Hillsborough Homes with Canyon View

Welcome to Hillsborough, California – a hidden gem nestled in the heart of San Mateo County. Known for its lush landscapes and serene atmosphere, Hillsborough is an affluent residential community that offers a perfect blend of suburban charm and natural beauty. With its tree-lined streets and meticulously manicured gardens, this picturesque town is a haven for those seeking tranquility and a touch of elegance.

One of the standout features of Hillsborough is its stunning homes with canyon views. Imagine waking up each morning to breathtaking vistas of rolling hills and lush canyons, where the beauty of nature greets you at your doorstep. These properties not only provide a sense of privacy and seclusion but also offer an unparalleled opportunity to enjoy the outdoors. Whether you’re sipping coffee on your balcony or hosting a gathering in your backyard, the stunning surroundings elevate everyday living to a new level.

Hillsborough is also renowned for its top-rated schools, making it an ideal locale for families. The community is committed to maintaining a high quality of life, with numerous parks and recreational facilities available for residents to enjoy. The proximity to San Francisco and Silicon Valley adds to the allure, providing easy access to urban amenities while allowing you to retreat to your serene oasis.

If you’re looking for a place that combines luxury living with natural beauty, Hillsborough’s homes with canyon views offer an exceptional opportunity. Discover the charm of this remarkable town and envision your future in a home that embraces both elegance and nature. Welcome to Hillsborough – where 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 Court, Hillsborough

$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 Road, Hillsborough

$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 Drive, Hillsborough

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Based on information from California Regional Multiple Listing Service, Inc. as of . This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.