5-Bedroom Houses for Sale in Hillsborough, CA

20 Pine Court, Hillsborough A Modern Architectural Masterpiece Nestled in the prestigious Skyfarm neighborhood, 20 Pine Court is a breathtaking 5 bedroom, 5 full bath, and 2 half bath modern estate envisioned by the acclaimed Sean Bailey Design. This architectural marvel seamlessly merges sophisticated elegance with unparalleled functionality, creating a living experience that redefines luxury.

Paul Zinchik Compass

In the Burlingame Country Club area, this stunning renovation combines chic sophistication with Spanish flair. Featuring 5 bedrooms and 5.5 baths across two levels, the home has espresso-hued hardwood and Saltillo tile floors complemented by updated lighting, 3 fireplaces with modern style. The floor plan features upstairs living areas and the primary suite opening to the resort-inspired rear

Alicia Sanguinetti Compass

This BRAND NEW (Built in 2024) never-lived-in ECO-FRIENDLY SMART HOME blends modern sophistication with sustainable living, offering breathtaking PANORAMIC VIEWS of the San Francisco Bay. The striking exterior showcases smooth white stucco, warm wood paneling, and expansive glass elements, including a grand entrance and a three-car garage. Soaring tray ceilings, recessed & cove lighting, and

Stanley Lo Green Banker Realty

Modern farmhouse in the coveted Carolands neighborhood of Hillsborough. Situated on a flat and spacious half-acre lot, this home has been remodeled and expanded from the studs to offer the ultimate in modern luxury. The main house features 4 bedrooms and 4 bathrooms, including a newly renovated primary suite with a walk-in closet and an expanded bath for a spa-like retreat. Inside, you'll be

Phil Chen Christie's International Real Estate Sereno

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

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

Modern Luxury Meets Cozy Elegance in Burlingame Park. This NEW BUILD home effortlessly combines sleek, modern design with natural materials to create a warm, inviting atmosphere. Every corner of this masterpiece has been meticulously crafted with high-end finishes, ensuring both style and comfort.Key Features-6 Spacious Bedrooms-8 Unique Bathrooms. The heart of the home features a gourmet kitchen

Beth Taylor Coldwell Banker Realty

Perfectly situated in the heart of South Hillsborough, 280 Uplands Drive offers a rare opportunity on an expansive, flat over half-acre lot surrounded by beautiful estates. Rebuilt and remodeled approximately 35 years ago, this 5-bedroom, 4.5-bath home spans nearly 5,000 square feet and features a generous floor plan, lush landscaping, and a swimming pool. While currently owner-occupied and not

Michael Haywood Jr. eXp Realty of California Inc

Architectural Gem! First time on the market in 60 years. Rarely available 5 bedroom 5 1/2 bath home in coveted lower north Hillsborough. Originally designed by renowned Mid Century modern architect Gardener Dailey with gardens designed by legendary landscape architect,Thomas Church. This classic home is the epitome of old world grace and elegance in a magical garden setting. The entry level

Lowrie Maclean Compass

DESIGN FOR LIVING: THE PERFECT MEETING OF SUN, CELEBRATION, AND SAVOIR FAIRE! Remodeled designer quality unfolds across multiple destinations, with minimal boundary between indoor and outdoor living. 5 bedrooms, 3 full baths, 2 half baths, plus large Office (or gym), and enormous recreation room of 21 x 26 feet. Majority of the home flows on one level, including four bedrooms all together

Geoffrey Nelson Coldwell Banker Realty

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

Experience the ultimate in luxury living at 60 Glengarry Way, a stunning 2021 new construction with breathtaking Mt. Diablo and Bay views. Meticulous attention to detail, mature landscaping, and a grand entrance set the tone for this exceptional property. Enjoy expansive entertaining spaces with a feature fireplace, European white oak flooring, and a gourmet kitchen equipped with high-end Miele

Eva Chen Compass

A private estate in the highly coveted Lower North Hillsborough, this trophy property spans 5.36 acres across four separate parcels, offering exceptional privacy, expansion potential, and investment value. Designed by renowned architects John Bakewell Jr. & Ernest Weihe, this French chateau-style masterpiece became home to Hollywood legend Bing Crosby. With ties to the legendary racehorse

Jenn Gilson Golden Gate Sotheby's International Realty

Welcome to 760 Chateau Dr., a stunning French Tudor-style estate that exudes timeless elegance while offering an inviting and comfortable living experience on 7,285 sqft of living area. The main residence spans 5,875 sq.ft of living area across three beautifully designed levels, featuring exquisite architectural details such as a grand fleur-de-lis spiral staircase, intricate cast iron light

Eva Sogotis KW Advisors

BEST DEAL IN TOWN! PRIVATE AND QUIET LOCATION! LARGE USABLE YARD! AMAZING SCHOOLS! A must-see breathtaking Hillsborough Park home! Top rated public schools: South Elementary School and Crocker Middle School/ Close to Downtown San Mateo shops and restaurants / Located at the end of a private cul-de-sac / 18 ft vaulted ceilings in the grand living room / Bright natural light / Primary suite + 2 en

Kathryn Gerhardt Gilmartin Group

A Rare Opportunity to Create Your Dream Home! Set on a large, sunny, and private lot, this well-maintained 5-bedroom, 4-bathroom French-style estate offers the perfect canvas for your vision. With timeless architectural details, soaring ceilings, and a grand southeast-facing entry, this home is filled with natural light and character just waiting to be reimagined. The main level features four

Alex Kononoff eXp Realty of Northern California, Inc.

Stop your search, this home has everything on your checklist: stunning, private views, a massive floor plan, high ceilings, and a prestigious Hillsborough address. The standout feature is the expansive downstairs media room. Once a concert hall for top artists, it can continue that legacy or be transformed into a home theater, fitness room(perfect for indoor pickleball!),or bonus living space.

Mary Bee Thrasher Remax Capital

APPROVED PLANS FOR A BRAND NEW MODERN HOME! ALL PERMITS COMPLETED, READY TO BUILD YOUR DREAM HOME!!! HUGE LOT WITH .621 ACRES OF USABLE LAND, SEATED IN THE PERFECT LOCATION / NEIGHBORHOOD. Plans include a 1 bed/1bath ADU with a full kitchen, dining, & living room, as well as a swimming pool. Close to top-rated schools, countless amenities, modern conveniences, Downtown Burlingame, and easy

Stanley Lo Green Banker Realty

LOWER HILLSBOROUGH'S PREMIER ESTATE! Rare listing, a once-in-a-lifetime property w/ one of the LARGEST LOTS in its neighborhood -- 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. There's a Detached 5-car garage with a

Stanley Lo Green Banker Realty

BEST CHOICE IN ALL OF LOWER HILLSBOROUGH - PRICE REDUCED $1 MILLION!!! Welcome to 1140 Bromfield, a stunning 5-bedroom estate set on 1.11 lush acres in the prestigious Lower Hillsborough neighborhood. This meticulously crafted home blends timeless elegance with modern convenience, offering an unparalleled living experience. Inside, discover 5 full bathrooms, 2 half bathrooms, and a gourmet

Stanley Lo Green Banker Realty

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

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

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