Capital
(If provided) CoList: from

Sold listing courtesy of Shuo Xiang from XLB

$5,795,000

Occupying a premier setting in one of Hillsboroughs most prestigious enclaves, 260 Robin Road showcases exceptional craftsmanship and timeless design. This completely rebuilt estate offers over 3,800 square feet of refined living space, blending modern luxury with effortless livability. Designed for todays discerning buyer, the home features four luxurious bedroom suites and five beautifully appointed bathrooms, each finished with thoughtful attention to detail. Expansive living spaces and walls of glass frame breathtaking Bay views while filling the home with natural light and creating a seamless connection between indoor and outdoor living. The open kitchen and family room serve as the heart of the home, designed for both everyday comfort and elegant entertaining. Set on a rare two-acre lot, the property offers an extraordinary sense of privacy and scale. A flat, fenced yard provides exceptional usable space for recreation, entertaining, or future amenities. With its elevated setting, stunning views, and beautifully rebuilt interiors, 260 Robin Road represents a rare opportunity to own a truly special Hillsborough estate.

4 Beds ⋅ 5 Baths ⋅ ML82037384 MLS

Occupying a premier setting in one of Hillsboroughs most prestigious enclaves, 260 Robin Road showcases exceptional craftsmanship and timeless design. This completely rebuilt estate offers over 3,800 square feet of refined living space, blending modern luxury with effortless livability. Designed for todays discerning buyer, the home features four luxurious bedroom suites and five beautifully appointed bathrooms, each finished with thoughtful attention to detail. Expansive living spaces and walls of glass frame breathtaking Bay views while filling the home with natural light and creating a seamless connection between indoor and outdoor living. The open kitchen and family room serve as the heart of the home, designed for both everyday comfort and elegant entertaining. Set on a rare two-acre lot, the property offers an extraordinary sense of privacy and scale. A flat, fenced yard provides exceptional usable space for recreation, entertaining, or future amenities. With its elevated setting, stunning views, and beautifully rebuilt interiors, 260 Robin Road represents a rare opportunity to own a truly special Hillsborough estate.

260 Robin RD, Hillsborough

Listed by The Laugesen Team, 650-465-5742 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

$5,800,000

Located on a private, tree-lined parcel in Hillsborough, this spacious residence offers beautiful canyon views and an inviting indoor-outdoor lifestyle. A grand two-story entry welcomes you into the home and leads to the formal living room featuring vaulted ceilings, a fireplace, and sliding doors that open to the rear deck, perfect for enjoying the scenic setting and outdoor entertaining. Just off the living room is an additional office or flexible space with a wet bar. The main level also features a formal dining room, a kitchen with breakfast area, and family room with vaulted ceilings, and fireplace. The primary suite is located on the main level and includes an en-suite bathroom. This level also offers a half bath and a guest quarters area complete with its own bathroom and kitchenette. A mudroom and attached 3-car garage provide added convenience. Upstairs are three additional bedrooms and a full bathroom. The backyard is designed for entertaining with a pool, expansive patio space, and artificial turf, all surrounded by mature trees for privacy. Conveniently located near shopping and dining in Burlingame as well as commute routes to San Francisco and along the Peninsula. Hillsborough is known for its peaceful residential setting and highly regarded public schools.

5 Beds ⋅ 4 Baths ⋅ ML82045371 MLS

Located on a private, tree-lined parcel in Hillsborough, this spacious residence offers beautiful canyon views and an inviting indoor-outdoor lifestyle. A grand two-story entry welcomes you into the home and leads to the formal living room featuring vaulted ceilings, a fireplace, and sliding doors that open to the rear deck, perfect for enjoying the scenic setting and outdoor entertaining. Just off the living room is an additional office or flexible space with a wet bar. The main level also features a formal dining room, a kitchen with breakfast area, and family room with vaulted ceilings, and fireplace. The primary suite is located on the main level and includes an en-suite bathroom. This level also offers a half bath and a guest quarters area complete with its own bathroom and kitchenette. A mudroom and attached 3-car garage provide added convenience. Upstairs are three additional bedrooms and a full bathroom. The backyard is designed for entertaining with a pool, expansive patio space, and artificial turf, all surrounded by mature trees for privacy. Conveniently located near shopping and dining in Burlingame as well as commute routes to San Francisco and along the Peninsula. Hillsborough is known for its peaceful residential setting and highly regarded public schools.

65 Falkirk LN, Hillsborough

Listed by Jenn Gilson, 650-642-6957 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Amarendra Kumar from SATV01

$12,500,000

5 Beds ⋅ 5 Baths ⋅ ML82045292 MLS

20 Denham CT, Hillsborough

Listed by Max Lo, 650-307-8816 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Max Lo from GRBA

$10,750,000

Modern Sanctuary in Lower South Hillsborough. Welcome to 655 Hayne Road, a newly completed modern residence offering privacy and refined California living in one of Hillsboroughs most desirable neighborhoods. Set behind a gated entrance on a mostly flat, usable parcel, the property is thoughtfully designed for seamless indoor-outdoor living. The main residence flows primarily across a single level, with an open-concept layout that connects effortlessly to the grounds and frames serene treetop views. Positioned just off the main living areas, the attached ADU offers a natural extension of the home, well suited for entertaining, guests, or extended stays. With easy access to the pool and outdoor kitchen, it lives as a cabana-style retreat, enhancing the indoor-outdoor lifestyle. A separate lower-level space offers flexibility for a home theater, gym, or game room. The grounds are carefully composed to create a true sense of escape, blending manicured landscaping, open turf areas, and a natural backdrop. Ideally located just moments from South School and with convenient access to Burlingame, San Mateo, and major commute routes. A rare offering that pairs modern design with usable land in a sought-after Hillsborough setting, ideal for refined indoor-outdoor living.

7 Beds ⋅ 6 Baths ⋅ ML82044447 MLS

Modern Sanctuary in Lower South Hillsborough. Welcome to 655 Hayne Road, a newly completed modern residence offering privacy and refined California living in one of Hillsboroughs most desirable neighborhoods. Set behind a gated entrance on a mostly flat, usable parcel, the property is thoughtfully designed for seamless indoor-outdoor living. The main residence flows primarily across a single level, with an open-concept layout that connects effortlessly to the grounds and frames serene treetop views. Positioned just off the main living areas, the attached ADU offers a natural extension of the home, well suited for entertaining, guests, or extended stays. With easy access to the pool and outdoor kitchen, it lives as a cabana-style retreat, enhancing the indoor-outdoor lifestyle. A separate lower-level space offers flexibility for a home theater, gym, or game room. The grounds are carefully composed to create a true sense of escape, blending manicured landscaping, open turf areas, and a natural backdrop. Ideally located just moments from South School and with convenient access to Burlingame, San Mateo, and major commute routes. A rare offering that pairs modern design with usable land in a sought-after Hillsborough setting, ideal for refined indoor-outdoor living.

655 Hayne RD, Hillsborough

Listed by Shaun Walter, 650-727-4888 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Shaun Walter from CBR

$7,172,500

Located in prime Lower South Hillsborough, this beautifully updated home sits on approximately 0.42 acres of flat, private, and meticulously landscaped grounds designed for effortless indoor-outdoor living. The front yard features manicured turf and a putting green, while the backyard offers a resort-like setting with a pool, built-in BBQ, outdoor TV, and multiple entertaining areas. Light-filled interiors showcase a seamless flow with a spacious kitchen/family room combination and formal living and dining rooms, all oriented toward the backyard. A rare highlight is the presence of two primary suites, providing exceptional flexibility. The upstairs primary retreat features dual closets, a private deck overlooking the pool, a spa-like bath with soaking tub, dual sinks, and high ceilings, plus an attached office with built-ins. A nursery is conveniently located adjacent to this suite. A second primary suite is located on the main level and overlooking the backyard. Alongside, is 2 additional bedroom suites, offering comfort and privacy for family and guests. Ideally located, mere blocks from Crystal Springs Uplands School, South Elementary, The Episcopal Day School, and just minutes to downtown San Mateo.

5 Beds ⋅ 5 Baths ⋅ ML82044375 MLS

Located in prime Lower South Hillsborough, this beautifully updated home sits on approximately 0.42 acres of flat, private, and meticulously landscaped grounds designed for effortless indoor-outdoor living. The front yard features manicured turf and a putting green, while the backyard offers a resort-like setting with a pool, built-in BBQ, outdoor TV, and multiple entertaining areas. Light-filled interiors showcase a seamless flow with a spacious kitchen/family room combination and formal living and dining rooms, all oriented toward the backyard. A rare highlight is the presence of two primary suites, providing exceptional flexibility. The upstairs primary retreat features dual closets, a private deck overlooking the pool, a spa-like bath with soaking tub, dual sinks, and high ceilings, plus an attached office with built-ins. A nursery is conveniently located adjacent to this suite. A second primary suite is located on the main level and overlooking the backyard. Alongside, is 2 additional bedroom suites, offering comfort and privacy for family and guests. Ideally located, mere blocks from Crystal Springs Uplands School, South Elementary, The Episcopal Day School, and just minutes to downtown San Mateo.

300 Uplands DR, Hillsborough

Listed by Sternsmith Group, 650-678-5455 from Compass
(If provided) CoList: from

Sold listing courtesy of Max Lo from GRBA

$6,400,000

Step into ultimate luxury with this spacious 6 BD, 5.5 BA home spanning +/- 4,746 SQFT on over 1/2 an acre of beautifully landscaped grounds. Perfect for entertaining and serene living, this home blends a versatile floorplan with thoughtful updates, including a significant 2017-2018 remodel and expansion. The main level is a showstopper, featuring a chef's kitchen with top-tier appliances, an oversized island, and seamless flow to the formal living & dining spaces. Sunlight pours through a wall of windows, framing views of the sparkling pool and lush gardens. This level also offers a private wing with two BDs, a shared BA and an ensuite BD with high ceilings, plus an additional BD, full BA, powder room, laundry room, and interior garage access. Upstairs, two ensuite retreats await, including the primary suite with a spa-like BA, a walk-in closet that dazzles and a 2nd W/D. The lower level living area opens to a tranquil patio & expansive lawn, ideal for outdoor entertaining or quiet mornings. High ceilings, hardwood floors, skylights, fruit trees and modern comforts like A/C, lots of storage and a spacious driveway complete the home. Located in a top-tier school district with easy access to 280 and 92, this home offers the perfect balance of convenience, elegance, and lifestyle.

6 Beds ⋅ 6 Baths ⋅ ML82042894 MLS

Step into ultimate luxury with this spacious 6 BD, 5.5 BA home spanning +/- 4,746 SQFT on over 1/2 an acre of beautifully landscaped grounds. Perfect for entertaining and serene living, this home blends a versatile floorplan with thoughtful updates, including a significant 2017-2018 remodel and expansion. The main level is a showstopper, featuring a chef's kitchen with top-tier appliances, an oversized island, and seamless flow to the formal living & dining spaces. Sunlight pours through a wall of windows, framing views of the sparkling pool and lush gardens. This level also offers a private wing with two BDs, a shared BA and an ensuite BD with high ceilings, plus an additional BD, full BA, powder room, laundry room, and interior garage access. Upstairs, two ensuite retreats await, including the primary suite with a spa-like BA, a walk-in closet that dazzles and a 2nd W/D. The lower level living area opens to a tranquil patio & expansive lawn, ideal for outdoor entertaining or quiet mornings. High ceilings, hardwood floors, skylights, fruit trees and modern comforts like A/C, lots of storage and a spacious driveway complete the home. Located in a top-tier school district with easy access to 280 and 92, this home offers the perfect balance of convenience, elegance, and lifestyle.

520 Darrell RD, Hillsborough

Listed by Becky Geller, 415-225-8172 from Compass
(If provided) CoList: from

Sold listing courtesy of Ryan LeDoux from APR

$10,200,000

6 Beds ⋅ 6 Baths ⋅ ML82042686 MLS

2077 Forest View AVE, Hillsborough

Listed by Chelsea Miller, 650-455-6551 from Miller/Steil Properties
(If provided) CoList: Joseph Miller from Miller/Steil Properties

Sold listing courtesy of Shaun Walter from CBR

$5,500,000

Privately set on a serene cul-de-sac, this gated estate is a refined expression of scale, light, and California indoor-outdoor living. A circular drive introduces a grand entry and sweeping staircase, with soaring ceilings elevating the formal living and dining spaces. At the heart of the home, a crisp white chefs kitchen flows effortlessly into the family room and out to curated gardens and expansive decks, mature trees, and a grassy play space, designed for effortless entertaining. Each of the 4 upstairs bedrooms opens to a balcony, while the primary suite unfolds as a true retreat complete with wraparound canyon views, a dressing area, and a spa-inspired bath. Don't miss this rare offering defined by privacy, elegance, and award-winning Hillsborough schools.

5 Beds ⋅ 5 Baths ⋅ ML82042651 MLS

Privately set on a serene cul-de-sac, this gated estate is a refined expression of scale, light, and California indoor-outdoor living. A circular drive introduces a grand entry and sweeping staircase, with soaring ceilings elevating the formal living and dining spaces. At the heart of the home, a crisp white chefs kitchen flows effortlessly into the family room and out to curated gardens and expansive decks, mature trees, and a grassy play space, designed for effortless entertaining. Each of the 4 upstairs bedrooms opens to a balcony, while the primary suite unfolds as a true retreat complete with wraparound canyon views, a dressing area, and a spa-inspired bath. Don't miss this rare offering defined by privacy, elegance, and award-winning Hillsborough schools.

10 Salmark CT, Hillsborough

Listed by Hope Pilch, 650-619-4732 from HP Properties
(If provided) CoList: from

Sold listing courtesy of Jingya Ji from CBR

$5,750,000

Regally situated on a majestic +/-0.58-acre lot, this classic colonial estate blends timeless architectural elegance with modern living space, and private, resort-like grounds designed for both comfort and enjoyment. Spanning +/-3,545sf, the 5-bedroom, 3.5-bath home welcomes you with an elegant marble foyer, a sophisticated living room with grand fireplace, and a graceful formal dining room. The sunny kitchen, complete with breakfast bar and cozy nook, flows seamlessly into a bright sunroom opening to the exceptional rear yard. Steps away, a family/media room with fireplace and bar offers relaxed living and effortless entertainment. The main level also features a private guest bedroom or office with full bath, a laundry room, and chic powder room. Upstairs, 3 sizeable bedrooms are serviced by a hall bath, while the lavish primary suite with large walk-in closet and spa-inspired bath provides a serene retreat. The resort-like grounds feature mature landscaping, a sweeping level lawn, pool, hot tub, BBQ, custom playhouse, and ample space to explore. Added highlights include a 3-car-attached garage with abundant storage and large attic. Located near top-rated schools and major commute routes, this distinguished estate delivers exceptional indoor-outdoor living in a tranquil setting.

5 Beds ⋅ 4 Baths ⋅ ML82042541 MLS

Regally situated on a majestic +/-0.58-acre lot, this classic colonial estate blends timeless architectural elegance with modern living space, and private, resort-like grounds designed for both comfort and enjoyment. Spanning +/-3,545sf, the 5-bedroom, 3.5-bath home welcomes you with an elegant marble foyer, a sophisticated living room with grand fireplace, and a graceful formal dining room. The sunny kitchen, complete with breakfast bar and cozy nook, flows seamlessly into a bright sunroom opening to the exceptional rear yard. Steps away, a family/media room with fireplace and bar offers relaxed living and effortless entertainment. The main level also features a private guest bedroom or office with full bath, a laundry room, and chic powder room. Upstairs, 3 sizeable bedrooms are serviced by a hall bath, while the lavish primary suite with large walk-in closet and spa-inspired bath provides a serene retreat. The resort-like grounds feature mature landscaping, a sweeping level lawn, pool, hot tub, BBQ, custom playhouse, and ample space to explore. Added highlights include a 3-car-attached garage with abundant storage and large attic. Located near top-rated schools and major commute routes, this distinguished estate delivers exceptional indoor-outdoor living in a tranquil setting.

740 Clydesdale DR, Hillsborough

Listed by Jim Arbeed, 650-558-4248 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Cullinan Luxury from KWPEN

$8,300,000

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.

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

Listed by Wen Guo RE Group, 650-817-5000 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Ben Jiang from GVFR

$6,000,000

4 Beds ⋅ 5 Baths ⋅ ML82042279 MLS

1162 Barroilhet DR, Hillsborough

Listed by The Dwyer Group, 650-703-1183 from Compass
(If provided) CoList: George Langford from Compass

Sold listing courtesy of The Laugesen Team from KWPEN

$8,700,000

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.

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

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

$7,895,000

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.

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

Listed by Jim Arbeed, 650-558-4248 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jenn Gilson from MCGR

$7,470,000

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.

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

Listed by Claire Chen, 510-754-0555 from Compass
(If provided) CoList: from

Sold listing courtesy of Stanley Lo from GRBA

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