5-Bedroom Houses for Sale in Hillsborough

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 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

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

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, &

Austin Herman Compass

Welcome to Casa La Cumbre, a warm & sophisticated modern home that is just as grand as it is inviting and laid back. Designed & re-built by renowned Bay Area builder, Craftsmen's Guild. At 7,789 sqft, this estate sits on a generous .75 acre lot. The home offers 8 bedrooms, 7.5 bathrooms, formal living & dining rooms, a great room with eat in kitchen, an upstairs den, movie theater, wine room,

Kia Amini Compass

A rare once-in-a-generation opportunity to own a true TROPHY PROPERTY in Hillsborough's coveted Homeplace neighborhood. This gated Mediterranean estate offers timeless architecture and modern luxury across approx. 6,880 sq ft on 1.22 acres. With 7 beds, 6 full baths, and 2 half baths, the home features elegant formal rooms, hardwood floors, French doors, and recessed lighting. The gourmet kitchen

Stanley Lo Green 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

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

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