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$70,000,000
6 Beds ⋅ 17 Baths ⋅ ML82024133 MLS
Set on more than 12 secluded acres, Villa de Verano is an ultra-exclusive Hillsborough estate inspired by the elegance of Lake Como. The gated compound offers exceptional privacy, symmetry and scale, with a tree-lined drive leading to a grand motor court & the main residence, guest quarters & sports pavilion. The 12,404 sqft main residence spans 3 levels serviced by an elevator & overlooks the pool, reflection pond & sweeping views of San Francisco Bay. The 4,612 sqft guest house & sports pavilion complement the estate. Interior amenities include a fitness center, theater, game room, spa, & saltwater aquarium. Custom furnishings & art create a unified aesthetic. The grounds include an amphitheater, event lawn, Asian garden with koi pond, swimming pool, reflection pond, open air pavilion, rose garden, redwood grove & English spiral mound. The Sports Pavilion includes a 2 story sports lounge with a viewing platform overlooking a sunken tennis court, pickleball court, volleyball court, badminton court, bocce ball court, horseshoe court, shuffleboard court & putting green. The estate also features an executive length golf course. Upon its completion, Villa de Verano received the CLCA annual Grand Sweepstakes Award for best residential estate completed in the state of California.

3000 Ralston AVE, Hillsborough

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

Sold listing courtesy of Jia Xu from TRNX
$19,800,000
6 Beds ⋅ 11 Baths ⋅ ML82037186 MLS
At a premier lower Hillsborough setting, this extraordinary estate stands as one of the finest in all of Hillsborough. This property delivers a lifestyle of luxury & scale across 1.3 level acres with exceptional privacy. The main residence unfolds over 3 expansive levels, each with generously proportioned rooms, elaborate architectural detailing & substantial volume. 6 bedroom suites, 2 offices, & a detached guesthouse provide outstanding flexibility for family, guests & extended stays. Grand public rooms are designed for formal entertaining supported by a chefs kitchen equipped to accommodate large-scale gatherings. The lower level is dedicated entirely to recreation & entertaining, offering multiple lounges, a commercial-quality cinema, an extensive wine cellar designed for a significant collection, a full bar, second kitchen, and a well-appointed gym w/steam shower & sauna. Outdoor amenities rival those found at private resorts. The grounds feature an oversized pool and spa with rock waterfall, expansive terraces, a covered loggia with full outdoor kitchen, and regulation-size tennis court currently surfaced for basketball. This is a property where scale, amenities, & location come together for an exceptional lifestyle.

925 Seabury RD, Hillsborough

Listed by Zach Trailer, 650-906-8008 from Compass
(If provided) CoList: from

Sold listing courtesy of Jim Arbeed from CBR
$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
$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
$14,500,000
5 Beds ⋅ 8 Baths ⋅ ML82037507 MLS
A beautifully reimagined estate on one of South Hillsborough's most coveted streets. Set behind a private gate and an expansive driveway, this exceptional property pairs timeless architecture with a sophisticated modern remodel. Elegant formal spaces flow effortlessly outdoors, creating a home designed for entertaining. The living room opens to the terrace and gardens, while the dining room, anchored by a sculptural designer fixture, invites memorable alfresco dinners. At the heart of the home, the architectural kitchen and great room showcase a dramatic 14-foot Cristallo island, Viking and Sub-Zero appliances, custom cabinetry, and exposed beam ceilings, all illuminated by striking designer lighting. Five en-suite bedrooms and eight spa-inspired baths are complemented by a media room, gym, two laundry rooms, and five fireplaces throughout. The resort-style grounds offer a pool, jacuzzi, cabana, outdoor kitchen, and multiple terraces, surrounded by mature trees and beautifully layered landscaping. With a solar composite slate roof, EV-charging, new electrical systems, and a new multi-zone HVAC, the home pairs luxury with thoughtful modern infrastructure. Minutes to top Hillsborough schools, Burlingame Avenue, and Burlingame Country Club, this is Hillsborough living at its finest.

729 Chiltern RD, Hillsborough

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

Sold listing courtesy of Austin Herman from APR
$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
$12,500,000
8 Beds ⋅ 8 Baths ⋅ ML82032610 MLS
Striking modern estate offering the perfect blend of luxury, scale, and design. This full scale renovation showcases soaring ceilings, dramatic floor-to-ceiling windows, and seamless indoor-outdoor living. The spacious floor plan features grand formal and casual living areas, a sleek chefs kitchen, and walls of glass opening to expansive terraces with serene tree-lined views. Luxury amenities include a private home theatre, gym, tasting room and wine cellar, elevator, and a resort-style backyard with pool house and built-in BBQ. The sparkling pool with water features, multiple lounge areas, and expansive patio create the ultimate setting for entertaining and relaxation.

1215 La Cumbre, Hillsborough

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

Sold listing courtesy of Jenny MacLeod from APR
$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
$11,800,000
6 Beds ⋅ 6 Baths ⋅ ML82047705 MLS
Located in desirable lower South Hillsborough, 255 Brentwood offers modern design, vaulted ceilings, exceptional natural light throughout, and seamless indoor-outdoor living. A striking front entry opens to a bright, welcoming foyer, leading into thoughtfully designed living spaces filled with natural light. The open kitchen and dining area serves as the heart of the homeperfect for both everyday living and entertainingfeaturing Miele appliances, two dishwashers, a pantry, and seamless flow to a built-in bar with wine fridge. The main level includes a casual living room, two en-suite bedrooms, and a stunning formal living room wrapped in glass doors and windows with direct access to the backyard. A private elevator connects all levels, offering ease and convenience throughout the home. The lower level offers added flexibility with a bedroom, mudroom, and wine room. Upstairs, the private primary suite features its own balcony, creating a peaceful retreat, while two additional en-suite bedrooms with generous closets complete the level. Outdoor spaces are designed for true California living, featuring a sport court, putting green, outdoor kitchen, sound system, curated lighting, four fireplaces, and beautifully landscaped grounds with a blend of turf and grass.

255 Brentwood RD, Hillsborough

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

Sold listing courtesy of Phil Chen from SGP
$10,750,000
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
$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
$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
$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
$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
$10,200,000
8 Beds ⋅ 7 Baths ⋅ ML82032410 MLS
Welcome to 45 Calaveras Court, a brand-new modern masterpiece nestled in the Hillsborough hills. Located at the end of a private cul-de-sac on a sizable 4-acre lot, this stunning residence offers approximately 7,000 square feet of elegantly designed living space. Enjoy unobstructed canyon views from every window, providing a breathtaking backdrop to your everyday life. Step inside to discover soaring ceilings that create an open and inviting atmosphere, complemented by an abundance of natural light that fills every corner. The expansive first floor features a massive entertainment deck, perfect for hosting gatherings or simply relaxing amidst nature. With a total of 8 bedrooms, including master suites on each level, this exceptional home is perfect for large families or multi-generation living.

45 Calaveras CT, Hillsborough

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

Sold listing courtesy of Greg Browman from 7A895
$9,540,000
6 Beds ⋅ 7 Baths ⋅ ML82032691 MLS
Almost fully rebuilt in 2022, this Santa Barbara-style Mediterranean in Hillsborough blends timeless architecture with modern systems and resort-style living. Interior design by JD Bartell creates a truly special & cohesive residence for daily living & entertaining. The home offers up to 6 bedrooms & 6.5 bathrooms with Venetian plaster throughout, custom white oak floors, seamless cabinetry & doors with a dramatic staircase. This home includes radiant heat and air conditioning with multiple zones, integrated security cameras, lighting & audio. The chef's kitchen features a huge custom book-matched island with top-of-the-line appliances, dual sinks, ample storage, plus a temperature-controlled wine cellar, open to the large family room. Extensive upgrades include 400-amp electrical service, new copper plumbing and wiring, dual internet, 19.5 kWh solar, a 22 kWh Generac backup generator, tankless water heaters, & whole-home water filtration. Resort-style grounds include fruit trees, drought-tolerant landscaping, smart irrigation, a resurfaced pebble pool with water features, travertine hardscape, circular paver driveway, iron gates, and an outdoor BBQ. A rare offering combining architectural character with a more transitional interior full of custom upgrades.

2950 Churchill DR, Hillsborough

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

Sold listing courtesy of Ramez Tabri from ALNC
$9,280,000
5 Beds ⋅ 5 Baths ⋅ ML82036409 MLS
Welcome home to your modern farmhouse in the coveted Carolands neighborhood of Hillsborough. Situated on a flat and usable .52-acre lot, this home was rebuilt and expanded in 2021 from the foundation up, ensuring a turnkey and comfortable living experience. The main house boasts 4 bedrooms and 4 bathrooms, plus a 1-bedroom, 1-bath ADU. Inside, discover 16-foot ceilings, stunning wood floors, abundant natural light, and premium upgrades. The chef's kitchen features Thermador appliances and an 11-foot island, with La Cantina doors for seamless indoor-outdoor flow to your outdoor oasis that includes a new pool/spa, BBQ, bocce ball, expansive lawn, and fruit trees. There is also a large side yard perfect for basketball, extra cars, or even a boat. This property combines rare single-level living with modern features, great natural light on a flat, usable lot, and a neighborhood that invites walks and bike rides.

588 Craig RD, Hillsborough

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

Sold listing courtesy of Amy Xiao from KWCU
$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
$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
$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
$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
$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
$8,000,000
5 Beds ⋅ 5 Baths ⋅ ML82036808 MLS
Situated in Lower North Hillsborough, this gated property encompasses approximately 30,348 square feet flat lot and represents a rare estate-caliber parcel for the discerning buyer. Mature landscaping, privacy, and abundant sun exposure define the setting, just moments from downtown San Mateo, Burlingame Avenues shopping and dining, and top-rated Hillsborough schools. The expansive grounds feature broad lawn areas, a sparkling pool and cabana, detached guest house, greenhouse, two-car garage, enclosed carport, and circular drive, creating a substantial footprint across the site. The existing residence, including a 1997 addition, is approximately 5,533 square feet, offers generous scale and presents an opportunity for significant renovation, reconfiguration, or potential redevelopment. See floor plans for details. Large, flat lot of this size are increasingly scarce in Lower North Hillsborough, providing the opportunity to create a customized estate in one of the Peninsulas most desirable neighborhoods with enduring long-term value.

730 Hillsborough BLVD, Hillsborough

Listed by Alex Hawkins, 408-348-5013 from Cronan Real Estate Services, Inc.
(If provided) CoList: from

Sold listing courtesy of Alex Hawkins from CRNAN
$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
$7,825,000
4 Beds ⋅ 5 Baths ⋅ ML82046534 MLS
For the first time in over half a century, this remarkable family estate is opening its doors to a new chapter. Built in 1967 and held by the same family ever since, this is more than just a homeit is a rare opportunity to acquire a residence of incredible character and complete seclusion. The expansive floor plan is thoughtfully designed for both grand entertaining and intimate daily life, featuring four generous bedrooms along with three full and two half baths. Among its many refined living spaces is a sophisticated library, offering the perfect sanctuary for a home office or quiet reflection. Every room is bathed in natural light, creating a seamless connection between the interior and the breathtaking grounds outside. Set within a lush, private envelope, the property is defined by stunning curated gardens that create a verdant oasis. These meticulously maintained outdoor spaces provide a level of privacy that is increasingly rare, ensuring a serene retreat. Meticulously cared for and brimming with potential, this is a once-in-a-generation opportunity to acquire this remarkable estate and steward its beautiful legacy into a new era.

1955 Parkside AVE, Hillsborough

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

Sold listing courtesy of Jenny MacLeod from APR
$7,600,000
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
$7,470,000
7 Beds ⋅ 9 Baths ⋅ ML82025914 MLS
https://1215TournamentDr.com/ Rare estate in the prestigious Tobin Clark area of Hillsborough.Set on a private,resort-like lot with mature trees, layered outdoor spaces,and a private walking trail.Surrounded by top private schools, the home is thoughtfully laid out with 7beds & 7.5baths, along with formal living and dining rooms that connect to a spacious family room and kitchen. A group of four bedrooms are located together in one area of the home, making it especially practical for families with multiple children.The primary suite itself feels like a quiet retreat,featuring a spa-like bath and an expansive walk-in closet.A wood-paneled office provides a dedicated workspace,while the au pair quarters offer additional privacy for guests or extended household needs. A large open area is designed for everyday enjoyment like watching movies,playing games,or hosting.With a wet bar,full kitchenette,nearby bedroom and bath,and direct access to the outdoors,this space can also function as a self-contained living area. Outside,the grounds unfold with lawns,terraces,and an outdoor fireplace.Creating places to sit,walk, and host.Additional highlights include a rare 5-car garage & dual laundry areas.A home where space,privacy, and everyday living come together in a way that simply works.

1215 Tournament DR, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA
$7,300,000
5 Beds ⋅ 6 Baths ⋅ ML82046420 MLS
Beyond the gates, perched atop a knoll w/ westerly hill views, a remarkable estate in the heart of Hillsborough. Fine luxury living is a timeless Craftsman built in 2009. Opulence begins at the front door to a grand foyer w/ soaring ceilings including a living room, a formal dining room, breakfast room, separate family room, & a gourmet chefs eat-in kitchen w/ custom cabinetry, Viking stainless steel appliances, a large custom island w/ prep sink & wine cooler, a 6-burner gas stove, & walk-in pantry plus office. Five en-suite bedrooms w/ a sumptuous primary bedroom suite complete w/ dual walk-in closets w/ closet organizers, & a spa-like bathroom w/ dual sinks w/ separate shower & tub. Impressive attention to detail throughout including French doors, wainscoting, crown moldings, baseboards, refinished hardwood floors, iron railings, & 2 mantled fireplaces plus central heating & air conditioning for added comfort. Additional library w/ coffered ceilings welcomes you to a garden oasis w/ mature landscaping, spacious faux grass area, dual patios, & your very own custom koi pond. Welcome home, to The Crown of Jewell Place.

15 Jewell PL, Hillsborough

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

Sold listing courtesy of Max Lo from GRBA
$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
$6,888,000
5 Beds ⋅ 6 Baths ⋅ ML82037136 MLS
Highly sought after property in the Tobin Clark Estate neighborhood, this property offers expansive, panoramic views overlooking the San Francisco Bay and Peninsula. Spanning over 6500 sq ft, this impressive east-facing residence offers 5 bedrooms, 5.5 bathrooms with a bonus media room, combining scale, elegance, and everyday functionality. A grand foyer welcomes you into the formal living and dining rooms, creating an immediate sense of sophistication. The main level's great room seamlessly integrates the kitchen and family room in an open-concept layout ideal for modern living, while a versatile flex room nearby enclosed by double french doors offers the perfect space for a playroom, secondary family room, office, or private gym. Panoramic bay views can be enjoyed from the kitchen, family room, formal living room, stairway, and primary suite. The expansive updated upstairs primary bedroom features multiple sitting areas and a private balcony showcasing some of the home's most breathtaking views of the Peninsula and water. A gated driveway leads to a spacious three-car garage with additional guest parking, offering both privacy and convenience.

140 Tobin Clark DR, Hillsborough

Listed by Andrew Law, 408-718-0767 from eXp Realty of Northern California, Inc.
(If provided) CoList: Scott Kao from eXp Realty of Northern California, Inc.

Sold listing courtesy of Sophia Wong from KWPEN

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