Hillsborough Homes with Pool for Sale - Larsen Real Estate Team

9 Beds ⋅ 7 Baths ⋅ ML82062082 MLS

GRANDEUR. MODERN LUXURY. OVER 2 ACRES + NEW ADU + EXTENSIVELY MODERNIZED A rare Hillsborough estate where irreplaceable old-world craftsmanship meets todays technology and comfort. Extensively modernized with a new kitchen, updated baths, new heating and air conditioning, generator, and sophisticated smart-home systems. Hundreds of LED lights, gates, climate, security and other home functions can be controlled remotely.******The craftsmanship of yesterdaybeautifully preserved. The technology and comfort of todayalready done. DONT LET THE AGE FOOL YOU. THIS IS A HISTORIC MASTERPIECE REIMAGINED FOR MODERN LIVING.

85 Fagan DR, Hillsborough

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

$5,998,000

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

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

$15,695,000

5 Beds ⋅ 8 Baths ⋅ ML82061925 MLS

An elegant study in Refined Modern Country architecture, this newly completed Hillsborough estate is defined by proportion, craftsmanship, & connection to the landscape. Set on a level 0.51-acre lot in Country Club Manor, top-tier schools & Downtown Burlingame are within easy reach. Classic covered porches, architectural details, & bespoke millwork establish a graceful rhythm. Inside, approximately 4,933 sq. ft. unfolds, balancing comfort & understated sophistication, encompassing 4 spacious bedrooms, 5 full baths, 2 powder rooms, 2 laundry rooms, & a beautifully appointed mudroom. Expansive glass doors draw the outdoors inward, opening the living spaces to grounds as an extension of the home. Al fresco living spaces invite long lunches & evening gatherings, while an outdoor kitchen, lush landscaping, & sparkling pool create an atmosphere that feels cultivated & relaxed. Set apart for privacy, the approximately 774 sq. ft. guest house offers 1 bedroom, 1 bath, & a private sauna retreat for guests, extended family, or work. Entirely custom-built & meticulously crafted, this exceptional estate embodies a rare level of California luxury: sophisticated yet welcoming, grand yet intimate, & designed to become the backdrop for a lifetime of unforgettable moments.

1950 Ralston AVE, Hillsborough

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

$4,398,000

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 DR, Hillsborough

Listed by Henry Chu, 650-918-8118 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$5,498,000

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 CT, Hillsborough

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

$12,000,000

7 Beds ⋅ 7 Baths ⋅ ML82059857 MLS

Offered as a rare presale opportunity with the ability to personalize select finishes, this modern architectural masterpiece is estimated for completion in Q3 2027. Privately situated on a level half-acre cul-de-sac lot, the residence offers approximately 5,722 square feet of refined living space, including an attached JADU and detached ADU . A dramatic double-height foyer with a full-height porcelain slab feature wall and statement chandelier creates a striking first impression. Soaring ceilings, premium engineered oak flooring, a dramatic floating staircase, and walls of glass create a striking sense of scale and effortless indoor-outdoor living. The showpiece kitchen features custom European-inspired cabinetry with warm natural wood finishes, natural quartzite surfaces, a waterfall island, and premium Miele appliances. A private balcony, spa-inspired primary bath, custom wine display, Control4 automation, and beautifully landscaped grounds complete the residence. Buy early for preferred pricing and design personalization.

20 Castle CT, Hillsborough

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

$4,099,000

4 Beds ⋅ 3 Baths ⋅ ML82059435 MLS

HILLSBOROUGH'S BEST JUST GOT BETTER WITH A NEW PRICE!!! A MUST SEE! Located in the sought-after Lakeview neighborhood, this private and inviting home is surrounded by mature trees and offers an abundance of indoor and outdoor spaces for comfortable living and entertaining. The main level features a spacious living room and family room combination connected to the dining area, with large windows and glass doors filling the home with natural light and creating a seamless connection to the outdoors. The kitchen offers all the essentials for everyday living, while three bedrooms on the main level include a generously sized primary suite. The lower level adds versatility with a recreation room and an additional guest en-suite bedroom. Behind the garage, a separate finished space provides even more flexibility and can serve as a media room, home office, gym, or whatever suits your needs. Outdoors, enjoy multiple patio areas, expansive open spaces, several decks, mature landscaping, and an ice-cold swimming pool / hot tub combo; creating a private setting for relaxing or entertaining. There is so much to offer and only so much space to say it all. Best of all, this exceptional location provides access to some of Californias finest schools & is just a short drive to downtown Burlingame.

1548 Kingswood DR, Hillsborough

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

$4,500,000

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

$18,770,000

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 AVE, Hillsborough

Listed by Joseph Miller, 650-455-6552 from Miller/Steil Properties
(If provided) CoList: Chelsea Miller from Miller/Steil Properties

Sold listing courtesy of Stanley Lo from GRBA

$10,300,000

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 LN, Hillsborough

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

Sold listing courtesy of Michele Oravec from APR

$4,400,000

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

Listed by Emma Elfving, 650-773-5115 from Compass
(If provided) CoList: Erik Elfving from Compass

Sold listing courtesy of Julie Boc from SGP

$14,995,000

6 Beds ⋅ 9 Baths ⋅ ML82056682 MLS

A rare offering in coveted South Hillsborough, 810 Lombardi Lane is a private, gated estate set on nearly one level acre of beautifully curated grounds at the end of an exclusive cul-de-sac. Timeless architecture, soaring ceilings, custom millwork, and walls of glass create light-filled interiors that flow effortlessly to the resort-inspired outdoor spaces. Designed for both everyday living and grand-scale entertaining, the home features an exceptional chef's kitchen, expansive gathering spaces, and seamless indoor-outdoor living with accordion glass doors opening to a saltwater pool, outdoor kitchen, custom fire pit, and lush architectural landscaping. The luxurious primary suite is a private retreat with a spa-inspired bath and tranquil garden patio, while each additional bedroom offers a beautifully appointed en suite with its own distinctive designer tilework. A detached ADU with dramatic 12-foot wood-beam ceilings overlooks the pool and provides exceptional flexibility for guests, a private office, wellness studio, or multigenerational living. Combining remarkable privacy, timeless craftsmanship, and an unrivaled South Hillsborough location, this exceptional estate embodies luxurious Peninsula living.

810 Lombardi LN, Hillsborough

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

$12,019,880

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

$8,999,000

3 Beds ⋅ 4 Baths ⋅ ML82044812 MLS

RARE OPPORTUNITY! Hurry, properties of this caliber, on this size lot, in this location rarely come on the market! You can remodel a home, but you can never recreate this location, this cul-de-sac, or this extraordinary lot. One of Hillsboroughs most sought-after and prestigious streets. Tucked away at the end of a quiet cul-de-sac, this extraordinary estate sits on one of the largest lots in the neighborhood, an exceptionally rare offering that will not become available again for years. Walking distance to vibrant downtown Burlingame and some of California's best public schools. Whether you choose to enjoy this beautiful estate as it is or create your own dream luxury residence, this is truly a once-in-a-lifetime opportunity in an irreplaceable location. Enjoy unmatched privacy surrounded by magnificent mature trees and lush landscaping, creating your own peaceful retreat. DO NOT WAIT, SERIOUSLY!!!

2155 Geri LN, Hillsborough

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

$7,600,000

5 Beds ⋅ 5 Baths ⋅ ML82054472 MLS

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

2245 Oakdale RD, Hillsborough

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

Sold listing courtesy of Sandra Comaroto from APR

$5,510,000

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

Listed by Mike Foor, 650-430-6500 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Eric Chu from SGP

$11,475,000

6 Beds ⋅ 8 Baths ⋅ ML82054575 MLS

Situated in one of the best locations in Hillsborough, 280 Uplands Dr is a rare opportunity on a flat, private, over-half-acre corner lot, steps from Crystal Springs Uplands School & South Elementary. This estate offers 6 bedrooms, 6 full baths & 2 half baths, all en-suite, with attached ADU. A dedicated office with fireplace, home theater with theatrical lighting and built-in refreshment station, and an adjoining bonus room. Upstairs, a bedroom suite is joined by a multi-purpose room with fireplace, ideal as a gym, bar, or rec space. All mechanical systems replaced, including new roof and four separate HVAC systems for comfort and efficiency. All-new interior finishes and a chef's kitchen with premium appliances, including Sub-Zero. Private rear driveway with automatic gate. Outdoor spaces offer true California entertaining: brand-new pool and spa with automatic safety cover, outdoor kitchen, Trex decking, new hardscape and paver walkways. Ideally suited for social events, with ample parking and a layout that flows seamlessly from indoors to out.

280 Uplands DR, Hillsborough

Listed by Michael Haywood Jr., 650-773-0266 from eXp Realty of California Inc
(If provided) CoList: from

$11,000,000

5 Beds ⋅ 7 Baths ⋅ ML82052749 MLS

Welcome to 433 El Centro, a newly remodeled luxury estate in Hillsborough. Situated on 0.41 acres, this exceptional property offers refined living designed for entertaining and everyday comfort. The home features 5 bedrooms (including the ADU), 5 full baths, 2 half baths, and a bonus room/den. The gourmet chef's kitchen boasts premium paneled appliances, a wine cooler, and opens to a spacious family room. Additional highlights include built-in speakers, a custom wet bar, dedicated media room, temperature-controlled wine cellar, and laundry rooms on both levels. The luxurious primary suite offers a private office, walk-in closet, and spa-inspired bath with heated floors, towel racks, soaking tub, and dual showers. All secondary bedrooms feature en-suite baths for added comfort and privacy. Designed for seamless indoor-outdoor living, the grounds showcase a pool, spa, fire pit, expansive lawn, outdoor TV, and covered BBQ pavilion with prep space, refrigerator, and ample seating. Conveniently located near top-rated Hillsborough schools, parks, Downtown Burlingame, and transportation, this turnkey estate presents a rare opportunity in one of the Peninsula's most sought-after communities.

433 El Centro RD, Hillsborough

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

$28,995,000

11 Beds ⋅ 15 Baths ⋅ ML82038870 MLS

A secluded trophy estate in the heart of highly coveted Lower North Hillsborough, this extraordinary 2.4+ acre property offers rare scale and privacy on one of the towns largest parcels. The French Chateau-inspired residence was once home to Hollywood icon Bing Crosby and is rich with storied provenance, including connections to the legendary Seabiscuit and curated antique details from the Hearst Collection. Thoughtfully updated by the current owner, the home spans four levels and features 11 bedrooms, 10 full baths, and 5 half baths, blending grand architectural presence with a warm, livable layout. Designed for both intimate daily living and elegant entertaining, the floor plan includes multiple salons, a formal dining room, a wood-paneled library, a private office, and a distinct guest wing. The park-like grounds showcase sweeping lawns, a resort-style pool with fountains, and expansive open space, creating a serene and majestic setting. With its remarkable history, refined craftsmanship, and exceptional acreage, this is a truly irreplaceable legacy estate an unparalleled opportunity to own a landmark property from California's Golden Era.

1200 Armsby DR, Hillsborough

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

$8,038,000

6 Beds ⋅ 4 Baths ⋅ ML82053844 MLS

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

820 Eucalyptus AVE, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA

$8,800,000

6 Beds ⋅ 6 Baths ⋅ ML82053405 MLS

FOR COMP PURPOSES ONLY

30 Bayberry PL, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR

$10,500,000

5 Beds ⋅ 5 Baths ⋅ ML82053151 MLS

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

1850 Brookvale RD, Hillsborough

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

Sold listing courtesy of Raziel A. Ungar from APR

$6,400,000

3 Beds ⋅ 3 Baths ⋅ ML82051604 MLS

Built in 1967 this home has retained its single level ranch layout while benefiting from a complete modern remodel. Gorgeous wide plank oak hardwood flooring runs throughout the public spaces. The beautifully landscaped front yard leads to a formal entry that opens onto the living room with a stunning view of the resort-style backyard complete with a pool and spa, a full outdoor kitchen with grill, a putting green, and a bocci ball court. This is all backdropped by sweeping views of the peninsula and the San Francisco Bay. Both the living room and family room overlook the backyard and feature modern working fireplaces. The spacious, bright kitchen features a large center island with room for seating, a SubZero refrigerator, a Wolf gas stove top and oven, and a Bosch dishwasher. Off of the kitchen are a full laundry room as well as an immaculate three-car garage. The opposite end of the home contains three bedrooms. The large, bright primary suite has french doors that open to the backyard. The suite also includes a spacious bathroom with two washstands and a luxurious shower as well as a large walk in closet. The additional two bedrooms overlook the lush front yard and share a full size bathroom. This home is in a perfect location with easy access to Highways 92, 280, and 101.

995 Woodland DR, Hillsborough

Listed by Mark Scafine, 650-222-4530 from The Scafine Group
(If provided) CoList: from

Sold listing courtesy of Jim Arbeed from CBR

$15,190,000

5 Beds ⋅ 6 Baths ⋅ ML82051492 MLS

-- COMP PURPOSES ONLY --

245 W Santa Inez AVE, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA

$3,700,000

4 Beds ⋅ 4 Baths ⋅ ML82051481 MLS

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

1407 Carlton RD, Hillsborough

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

Sold listing courtesy of Minh-Ngoc Nguyen from KINOKO

$6,300,000

5 Beds ⋅ 4 Baths ⋅ ML82041280 MLS

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

973 Baileyana RD, Hillsborough

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

Sold listing courtesy of Rachel Sudano from CBR

$6,421,000

4 Beds ⋅ 3 Baths ⋅ ML82051272 MLS

Nestled in prestigious Lower North Hillsborough, this distinguished single level residence offers a bright, airy & luxurious living style. The over half acre level lot offers European inspired gardens with flowering plants and meandering foot paths. The impressive front courtyard enters to a grand formal living room with walls of windows overlooking the spectacular gardens & pool area. The spacious family room with fireplace also looks out to the resort style grounds. A formal dining room, ideal for entertaining, is off the beautifully updated kitchen with its comfortable eating area. The laundry room and half bath, so handy off the kitchen, leads to the oversize attached three car garage. The primary suite with access to the gardens, has multiple closets including a large walk in style, and an updated bathroom. Other bedrooms are roomy & cheerful. The grounds feature multiple inviting gathering areas & remarkable landscaping, a large level lawn area, children's play area all with charming winding footpaths throughout. The beautiful pool/spa setting offers exceptional privacy creating a serene retreat space This truly special home offers it all and is so close to all the Burlingame shops, services & restaurants, and all transportation options nearby too! An enchanting home!

2140 Carmelita AVE, Hillsborough

Listed by Brian Boisson, 650-302-6458 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Sandra Comaroto from APR

$8,250,000

4 Beds ⋅ 6 Baths ⋅ ML82051234 MLS

15 Annescourt, Hillsborough

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

Sold listing courtesy of Geoffrey Nelson from CBR

$10,500,000

7 Beds ⋅ 8 Baths ⋅ ML82050881 MLS

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

225 TOBIN CLARK DR, Hillsborough

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

Sold listing courtesy of Shaun Walter from CBR

$6,500,000

5 Beds ⋅ 8 Baths ⋅ ML82050602 MLS

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

452 Roblar AVE, Hillsborough

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

Sold listing courtesy of Serena Conti from APR

$6,998,000

4 Beds ⋅ 4 Baths ⋅ ML82048818 MLS

Sprawling Privacy Meets Elegant Living Hillsborough Welcome to your private estate, a secluded sanctuary tailored for multi-generational family living & spectacular entertaining. Tucked behind a gated driveway on a premier 2-acre lot, this single-family residence offers a blend of luxury, space, & serenity in one of Hillsboroughs most coveted enclaves. Built in 1974, the home spans a generous 3,230 sq. ft. of living space, beautifully designed to celebrate a seamless indoor-outdoor lifestyle amidst lush landscapes. Step inside to discover a bright, expansive floor plan featuring 4 bedrooms, 3 full bathrooms, and 1 half bathroom. Every room offers room to breathe and space to thrive, with large windows inviting natural light and framing views of the verdant, tree-lined grounds. The crown jewel of this estate is its backyard resort. The sprawling, ultra-private acreage features a sparkling pool and outdoor entertaining spaces, creating an idyllic backdrop for weekend barbecues, sophisticated cocktail parties, or quiet mornings listening to the birds.Here, graceful living meets absolute peace of mind. You are minutes from top-rated schools and world-class dining, yet worlds away from the hustle and bustle. Embrace the pinnacle of Hillsborough luxury. Your private sanctuary awaits.

220 Robin RD, Hillsborough

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

$5,900,000

4 Beds ⋅ 4 Baths ⋅ ML82048225 MLS

Set on a half-acre, this beautifully appointed home embodies refined California living, introduced by lush landscaping and a striking column-framed entrance. Inside, nearly 3,500 square feet unfold with dramatic architectural design, where soaring ceilings, exposed beams, and expansive glass create a light-filled, open feel. Hardwood and tile floors span thoughtfully designed spaces, including a stunning living room with a floor-to-ceiling brick fireplace, a dining room with a two-way fireplace, a gourmet kitchen with Gaggenau appliances, and a spacious family room. Four bedrooms, many en suite, include a luxurious primary with a jetted tub and steam shower. The backyard offers a resort-like escape with a pool, lawn, patio, and putting green, all in a private setting near parks, downtown San Mateo, downtown Burlingame, and top schools.

34 Roberts WAY, Hillsborough

Listed by DeLeon Team, 650-300-0888 from Deleon Realty
(If provided) CoList: from

Sold listing courtesy of Eric Chu from SGP

$5,350,000

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

Listed by Judy Citron, 650-400-8424 from Compass
(If provided) CoList: Talia Citron from Compass

Sold listing courtesy of Geoffrey Nelson from CBR

$5,800,000

5 Beds ⋅ 4 Baths ⋅ ML82045371 MLS

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

65 Falkirk LN, Hillsborough

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

Sold listing courtesy of Amarendra Kumar from SATV01

$12,500,000

5 Beds ⋅ 5 Baths ⋅ ML82045292 MLS

20 Denham CT, Hillsborough

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

Sold listing courtesy of Max Lo from GRBA

$6,380,000

4 Beds ⋅ 3 Baths ⋅ ML82043385 MLS

Guest House with full bath, laundry and kitchen on property.

2105 Forest View AVE, Hillsborough

Listed by Emily Smith Silvestri, 650-346-1361 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Christina Ng from APR

$10,750,000

7 Beds ⋅ 6 Baths ⋅ ML82044447 MLS

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

655 Hayne RD, Hillsborough

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

Sold listing courtesy of Shaun Walter from CBR

$7,172,500

5 Beds ⋅ 5 Baths ⋅ ML82044375 MLS

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

300 Uplands DR, Hillsborough

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

Sold listing courtesy of Max Lo from GRBA

$6,400,000

6 Beds ⋅ 6 Baths ⋅ ML82042894 MLS

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

520 Darrell RD, Hillsborough

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

Sold listing courtesy of Ryan LeDoux from APR

$10,200,000

6 Beds ⋅ 6 Baths ⋅ ML82042686 MLS

2077 Forest View AVE, Hillsborough

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

Sold listing courtesy of Shaun Walter from CBR

$4,800,000

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

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

Sold listing courtesy of Mary Jo McCarthy from DP

$5,750,000

5 Beds ⋅ 4 Baths ⋅ ML82042541 MLS

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

740 Clydesdale DR, Hillsborough

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

Sold listing courtesy of Cullinan Luxury from KWPEN

$8,300,000

6 Beds ⋅ 7 Baths ⋅ ML82039635 MLS

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

200 Tobin Clark DR, Hillsborough

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

Sold listing courtesy of Ben Jiang from GVFR

$6,000,000

4 Beds ⋅ 5 Baths ⋅ ML82042279 MLS

1162 Barroilhet DR, Hillsborough

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

Sold listing courtesy of The Laugesen Team from KWPEN

$8,700,000

6 Beds ⋅ 9 Baths ⋅ ML82039853 MLS

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

15 Boroughwood PL, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA

$4,750,000

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

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

Sold listing courtesy of Candace Stadelmann from APR

$7,895,000

5 Beds ⋅ 4 Baths ⋅ ML82041699 MLS

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

335 El Portal AVE, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR

$4,950,000

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

$6,500,000

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

$4,550,000

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

View All Hillsborough CA Homes with Pool Listings