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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 DR, Hillsborough

$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

$5,485,000

Arrive through a grand circular driveway to this beautifully expanded and remodeled 4-bedroom + office, 3.5-bath residence set on a .41-acre flat lot in sought-after Lower South Hillsborough. Inside, classic elegance meets open modern living. The chefs kitchen flows seamlessly into the family, dining, and breakfast areas, overlooking the private backyard with lawn, patio, and mature gardens perfect for entertaining or quiet afternoons at home. The main level also features a formal living room, private office, guest suite with adjacent full bath, and a custom laundry room. Upstairs, the primary suite offers a spa-like retreat with a soaking tub, standing shower, dual sinks, and two additional sun-filled bedrooms sharing a remodeled bath. Located just moments from Burlingame Avenue and downtown San Mateo, and within top-rated South Elementary School and Crocker Middle School, this is timeless Hillsborough livingrefined, walkable, and effortlessly elegant.

4 Beds ⋅ 4 Baths ⋅ ML82025814 MLS

Arrive through a grand circular driveway to this beautifully expanded and remodeled 4-bedroom + office, 3.5-bath residence set on a .41-acre flat lot in sought-after Lower South Hillsborough. Inside, classic elegance meets open modern living. The chefs kitchen flows seamlessly into the family, dining, and breakfast areas, overlooking the private backyard with lawn, patio, and mature gardens perfect for entertaining or quiet afternoons at home. The main level also features a formal living room, private office, guest suite with adjacent full bath, and a custom laundry room. Upstairs, the primary suite offers a spa-like retreat with a soaking tub, standing shower, dual sinks, and two additional sun-filled bedrooms sharing a remodeled bath. Located just moments from Burlingame Avenue and downtown San Mateo, and within top-rated South Elementary School and Crocker Middle School, this is timeless Hillsborough livingrefined, walkable, and effortlessly elegant.

310 Ranelagh RD, Hillsborough

$5,350,000

Extremely rare opportunity available to build your dream home on this flat, over-half an acre south facing lot with perimeter foliage and surrounded by estate homes. No trees obstructing the buildable area, Outstanding location surrounded by estate home in lower South Hillsborough, just minutes to Burlingame, top-rated public and private schools and local country clubs. Enjoy the convenience of being located near the San Francisco Airport and Silicon Valley. First time available in 50 +- years.

3 Beds ⋅ 2 Baths ⋅ ML82046633 MLS

Extremely rare opportunity available to build your dream home on this flat, over-half an acre south facing lot with perimeter foliage and surrounded by estate homes. No trees obstructing the buildable area, Outstanding location surrounded by estate home in lower South Hillsborough, just minutes to Burlingame, top-rated public and private schools and local country clubs. Enjoy the convenience of being located near the San Francisco Airport and Silicon Valley. First time available in 50 +- years.

135 Stonehedge RD, Hillsborough

$5,325,000

A stunning bucolic estate within the exclusive Hillsborough hills perches at the end of a long, private cobblestone drive. This well-appointed home offers 4,240 sq ft of living space on 2.24 acres with views from virtually every room. Backyards large entertaining patio includes a pool/spa, BBQ area and lifesize Kung Fu Panda statue. Kitchens picture windows let natural light gleam off long granite counters and Viking stove. Sizable vaulted family room adjoins for casual dining. A door off the kitchen leads to dining and living rooms, both with coffered ceilings and wainscotting. Primary Suite impresses with marble-appointed bath, while 2 guest beds have ample closets and share a marbled hall bath that offers much space. Lower level offers a spacious media room, home gym and ensuite bedroom. Mud room off the 3-car garage offers laundry, storage and full bath with sauna. Tremendous grounds and ideal floor-plan in a prized neighborhood make this Hillsborough property a must-see.

4 Beds ⋅ 4 Baths ⋅ ML81990249 MLS

A stunning bucolic estate within the exclusive Hillsborough hills perches at the end of a long, private cobblestone drive. This well-appointed home offers 4,240 sq ft of living space on 2.24 acres with views from virtually every room. Backyards large entertaining patio includes a pool/spa, BBQ area and lifesize Kung Fu Panda statue. Kitchens picture windows let natural light gleam off long granite counters and Viking stove. Sizable vaulted family room adjoins for casual dining. A door off the kitchen leads to dining and living rooms, both with coffered ceilings and wainscotting. Primary Suite impresses with marble-appointed bath, while 2 guest beds have ample closets and share a marbled hall bath that offers much space. Lower level offers a spacious media room, home gym and ensuite bedroom. Mud room off the 3-car garage offers laundry, storage and full bath with sauna. Tremendous grounds and ideal floor-plan in a prized neighborhood make this Hillsborough property a must-see.

2530 Skyfarm DR, Hillsborough

$5,300,000

A Modern Transformation with Sweeping Bay Views! Beautifully remodeled for modern living, this Lower Hillsborough home showcases an open-concept design with wide expanses of glass that frame views across the San Francisco Bay and out to the Bay Bridge and East Bay hills. Natural light fills every room, two gas fireplaces add warmth, and wood-like tile floors unify the open living areas. Expansive formal rooms are complemented by a designer kitchen and family room combination, creating an ideal layout for entertaining and everyday comfort. Rounding out the main level are three spacious bedrooms, including a primary suite that takes full advantage of the views, plus there is a flexible-use lower level with large bonus room and adjoining bath. Outside, an expansive view deck with cable-strung railings and terraced lawns extend the living space, providing ample room for entertaining and play. With its modern transformation, dazzling views, and sought-after Lower Hillsborough setting, this home presents the perfect place to live midway between San Francisco and Silicon Valley.

3 Beds ⋅ 4 Baths ⋅ ML82026991 MLS

A Modern Transformation with Sweeping Bay Views! Beautifully remodeled for modern living, this Lower Hillsborough home showcases an open-concept design with wide expanses of glass that frame views across the San Francisco Bay and out to the Bay Bridge and East Bay hills. Natural light fills every room, two gas fireplaces add warmth, and wood-like tile floors unify the open living areas. Expansive formal rooms are complemented by a designer kitchen and family room combination, creating an ideal layout for entertaining and everyday comfort. Rounding out the main level are three spacious bedrooms, including a primary suite that takes full advantage of the views, plus there is a flexible-use lower level with large bonus room and adjoining bath. Outside, an expansive view deck with cable-strung railings and terraced lawns extend the living space, providing ample room for entertaining and play. With its modern transformation, dazzling views, and sought-after Lower Hillsborough setting, this home presents the perfect place to live midway between San Francisco and Silicon Valley.

442 El Arroyo RD, Hillsborough

$5,280,000

Modern California luxury with timeless architectural pedigree this home captures sweeping Bay views from every room of this private, gated Hillsborough retreat. Designed by renowned architect Angus McSweeney, the home showcases open, light-filled spaces anchored by a grand foyer, a striking great room with two fireplaces, and walls of glass framing the horizon. The chef's kitchen features a luminous agate island, Wolf range and a seamless connection to the dining and living areas, perfect for everyday living and effortless entertaining. The primary suite offers floor-to-ceiling windows, fitted closets, and a stone spa bath. Set on nearly an acre of landscaped grounds, this estate includes a new turf lawn, expansive deck, pool, BBQ area, and modern glass-door garage. Ideally located just minutes from Burlingame Avenues vibrant shops and dining, top-rated Hillsborough schools, and convenient access to SFO and Silicon Valley, this residence epitomizes Peninsula living at its most refined.

4 Beds ⋅ 3 Baths ⋅ ML82024529 MLS

Modern California luxury with timeless architectural pedigree this home captures sweeping Bay views from every room of this private, gated Hillsborough retreat. Designed by renowned architect Angus McSweeney, the home showcases open, light-filled spaces anchored by a grand foyer, a striking great room with two fireplaces, and walls of glass framing the horizon. The chef's kitchen features a luminous agate island, Wolf range and a seamless connection to the dining and living areas, perfect for everyday living and effortless entertaining. The primary suite offers floor-to-ceiling windows, fitted closets, and a stone spa bath. Set on nearly an acre of landscaped grounds, this estate includes a new turf lawn, expansive deck, pool, BBQ area, and modern glass-door garage. Ideally located just minutes from Burlingame Avenues vibrant shops and dining, top-rated Hillsborough schools, and convenient access to SFO and Silicon Valley, this residence epitomizes Peninsula living at its most refined.

745 Endfield WAY, Hillsborough

$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

$5,150,000

Elevated on nearly one acre of landscaped grounds, this newly updated single-level property offers exceptional scale, flexibility, and presence in a close-in setting. Updates include brand new European white oak engineered floors throughout, newly painted interiors and cabinetry, plus recently remodeled baths and updated HVAC. The foyer opens to a light-filled living room with waterfall view and dramatic two-way fireplace with carved marble surround flanked by built-ins. A generous great room follows, featuring a barrel-vaulted ceiling, expansive wall of glass, formal dining area, and a well-appointed kitchen with granite countertops, large island beneath an operable skylight, premium appliances, and banquette seating. A separate wing has 4 bedrooms and 2.5 baths, including a spacious primary suite with remodeled luxury bath. 3 additional bedrooms include one customized for office use and two with outside access and shared bath. A detached ADU with full kitchen, bath, walk-in closet, and private 2-car garage (in addition to the main home 2-car garage) adds outstanding flexibility. Outdoor living includes paver patios, synthetic lawn, and an outdoor kitchen with gas and conventional barbecues. Excellent Hillsborough schools and just over one mile from Broadway shops and dining.

4 Beds ⋅ 4 Baths ⋅ ML82037294 MLS

Elevated on nearly one acre of landscaped grounds, this newly updated single-level property offers exceptional scale, flexibility, and presence in a close-in setting. Updates include brand new European white oak engineered floors throughout, newly painted interiors and cabinetry, plus recently remodeled baths and updated HVAC. The foyer opens to a light-filled living room with waterfall view and dramatic two-way fireplace with carved marble surround flanked by built-ins. A generous great room follows, featuring a barrel-vaulted ceiling, expansive wall of glass, formal dining area, and a well-appointed kitchen with granite countertops, large island beneath an operable skylight, premium appliances, and banquette seating. A separate wing has 4 bedrooms and 2.5 baths, including a spacious primary suite with remodeled luxury bath. 3 additional bedrooms include one customized for office use and two with outside access and shared bath. A detached ADU with full kitchen, bath, walk-in closet, and private 2-car garage (in addition to the main home 2-car garage) adds outstanding flexibility. Outdoor living includes paver patios, synthetic lawn, and an outdoor kitchen with gas and conventional barbecues. Excellent Hillsborough schools and just over one mile from Broadway shops and dining.

2260 Summit DR, Hillsborough

$5,000,000

Incredible opportunity to build your dream home in one of the San Francisco Peninsula's most desired towns! Located at the end of a cul-de-sac in Lower North Hillsborough, experience an expansive sun-drenched lot on half an acre. Flat and entirely usable, this rare rectangular parcel is perfectly setup to maximize design and use of an incredible home. Enjoy use of top-rated Hillsborough schools, and a fantastic location near downtown areas and commute routes. An opportunity not to be missed!

ML82019305 MLS

Incredible opportunity to build your dream home in one of the San Francisco Peninsula's most desired towns! Located at the end of a cul-de-sac in Lower North Hillsborough, experience an expansive sun-drenched lot on half an acre. Flat and entirely usable, this rare rectangular parcel is perfectly setup to maximize design and use of an incredible home. Enjoy use of top-rated Hillsborough schools, and a fantastic location near downtown areas and commute routes. An opportunity not to be missed!

8 Reynolds CT, Hillsborough

$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

$4,900,000

5 Beds ⋅ 4 Baths ⋅ ML82028079 MLS

1015 Woodland DR, Hillsborough

$4,800,000

Experience the privacy and tranquility of an estate setting, where serene surroundings are complemented by views of San Francisco and the East Bay. A formal entry welcomes you into expansive living and family rooms filled with natural light, highlighted by soaring ceilings and skylights throughout. The well-appointed floor plan features four bedrooms and three baths, including a spacious primary suite with its own private balconyperfect for enjoying the stunning views. The bright kitchen offers a charming breakfast area, ideal for casual dining and everyday living. Outdoors, a grand patio and pool provide an exceptional setting for entertaining or relaxing in complete privacy. Thoughtfully curated landscaping and mature plantings create a lush, picturesque environment, enhancing the homes sense of retreat. Located within the highly regarded Hillsborough school district, this property offers a rare blend of elegance, comfort, and convenience.

4 Beds ⋅ 3 Baths ⋅ ML82042683 MLS

Experience the privacy and tranquility of an estate setting, where serene surroundings are complemented by views of San Francisco and the East Bay. A formal entry welcomes you into expansive living and family rooms filled with natural light, highlighted by soaring ceilings and skylights throughout. The well-appointed floor plan features four bedrooms and three baths, including a spacious primary suite with its own private balconyperfect for enjoying the stunning views. The bright kitchen offers a charming breakfast area, ideal for casual dining and everyday living. Outdoors, a grand patio and pool provide an exceptional setting for entertaining or relaxing in complete privacy. Thoughtfully curated landscaping and mature plantings create a lush, picturesque environment, enhancing the homes sense of retreat. Located within the highly regarded Hillsborough school district, this property offers a rare blend of elegance, comfort, and convenience.

965 Parrott DR, Hillsborough

$4,800,000

For the very first time in its storied history, this 1936 family estate is being offered to the public. This classic English Tudor is a landmark in its own right, a home that gracefully bridges Hillsborough's past and present. Set on nearly an acre of level land with views of the Bay and San Francisco skyline, the residence embodies timeless elegance. Its centerpiece is a remarkable floating spiral staircase anchored only at the bottom and top. With a large open kitchen connecting to the family room, plus 5 bedrooms and 5 full bathrooms (2 half baths), the estate is ready and waiting for its next owner (some photos are virtually staged)! There is a bedroom, library and full bathroom on the main level. The primary bedroom and 3 add'l bedrooms are upstairs. Outdoors, the gardens carry the signature of renowned landscape architect Thomas Church, whose designs shaped much of California's most beautiful private estates with broad lawns, graceful plantings and private spaces. Built by the Wisnoms, one of the founding families of San Mateo, The National Bank of San Mateo and cousins of Wisnoms Hardware family. This offering represents a rare opportunity: to own a piece of Hillsborough history and to become the next steward of a home designed with both legacy and livability at its core.

5 Beds ⋅ 7 Baths ⋅ ML82022191 MLS

For the very first time in its storied history, this 1936 family estate is being offered to the public. This classic English Tudor is a landmark in its own right, a home that gracefully bridges Hillsborough's past and present. Set on nearly an acre of level land with views of the Bay and San Francisco skyline, the residence embodies timeless elegance. Its centerpiece is a remarkable floating spiral staircase anchored only at the bottom and top. With a large open kitchen connecting to the family room, plus 5 bedrooms and 5 full bathrooms (2 half baths), the estate is ready and waiting for its next owner (some photos are virtually staged)! There is a bedroom, library and full bathroom on the main level. The primary bedroom and 3 add'l bedrooms are upstairs. Outdoors, the gardens carry the signature of renowned landscape architect Thomas Church, whose designs shaped much of California's most beautiful private estates with broad lawns, graceful plantings and private spaces. Built by the Wisnoms, one of the founding families of San Mateo, The National Bank of San Mateo and cousins of Wisnoms Hardware family. This offering represents a rare opportunity: to own a piece of Hillsborough history and to become the next steward of a home designed with both legacy and livability at its core.

923 Hayne RD, Hillsborough

$4,780,000

Exceptional private and gated estate on a rare 25,990 sq ft corner lot in Hillsboroughs most prestigious enclave. Elevated and secluded with lush landscaping, soaring trees, and a grand presence. Two luxurious primary bedroom suites on the main level feature spa-style baths with Jacuzzi tubs, glass showers, dual vanities, large walk-in closets, wet bars in the 2 masters bedroom and 1 in the family room, offering the ultimate in comfort and convenience. Ideal for multi-generational living or hosting in style. Dramatic foyer with high ceiling, sweeping staircase, elegant column accents, formal living and dining rooms, and a sun-filled family room with a built-in wet bar, perfect for entertaining. The gourmet kitchen boasts granite counters, high-end appliances, an island with a second sink, and a cozy breakfast nook. Upstairs offers an additional primary suite, a spacious loft, and a private balcony. Resort-inspired amenities include a rooftop lounge, private courtyard, sports court, detached three-car garage, and a gated driveway. A rare opportunity for luxury, privacy, and seamless indoor-outdoor living.

5 Beds ⋅ 6 Baths ⋅ ML82022295 MLS

Exceptional private and gated estate on a rare 25,990 sq ft corner lot in Hillsboroughs most prestigious enclave. Elevated and secluded with lush landscaping, soaring trees, and a grand presence. Two luxurious primary bedroom suites on the main level feature spa-style baths with Jacuzzi tubs, glass showers, dual vanities, large walk-in closets, wet bars in the 2 masters bedroom and 1 in the family room, offering the ultimate in comfort and convenience. Ideal for multi-generational living or hosting in style. Dramatic foyer with high ceiling, sweeping staircase, elegant column accents, formal living and dining rooms, and a sun-filled family room with a built-in wet bar, perfect for entertaining. The gourmet kitchen boasts granite counters, high-end appliances, an island with a second sink, and a cozy breakfast nook. Upstairs offers an additional primary suite, a spacious loft, and a private balcony. Resort-inspired amenities include a rooftop lounge, private courtyard, sports court, detached three-car garage, and a gated driveway. A rare opportunity for luxury, privacy, and seamless indoor-outdoor living.

1531 Wedgewood DR, Hillsborough

$4,750,000

Commanding sweeping views of San Francisco, the Bay Bridge, and a glittering skyline, 1340 View Haven is a contemporary Hillsborough retreat designed to showcase its extraordinary vantage point. A private tree lined setting, the home unfolds through a dramatic double-height foyer with a glass-encased staircase and suspended artistic wine display. The house unfolds to expansive, light-filled living areas framed by walls of glass blurring the line between indoors and out. A sleek, European-style kitchen is anchored by a sculptural quartz island and premium appliancesseamlessly flows into dining and family areas, all opening to view terraces designed for elevated entertaining. The house has five bedrooms with a stunning primary bedroom retreat with panoramic outlooks, private balcony, fireplace, and spa-like bath. Outside, a view-facing pool and spa, fire pit, and heated terraces create a space for year round enjoyment. Recent structural enhancements include retrofitting to the deck, foundation, and retaining walls, reinforcing both integrity and longevity.

5 Beds ⋅ 5 Baths ⋅ ML82041555 MLS

Commanding sweeping views of San Francisco, the Bay Bridge, and a glittering skyline, 1340 View Haven is a contemporary Hillsborough retreat designed to showcase its extraordinary vantage point. A private tree lined setting, the home unfolds through a dramatic double-height foyer with a glass-encased staircase and suspended artistic wine display. The house unfolds to expansive, light-filled living areas framed by walls of glass blurring the line between indoors and out. A sleek, European-style kitchen is anchored by a sculptural quartz island and premium appliancesseamlessly flows into dining and family areas, all opening to view terraces designed for elevated entertaining. The house has five bedrooms with a stunning primary bedroom retreat with panoramic outlooks, private balcony, fireplace, and spa-like bath. Outside, a view-facing pool and spa, fire pit, and heated terraces create a space for year round enjoyment. Recent structural enhancements include retrofitting to the deck, foundation, and retaining walls, reinforcing both integrity and longevity.

1340 View Haven RD, Hillsborough

$4,700,000

4 Beds ⋅ 3 Baths ⋅ ML82059590 MLS

1520 Tartan Trail RD, Hillsborough

$4,580,000

ONE OF HILLSBOROUGH'S BEST DEALS, SERIOUSLY! Set on an oversized lot of nearly 1 acre, this single-story home was recently remodeled with sleek contemporary designs and modern amenities. The open layout seamlessly connects the living room and high-end chefs kitchen, ideal for entertaining. Enjoy spa-like bathrooms, a luxurious master suite, a versatile bonus room downstairs, recessed lighting, tasteful flooring, coffered ceilings, and stone fireplaces as striking centerpieces. An integrated Sonos sound system complements the expansive indoor-outdoor flow, with a huge flat backyard offering bay views and endless potential for expansion, an ADU, or additional deck space well beyond the back fence. Complete with a 3-car garage, access to top-rated schools, and easy commuting via Highway 280, all just minutes from downtown Burlingame. This home offers it all, YOU HAVE TO SEE IT TO EXPERIENCE JUST HOW GREAT IT IS!

3 Beds ⋅ 2 Baths ⋅ ML82012139 MLS

ONE OF HILLSBOROUGH'S BEST DEALS, SERIOUSLY! Set on an oversized lot of nearly 1 acre, this single-story home was recently remodeled with sleek contemporary designs and modern amenities. The open layout seamlessly connects the living room and high-end chefs kitchen, ideal for entertaining. Enjoy spa-like bathrooms, a luxurious master suite, a versatile bonus room downstairs, recessed lighting, tasteful flooring, coffered ceilings, and stone fireplaces as striking centerpieces. An integrated Sonos sound system complements the expansive indoor-outdoor flow, with a huge flat backyard offering bay views and endless potential for expansion, an ADU, or additional deck space well beyond the back fence. Complete with a 3-car garage, access to top-rated schools, and easy commuting via Highway 280, all just minutes from downtown Burlingame. This home offers it all, YOU HAVE TO SEE IT TO EXPERIENCE JUST HOW GREAT IT IS!

1620 Marlborough RD, Hillsborough

$4,579,000

Fresh updates, incredible Bay and airport runway views, and impressive scale on more than one-half acre. Predominantly arranged on one level, the 6-bedroom, 5.5-bath floor plan has remarkable flexibility with options to accommodate offices, guest quarters, recreation, fitness, and more. Every room opens to the outdoors with 3 front terraces overlooking the Bay plus a tremendous newly built deck in clear redwood. Freshly painted inside, refinished hardwood floors, and new carpet in some rooms ready for immediate enjoyment and also an opportunity to further transform. Grand entertaining spaces include a vast living room, formal dining room, kitchen designed for a true chef with both gas and electric cooktops plus wok burner, and a tremendous family room. Peaceful non-through street just minutes from top Hillsborough schools including West and Crocker, hiking trails, and Highway 280 to San Francisco and Silicon Valley.

6 Beds ⋅ 6 Baths ⋅ ML82025146 MLS

Fresh updates, incredible Bay and airport runway views, and impressive scale on more than one-half acre. Predominantly arranged on one level, the 6-bedroom, 5.5-bath floor plan has remarkable flexibility with options to accommodate offices, guest quarters, recreation, fitness, and more. Every room opens to the outdoors with 3 front terraces overlooking the Bay plus a tremendous newly built deck in clear redwood. Freshly painted inside, refinished hardwood floors, and new carpet in some rooms ready for immediate enjoyment and also an opportunity to further transform. Grand entertaining spaces include a vast living room, formal dining room, kitchen designed for a true chef with both gas and electric cooktops plus wok burner, and a tremendous family room. Peaceful non-through street just minutes from top Hillsborough schools including West and Crocker, hiking trails, and Highway 280 to San Francisco and Silicon Valley.

30 Live Oak LN, Hillsborough

$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

$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

$4,500,000

3 Beds ⋅ 3 Baths ⋅ ML82032145 MLS

571 Craig RD, Hillsborough

$4,423,560

Hillsborough opportunity on expansive 21,789+/- SF mostly flat lot. Classic 2-story SFR offers 2,890+/- SF, 4BD, 3.5BA incl 2 en-suites + 1 BD on main level ideal for guests, office or multi-gen living. Vaulted entry, formal living rm w/wood-burning FP, sep family rm w/2nd wood-burning FP & wet bar w/sink. Spacious eat-in kitchen w/abundant natural light, lg pantry & views of backyard & pool. Formal dining rm overlooks yard & mature trees. South-facing rear exposure provides all-day sun. Private backyard w/functioning in-ground pool serviced weekly. Upstairs primary suite w/updated wood flrs & balcony overlooking backyard; addl BD w/private balcony facing street. 3-car garage w/high-end custom wood garage doors. Comp shingle roof. Fresh interior paint, deep cleaned, ext power washed. Property needs loving care & thoughtful updatesrare chance to customize in prime Lakeview location where updated homes command significantly higher values. Excellent Hillsborough public schools. Minutes to Burlingame Ave, Hwy 280/92, top Peninsula amenities. Exceptional upside, setting & scale.

4 Beds ⋅ 4 Baths ⋅ ML82032273 MLS

Hillsborough opportunity on expansive 21,789+/- SF mostly flat lot. Classic 2-story SFR offers 2,890+/- SF, 4BD, 3.5BA incl 2 en-suites + 1 BD on main level ideal for guests, office or multi-gen living. Vaulted entry, formal living rm w/wood-burning FP, sep family rm w/2nd wood-burning FP & wet bar w/sink. Spacious eat-in kitchen w/abundant natural light, lg pantry & views of backyard & pool. Formal dining rm overlooks yard & mature trees. South-facing rear exposure provides all-day sun. Private backyard w/functioning in-ground pool serviced weekly. Upstairs primary suite w/updated wood flrs & balcony overlooking backyard; addl BD w/private balcony facing street. 3-car garage w/high-end custom wood garage doors. Comp shingle roof. Fresh interior paint, deep cleaned, ext power washed. Property needs loving care & thoughtful updatesrare chance to customize in prime Lakeview location where updated homes command significantly higher values. Excellent Hillsborough public schools. Minutes to Burlingame Ave, Hwy 280/92, top Peninsula amenities. Exceptional upside, setting & scale.

100 Rizal DR, Hillsborough

$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 PL, Hillsborough

$4,300,000

COMP PURPOSES ONLY

5 Beds ⋅ 4 Baths ⋅ ML82036641 MLS

COMP PURPOSES ONLY

30 Inverness WAY, Hillsborough

$4,195,000

This turn-key, single-level ranch-style residence offers a functional layout with a spacious floor plan that flows seamlessly for both everyday living and effortless entertaining. The expansive grounds are designed for relaxation and recreation, featuring a sparkling pool with a dedicated pool bathhouse, a fire pit with built-in seating, generous yard with great lawn space framed by mature landscaping. A three-car garage provides ample parking and storage. While move-in ready today, the property also presents an exciting opportunity to update or reimagine, creating your dream Hillsborough retreat.

4 Beds ⋅ 4 Baths ⋅ ML82023761 MLS

This turn-key, single-level ranch-style residence offers a functional layout with a spacious floor plan that flows seamlessly for both everyday living and effortless entertaining. The expansive grounds are designed for relaxation and recreation, featuring a sparkling pool with a dedicated pool bathhouse, a fire pit with built-in seating, generous yard with great lawn space framed by mature landscaping. A three-car garage provides ample parking and storage. While move-in ready today, the property also presents an exciting opportunity to update or reimagine, creating your dream Hillsborough retreat.

1430 Lakeview DR, Hillsborough

$3,900,000

Set on a generous and private 0.69-acre lot with breathtaking views, this lovely updated 4-bedroom, 2.5-bath home offers the perfect blend of modern comfort and timeless elegance. Designed for today's lifestyle, it features light-filled interior spaces and a seamless flow ideal for entertaining. Highlights include chic flooring, tray ceilings, recessed lighting, and expansive picture windows framing the lush, natural surroundings. The open-concept dining area, complete with a fireplace, is accented by French doors that open to a sizable patio and level lawn, perfect for indoor-outdoor living. The chef's kitchen boasts a center island and top-of-the-line appliances, flowing effortlessly into a spacious great room with direct access to a large deck showcasing spectacular views. 3 bedrooms and 2.5 baths are conveniently located on the main level, including a luxurious primary suite with a large walk-in closet and a spa-inspired bath. A 4th bedroom is located on the lower level, offering flexibility for guests, a home office, or additional living space. A long, sweeping driveway bordered by manicured boxwood hedges, vibrant rose bushes, and elegant Japanese maples leads to a 2-car garage with additional storage, completing the appeal of this exceptional, turnkey property.

4 Beds ⋅ 3 Baths ⋅ ML82031459 MLS

Set on a generous and private 0.69-acre lot with breathtaking views, this lovely updated 4-bedroom, 2.5-bath home offers the perfect blend of modern comfort and timeless elegance. Designed for today's lifestyle, it features light-filled interior spaces and a seamless flow ideal for entertaining. Highlights include chic flooring, tray ceilings, recessed lighting, and expansive picture windows framing the lush, natural surroundings. The open-concept dining area, complete with a fireplace, is accented by French doors that open to a sizable patio and level lawn, perfect for indoor-outdoor living. The chef's kitchen boasts a center island and top-of-the-line appliances, flowing effortlessly into a spacious great room with direct access to a large deck showcasing spectacular views. 3 bedrooms and 2.5 baths are conveniently located on the main level, including a luxurious primary suite with a large walk-in closet and a spa-inspired bath. A 4th bedroom is located on the lower level, offering flexibility for guests, a home office, or additional living space. A long, sweeping driveway bordered by manicured boxwood hedges, vibrant rose bushes, and elegant Japanese maples leads to a 2-car garage with additional storage, completing the appeal of this exceptional, turnkey property.

30 Calaveras CT, Hillsborough

$3,900,000

Situated in the prestigious Carolands, 530 Darrell Rd combines timeless character with modern convenience. With easy access to I-280, it offers equal commute times to San Francisco and Silicon Valley, lies within a top-rated school district, and is just 2.5 miles from Downtown Burlingame. Double wooden entry doors with custom leaded glass (sold separately) open to a bright living room with stone fireplace, wood-paneled ceiling, recessed lighting, and wall of glass to the covered lanai. The dining room, framed by Japanese-inspired sliding doors, is lit by skylights that reflect off hardwood floors. The eat-in kitchen has a breakfast nook, pantry, butler's pass-through, granite island with sink and bar, built-ins including dual ovens, cooktop with hood, paneled refrigerator, and a rare cooking fireplace. Off the kitchen are an en-suite guest room with outdoor access, maid's room, and garage. A bedroom/office and powder room complement the foyer, while the opposite wing hosts 3 bedrooms and 2 baths, including the primary suite with high ceilings, fireplace, patio, and spa-like bath. Outdoors enjoy a lanai with pond, fountains, waterfall, sparkling pool, patios, lawn, mature trees, outdoor powder, paver driveway, 2-car garage, and shed.

5 Beds ⋅ 5 Baths ⋅ ML82022122 MLS

Situated in the prestigious Carolands, 530 Darrell Rd combines timeless character with modern convenience. With easy access to I-280, it offers equal commute times to San Francisco and Silicon Valley, lies within a top-rated school district, and is just 2.5 miles from Downtown Burlingame. Double wooden entry doors with custom leaded glass (sold separately) open to a bright living room with stone fireplace, wood-paneled ceiling, recessed lighting, and wall of glass to the covered lanai. The dining room, framed by Japanese-inspired sliding doors, is lit by skylights that reflect off hardwood floors. The eat-in kitchen has a breakfast nook, pantry, butler's pass-through, granite island with sink and bar, built-ins including dual ovens, cooktop with hood, paneled refrigerator, and a rare cooking fireplace. Off the kitchen are an en-suite guest room with outdoor access, maid's room, and garage. A bedroom/office and powder room complement the foyer, while the opposite wing hosts 3 bedrooms and 2 baths, including the primary suite with high ceilings, fireplace, patio, and spa-like bath. Outdoors enjoy a lanai with pond, fountains, waterfall, sparkling pool, patios, lawn, mature trees, outdoor powder, paver driveway, 2-car garage, and shed.

530 Darrell RD, Hillsborough

$3,820,000

A rare gem on a quaint street in Lower Hillsborough. This 3-bedroom, 3-bath home features abundant light, oversized windows, and high ceilings on the second level, seamlessly connecting the indoors to the serene outdoor yard. Look for partial bay views from the living and dining rooms. The updated kitchen offers quality appliances, generous counter space, and a cozy dining area overlooking the side yard. Lovingly cared for by the same owners for over 20 years, the home combines warmth, functionality, and privacy. A circular driveway adds convenience, completing this elegant, tranquil setting.

3 Beds ⋅ 3 Baths ⋅ ML82025890 MLS

A rare gem on a quaint street in Lower Hillsborough. This 3-bedroom, 3-bath home features abundant light, oversized windows, and high ceilings on the second level, seamlessly connecting the indoors to the serene outdoor yard. Look for partial bay views from the living and dining rooms. The updated kitchen offers quality appliances, generous counter space, and a cozy dining area overlooking the side yard. Lovingly cared for by the same owners for over 20 years, the home combines warmth, functionality, and privacy. A circular driveway adds convenience, completing this elegant, tranquil setting.

465 El Centro RD, Hillsborough

$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