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Set on approximately 0.62 acres in desirable Lower South Hillsborough, this inviting ranch-style residence offers an exceptional combination of privacy, space, convenience, and tremendous potential. The home features three bedrooms and two-and-a-half bathrooms, with beautiful hardwood floors, freshly painted interiors, and newly refinished flooring creating a bright and welcoming backdrop. A generously sized family room and separate dining room both open directly to the expansive backyard, providing wonderful indoor-outdoor flow and effortless access to the patio and lawn. The private grounds are a standout feature, offering a large outdoor patio, expansive grassy areas, and ample room to reimagine the property over time. The generous lot also provides potential for an ADU or additional improvements, subject to applicable approvals. A two-car garage plus additional carport provides excellent parking and storage. Ideally situated in Lower South Hillsborough, the property enjoys convenient access to South School, Crystal Springs Uplands School, downtown San Mateo, shopping, dining, and major commute routes.

3 Beds ⋅ 3 Baths ⋅ ML82063576 MLS

Set on approximately 0.62 acres in desirable Lower South Hillsborough, this inviting ranch-style residence offers an exceptional combination of privacy, space, convenience, and tremendous potential. The home features three bedrooms and two-and-a-half bathrooms, with beautiful hardwood floors, freshly painted interiors, and newly refinished flooring creating a bright and welcoming backdrop. A generously sized family room and separate dining room both open directly to the expansive backyard, providing wonderful indoor-outdoor flow and effortless access to the patio and lawn. The private grounds are a standout feature, offering a large outdoor patio, expansive grassy areas, and ample room to reimagine the property over time. The generous lot also provides potential for an ADU or additional improvements, subject to applicable approvals. A two-car garage plus additional carport provides excellent parking and storage. Ideally situated in Lower South Hillsborough, the property enjoys convenient access to South School, Crystal Springs Uplands School, downtown San Mateo, shopping, dining, and major commute routes.

140 Rockridge Road, Hillsborough

Listing courtesy of Emma Elfving from Compass. 650-773-5115

Selling Office: Quest Real Estate.

$6,175,000

Commanding a 0.721-acre promontory in Hillsboroughs coveted Skyfarm neighborhood, this exceptional five-bedroom, five-bathroom residence is defined by scale, privacy, and an intimate connection to the landscape. Framed by breathtaking, unobstructed canyon views, the property delivers a private resort experience right at home, complete with a crystal-clear pool set against sweeping natural vistas. Designed for both grand entertaining and effortless daily living, the generous floor plan features a custom wine room and a convenient elevator, offering exceptional comfort, privacy, and seamless indoor-outdoor flow. Exceptional storage and vehicle accommodation abound with an oversized 4-car garage, ideal for car enthusiasts, extra storage, or potential workshop space. Situated on premier grounds in one of Northern Californias most coveted enclaves, this residence seamlessly unites architectural scale, ultimate privacy, and an idyllic natural setting. Offering access to Hillsboroughs top-rated public schools, the home stands as a refined expression of contemporary California luxury where architecture, landscape, and everyday life harmoniously converge high above the canyon.

5 Beds ⋅ 5 Baths ⋅ ML82061953 MLS

Commanding a 0.721-acre promontory in Hillsboroughs coveted Skyfarm neighborhood, this exceptional five-bedroom, five-bathroom residence is defined by scale, privacy, and an intimate connection to the landscape. Framed by breathtaking, unobstructed canyon views, the property delivers a private resort experience right at home, complete with a crystal-clear pool set against sweeping natural vistas. Designed for both grand entertaining and effortless daily living, the generous floor plan features a custom wine room and a convenient elevator, offering exceptional comfort, privacy, and seamless indoor-outdoor flow. Exceptional storage and vehicle accommodation abound with an oversized 4-car garage, ideal for car enthusiasts, extra storage, or potential workshop space. Situated on premier grounds in one of Northern Californias most coveted enclaves, this residence seamlessly unites architectural scale, ultimate privacy, and an idyllic natural setting. Offering access to Hillsboroughs top-rated public schools, the home stands as a refined expression of contemporary California luxury where architecture, landscape, and everyday life harmoniously converge high above the canyon.

40 Eugenia Way, Hillsborough

Listing courtesy of Gina Haggarty from Compass. 650-207-5192

Selling Office: Golden Gate Sotheby's International Realty.

$4,168,000

Owned since new, offered for the first time since 1976, this exceptional home represents a rare opportunity more than five decades in the making. Set behind a gated driveway amid beautifully landscaped grounds, distinguished by its single-level design & connection to the outdoors. The thoughtfully designed floor plan features 4 bedrooms & 2.5 bathrooms, elegant living & dining rooms, a light-filled family room w/vaulted ceiling, kitchen with breakfast nook, & a spacious primary suite. A defining feature is the dramatic sunroom extending across the rear of the home. Accessible from the family room, breakfast area, & primary suite, walls & ceiling of glass overlook the swimming pool, deck, mature trees, & surrounding greenery. Beautifully established grounds feature sweeping lawns, mature landscaping, a swimming pool, recreation court, expansive deck, three-car garage, & generous parking - an inviting setting for relaxation and entertaining. A separate lower-level bonus area with a bedroom, bathroom, & living room provides flexibility for guests, a home office, or recreation. With its privacy, single-level living, indoor-outdoor connection, & impressive grounds, this distinctive home offers a rare opportunity to enjoy Hillsborough living & envision its possibilities for the future.

4 Beds ⋅ 3 Baths ⋅ ML82061870 MLS

Owned since new, offered for the first time since 1976, this exceptional home represents a rare opportunity more than five decades in the making. Set behind a gated driveway amid beautifully landscaped grounds, distinguished by its single-level design & connection to the outdoors. The thoughtfully designed floor plan features 4 bedrooms & 2.5 bathrooms, elegant living & dining rooms, a light-filled family room w/vaulted ceiling, kitchen with breakfast nook, & a spacious primary suite. A defining feature is the dramatic sunroom extending across the rear of the home. Accessible from the family room, breakfast area, & primary suite, walls & ceiling of glass overlook the swimming pool, deck, mature trees, & surrounding greenery. Beautifully established grounds feature sweeping lawns, mature landscaping, a swimming pool, recreation court, expansive deck, three-car garage, & generous parking - an inviting setting for relaxation and entertaining. A separate lower-level bonus area with a bedroom, bathroom, & living room provides flexibility for guests, a home office, or recreation. With its privacy, single-level living, indoor-outdoor connection, & impressive grounds, this distinctive home offers a rare opportunity to enjoy Hillsborough living & envision its possibilities for the future.

1345 Lakeview Drive, Hillsborough

Listing courtesy of Henry Chu from Golden Gate Sotheby's International Realty. 650-918-8118

Selling Office: Real Brokerage Technologies.

$8,250,000

A rare Lower Hillsborough opportunity awaits at 701 Chester Way, an extraordinary 40,083-square-foot property that has been held by the same family for 52 years. Originally built in 1917, this approximately 8,170-square-foot Mediterranean-style residence offers eight bedrooms, 6.5 baths, a four-car garage, swimming pool, and squash court. While the residence presents some deferred maintenance, its remarkable scale, expansive grounds, sought-after Lower Hillsborough location, and long private approach create an exceptional canvas for restoration, renovation, or a visionary redevelopment plan, subject to applicable approvals and buyer investigation.

8 Beds ⋅ 7 Baths ⋅ ML82065500 MLS

A rare Lower Hillsborough opportunity awaits at 701 Chester Way, an extraordinary 40,083-square-foot property that has been held by the same family for 52 years. Originally built in 1917, this approximately 8,170-square-foot Mediterranean-style residence offers eight bedrooms, 6.5 baths, a four-car garage, swimming pool, and squash court. While the residence presents some deferred maintenance, its remarkable scale, expansive grounds, sought-after Lower Hillsborough location, and long private approach create an exceptional canvas for restoration, renovation, or a visionary redevelopment plan, subject to applicable approvals and buyer investigation.

701 Chester Way, Hillsborough

Listing courtesy of Jose Dos Ramos from Berkshire Hathaway HomeServices Drysdale Propertie. 650-787-5568

Selling Office: KW Advisors.

$4,750,000

Located in one of Hillsborough's desirable residential neighborhoods, this approximately 3,570-square-foot residence sits on a generous 18,344-square-foot lot. Offering an exceptional opportunity in an established Hillsborough setting, the property was sold off-market and entered into the MLS for comparable purposes only.

4 Beds ⋅ 3 Baths ⋅ ML82065236 MLS

Located in one of Hillsborough's desirable residential neighborhoods, this approximately 3,570-square-foot residence sits on a generous 18,344-square-foot lot. Offering an exceptional opportunity in an established Hillsborough setting, the property was sold off-market and entered into the MLS for comparable purposes only.

25 Annescourt Place, Hillsborough

Listing courtesy of Alexandra Gilmartin from Gilmartin Group. 650-454-0575

Selling Office: Christie's International Real Estate Sereno.

$5,800,000

Set on a private, gated .86 acres of stunningly landscaped grounds, this exceptional contemporary residence was extensively remodeled to perfection in 2017. Floor-to-ceiling glass walls throughout fill the interior spaces with natural light and create a seamless connection to the serene outdoors. A gracious foyer leads to an elegant living and dining room ensemble wrapped in walls of glass, with a chic fireplace adding warmth and intimacy. The amazing chefs kitchen is anchored by a dramatic center island, ample cabinetry, and generous counter space. Huge sliding glass doors open to a large deck, creating an idyllic setting for morning coffee, dining, or relaxed entertaining. The primary suite features an expansive glass wall with sliding door, a romantic fireplace, huge walk-in closet, and remote-controlled blinds. Two additional bedrooms with dedicated bathrooms offer flexibility, with one beautifully arranged as an office with custom cabinetry and desks. Outside, majestic trees, meandering creek, incredible landscaping, expansive synthetic turf, and wrap-around decking create a truly magical park setting. Extending from El Cerrito to Rockridge Drive, this property offers a rare sanctuary where architecture, light, landscape, and contemporary luxury exist in effortless harmony.

3 Beds ⋅ 3 Baths ⋅ ML82061884 MLS

Set on a private, gated .86 acres of stunningly landscaped grounds, this exceptional contemporary residence was extensively remodeled to perfection in 2017. Floor-to-ceiling glass walls throughout fill the interior spaces with natural light and create a seamless connection to the serene outdoors. A gracious foyer leads to an elegant living and dining room ensemble wrapped in walls of glass, with a chic fireplace adding warmth and intimacy. The amazing chefs kitchen is anchored by a dramatic center island, ample cabinetry, and generous counter space. Huge sliding glass doors open to a large deck, creating an idyllic setting for morning coffee, dining, or relaxed entertaining. The primary suite features an expansive glass wall with sliding door, a romantic fireplace, huge walk-in closet, and remote-controlled blinds. Two additional bedrooms with dedicated bathrooms offer flexibility, with one beautifully arranged as an office with custom cabinetry and desks. Outside, majestic trees, meandering creek, incredible landscaping, expansive synthetic turf, and wrap-around decking create a truly magical park setting. Extending from El Cerrito to Rockridge Drive, this property offers a rare sanctuary where architecture, light, landscape, and contemporary luxury exist in effortless harmony.

739 El Cerrito Avenue, Hillsborough

Listing courtesy of Jim Arbeed from Coldwell Banker Realty. 650-558-4248

Selling Office: KW Advisors.

$6,150,000

HILLSBOROUGH'S TOP LOCATION! This rare and exceptional Mid-Century Modern architectural gem, designed in 1958 by acclaimed architect Charles Bolton White, is tucked away on one of Lower South Hillsboroughs most private and sought-after cul-de-sacs, with just three homes on the court. Set on a mostly level, sun-filled half acre, this graceful 6-bedroom, 4-bath residence is surrounded by Japanese-inspired gardens, graceful maples, mature oaks and towering redwoods, creating a serene, park-like setting. Designed for architecture and nature to exist in perfect harmony, the home features soaring ceilings, walls of windows opening to the rear gardens, warm redwood walls, a spacious family room and generously sized bedrooms. The private primary suite enjoys beautiful pool and garden views and an ensuite bath. Outdoors, a sparkling pool, expansive entertaining patios and generous level play areas capture quintessential indoor-outdoor California living. A separate fruit-tree meadow offers added privacy and an ideal setting for a future ADU. Meticulously maintained and beautifully preserved, this extraordinary Hillsborough residence is ready for its next chapter.

6 Beds ⋅ 4 Baths ⋅ ML82061801 MLS

HILLSBOROUGH'S TOP LOCATION! This rare and exceptional Mid-Century Modern architectural gem, designed in 1958 by acclaimed architect Charles Bolton White, is tucked away on one of Lower South Hillsboroughs most private and sought-after cul-de-sacs, with just three homes on the court. Set on a mostly level, sun-filled half acre, this graceful 6-bedroom, 4-bath residence is surrounded by Japanese-inspired gardens, graceful maples, mature oaks and towering redwoods, creating a serene, park-like setting. Designed for architecture and nature to exist in perfect harmony, the home features soaring ceilings, walls of windows opening to the rear gardens, warm redwood walls, a spacious family room and generously sized bedrooms. The private primary suite enjoys beautiful pool and garden views and an ensuite bath. Outdoors, a sparkling pool, expansive entertaining patios and generous level play areas capture quintessential indoor-outdoor California living. A separate fruit-tree meadow offers added privacy and an ideal setting for a future ADU. Meticulously maintained and beautifully preserved, this extraordinary Hillsborough residence is ready for its next chapter.

15 Mc Kenzie Court, Hillsborough

Listing courtesy of Hope Pilch from HP Properties. 650-619-4732

Selling Office: KW Advisors.

$6,000,000

This gated Hillsborough estate commands one of the finest views in town. Sweeping San Francisco vistas from the living room, dining room, and kitchen even dishwashing becomes a moment to savor as city lights twinkle! The expansive main deck one of four throughout the home provides views stretching from San Francisco to San Mateo and beyond. The primary suite offers a walk-in dressing room and spa-like bathroom, joined by two additional en-suite bedrooms and a versatile bonus room, currently staged as a 4th bedroom with sitting area. A 2-car attached garage with private gated entry completes this rare offering where every day is a room with a view! All that, plus award-winning schools, close to San Francisco and Silicon Valley and minutes to 92, 101 and 280.

3 Beds ⋅ 4 Baths ⋅ ML82062299 MLS

This gated Hillsborough estate commands one of the finest views in town. Sweeping San Francisco vistas from the living room, dining room, and kitchen even dishwashing becomes a moment to savor as city lights twinkle! The expansive main deck one of four throughout the home provides views stretching from San Francisco to San Mateo and beyond. The primary suite offers a walk-in dressing room and spa-like bathroom, joined by two additional en-suite bedrooms and a versatile bonus room, currently staged as a 4th bedroom with sitting area. A 2-car attached garage with private gated entry completes this rare offering where every day is a room with a view! All that, plus award-winning schools, close to San Francisco and Silicon Valley and minutes to 92, 101 and 280.

100 Southdown Court, Hillsborough

Listing courtesy of from Compass. 650-703-1183

Selling Office: Compass.

$12,500,000

5 Beds ⋅ 6 Baths ⋅ ML82064115 MLS

1545 Bellevue Avenue, Hillsborough

Listing courtesy of Max Lo from Green Banker Realty. 650-307-8816

Selling Office: Compass.

$6,150,000

Set against stunning Bay views, this Ranch style home blends timeless mid-century modern character with spacious, light filled living. Approximately 4,560 square feet of living space offers five bedrooms and four-and-a-half baths, with an inviting combination of formal and informal rooms. The main bedroom wing is thoughtfully arranged with a spacious primary suite, plus two additional bedrooms connected by a bathroom. A guest suite is conveniently located off the kitchen and laundry area, while the lower level -- with its own exterior access offers a potential fifth bedroom and full bath. The lower level provides even more flexibility, with an additional room perfect for an office, second family room or game room. Abundant natural light fills the home, while expansive windows capture the spectacular Bay outlook and create a strong connection to the private, mostly level grounds. The formal dining room and family room both have access to the backyard with a swimming pool and generous outdoor spaces. Architectural character, generous scale, versatile living spaces, privacy, and breathtaking views all paired with top-rated public schools. Perfect Mid-Peninsula location.

5 Beds ⋅ 5 Baths ⋅ ML82060425 MLS

Set against stunning Bay views, this Ranch style home blends timeless mid-century modern character with spacious, light filled living. Approximately 4,560 square feet of living space offers five bedrooms and four-and-a-half baths, with an inviting combination of formal and informal rooms. The main bedroom wing is thoughtfully arranged with a spacious primary suite, plus two additional bedrooms connected by a bathroom. A guest suite is conveniently located off the kitchen and laundry area, while the lower level -- with its own exterior access offers a potential fifth bedroom and full bath. The lower level provides even more flexibility, with an additional room perfect for an office, second family room or game room. Abundant natural light fills the home, while expansive windows capture the spectacular Bay outlook and create a strong connection to the private, mostly level grounds. The formal dining room and family room both have access to the backyard with a swimming pool and generous outdoor spaces. Architectural character, generous scale, versatile living spaces, privacy, and breathtaking views all paired with top-rated public schools. Perfect Mid-Peninsula location.

860 Longview Road, Hillsborough

Listing courtesy of from Compass. 650-703-1183

Selling Office: Compass.

$7,100,000

Set in coveted lower North Hillsborough, 2801 Easton Drive offers timeless French Country character in a prime location just moments from downtown Brodaway Burlingame. This gracious home blends classic architectural appeal with an inviting sense of warmth and sophistication, creating an exceptional opportunity in one of the Peninsulas most desirable neighborhoods. Enjoy the convenience of being within walking distance of downtown Broadway Burlingames acclaimed shops, restaurants, caf s and everyday amenities, while nearby parks and neighborhood streets provide a peaceful residential setting. The property is located in the North Elementary, Crocker Middle Schools, and Burlingame High School attendance areas. A rare combination of distinctive style, sought-after location and exceptional walkability. 2801 Easton Drive embodies the best of Lower North Hillsborough living.

4 Beds ⋅ 5 Baths ⋅ ML82058766 MLS

Set in coveted lower North Hillsborough, 2801 Easton Drive offers timeless French Country character in a prime location just moments from downtown Brodaway Burlingame. This gracious home blends classic architectural appeal with an inviting sense of warmth and sophistication, creating an exceptional opportunity in one of the Peninsulas most desirable neighborhoods. Enjoy the convenience of being within walking distance of downtown Broadway Burlingames acclaimed shops, restaurants, caf s and everyday amenities, while nearby parks and neighborhood streets provide a peaceful residential setting. The property is located in the North Elementary, Crocker Middle Schools, and Burlingame High School attendance areas. A rare combination of distinctive style, sought-after location and exceptional walkability. 2801 Easton Drive embodies the best of Lower North Hillsborough living.

2801 Easton Drive, Hillsborough

Listing courtesy of Max Lo from Green Banker Realty. 650-307-8816

Selling Office: Gaea Realty.

$18,770,000

This English Tudor set on over one flat acre in prime lower North Hillsborough is surrounded by three sides of the Burlingame Country Club Golf Course, making it one of the areas most iconic estates. This fully custom private gated architectural masterpiece is the epitome of California living. Constructed in 2005 with many recent improvements including a remodeled kitchen, refinished floors throughout, updated light fixtures & new landscaping that blend old-world charm with modern aesthetics to create an immediate sense of arrival upon entering.An entertainer's dream, this property features formal rooms and multiple entertaining spaces on both floors. The 6 bedrooms and 7 full bathrooms are thoughtfully designed with a primary bedroom on each level. The French doors throughout create the ultimate indoor-outdoor flow as they lead to the resort style backyard that is complemented by a pool house with a full bath. The backyard features a stunning Pebbletec pool with dual waterfall and a separate spa. The lush landscaping lends privacy to the property and creates a park like setting throughout with the serene courtyard and garden walking path. This property is walking distance to Burlingame Avenue and one block to North Elementary and Crocker Middle School.

6 Beds ⋅ 9 Baths ⋅ ML82057167 MLS

This English Tudor set on over one flat acre in prime lower North Hillsborough is surrounded by three sides of the Burlingame Country Club Golf Course, making it one of the areas most iconic estates. This fully custom private gated architectural masterpiece is the epitome of California living. Constructed in 2005 with many recent improvements including a remodeled kitchen, refinished floors throughout, updated light fixtures & new landscaping that blend old-world charm with modern aesthetics to create an immediate sense of arrival upon entering.An entertainer's dream, this property features formal rooms and multiple entertaining spaces on both floors. The 6 bedrooms and 7 full bathrooms are thoughtfully designed with a primary bedroom on each level. The French doors throughout create the ultimate indoor-outdoor flow as they lead to the resort style backyard that is complemented by a pool house with a full bath. The backyard features a stunning Pebbletec pool with dual waterfall and a separate spa. The lush landscaping lends privacy to the property and creates a park like setting throughout with the serene courtyard and garden walking path. This property is walking distance to Burlingame Avenue and one block to North Elementary and Crocker Middle School.

600 Eucalyptus Avenue, Hillsborough

Listing courtesy of Joseph Miller from Miller/Steil Properties. 650-455-6552

Selling Office: Green Banker Realty.

$6,000,000

Located in Lower South Hillsborough, this spacious 3,440 sq ft home offers four bedrooms, three full bathrooms and separate office. The living room and an additional area feature wood-burning fireplaces, adding warmth and charm to the space. The home includes a separate family room and multiple dining options, such as a breakfast room, dining area in the living room, and an eat-in kitchen, All with access to a large sun lit flat back yard. The property comes with a two-car garage and is situated within the Hillsborough City Elementary school district. This residence combines functional living spaces with key amenities in a desirable location.

4 Beds ⋅ 4 Baths ⋅ ML82055379 MLS

Located in Lower South Hillsborough, this spacious 3,440 sq ft home offers four bedrooms, three full bathrooms and separate office. The living room and an additional area feature wood-burning fireplaces, adding warmth and charm to the space. The home includes a separate family room and multiple dining options, such as a breakfast room, dining area in the living room, and an eat-in kitchen, All with access to a large sun lit flat back yard. The property comes with a two-car garage and is situated within the Hillsborough City Elementary school district. This residence combines functional living spaces with key amenities in a desirable location.

336 Brentwood Road, Hillsborough

Listing courtesy of Max Lo from Green Banker Realty. 650-307-8816

Selling Office: Compass.

$6,000,000

Offered for the first time in over 40 years, this iconic Hillsborough estate presents a rare opportunity to own a piece of local history. Set within the coveted Lakeview neighborhood on a private cul-de-sac, the home is thoughtfully designed to embrace its breathtaking surroundings, where panoramic Bay and canyon views are showcased through dramatic walls of windows and enjoyed from multiple view decks. Light-filled interiors offer seamless indoor/outdoor living with expansive gathering spaces, four bedrooms, each with an en suite bathroom, a fitness/yoga studio with sauna, and a dedicated media room ready to become the ultimate home theater. Set on an expansive 25,000 sq. ft. lot with over 7,000 sq. ft. of living space, this timeless estate blends privacy, scale, and natural beauty. Ideally located between San Francisco and Silicon Valley, just minutes from SFO, Highway 280, and top-rated public and private schools. A truly rare opportunity to call one of the Peninsula's most prestigious neighborhoods home.

4 Beds ⋅ 7 Baths ⋅ ML82054112 MLS

Offered for the first time in over 40 years, this iconic Hillsborough estate presents a rare opportunity to own a piece of local history. Set within the coveted Lakeview neighborhood on a private cul-de-sac, the home is thoughtfully designed to embrace its breathtaking surroundings, where panoramic Bay and canyon views are showcased through dramatic walls of windows and enjoyed from multiple view decks. Light-filled interiors offer seamless indoor/outdoor living with expansive gathering spaces, four bedrooms, each with an en suite bathroom, a fitness/yoga studio with sauna, and a dedicated media room ready to become the ultimate home theater. Set on an expansive 25,000 sq. ft. lot with over 7,000 sq. ft. of living space, this timeless estate blends privacy, scale, and natural beauty. Ideally located between San Francisco and Silicon Valley, just minutes from SFO, Highway 280, and top-rated public and private schools. A truly rare opportunity to call one of the Peninsula's most prestigious neighborhoods home.

95 Southdown Court, Hillsborough

Listing courtesy of Madelyn Brown from KW Bay Area Estates. 408-761-7776

Selling Office: KW Bay Area Estates.

$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 Road, Hillsborough

Listing courtesy of Samia Morgan from eXp Realty of Northern California, Inc.. 650-678-3633

Selling Office: Kinoko.

$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 Road, Hillsborough

Listing courtesy of Phil Chen from Christie's International Real Estate Sereno. 415-271-1920

Selling Office: Compass.

$12,019,880

Extraordinary gardens and complete privacy create one of South Hillsborough's most exceptional residences. This circa 1931 Spanish Hacienda home presents a compelling blend of enduring architecture and recently completed updates. Surrounding this gated estate are approximately 2.55 acres of park-like grounds with a separate guest home, cabana, pool, spa and sports court. Signature details of the era remain beautifully intact, from vaulted ceilings, Gothic arched doorways, and all-wood beamed ceilings. Recent improvements introduce a fresh aesthetic, including a remodeled designer kitchen and service area, updated lighting, and refinished hardwood floors. The home balances impressive scale with comfortable livability through a collection of elegant formal rooms, a dedicated office, a tremendous kitchen and family room combination, and lower-level spaces for fitness and staff accommodations. The 5 bedrooms and 5.5 baths in the main residence are complemented by a detached one bedroom guest house plus a pool cabana, while the grounds unfold with meandering pathways, mature trees, and abundant privacy. Bay views from the primary suite add another dimension to this distinguished Hillsborough estate.

6 Beds ⋅ 7 Baths ⋅ ML82055882 MLS

Extraordinary gardens and complete privacy create one of South Hillsborough's most exceptional residences. This circa 1931 Spanish Hacienda home presents a compelling blend of enduring architecture and recently completed updates. Surrounding this gated estate are approximately 2.55 acres of park-like grounds with a separate guest home, cabana, pool, spa and sports court. Signature details of the era remain beautifully intact, from vaulted ceilings, Gothic arched doorways, and all-wood beamed ceilings. Recent improvements introduce a fresh aesthetic, including a remodeled designer kitchen and service area, updated lighting, and refinished hardwood floors. The home balances impressive scale with comfortable livability through a collection of elegant formal rooms, a dedicated office, a tremendous kitchen and family room combination, and lower-level spaces for fitness and staff accommodations. The 5 bedrooms and 5.5 baths in the main residence are complemented by a detached one bedroom guest house plus a pool cabana, while the grounds unfold with meandering pathways, mature trees, and abundant privacy. Bay views from the primary suite add another dimension to this distinguished Hillsborough estate.

862 Chiltern Road, Hillsborough

Listing courtesy of Lori Buecheler from Compass. 650-387-2716

Selling Office: Compass.

$3,250,000

Tucked along a private paved brick lane just off coveted Crystal Springs Road, 1050 Merner is a serene retreat surrounded by mature trees and lush landscaping. Offering 4 bedrooms main plus a 1-bedroom ADU, the home is filled with natural light and features recessed lighting throughout, creating a warm and inviting atmosphere. Designed for both comfortable living and effortless entertaining, the outdoor spaces are equally impressive. The expansive wood patio provides the perfect setting for al fresco dining and gatherings beneath the trees, while stairs lead down to a secondary yard complete with a playground and sandbox, creating endless opportunities for recreation and relaxation. Inside, the spacious primary suite offers a relaxing escape with a walk-in closet and beautifully appointed en-suite bath. The versatile ADU and separate studio/office provide exceptional flexibility for guests, a gym, creative workspace, or au pair quarters. A two-car garage offers ample storage and convenient parking. Ideally located with easy access to Alameda de las Pulgas, Highways 92 and 280, and just minutes from both downtown San Mateo and downtown Burlingame, this property combines privacy, functionality, and convenience in one exceptional offering.

4 Beds ⋅ 5 Baths ⋅ ML82048490 MLS

Tucked along a private paved brick lane just off coveted Crystal Springs Road, 1050 Merner is a serene retreat surrounded by mature trees and lush landscaping. Offering 4 bedrooms main plus a 1-bedroom ADU, the home is filled with natural light and features recessed lighting throughout, creating a warm and inviting atmosphere. Designed for both comfortable living and effortless entertaining, the outdoor spaces are equally impressive. The expansive wood patio provides the perfect setting for al fresco dining and gatherings beneath the trees, while stairs lead down to a secondary yard complete with a playground and sandbox, creating endless opportunities for recreation and relaxation. Inside, the spacious primary suite offers a relaxing escape with a walk-in closet and beautifully appointed en-suite bath. The versatile ADU and separate studio/office provide exceptional flexibility for guests, a gym, creative workspace, or au pair quarters. A two-car garage offers ample storage and convenient parking. Ideally located with easy access to Alameda de las Pulgas, Highways 92 and 280, and just minutes from both downtown San Mateo and downtown Burlingame, this property combines privacy, functionality, and convenience in one exceptional offering.

1050 Merner Road, Hillsborough

Listing courtesy of Phil Chen from Christie's International Real Estate Sereno. 415-271-1920

Selling Office: KW Advisors.

$4,700,000

4 Beds ⋅ 3 Baths ⋅ ML82059590 MLS

1520 Tartan Trail Road, Hillsborough

Listing courtesy of Stanley Lo from Green Banker Realty. 650-373-0007

Selling Office: Green Banker Realty.

$10,300,000

Located in one of Hillsborough's most coveted neighborhoods, 19 Farm Lane is an exceptional residence set along tree-lined streets amid extraordinary privacy & beautifully manicured grounds. Flowering plants, mature landscaping, & a massive flat lot create an impressive sense of arrival, complemented by an expansive driveway & 3-car garage. Inside, large windows, high ceilings, skylights, & recessed lighting create an airy, light-filled atmosphere. The thoughtfully designed floor plan offers effortless everyday living & entertaining, with a well-equipped kitchen, formal dining room, & generous living spaces. The lower level features a spacious living room & family room, two en-suite bedrooms with walk-in closets, & an additional bedroom ideal for guests or extended living. Upstairs, the luxurious primary suite offers two walk-in closets & a spa-like bathroom. Outside, the expansive backyard is a private sanctuary surrounded by lush landscaping & centered around a sparkling pool. Just minutes by bike from Downtown Burlingame's shops & restaurants, the home also offers access to some of California's finest schools. With its exceptional setting, privacy, flat lot, pool, and versatile floor plan, 19 Farm Lane presents a rare opportunity to experience the best of Hillsborough living.

6 Beds ⋅ 5 Baths ⋅ ML82057038 MLS

Located in one of Hillsborough's most coveted neighborhoods, 19 Farm Lane is an exceptional residence set along tree-lined streets amid extraordinary privacy & beautifully manicured grounds. Flowering plants, mature landscaping, & a massive flat lot create an impressive sense of arrival, complemented by an expansive driveway & 3-car garage. Inside, large windows, high ceilings, skylights, & recessed lighting create an airy, light-filled atmosphere. The thoughtfully designed floor plan offers effortless everyday living & entertaining, with a well-equipped kitchen, formal dining room, & generous living spaces. The lower level features a spacious living room & family room, two en-suite bedrooms with walk-in closets, & an additional bedroom ideal for guests or extended living. Upstairs, the luxurious primary suite offers two walk-in closets & a spa-like bathroom. Outside, the expansive backyard is a private sanctuary surrounded by lush landscaping & centered around a sparkling pool. Just minutes by bike from Downtown Burlingame's shops & restaurants, the home also offers access to some of California's finest schools. With its exceptional setting, privacy, flat lot, pool, and versatile floor plan, 19 Farm Lane presents a rare opportunity to experience the best of Hillsborough living.

19 Farm Lane, Hillsborough

Listing courtesy of Stanley Lo from Green Banker Realty. 650-373-0007

Selling Office: Compass.

$4,400,000

Nestled in Hillsborough's prestigious Skyfarm neighborhood, this expansive single-level residence sits on an exceptionally private half-acre lot with sweeping panoramic Bay views and extraordinary potential. Thoughtfully designed for comfortable living and effortless entertaining, the home features four generously sized bedrooms, three-and-one-half bathrooms, soaring vaulted ceilings, floor-to-ceiling windows, rich hardwood flooring, and a wood-burning fireplace. The well-appointed kitchen offers picturesque Bay views, a breakfast bar, and an adjoining breakfast room, while a separate office provides an ideal work-from-home space. Outside, the sprawling grounds showcase a sparkling pool, remarkable privacy, and an expansive backyard with endless possibilities for a sport court, gardens, outdoor entertaining, or a future ADU or guest house (buyer to verify). Additional highlights include owned solar, a spacious three-car garage, abundant storage, and a highly desirable single-level floor plan. Combining timeless architecture, breathtaking views, exceptional privacy, and incredible opportunity, this is a rare chance to personalize a premier property in one of Hillsborough's most coveted neighborhoods.

4 Beds ⋅ 4 Baths ⋅ ML82056870 MLS

Nestled in Hillsborough's prestigious Skyfarm neighborhood, this expansive single-level residence sits on an exceptionally private half-acre lot with sweeping panoramic Bay views and extraordinary potential. Thoughtfully designed for comfortable living and effortless entertaining, the home features four generously sized bedrooms, three-and-one-half bathrooms, soaring vaulted ceilings, floor-to-ceiling windows, rich hardwood flooring, and a wood-burning fireplace. The well-appointed kitchen offers picturesque Bay views, a breakfast bar, and an adjoining breakfast room, while a separate office provides an ideal work-from-home space. Outside, the sprawling grounds showcase a sparkling pool, remarkable privacy, and an expansive backyard with endless possibilities for a sport court, gardens, outdoor entertaining, or a future ADU or guest house (buyer to verify). Additional highlights include owned solar, a spacious three-car garage, abundant storage, and a highly desirable single-level floor plan. Combining timeless architecture, breathtaking views, exceptional privacy, and incredible opportunity, this is a rare chance to personalize a premier property in one of Hillsborough's most coveted neighborhoods.

35 Silk Tree Place, Hillsborough

Listing courtesy of Emma Elfving from Compass. 650-773-5115

Selling Office: Christie's International Real Estate Sereno.

$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 Avenue, Hillsborough

Listing courtesy of Andrew J. Klink from Compass. 650-222-9999

Selling Office: Compass.

$4,500,000

Tucked away on a peaceful cul-de-sac just moments from Vista Park, this Chuck Winslow-designed residence masterfully blends the warmth and romance of an Italian villa with refined California living. A dramatic living room welcomes guests with soaring 10-foot ceilings, exposed mahogany beams, rich inlaid hardwood floors, and walls of French doors that frame the sun-drenched pool courtyard, seamlessly blending indoor and outdoor living. At the heart of the home is a truly one-of-a-kind gourmet kitchen inspired by Henri Matisse's celebrated Jazz series. Outdoor living is equally exceptional, with an enclosed courtyard centering around a poured swimming pool and outdoor fireplace. A residence of uncommon character and enduring elegance, this is a home where architecture, art, comfort, and lifestyle come together to create one of Hillsborough's truly distinctive offerings.

4 Beds ⋅ 3 Baths ⋅ ML82058818 MLS

Tucked away on a peaceful cul-de-sac just moments from Vista Park, this Chuck Winslow-designed residence masterfully blends the warmth and romance of an Italian villa with refined California living. A dramatic living room welcomes guests with soaring 10-foot ceilings, exposed mahogany beams, rich inlaid hardwood floors, and walls of French doors that frame the sun-drenched pool courtyard, seamlessly blending indoor and outdoor living. At the heart of the home is a truly one-of-a-kind gourmet kitchen inspired by Henri Matisse's celebrated Jazz series. Outdoor living is equally exceptional, with an enclosed courtyard centering around a poured swimming pool and outdoor fireplace. A residence of uncommon character and enduring elegance, this is a home where architecture, art, comfort, and lifestyle come together to create one of Hillsborough's truly distinctive offerings.

1032 La Cuesta Road, Hillsborough

Listing courtesy of from Compass. 650-400-1188

Selling Office: Christie's International Real Estate Sereno.

$5,510,000

Exceptional location in a coveted community. Captivating views. Prestigious schools. Stunning pool and spa. Perfect for indoor-outdoor living designed for entertaining - feels like your own personal resort. Open floor plan flooded with natural light. 4 bedrooms with 2.5 baths, huge living room with wood burning fireplace, plus big family room and kitchen breakfast area. The family room, kitchen, and primary bedroom suite, all have sweeping views and direct access to the pool and spa. Extra large laundry room on the bedroom level, expansive 3 car garage with additional work spaces and two very large storage rooms attached. For those few who want to start fresh with a complete custom rebuild, this homes highly desirable expansive lot would be exceptional for a dramatic new design! Do not miss out on your rare opportunity to create a custom estate from the ground up in a highly desirable Hillsborough setting!

4 Beds ⋅ 3 Baths ⋅ ML82054648 MLS

Exceptional location in a coveted community. Captivating views. Prestigious schools. Stunning pool and spa. Perfect for indoor-outdoor living designed for entertaining - feels like your own personal resort. Open floor plan flooded with natural light. 4 bedrooms with 2.5 baths, huge living room with wood burning fireplace, plus big family room and kitchen breakfast area. The family room, kitchen, and primary bedroom suite, all have sweeping views and direct access to the pool and spa. Extra large laundry room on the bedroom level, expansive 3 car garage with additional work spaces and two very large storage rooms attached. For those few who want to start fresh with a complete custom rebuild, this homes highly desirable expansive lot would be exceptional for a dramatic new design! Do not miss out on your rare opportunity to create a custom estate from the ground up in a highly desirable Hillsborough setting!

1176 Tournament Drive, Hillsborough

Listing courtesy of Mike Foor from Intero Real Estate Services. 650-430-6500

Selling Office: Christie's International Real Estate Sereno.

$70,000,000

Set on more than 12 secluded acres, Villa de Verano is an ultra-exclusive Hillsborough estate inspired by the elegance of Lake Como. The gated compound offers exceptional privacy, symmetry and scale, with a tree-lined drive leading to a grand motor court & the main residence, guest quarters & sports pavilion. The 12,404 sqft main residence spans 3 levels serviced by an elevator & overlooks the pool, reflection pond & sweeping views of San Francisco Bay. The 4,612 sqft guest house & sports pavilion complement the estate. Interior amenities include a fitness center, theater, game room, spa, & saltwater aquarium. Custom furnishings & art create a unified aesthetic. The grounds include an amphitheater, event lawn, Asian garden with koi pond, swimming pool, reflection pond, open air pavilion, rose garden, redwood grove & English spiral mound. The Sports Pavilion includes a 2 story sports lounge with a viewing platform overlooking a sunken tennis court, pickleball court, volleyball court, badminton court, bocce ball court, horseshoe court, shuffleboard court & putting green. The estate also features an executive length golf course. Upon its completion, Villa de Verano received the CLCA annual Grand Sweepstakes Award for best residential estate completed in the state of California.

6 Beds ⋅ 17 Baths ⋅ ML82024133 MLS

Set on more than 12 secluded acres, Villa de Verano is an ultra-exclusive Hillsborough estate inspired by the elegance of Lake Como. The gated compound offers exceptional privacy, symmetry and scale, with a tree-lined drive leading to a grand motor court & the main residence, guest quarters & sports pavilion. The 12,404 sqft main residence spans 3 levels serviced by an elevator & overlooks the pool, reflection pond & sweeping views of San Francisco Bay. The 4,612 sqft guest house & sports pavilion complement the estate. Interior amenities include a fitness center, theater, game room, spa, & saltwater aquarium. Custom furnishings & art create a unified aesthetic. The grounds include an amphitheater, event lawn, Asian garden with koi pond, swimming pool, reflection pond, open air pavilion, rose garden, redwood grove & English spiral mound. The Sports Pavilion includes a 2 story sports lounge with a viewing platform overlooking a sunken tennis court, pickleball court, volleyball court, badminton court, bocce ball court, horseshoe court, shuffleboard court & putting green. The estate also features an executive length golf course. Upon its completion, Villa de Verano received the CLCA annual Grand Sweepstakes Award for best residential estate completed in the state of California.

3000 Ralston Avenue, Hillsborough

Listing courtesy of Jenn Gilson from Golden Gate Sotheby's International Realty. 650-642-6957

Selling Office: J West Investments Inc.

$7,600,000

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.

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 Road, Hillsborough

Listing courtesy of from Compass. 650-678-5455

Selling Office: Compass.

$10,200,000

Welcome to 45 Calaveras Court, a brand-new modern masterpiece nestled in the Hillsborough hills. Located at the end of a private cul-de-sac on a sizable 4-acre lot, this stunning residence offers approximately 7,000 square feet of elegantly designed living space. Enjoy unobstructed canyon views from every window, providing a breathtaking backdrop to your everyday life. Step inside to discover soaring ceilings that create an open and inviting atmosphere, complemented by an abundance of natural light that fills every corner. The expansive first floor features a massive entertainment deck, perfect for hosting gatherings or simply relaxing amidst nature. With a total of 8 bedrooms, including master suites on each level, this exceptional home is perfect for large families or multi-generation living.

8 Beds ⋅ 7 Baths ⋅ ML82032410 MLS

Welcome to 45 Calaveras Court, a brand-new modern masterpiece nestled in the Hillsborough hills. Located at the end of a private cul-de-sac on a sizable 4-acre lot, this stunning residence offers approximately 7,000 square feet of elegantly designed living space. Enjoy unobstructed canyon views from every window, providing a breathtaking backdrop to your everyday life. Step inside to discover soaring ceilings that create an open and inviting atmosphere, complemented by an abundance of natural light that fills every corner. The expansive first floor features a massive entertainment deck, perfect for hosting gatherings or simply relaxing amidst nature. With a total of 8 bedrooms, including master suites on each level, this exceptional home is perfect for large families or multi-generation living.

45 Calaveras Court, Hillsborough

Listing courtesy of from Compass. 650-400-1188

Selling Office: Corcoran Global Living.

$8,038,000

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 Avenue, Hillsborough

Listing courtesy of from Compass. 650-703-1183

Selling Office: Green Banker Realty.

$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 Drive, Hillsborough

Listing courtesy of Claire Chen from Compass. 510-754-0555

Selling Office: Green Banker Realty.

$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 Road, Hillsborough

Listing courtesy of from KW Advisors. 650-766-5333

Selling Office: Christie's International Real Estate Sereno.

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