255 Brentwood Road, Hillsborough
Offered at $10,995,000
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Snapshot

6 Bedrooms
6 Baths
5,290 Sq Ft
25,921 Lot
Offered at $10,995,000

Modern Living in the Heart of Hillsborough

Modern Architecture | Exceptional Natural Light Throughout | Open-Concept Kitchen + Dining | Chef’s Kitchen with Miele Appliances | Two Dishwashers | Walk-in Pantry | Built-in Bar with Wine Fridge | Formal Living Room with Glass Doors | Casual Living Room | Elevator Connecting All Levels | Six En-Suite Bedrooms | Private Primary Suite with Balcony | Mudroom | Dedicated Wine Room | Expansive Grounds | Seamless Indoor-Outdoor Living | Outdoor Kitchen | Custom Sport Court | Putting Green | Turf + Grass Landscaping | Architectural Plantings | Close to South School + Crystal Springs Uplands


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Features

Set in the coveted lower South Hillsborough neighborhood, 255 Brentwood is a striking expression of modern design—where natural light, clean architecture, and thoughtful functionality come together in perfect balance.

Beautifully positioned to capture both openness and views, the home offers a rare blend of scale, privacy, and everyday convenience—just moments to top-rated schools including South School and Crystal Springs Uplands, as well as nearby tennis courts, fields, and recreation.

A bold, contemporary front door opens to a luminous foyer, where soaring vaulted ceilings and expansive sightlines immediately set the tone. Natural light pours through the home, highlighting designer lighting, curated finishes, and a seamless indoor-outdoor connection that defines the living experience.

At the heart of the home, the open-concept kitchen and dining area create a true gathering space—designed for both effortless daily living and elevated entertaining. The chef’s kitchen features warm walnut accents, premium Miele appliances, dual dishwashers, and a generous pantry. A built-in bar with wine fridge enhances the entertaining experience with both function and style.

The main level offers a relaxed yet refined flow, anchored by a casual living room and complemented by two en-suite bedrooms. A separate formal living room, wrapped in glass doors and windows, opens seamlessly to the backyard—creating a true indoor-outdoor lifestyle with multiple access points and natural flow.

Thoughtfully designed for comfort and longevity, a private elevator connects all levels of the home, offering ease and convenience throughout.

The lower level adds versatility with an additional bedroom, mudroom, and a dedicated wine room—perfectly suited for both everyday function and entertaining.

Upstairs, the primary suite is a private retreat, complete with its own balcony, serene outlooks, and a spa-like en-suite. Two additional en-suite bedrooms with generous closets complete the level.

Outdoor living is elevated at every turn. Designed for both relaxation and recreation, the grounds feature a seamless blend of turf and grass, architectural plantings, and multiple zones for gathering. A fully equipped outdoor kitchen, integrated sound system, curated lighting, and four fireplaces create a true resort-like setting, while a custom sport court and putting green complete the experience.

Just minutes to downtown Burlingame’s premier dining and shopping, top-rated schools, and major commute routes including Highway 101, 280, and SFO, the location delivers both lifestyle and connectivity at an exceptional level.

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Hillsborough Photo

About Hillsborough

Offering a rare combination of tranquil seclusion and access to one of the most vibrant economic areas in the world, Hillsborough is a coveted neighborhood to live in. With its neighboring town, Burlingame, this area provides a unique combination of city sophistication and rural beauty. A quick drive to the San Francisco International Airport (about ten minutes from most points in Hillsborough) puts the world at your fingertips. Some of the most exclusive homes and top-rated schools in San Mateo County are found in the community of Hillsborough.  

Hillsborough is an ideal community location, situated between two major freeways, Highway 101 and Interstate 280. Hillsborough provides a link with San Francisco to the north, Silicon Valley to the south and the East Bay just across the San Mateo-Hayward Bridge.