Refine Search
Map
Sort by
2265 Ralston AVE, Hillsborough
$19,500,000
5 Beds ⋅ 7 Baths ⋅ ML82062674 MLS
New construction in progress and will be completed in Mid 2027. This is An exceptional new estate in coveted Lower North Hillsborough.

2265 Ralston AVE, Hillsborough

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

40 Eugenia WAY, Hillsborough
$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

1950 Ralston AVE, Hillsborough
$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
860 Longview RD, Hillsborough
$6,150,000
5 Beds ⋅ 5 Baths ⋅ ML82060425 MLS
Set against stunning Bay views, this Ranch style home blends timeless mid-century modern character with spacious, light filled living. Approximately 4,560 square feet of living space offers five bedrooms and four-and-a-half baths, with an inviting combination of formal and informal rooms. The main bedroom wing is thoughtfully arranged with a spacious primary suite, plus two additional bedrooms connected by a bathroom. A guest suite is conveniently located off the kitchen and laundry area, while the lower level -- with its own exterior access offers a potential fifth bedroom and full bath. The lower level provides even more flexibility, with an additional room perfect for an office, second family room or game room. Abundant natural light fills the home, while expansive windows capture the spectacular Bay outlook and create a strong connection to the private, mostly level grounds. The formal dining room and family room both have access to the backyard with a swimming pool and generous outdoor spaces. Architectural character, generous scale, versatile living spaces, privacy, and breathtaking views all paired with top-rated public schools. Perfect Mid-Peninsula location.

860 Longview RD, Hillsborough

Listed by The Dwyer Group, 650-759-1593 from Compass
(If provided) CoList: from

Sold listing courtesy of Heather Hansen from APR
901 Hillsborough BLVD, Hillsborough
$7,280,000
5 Beds ⋅ 6 Baths ⋅ ML82057580 MLS
$715,000 Price Reduction! Lowest price home in Lower North Hillsborough! Welcome to this exceptional lower North Hillsborough estate that blends timeless architectural charm with sophisticated modern living. Spanning over 5180sf, this 5 bedroom 6 bath home has it all! A welcoming front porch with dormer windows enhance the homes inviting exterior. The chef's kitchen is thoughtfully appointed for both everyday living and entertaining, with two sets of French doors opening to an expansive patio complete with a built-in grill and full-length pergola. The grand room is truly designed to impress, featuring dual fireplaces and multiple French doors. . The abundant natural light throughout the home creates a rich environment for family living and guest entertainment. The primary suite, along with two additional bedrooms on the main level, features vaulted ceilings and custom-designed closets. The lower level provides an exceptional extension of the living space, offering a spacious media room, two additional bedrooms, a butler's pantry, and a dedicated artist studio or gym. Additional luxuries include central air conditioning, backup generator, and a whole-home audio system. Just minutes to downtown Burlingame, North Elementary and Crocker Middle School, this wonderful home has it all!

901 Hillsborough BLVD, Hillsborough

Listed by Nick Corcoleotes, 650-207-2758 from Coldwell Banker Realty
(If provided) CoList: from

2245 Oakdale RD, Hillsborough
$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
433 El Centro RD, Hillsborough
$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

1850 Brookvale RD, Hillsborough
$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
36 Eugenia WAY, Hillsborough
$5,280,000
5 Beds ⋅ 4 Baths ⋅ ML82053052 MLS
An exquisite property located in the exclusive Skyfarm neighborhood of Hillsborough. Set on over 0.69 acres, this home offers breathtaking views of the Bay, the airport, and downtown San Francisco. It creates a perfect setting for indoor / outdoor living in Hillsborough. The formal dining room and living room open onto the back deck, while the chef's kitchen combines a family room and an eat-in formal dining area with a private patio. The primary bedroom features an ensuite bathroom and a walk-in closet. Top-rated West Elementary School and Crocker Middle School. County records show 3,500 SqFt. 4 Bedrooms, 3 Full Baths. Seller converted the home to 5 Bedrooms, 4 Full Baths, which are permitted.

36 Eugenia WAY, Hillsborough

Listed by John Pang, 650-699-2838 from Realty One Group Extreme
(If provided) CoList: from

245 W Santa Inez AVE, Hillsborough
$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
973 Baileyana RD, Hillsborough
$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
452 Roblar AVE, Hillsborough
$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
15 Jewell PL, Hillsborough
$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
65 Falkirk LN, Hillsborough
$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
20 Denham CT, Hillsborough
$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
300 Uplands DR, Hillsborough
$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
10 Salmark CT, Hillsborough
$5,500,000
5 Beds ⋅ 5 Baths ⋅ ML82042651 MLS
Privately set on a serene cul-de-sac, this gated estate is a refined expression of scale, light, and California indoor-outdoor living. A circular drive introduces a grand entry and sweeping staircase, with soaring ceilings elevating the formal living and dining spaces. At the heart of the home, a crisp white chefs kitchen flows effortlessly into the family room and out to curated gardens and expansive decks, mature trees, and a grassy play space, designed for effortless entertaining. Each of the 4 upstairs bedrooms opens to a balcony, while the primary suite unfolds as a true retreat complete with wraparound canyon views, a dressing area, and a spa-inspired bath. Don't miss this rare offering defined by privacy, elegance, and award-winning Hillsborough schools.

10 Salmark CT, Hillsborough

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

Sold listing courtesy of Jingya Ji from CBR
740 Clydesdale DR, Hillsborough
$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
1340 View Haven RD, Hillsborough
$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
335 El Portal AVE, Hillsborough
$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
729 Chiltern RD, Hillsborough
$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
140 Tobin Clark DR, Hillsborough
$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
730 Hillsborough BLVD, Hillsborough
$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
2323 Summit DR, Hillsborough
$5,628,000
5 Beds ⋅ 5 Baths ⋅ ML82036647 MLS
Classic elegance and timeless character define this exceptional three-level Mission Spanishstyle estate set on approximately 0.48 acres in sought-after Lower North Hillsborough. Rich in architectural charm, the home welcomes you with a grand entry hall and sweeping staircase leading to expansive living spaces designed for both refined entertaining and comfortable everyday living. The impressive living room features a dramatic high beamed ceiling and fireplace, while the living and formal dining rooms open to a covered porch capturing filtered Bay views. The formal dining room accommodates large gatherings and flows seamlessly into a gourmet eat-in kitchen with island and top-of-the-line appliances. A main-level bedroom and full bath offer flexibility for guests or extended family. Upstairs are three spacious bedrooms and beautifully updated baths providing peaceful private quarters. The lower level includes a large family room with fireplace and access to a secluded patio, plus an additional bedroom, bath, and versatile bonus space ideal for a gym, office, or game room. Mature landscaping, fruit trees, and multiple seating areas create a serene outdoor retreat. A rare opportunity to enjoy privacy, space, and classic Hillsborough elegance.

2323 Summit DR, Hillsborough

Listed by Disen Cai RE Group, 650-622-2156 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Kristin Lum from SGP
30 Inverness WAY, Hillsborough
$4,300,000
5 Beds ⋅ 4 Baths ⋅ ML82036641 MLS
COMP PURPOSES ONLY

30 Inverness WAY, Hillsborough

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

Sold listing courtesy of The Patty Dwyer Group from APR
588 Craig RD, Hillsborough
$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
25 Searsville CT, Hillsborough
$7,100,000
5 Beds ⋅ 4 Baths ⋅ ML82033175 MLS
EPIC HOMAGE TO CRAFTSMANSHIP AND LIFE IN THE SUN...One of Hillsborough's Most Elite Custom Remodels, steeped in the Magic of Montecito and Palm Beach. Every inch meticulously curated of high-end caliber inside and out. Ultimate privacy heightens soaring views above canyon, ridgelines, and sun-blessed luminosity. Top flight luxury designer elements of Venetian plaster walls, vaulted ceilings of 14-15 feet, European tilework, mahogany doors, and made-to-order light fixtures by Steven Handelman of Santa Barbara. Wolf, Sub-Zero, Miele, exquisite custom cabinetry, & more. Indoor/Outdoor celebration as a personal resort with saltwater PebbleSheen pool, 3 waterfalls & raised spa. Flat grassy yards, barbecue cove, secret Napa garden of fruit orchard & irrigated veggie beds. The beauty of the floorplan includes 4 bedrooms on the main level, plus private lower level for 5th bedroom, huge media room & 2nd kitchen. This level is the perfect in-law apartment, teen hangout, or poolside media lounge. And shhhh, don't forget the world-class temp-controlled wine cellar as your own speakeasy! Prestige cul-de-sac location within minutes of Nueva & West Schools, & easy Hwy 280 connection to VC realm of Silicon Valley, plus AI, private equity, & biotech of South San Francisco and Financial District.

25 Searsville CT, Hillsborough

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Chris Iverson from DP
1080 Macadamia DR, Hillsborough
$6,750,000
5 Beds ⋅ 6 Baths ⋅ ML82031249 MLS
An architectural statement of grand scale and enduring quality, this stately Skyfarm residence is nestled behind a mature landscape of majestic evergreens, offering privacy and a seamless connection to its natural grounds. Spanning 5,770± sq. ft. on an expansive 32,633+/- sq. ft. lot, the home is in pristine original condition and is poised for the next generation family to infuse with their own vision. The interior is defined by classic precision: refinished hardwood floors, raised wood paneling, crown molding, bay windows and Old World quality. A two-story foyer with chandelier leads to the grand living room, featuring a distinguished fireplace and backyard views, a formal dining room for refined venues, an eat-in kitchen, anchored by a center island, and an adjoining family room with a masonry fireplace and window wall blurring the boundary between indoors and the sprawling rear grounds. A spacious primary suite featuring generous wardrobe space and a scenic view headlines the upper level. Beyond the residence, irrigated grounds with sweeping lawns and patios create a private, park-like retreat. 1080 Macadamia Drive is a rare convergence of scale, land, and lifestyle.

1080 Macadamia DR, Hillsborough

Listed by Julie Baumann, 650-576-8889 from Compass
(If provided) CoList: from

Sold listing courtesy of Sandra Comaroto from APR
460 Barbara WAY, Hillsborough
$7,300,000
5 Beds ⋅ 3 Baths ⋅ ML82029393 MLS

460 Barbara WAY, Hillsborough

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

Sold listing courtesy of Gina Haggarty from APR
171 Tobin Clark DR, Hillsborough
$11,000,000
5 Beds ⋅ 6 Baths ⋅ ML82014791 MLS
Experience timeless luxury at this grand Mediterranean estate, ~7,700 sqft total living space set on ~1.5 acres in the prestigious Tobin Clark area of Hillsborough. Showcasing panoramic views of the Bay and Peninsula. This exceptional property offers an unparalleled lifestyle of elegance, comfort, and privacy. The main residence features ~6,500 square feet of living space, including 5 ensuite bedrooms, each w/ access to a private terrace. A sweeping staircase, custom chandeliers, and soaring ceilings create a dramatic welcome, while the formal living and dining rooms, gourmet kitchen, & wine room provide elegant spaces for entertaining. The primary suite is a private retreat with a sitting area, custom walk-in closet, and spa-like bath. A separate 2 bed 2 bath guest house (~1,200 Sqft) includes its own kitchen, living area w/ fireplace, & private balcony and private garage, perfect for extended stays or multigenerational living. Outdoor amenities include an infinity-edge pool and spa, full-size tennis court, putting green, and multiple entertaining patios surrounded by mature landscaping. Located just minutes from top-rated Hillsborough schools, downtown Burlingame, SFO, and Silicon Valley, this is a rare opportunity to own one of Hillsborough's most iconic view properties.

171 Tobin Clark DR, Hillsborough

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

Sold listing courtesy of Chris Hylton from APR

board logoThe data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Real Estate Company are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.


Copyright 2026 MLSListings Inc. All rights reserved