Hillsborough Homes with Canyon View

Welcome to Hillsborough, California—where charm meets elegance in one of the most coveted neighborhoods in San Mateo County. Nestled between the bustling city of San Mateo and the serene beauty of the San Francisco Peninsula, Hillsborough is a hidden gem that boasts a unique blend of natural beauty and suburban sophistication. With its tree-lined streets, manicured lawns, and stately homes, this picturesque town offers a tranquil escape from the hustle and bustle of city life.

One of the standout features of Hillsborough is its breathtaking canyon views. Many homes in this affluent community are designed to take full advantage of the stunning vistas that stretch across the lush hillsides and valleys. Imagine waking up each morning to the sight of rolling canyons bathed in golden sunlight, or enjoying a glass of wine on your patio as the sun sets, painting the sky in hues of orange and pink. Homes with canyon views in Hillsborough are not just residences; they are a lifestyle choice that embraces the beauty of nature while providing the luxury and comfort that discerning homeowners desire.

In addition to its scenic landscapes, Hillsborough is renowned for its top-rated schools, upscale shopping, and a strong sense of community. Residents enjoy a plethora of recreational activities, from hiking and biking in nearby parks to hosting neighborhood gatherings in the local community centers. Whether you’re raising a family or looking for a peaceful retreat, Hillsborough offers an unparalleled quality of life.

Explore the enchanting homes with canyon views in Hillsborough, and discover the perfect blend of luxury, comfort, and breathtaking natural beauty. Your dream home awaits!

Newest Hillsborough Homes with Canyon View

$5,995,000

4 Beds ⋅ 7 Baths ⋅ ML82054112 MLS

Offered for the first time in over 40 years, this iconic Hillsborough estate presents a rare opportunity to own a piece of local history. Set within the coveted Lakeview neighborhood on a private cul-de-sac, the home is thoughtfully designed to embrace its breathtaking surroundings, where panoramic Bay and canyon views are showcased through dramatic walls of windows and enjoyed from multiple view decks. Light-filled interiors offer seamless indoor/outdoor living with expansive gathering spaces, four bedrooms, each with an en suite bathroom, a fitness/yoga studio with sauna, and a dedicated media room ready to become the ultimate home theater. Set on an expansive 25,000± sq. ft. lot with over 7,000 sq. ft. of living space, this timeless estate blends privacy, scale, and natural beauty. Ideally located between San Francisco and Silicon Valley, just minutes from SFO, Highway 280, and top-rated public and private schools. A truly rare opportunity to call one of the Peninsula's most prestigious neighborhoods home.

95 Southdown CT, Hillsborough

Listed by Madelyn Brown, 408-761-7776 from KW Bay Area Estates
(If provided) CoList: Scott C. Poncetta from KW Bay Area Estates

$39,888,000

8 Beds ⋅ 13 Baths ⋅ ML82036796 MLS

Sitting on a commanding 2.5 acres atop a Hillsborough promontory with panoramic views, this bespoke estate reflects the vision of MAK Studios authority in modern design. Defined by a sculptural stone, glass and wood facade and a dramatic 22-foot high entry that frames the horizon, this home has 8BR's and options for 2 offices. The culinary program is exceptional: a statement kitchen appointed with Gaggenau appliances and supported by a fully equipped staff dirty kitchen for seamless entertaining at scale. The primary suite is conceived as a five-star retreat, enveloped in full slab marble with a steam shower and integrated smart amenities. Leisure and lifestyle spaces rival those of a private club multiple grand lounges, a state-of-the-art theater, executive office, fitness studio, bar, golf simulator, and a 1,620-bottle wine cellar. Advanced Crestron automation orchestrates lighting, climate, window treatments, and security, while radiant heat, owned solar, tankless systems, and a standby generator ensure efficiency and resilience. Resort-level grounds unfold with a 50-foot pool and spa, fire-lit terraces, manicured lawn, putting green, expansive motor court, and dual two-car garages a rare convergence of design, scale, and setting in Hillsborough.

455 Pinehill RD, Hillsborough

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

$9,800,000

7 Beds ⋅ 8 Baths ⋅ ML82032512 MLS

*NO SHOWINGS UNTIL AUGUST 2026* Set behind private gates on a 0.645-acre parcel in Hillsborough's prestigious neighborhood, this 9,035 sq ft estate offers sweeping San Francisco Bay views & exceptional scale. A grand double-door entry opens to a dramatic foyer with a stained-glass dome skylight, leading to an expansive main level defined by floor-to-ceiling glass and abundant natural light. Custom coved & vaulted tray ceilings with architectural pillars enhance the living room, formal dining room, and family room, all unified by rich hardwood floors. Refined details include stained glass accents, skylights, crown molding, wainscoting, recessed lighting, and a multi-room audio system. The formal living and dining rooms feature fireplaces, with roof deck access ideal for entertaining. The family room includes a custom wet bar with wine cooler and built-ins. The chef's kitchen offers granite counters, center island, pantry, high-end appliances, and breakfast nook. The main level includes a paneled office, powder rooms, laundry, garage access, and a spacious primary suite. The lower level offers six additional bedrooms, staff quarters, wine cellars, a second kitchen, and access to a glass-enclosed indoor pool with spa. Expansive patios, synthetic lawn, walking paths, and motor court.

2930 Privet DR, Hillsborough

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

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Intero are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.