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$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 RD, Hillsborough

Listed by Lori Buecheler, 650-387-2716 from Compass
(If provided) CoList: Olivia Maggi from Compass

Sold listing courtesy of Gary Johnson from COMP

$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

$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

$6,500,000

Tucked at the end of a private cul-de-sac, 720 Endfield Way offers a rare blend of privacy, scale, and panoramic Bay views. This meticulously maintained all ensuite 4-bedroom, 4-bath residence is filled with natural light. Expansive windows frame stunning vistas from Oakland to the San Mateo Bridge viewed from almost every room. Offering 3779 square feet of generous living spaces for refined entertainment and everyday living, including a family room with wet bar and large primary suite with fireplace, sitting area and walk-in closets. Hardwood floors, updated kitchen with quartz countertops and high end appliances. Cultivated gardens, pool, jacuzzi and dedicated raised vegetable beds are situated on the .75 acre lot. A sprawling view deck provides the perfect setting for sunset dinners, morning coffee, and effortless indoor-outdoor living. Rarely does a home combine such privacy, breathtaking views, and lifestyle appeal in one exceptional setting. Located moments from top-rated schools, Burlingame Avenue, and major commute routes, this is an extraordinary opportunity to experience elevated Peninsula living.

4 Beds ⋅ 4 Baths ⋅ ML82040481 MLS

Tucked at the end of a private cul-de-sac, 720 Endfield Way offers a rare blend of privacy, scale, and panoramic Bay views. This meticulously maintained all ensuite 4-bedroom, 4-bath residence is filled with natural light. Expansive windows frame stunning vistas from Oakland to the San Mateo Bridge viewed from almost every room. Offering 3779 square feet of generous living spaces for refined entertainment and everyday living, including a family room with wet bar and large primary suite with fireplace, sitting area and walk-in closets. Hardwood floors, updated kitchen with quartz countertops and high end appliances. Cultivated gardens, pool, jacuzzi and dedicated raised vegetable beds are situated on the .75 acre lot. A sprawling view deck provides the perfect setting for sunset dinners, morning coffee, and effortless indoor-outdoor living. Rarely does a home combine such privacy, breathtaking views, and lifestyle appeal in one exceptional setting. Located moments from top-rated schools, Burlingame Avenue, and major commute routes, this is an extraordinary opportunity to experience elevated Peninsula living.

720 Endfield WAY, Hillsborough

Listed by Runa Magowan, 415-412-4480 from Coldwell Banker Realty
(If provided) CoList: Amy Conn from Coldwell Banker Realty

Sold listing courtesy of Serena Conti from APR

$4,950,000

THE BEST OF HILLSBOROUGH! 815 Crystal Springs Rd presents an exceptional blend of luxury, privacy, & resort-style living in one of Hillsborough's most desirable settings. Thoughtfully remodeled in 2016, this 3,345 sq ft residence sits on an expansive 19,598 sq ft lot and offers 4 bedrooms and 3.5 baths, including a beautifully appointed pool house, versatile studio/bonus room, and finished basement. A gated entry opens to a generous paver motor court and oversized finished 2-car garage with EV charging, sink, and refrigerator. Inside, an open-concept layout showcases a formal living room with fireplace, dining area, & a chef's kitchen is with a six-burner gas range, built-in refrigerator, wine refrigeration, and a center island with prep sink & breakfast bar, and family room with wet bar and fireplace. A private office with separate entrance adds flexibility. The covered outdoor living area features a full kitchen, fireplace, TV, heaters, and built-in speakers for year-round enjoyment. The primary suite offers vaulted ceilings, dual closets, and a spa-like bath with heated floors. Grounds include lawn, gardens, fruit trees, peaceful stream, redwoods, and a pool/spa retreat. Close to downtown San Mateo and many top schools. TOO MANY DETAILS TO LIST HERE, a must see so don't wait!

4 Beds ⋅ 4 Baths ⋅ ML82040633 MLS

THE BEST OF HILLSBOROUGH! 815 Crystal Springs Rd presents an exceptional blend of luxury, privacy, & resort-style living in one of Hillsborough's most desirable settings. Thoughtfully remodeled in 2016, this 3,345 sq ft residence sits on an expansive 19,598 sq ft lot and offers 4 bedrooms and 3.5 baths, including a beautifully appointed pool house, versatile studio/bonus room, and finished basement. A gated entry opens to a generous paver motor court and oversized finished 2-car garage with EV charging, sink, and refrigerator. Inside, an open-concept layout showcases a formal living room with fireplace, dining area, & a chef's kitchen is with a six-burner gas range, built-in refrigerator, wine refrigeration, and a center island with prep sink & breakfast bar, and family room with wet bar and fireplace. A private office with separate entrance adds flexibility. The covered outdoor living area features a full kitchen, fireplace, TV, heaters, and built-in speakers for year-round enjoyment. The primary suite offers vaulted ceilings, dual closets, and a spa-like bath with heated floors. Grounds include lawn, gardens, fruit trees, peaceful stream, redwoods, and a pool/spa retreat. Close to downtown San Mateo and many top schools. TOO MANY DETAILS TO LIST HERE, a must see so don't wait!

815 Crystal Springs RD, Hillsborough

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

Sold listing courtesy of Phil Houston from APR

$4,550,000

Tucked away, this graceful single-level home exudes timeless charm and quiet sophistication. Sunlight streams through the windows, highlighting elegant hardwood floors and a thoughtfully designed layout that blends comfort with effortless entertaining. A long paver driveway welcomes guests, while 2 fireplaces provide warmth and a sense of home. The kitchen features double ovens and ample space for cooking and gathering. A separate laundry room with access to the backyard adds practical convenience. Step into the serene primary suite with angled ceilings, built ins, and two true walk in closets, complemented by a junior suite and two additional bedrooms. The primary bath features double sinks, a soaking tub, and a walk-in shower, while 2 additional bathrooms serve the home with ease. Outdoors, the property becomes a private sanctuary with mature trees frame a solar-heated pool. A detached garden or art house with skylight and sink provides a charming space for creativity or reflection, while an adjoining wine room offers the ideal setting for storage and tastings. With nearly 2,800 square feet of living space on a half-acre lot, this Hillsborough home offers a rare combination of elegance, privacy, and enduring appeal in one of the Peninsulas most prestigious communities.

4 Beds ⋅ 3 Baths ⋅ ML82037477 MLS

Tucked away, this graceful single-level home exudes timeless charm and quiet sophistication. Sunlight streams through the windows, highlighting elegant hardwood floors and a thoughtfully designed layout that blends comfort with effortless entertaining. A long paver driveway welcomes guests, while 2 fireplaces provide warmth and a sense of home. The kitchen features double ovens and ample space for cooking and gathering. A separate laundry room with access to the backyard adds practical convenience. Step into the serene primary suite with angled ceilings, built ins, and two true walk in closets, complemented by a junior suite and two additional bedrooms. The primary bath features double sinks, a soaking tub, and a walk-in shower, while 2 additional bathrooms serve the home with ease. Outdoors, the property becomes a private sanctuary with mature trees frame a solar-heated pool. A detached garden or art house with skylight and sink provides a charming space for creativity or reflection, while an adjoining wine room offers the ideal setting for storage and tastings. With nearly 2,800 square feet of living space on a half-acre lot, this Hillsborough home offers a rare combination of elegance, privacy, and enduring appeal in one of the Peninsulas most prestigious communities.

915 Link RD, Hillsborough

Listed by Julie Flouty, 650-504-6900 from Compass
(If provided) CoList: from

Sold listing courtesy of Max Lo from GRBA

$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 RD, Hillsborough

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

Sold listing courtesy of Rachel DiNapoli from DWELL

$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 RD, Hillsborough

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

Sold listing courtesy of Rob Decontreras from KWPEN