Hillsborough CA 5 Bedroom Real Estate, Homes, Condos for Sale

5 Beds ⋅ 5 Baths ⋅ ML82057153 MLS

Nestled behind private gates on approximately one-half acre in coveted Hillsborough, 380 Robinwood Lane is a thoughtfully remodeled estate blending modern design with effortless resort-style living. Surrounded by mature trees, lush landscaping, expansive turf lawn areas, and beautifully manicured grounds, the home offers exceptional privacy and seamless indoor-outdoor living. Light-filled interiors feature vaulted ceilings, walls of glass, and an expansive great room designed for everyday living and entertaining. The state-of-the-art chef's kitchen is anchored by a striking Taj Mahal quartzite waterfall island, professional-grade appliances, extensive custom cabinetry, and abundant storage. The home offers four en suite bedrooms plus one additional bedroom, including a private primary retreat with multiple fitted closets, a heated stone bath, and tranquil backyard views. A tucked away lower level en suite provides added flexibility for guests and multigenerational living. The lower level also includes a media room and family room with direct access to the backyard retreat. Outside, enjoy a sparkling pool, outdoor kitchen, expansive turf lawn, architectural landscaping, and multiple spaces for relaxing and entertaining.

380 Robinwood LN, Hillsborough

Listed by The Sharp Group, 650-766-5333 from KW Advisors
(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

$11,500,000

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

$11,350,000

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

$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

$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

$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

$6,880,000

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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$12,400,000

5 Beds ⋅ 7 Baths ⋅ ML82028559 MLS

Stunning Custom Built New Construction Home with Breathtaking Views. Formal Entry. Elegant Living Room with High Ceilings and Floor-to-Ceiling Windows. Chef's Eat-in Kitchen with Center Island with Sink, Pantry, and Ample Natural Light. 5 Spacious Bedrooms. 5 Beautifully Designed Full Bathrooms and 2 Half Bathrooms. Primary Suite Retreat Features Double Sinks, Standalone Tub, Stall Shower, and Walk-in Closet. Main Floor Bedroom Suite. Upper Level Features Separate Family Room with Bar and Half Bathroom. Exterior Features Includes Sparkling Pool, Outdoor Kitchen, and Floating Deck. Lovely Landscaped 1.33+/- Acre Lot with Breathtaking Views. Award Winning Hillsborough Schools

20 Pine CT, Hillsborough

Listed by Keri Nicholas, 650-533-7373 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Kalina Wasman from COMPS

$4,900,000

5 Beds ⋅ 4 Baths ⋅ ML82028079 MLS

1015 Woodland DR, Hillsborough

Listed by Stephanie Nash, 650-995-3820 from Compass
(If provided) CoList: from

Sold listing courtesy of Nicholas Delis from APR

$7,780,000

5 Beds ⋅ 7 Baths ⋅ ML82027382 MLS

Built in 2021, this showstopping modern estate captures the essence of California living. Soaring ceilings and walls of glass open completely to reveal breathtaking hillside and Bay views, blurring the line between indoors and out. The designer kitchen stuns with custom rift-oak cabinetry, marble island, and top-tier appliances. An entertainers dream, the outdoor terrace features a built-in BBQ, spa, fire pit, and endless views. Smart home technology, solar power, and a premier Hillsborough location complete this rare modern masterpiece.

60 Glengarry WAY, Hillsborough

Listed by Victoria Yang Surles, 415-818-3603 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jennifer Griessel from CCPCR1

$5,860,000

5 Beds ⋅ 5 Baths ⋅ ML82026911 MLS

LOWER SOUTH CHALET: ARCHITECTURAL SIGNIFICANCE MEETS FAMILY WARMTH! Homes are simply not built with this high style anymore! A rarity to the market, this is an architecturally significant statement equally at home as a fine art gallery or warm and cozy family retreat. Sophistication cascades throughout truly ENORMOUS room sizes, while never compromising daily function and inviting indoor/outdoor character. In the heart of Lower South Hillsborough, we celebrate one of the San Francisco Peninsula's top luxury enclaves, a neighborhood ranking within the Top 10 on median sales price in the United States, decade after decade. Around the corner from $18,000,000 estates, less than a mile from Crystal Springs Uplands, just 1.4 mile from North Elementary, 1.7 mile to downtown Burlingame Ave Apple Store. The romance of the Chalet is the theme: rustic charm with contemporary features. Sequestered within noble trees, imbued with spirit of a special-occasion getaway, & arresting in design flair, this is your conversation piece. | 5 beds, 4.5 baths | Expanded & Updated by acclaimed architect John A. Matthews, AIA | Huge Master Suite | Side Party Terrace | Separate Pool Area | Mill Valley-style woodsy vibes w/easy ADU potential | 4-car attached garage + motor court for basketball & yard access

300 Glendale RD, Hillsborough

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

Sold listing courtesy of Disen Cai RE Group from KWPEN

$7,318,000

5 Beds ⋅ 6 Baths ⋅ ML82025896 MLS

THE BEST OF THE BEST IN HILLSBOROUGH. Award-Winning architectural design meets timeless farmhouse elegance. Previously featured in Modern Luxury Silicon Valley Magazine, this home was meticulously remodeled & redesigned in 2017 by both an award-winning designer & architect. A stunning blend of modern farmhouse designs and contemporary elements, this exceptional estate is crafted for stylish living and effortless entertaining. Eco-minded design and sustainable elements create a healthy, harmonious environment throughout. The expansive indoor-outdoor layout offers formal and informal living and dining areas, a grand kitchen with a Taj Mahal quartzite island that seats 12, plus 5 bedrooms, 5.5 spa-inspired bathrooms, a loft, office, and soaring vaulted beam ceilings. Enjoy multiple en-suites, sliding barn doors, large windows / glass doors, and a seamless kitchen/family room retreat. The resort-style grounds include a terraced garden, lush lawn, outdoor kitchen, fire-pit lounge, hot tub with natural rock waterfall, pool, sport court, & a spacious outdoor gym / pool house with full bath. Approved plans for an 800 sq. ft. ADU add even more opportunity. Moments to top-rated schools including Nueva, Crystal Springs Uplands, and other acclaimed schools. TOO MUCH TO LIST HERE.

1485 Oak Rim DR, Hillsborough

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

Sold listing courtesy of Mitch Wong from APR

$7,500,000

5 Beds ⋅ 7 Baths ⋅ ML82025050 MLS

Regally set on a private +/-0.71-acre lot with sweeping San Francisco Bay views, this +/-7,435s.f. residence offers luxury, privacy, and an exceptional floor plan. The impressive two-story foyer sets the tone for the elegant formal living and dining rooms, complemented by a rich wood-paneled library. The expansive chef's kitchen features a large island, butlers pantry, and sizable breakfast room, and opens to an enormous family room with built-in bookcases, full bar, and direct access to the stunning rear yard. The main level also offers a game room, guest suite with marble bath, laundry room, powder room, and a wide rear staircase. Upstairs are three spacious en-suite secondary bedrooms, plus a versatile bonus room ideal as a 2nd office, nursery, or gym; and the huge primary suite with Bay views, a fireplace with sitting area, private balcony, spa-like bath with steam shower, and dual custom walk-in closets. The beautifully landscaped grounds offer sweeping patios, level lawns, a pool with spa, play/garden area, and an impressive pool house with kitchenette and full bath. A gated driveway leads to a 3-car garage and motor court. With awe-inspiring views, complete privacy, and resort-style amenities, this grand estate offers an unparalleled lifestyle in an extraordinary setting.

1111 Tournament DR, Hillsborough

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

Sold listing courtesy of Jim Arbeed from CBR

$7,495,000

5 Beds ⋅ 5 Baths ⋅ ML82023917 MLS

Situated on a serene cul-de-sac, this stunning, fully renovated modern farmhouse offers resort-style living on a mostly level +/-0.52-acre lot. With +/-4,200 s.f. of bright open space, the 5BR/4.5BA Napa Valley-style home features soaring ceilings, wide-plank hardwood floors, and walls of windows that flood the interior with light. A striking glass front door opens to the living room with dramatic fireplace and verdant views. The elegant dining room includes a sleek, temperature-controlled wine display, while the chef's kitchen with top-tier appliances, large island, and breakfast nook flows into the expansive great room with access to the backyard. The private bedroom wing offers 4 sizeable bedrooms, one with an ensuite bath, a separate hall bath, powder room, laundry, and the lavish primary suite with custom walk-in closet and spa-inspired bath with soaking tub & oversized shower. Additional spaces include an attached ADU with kitchenette, full bath which opens to the pool patio, and loft, plus a versatile lower-level bonus room ideal as an office or gym, and 3-car garage. Resort-like grounds boast mature olive trees, stunning landscaping, sprawling patio, level lawn, outdoor kitchen, and new pool with spa. A rare opportunity to own a virtually new home in a remarkable setting.

35 Bel Aire CT, Hillsborough

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

Sold listing courtesy of Vikrant Goel from SFLT01

$7,300,000

5 Beds ⋅ 7 Baths ⋅ ML82022917 MLS

This beautifully designed 5-bedroom, 5 full and 2 half-bath home blends timeless sophistication with modern comfort in one of Hillsboroughs most sought-after neighborhoods. A grand two-story foyer welcomes you in, leading to formal living and dining rooms perfect for entertaining. A private guest suite on the main level adds flexibility, while a butlers pantry hallway and separate walk-in pantry provide smart, functional storage. The expansive great room unites the family area, breakfast nook, and chefs kitchen, opening through folding glass doors to a spacious deck with a tranquil fountain and outdoor fireplaceideal for indoor-outdoor living. Downstairs, a media room with wet bar, temperature-controlled wine cellar, full bath, and additional bedroom offer space to relax and unwind. Upstairs, the luxurious primary suite features a sitting area, two walk-in closets, and a sunlit balcony. Two additional en-suite bedrooms and a handsome wood-paneled office complete the home. Premium finishes include motorized Hunter Douglas blinds and outdoor privacy screens and a full Savant Smart Home System for effortless control of lighting, climate, media, and music.

625 W Santa Inez AVE, Hillsborough

Listed by Vivian Shao, 650-307-7311 from Green Banker Realty
(If provided) CoList: Chi-hwa Shao from Green Banker Realty

Sold listing courtesy of Jim Arbeed from CBR

$5,900,000

5 Beds ⋅ 5 Baths ⋅ ML82022735 MLS

THE RULES OF REAL ESTATE ATTRACTION: LOCATION, LIVABILITY, MOVE RIGHT IN! The great lifestyles always seem to have a universal appeal and purity of function. Here, in the heart of Lower North Hillsborough estate country, we find a smooth single-story design, totally renovated, ready to purvey the universal luxury of the Peninsula. How rare art thou? Let me count the ways...this single-story design is surely scarce at any price point: no stairs to worry about, all remodeled condition, and a 5-bedroom, 4.5 bath floorplan opening out to flat private garden. These picturesque environs, dappled by vintage oaks & timeless mansions, are within a 30 minute stroll of downtown Burlingame Avenue. | Dramatic Lobby of 12 ft +\- ceilings | Living and Dining Rooms are elegant statements with 10 ft. 4 inch ceilings & bay windows | Grand size open rooms treated with hardwood floors, crisp white moldings, designer palette | Large updated chef's kitchen open with bistro nook | Huge Family Room Opens to Flat Yard | Separate Bedroom Suite ideal for Office or In-Law|Au Pair with private entry | Immense Master Suite with 2 walk-in closets & marble bathroom + soothing green garden view | Immaculate condition and perfect Floorplan | Walk to Burlingame Ave | Top Schools | #1 Neighborhood amongst mansions

515 N San Raymundo RD, Hillsborough

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

Sold listing courtesy of Raziel A. Ungar from APR

$12,000,000

5 Beds ⋅ 7 Baths ⋅ ML82010473 MLS

Rare, once-in-a-lifetime luxury estate in the prestigious Ryan Tract of Lower Hillsborough. Set on a flat 42,304 sq ft gated lot, this property offers 5 beds, 6.5 baths, solar, regulation tennis court, large pool + separate spa, lush gardens, expansive lawns, multiple patios, putting green, outdoor BBQ, long private driveway, motor court, and 3-car garage. The main residence features an elevator; all bedrooms en-suite; chefs kitchen with butlers pantry; family room; living room; formal dining room; multiple office/workshop spaces; and more. Additional structures include a pool house and a full guest house attached to the garage. Total advertised living space of 7,950 sq ft includes the main house, 945 sq ft 2-bed/2-bath guest house with full kitchen and living/dining area, and a 685 sq ft pool house with living space, kitchenette, laundry, full bath, and sauna. Walking distance to Downtown Burlingame and access to top-rated California schools. A true blend of elegance, scale, and resort-style living.

818 Irwin DR, Hillsborough

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

Sold listing courtesy of Stanley Lo from GRBA

$4,780,000

5 Beds ⋅ 6 Baths ⋅ ML82022295 MLS

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

1531 Wedgewood DR, Hillsborough

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

Sold listing courtesy of Alex Buljan from APR

$4,800,000

5 Beds ⋅ 7 Baths ⋅ ML82022191 MLS

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

923 Hayne RD, Hillsborough

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

Sold listing courtesy of Serena Conti from APR

$3,900,000

5 Beds ⋅ 5 Baths ⋅ ML82022122 MLS

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

530 Darrell RD, Hillsborough

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

Sold listing courtesy of Chuan-heng Lin from BQG

$12,600,000

5 Beds ⋅ 5 Baths ⋅ ML82021202 MLS

HILLSBOROUGH'S MOST EXCITING NEW CONSTRUCTION! Brand New Designer Showcase Overlooking the Bay near Nueva School. Dream Team of design and craftsmanship: award-winning San Francisco designer Studio Michael Hilal infuses cutting-edge modern DNA with warmth, livability, and a symphony of handpicked accoutrements. Custom builder Nejasmich Developments delivers renowned detail and artistry to a sleek canvas by Sausalito architect Brooks McDonald. The INNOVATION begins with a one-story building envelope. This platform sets the stage for ceilings over 12 feet, and 360 DEGREES OF LUXURY, with dynamic flow to usable flat lands at both front & rear. SEAMLESS is a most fitting theme for this lifestyle. Minimize the boundaries of indoors & outdoors, seamless attention to clean lines & finishes harmonizes as organic ambiance. | European Luxe meets Eastern Minimalism| Showstopper Great Room | Bay-View Party Terrace off Dining Room | 4 beds, 3.5 baths, plus Office, + Family Den in main home | Deluxe ADU for sleeping quarters, kitchen/laundry | Pro quality Gym w/ morning bar, German Sauna, backlit mirrors | Decadent Wine Pantry | Premium millwork of white oak & walnut, curated designer lighting | 3 Steam Showers | Pewter-Flamed Limestone hardscape | Gated Entry | Fire Pit | Outdoor Grilling Hub

55 Del Monte DR, Hillsborough

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

Sold listing courtesy of Kristopher Mares from KWPEN

$8,000,000

5 Beds ⋅ 5 Baths ⋅ ML82020606 MLS

Experience the perfect blend of luxury, elegance & California living in this breathtaking Mediterranean estate. This residence offers unparalleled privacy & sweeping views of the San Francisco Bay & surrounding mountains. A long, gated driveway welcomes you setting the stage for the home's elegant interior. Step inside to a dramatic, light-filled foyer featuring a graceful winding staircase that leads into an expansive living room framed by floor-to-ceiling windows showcasing the spectacular views.The gourmet chef's kitchen is comes complete with a large center island, elegant stone countertops, & top-of-the-line Viking stainless steel appliances. A richly wood-paneled library/office & spacious formal living & dining areas add sophistication, while new double-pane windows enhance comfort & energy efficiency throughout the home.Upstairs a primary suite awaits, featuring a spa-inspired bath with a jetted soaking tub, alongside generously sized bedrooms offering comfort & privacy. The impeccably landscaped grounds create a true oasis, featuring a resort-style pool & spa, & private tennis court. Perfect for both relaxation & entertaining, this property offers an unmatched lifestyle in one of California's most coveted settings.

75 Eugenia WAY, Hillsborough

Listed by Donald Kung, 650-219-8700 from Remax Capital
(If provided) CoList: from

Sold listing courtesy of Cici Wang from CBR

$9,350,000

5 Beds ⋅ 6 Baths ⋅ ML82012753 MLS

Welcome to Villa De Pinehill an exceptional Mediterranean masterpiece nestled on nearly two acres of enchanting, Italian-inspired gardens. Spanning three stories, this estate is a harmonious blend of timeless elegance and modern sophistication. Inside, exquisite craftsmanship is on full display with custom woodwork, premium natural stone, and globally sourced materials that infuse each space with old-world charm and refined luxury. A grand entrance sets the tone for the expansive interiors, featuring soaring ceilings, generously scaled rooms, and a chefs kitchen with a large island that flows seamlessly to the outdoor lawn and detached guest house. The lower level is designed for entertaining, complete with a wine room, full bar, and flexible bonus space. Multiple balconies and terraces overlook the gated, resort-like grounds. Additional amenities include radiant heating, a security system, an outdoor kitchen, three fireplaces, and a hot tub. A private one-bedroom guest house, with its own eat-in kitchen offers an ideal retreat for guests all set within a coveted enclave of equally stunning estates. Main house 7710sqft + guest house 640 sqft

414 Pinehill RD, Hillsborough

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

Sold listing courtesy of Phil Chen from SGP

$9,300,000

5 Beds ⋅ 4 Baths ⋅ ML82016912 MLS

Privately situated at the end of a gated cul-de-sac, this beautifully remodeled home offers the rare combination of complete privacy and accessibility. Set just 0.2 miles from Downtown Burlingame, it is the only Hillsborough home on the market with such close proximity to Burlingame Avenue less than five minutes (+/-) from fine dining, shopping, cafes, and local events. Families will also appreciate the quick access to top-rated North and Crocker Schools, Burlingame High, Crocker Fields and Tennis Courts, and the Burlingame Country Club. Inside, soaring ceilings, Fleetwood doors, skylights, and engineered wood floors set a sophisticated tone. The chefs kitchen features Wolf, Gaggenau, and Sub-Zero appliances, a marble island, and custom Segale Brothers cabinetry connecting seamlessly to both formal and casual living areas. Five bedrooms are located along a skylit hallway, including a serene primary suite with backyard access, spa-style bath, and fitted walk-in closet. Outdoors, enjoy a custom pool and spa, water features and a fully equipped pavilion with heat, lighting, and AV. A turf and grass lawn, mature trees, and curated plantings complete the backyard retreat. Additional highlights include multiple fireplaces, a mudroom/laundry room, and a 2-car garage.

45 Kammerer CT, Hillsborough

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

Sold listing courtesy of Kalina Wasman from COMPS

$7,486,250

5 Beds ⋅ 5 Baths ⋅ ML82016885 MLS

Main 3770, guesthouse 726, garage 405 = 4901. The picture of storybook charm is in this desirable lower Hillsborough, single level home. Main house is 4 bedrms, 4 baths, 2 offices, 1 spacious overlooking front gardens, & other attached to the primary ensuite. Newly built custom guest house. Guest house is 1 bed/1 bath. It includes a living rm w/fireplace, kitchen, & Nana doors opening to the backyard w/ a sunny bedrm, gorgeous bathrm, & relaxing sauna. The interiors of the main home include formal spaces w/an open family/great room. Formal living rm boasts a large gas fireplace & sliding French doors to the backyard. The chefs kitchen is open to the family rm & includes a separate wet bar, counter dining, & wine closet, all surrounded by handsome cabinetry. The lavish primary bedrm wing features a fireplace, an adjacent office, a custom bathrm w/oversized shower & heated floors, large walk-in closet, & sliding doors leading to the backyard. There are three additional bedrms, 1 is ensuite. The backyard is quintessential California living at its finest w/sparkling pool & spa, a built-in BBQ, dining & lounging areas, a fabulous firepit & seating area, cold plunge pool & incredible gardens. Blocks to downtown Burlingame & Broadway Aves, close to airports, SF, excellent schools

1715 Forest View AVE, Hillsborough

Listed by Valerie Soltau, 650-464-3896 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of The Sharp Group from KWPEN

$5,050,000

5 Beds ⋅ 6 Baths ⋅ ML82016683 MLS

Welcome to 2855 Churchill Drive, a serene retreat in the prestigious Hillsborough community. This elegant 4,340 sqft home offers 5 spacious bedrooms and 5.5 bathrooms, blending timeless design with modern comfort. Inside, hardwood floors, recessed lighting, and statement chandeliers create a warm, refined atmosphere. The chefs kitchen boasts a large center island, breakfast nook, and top-tier appliances ideal for everyday meals or entertaining. Natural light pours through dual-pane windows, enhancing the open layout and cozy fireplace. Host in the formal dining room, work from the home office, or unwind in the media/recreation room. The primary suite features a spa-like ensuite with soaking tub, separate shower, and dual vanities. All bedrooms include generous space and walk-in closets. Outside, enjoy a private backyard oasis perfect for relaxing or gathering with friends. Additional perks include central heating and a full laundry room with washer and dryer. Experience luxury, comfort, and California living at its finest.

2855 Churchill DR, Hillsborough

Listed by Curtis Lim, 650-678-6805 from Compass
(If provided) CoList: from

Sold listing courtesy of DeLeon Team from DLRPA

$11,000,000

5 Beds ⋅ 6 Baths ⋅ ML82016282 MLS

Classic Georgian colonial architecture and modern sophistication are masterfully blended in this gorgeous lower Hillsborough home, located at the end of a quiet cul-de-sac. With a perfect floor plan for any family, this 5 bedroom, 5.5 bathroom property was recently reimagined by designer Jon De La Cruz. The kitchen features custom oiled rift-sawn walnut cabinets, marble island, Pietra Cardoza countertops and backsplash, and a standing seam hood surround. A custom metal see-through fireplace adjoins the living room to the family room, which leads to the fully closable poolside lanai that is ideal for indoor/outdoor living. This property is the perfect balance of tasteful design and modern technology, with new curved standing seam metal roof, copper gutters, solar panels, Tesla battery back-up, and overhauled electrical/fiber internet network/entertainment systems. Walk to downtown Burlingame and Hillsborough's award-winning schools!

615 Devon DR, Hillsborough

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

Sold listing courtesy of The Patty Dwyer Group from APR

$11,100,000

5 Beds ⋅ 6 Baths ⋅ ML82010101 MLS

BRAND NEW, COMPLETELY REBUILT MID-CENTURY SMART HOME (COMPLETED IN 2025) LOCATED IN PRIME LOWER HILLSBOROUGH, IN THE PRESTIGIOUS RYAN TRACT NEIGHBORHOOD! This split-level home boasts a sleek exterior, new interior with all the latest smart home technology, a lower level attached basement ADU (included in total square footage) with a full kitchen, bedroom, and bathroom. ABSOLUTELY NO EXPENSE WAS SPARED in this one-of-a-kind, showcase home. This Mid-Century home effortlessly blends living, dining, and kitchen areas into one expansive, light-filled space, perfect for both entertaining and everyday living. Each bedroom is designed as a private retreat, complete with its own ensuite bath, offering comfort and convenience w/ a touch of luxury. The property itself sits on a rare, all-flat lot of almost half acre of land, offering both expansive outdoor space and total privacy. This home redefines elegance, standing as one the most luxurious estates in all of Hillsborough. Highlights include: a sparkling pool, outdoor kitchen, wine cellar, game room, office/study, 20 skylights, heated bathroom floors, solar, a chef's kitchen, formal dining room, luxurious primary suite, access to top schools, & SO MUCH MORE - TOO MANY DETAILS TO LIST, this is a MUST SEE in person!

695 Fairway CIR, Hillsborough

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

Sold listing courtesy of Jenn Gilson from MCGR

$6,710,000

5 Beds ⋅ 7 Baths ⋅ ML82012120 MLS

Contemporary Wow Factor, hidden Bay-view retreat. Barely visible from the road, this sophisticated haven in the hills commands utmost privacy, vistas, and epic volume.

10 Fawn CT, Hillsborough

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

Sold listing courtesy of Geoffrey Nelson from CBR

$5,050,000

5 Beds ⋅ 4 Baths ⋅ ML82011157 MLS

Perched on almost an acre in Hillsborough, this expansive property offers the perfect balance of luxury, privacy, and breathtaking surroundings. Tastefully updated in 2003, the 4 bedroom, 2.5-bathroom residence plus a separate 1BR & 1BA ADU with its own attached two-car garage, providing an excellent space for extended family, guests, or private accommodations. The main house also features an additional two-car garage, bringing the total to four. Designed for both comfort and sophistication, the home features a spacious primary suite with a Jacuzzi tub. Distinct formal dining, family, and living areas create an inviting yet functional layout. The gourmet kitchen is equipped with a central island, perfect for both everyday cooking and entertaining. Hardwood flooring extends throughout, enhancing the homes warmth and refinement. The beautifully landscaped grounds, boasts partial views and a secure gated entry. This exceptional home presents a rare opportunity to experience premier Hillsborough living, where space, style, and serenity come together effortlessly.

2260 Summit DR, Hillsborough

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

Sold listing courtesy of Leon Hu from SEHU01

$6,530,000

5 Beds ⋅ 5 Baths ⋅ ML82010779 MLS

NEW PRICE!! Nestled on .66 acres in Lower North Hillsborough, this stunning home is located near North Hillsborough School. The 2-story foyer leads to a spacious LR w/ fireplace insert, recessed lighting, built-in speakers, & large windows framing tranquil views of lush greenery. The formal DR offers picturesque views of patio & pool. The oversized eat-in kitchen boasts granite countertops, & custom wooden cabinetry. It comes equipped w/high-end appliances, including 2 dishwashers, Viking refrigerator, 6-burner range, & double ovens. The breakfast area opens rear patio, enhancing the kitchen's flow. The spacious family rm has soaring ceilings, 2 skylights, built-in speakers, fireplace, & bar w/ wine fridge, sink, & an add'l refrigerator. A powder room is situated off the entry. Also on main level is office or 5th BR, w/its own full bath. Upstairs, a generously sized primary BR suite features luxurious walk-in closet, fireplace, & access to private balcony. The attached bathroom has skylight, double-headed shower, & double sinks. 3 add'l BRs, 2 more bathrooms, & a laundry rm complete the 2nd level. Add'l features include a 3-car garage w/built-ins, 2 furnaces, & 2 AC units. The rear patio & yard offer a serene oasis, w/ pool, 2 spas, & outdoor kitchen w/BBQ area.

801 Eucalyptus AVE, Hillsborough

Listed by Austin Herman, 650-773-8652 from Compass
(If provided) CoList: Susan Herman from Compass

Sold listing courtesy of Vahid Firouzdor from COMPS

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