5-Bedroom Houses for Sale in Hillsborough, CA

Step into a piece of history w/ this extraordinary Hillsborough property, originally the 5-stall carriage house for the infamous 16-acre Fagan Estate. Transformed in 1971, the carriage house is now a luxurious single-family residence, designed to cater to modern living, while beautifully preserving the historic charm. Spanning approximately 7,000 square feet, the home includes 7 bedrooms, 4.5

Emily Patterson KW Advisors

A symphony of modern architecture and refined design, 855 Darrell Road is a one-of-a-kind contemporary estate where form meets function in the most breathtaking way. Crafted by Kelland Architects and built by Thorenfeldt Construction, every inch of this 7,370-square-foot residence pulses with innovation, artistry, and intention. From the moment you step inside, youre greeted by soaring ceilings,

Bedbury Group Golden Gate Sotheby's International Realty

Welcome to this stunning, newly remodeled 6-bedroom, 6.5-bathroom home located in the desirable city of Hillsborough. This expansive residence boasts 6,690 sq. ft. of luxurious living space on a generous 36,920 sq. ft. lot. The gourmet kitchen is a chef's dream, featuring a gas cooktop, island with sink, quartz countertops, multiple wine refrigerators, freezer, and additional high-end appliances,

Kara Lee Compass

Welcome to 20 Pine Court, where sleek modern design meets the warmth of everyday life. Tucked at the end of a quiet cul de sac in Hillsborough, this 5 bedroom, 5 full bath, 2 half bath home was designed by acclaimed architect Sean Bailey to invite both connection and calm. Picture your mornings here, light pouring through floor to ceiling glass, enjoying breakfast at the oversized kitchen island

Paul Zinchik Compass

Step into your modern farmhouse masterpiece in the coveted Carolands neighborhood of Hillsborough. Situated on a flat and spacious half-acre lot, this home has undergone a complete renovation and expansion, ensuring a modern and comfortable living experience. The main house offers 4 bedrooms and 4 bathrooms, with the added bonus of a brand new ADU that includes a 5th bedroom and additional bath.

Phil Chen Christie's International Real Estate Sereno

LOWER HILLSBOROUGH'S PREMIER ESTATE! LUXURY, DESIGN, & PRIVACY! Rare listing, a once-in-a-lifetime property w/ one of the LARGEST LOTS in its area -- 1.286 ACRES OF TOTALLY FLAT LAND! European style Italian Villa, constructed to perfection resembling the work of "turn-of-the-century" architect George Howard. UPDATED & RENOVATED throughout the years. EXTENSIVE STREET SETBACK. Detached 5-car garage

Stanley Lo Green Banker Realty

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

Phil Chen Christie's International Real Estate Sereno

A modern sanctuary of luxurious California living, 655 Hayne Road is nestled in Hillsboroughs coveted Lower South neighborhood. Offered pre-completion with an estimated finish date of November, this gated estate sits on a sprawling, fully usable lot and blends sophisticated design with resort-style amenities. The open-concept main residence level embraces indoor-outdoor living and showcases

Shaun Walter Coldwell Banker Realty

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

Stanley Lo Green Banker Realty

Situated on a private side street, this grand estate sits on a majestic 2-acres with jaw-dropping panoramic bay views, some of the best in all of Hillsborough. Exquisite architectural detailing and finishes throughout, including inlaid parquet walnut floors, hand carved fireplaces, and walls of glass framing iconic bay views and landscaping. The main level includes a stunning office, billiard

Pierre & Alex Buljan Compass

ICONIC 1920'S DUTCH COLONIAL-STYLE HOME LOCATED ON ONE OF HILLSBOROUGH'S MOST COVETED STREETS. THIS ELEGANT HOME HAS BEEN THOUGHTFULLY REMODELED WITH TOP-OF-THE-LINE MATERIALS AND FINISHES. THIS 6800+SF ESTATE OFFERS 6 BEDROOMS 5 FULL AND 2 HALF BATHS, AN AU PAIR SUITE, AND A SPACIOUS LAYOUT. ABUNDANT NATURAL LIGHT CAPTIVATES THE INVITING AMBIANCE SHOWCASING THE AMAZING DETAIL THROUGHOUT THE

Nick Corcoleotes Coldwell Banker Realty

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

Donald Kung Remax Capital

Completely transformed with a sophisticated modern aesthetic, this Hillsborough home showcases sweeping and spectacular Bay and San Francisco skyline views. High end down to the studs remodel in 2013 with no expense spared. Located in the coveted Lakeview neighborhood on just over one-half acre, features a striking two-story facade and generous outdoor spaces designed for entertaining around a

Judy Citron Compass

Tucked at the end of a quiet cul-de-sac on approximately 2 private acres, The Koshland Estate is a once-in-a-lifetime offering in one of the Peninsulas most prestigious enclaves. Designed in 1961 by Frank Lloyd Wright disciple Howard Friedman for his father-in-law, Levi Strauss & Co. President and CEO Daniel Koshland, the home was constructed to exceptional commercial-grade standards, rarely seen

Pierre & Alex Buljan Compass

NEW LISTING AND RECENTLY REFRESHED!!! ONE OF HILLSBOROUGH'S FINEST PROPERTIES!!! Breathtaking views of the San Francisco bay & beyond. HUGE MOSTLY LEVEL LOT WITH OVER .5 ACRES. Exquisite Mediterranean designs with a red-tiled roof and circular paver driveway. A grand foyer welcomes you in with soaring ceilings. Throughout, you'll find hardwood flooring, carpeting, and recessed lighting. To the

Stanley Lo Green Banker Realty

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

Geoffrey Nelson Coldwell Banker Realty

Welcome to 45 Calaveras Court, a brand-new modern masterpiece nestled in the Hillsborough hills. Located at the end of a private cul-de-sac on a sizable 4-acre lot, this stunning residence offers approximately 7,000 square feet of elegantly designed living space. Enjoy unobstructed canyon views from every window, providing a breathtaking backdrop to your everyday life. Step inside to discover

Pierre & Alex Buljan Compass

Custom-crafted French Country-style home built in 2001 on a large lot in highly desirable Easton Addition near Broadway, top schools and the beloved neighborhood library. The classic French Country facade has timeless curb appeal with a stucco exterior, slate tile roof, copper gutters and downspouts, true divided-light windows and an arched front door. Blending traditional elements with modern

Stephen Johnson Capital Realty Group

Welcome to 11 La Strada Ct, Burlingame—a stunning, Mediterranean-style home located in an exclusive gated community. Built in 1999, this luxurious residence blends timeless elegance with modern comforts. As you enter, you're greeted by a grand, marble-tiled entrance, setting the tone for the sophisticated interiors. The home features soaring high ceilings that enhance the sense of space and

Andrew Fung Ramsell Real Estate Inc