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Hillsborough

Hillsborough, CA
Hillsborough, CA

You found the right website if you are searching for homes for sale in Hillsborough CA. Our website has EVERY Hillsborough home for sale in California listed in the MLSListings Inc. MLS.

Hillsborough is an incorporated town in San Mateo County, California, in the San Francisco Bay Area. It is located 17 miles (27 km) south of San Francisco on the San Francisco Peninsula, bordered by Burlingame to the north, San Mateo to the east, Highlands-Baywood Park to the south, and Interstate 280 to the west. The population was 11,273 as of 2013

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Hillsborough Real Estate


Hillsborough is located on the Rancho San Mateo Mexican land grant which was purchased by William Davis Merry Howard, son of a wealthy Hillsborough, New Hampshire, shipping magnate, in 1846. Howard settled his family in this area, which attracted wealthy San Franciscans. Hillsborough is near Burlingame. In 1910, Hillsborough residents voted to incorporate.

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Geography and environment

According to the United States Census Bureau, the town has a total area of 6.2 square miles (16 km2), all of it land. The area’s considerably winding, hilly topography, and impossibility of a grid layout make Hillsborough notoriously challenging to navigate. Many lots include fairly steep slopes, particularly the western side of the town, with the landscape generally flattening to the east as it descends from the 280 freeway to El Camino Real and the towns of Burlingame and San Mateo.

Two prominent streams drain the mostly wooded slopes of Hillsborough: San Mateo Creek and Cherry Creek. In both cases the upper watersheds are closed-canopy California oak woodlands, with dominant trees of Coast Live Oak, Pacific Madrone and California Bay.

The upper drainage area of San Mateo Creek in Hillsborough contains significant serpentinite outcrops, which are known habitats for several rare plant species including the San Mateo woolly sunflower. Other common plants include toyon, gooseberry, lupine, monkeyflower and coffeeberry. Commonly observed mammals include California mule deer, raccoons, opossum, coyotes, rabbits, squirrels, and skunks.

Hillsborough is bordered by Burlingame to the north, San Mateo to the east, Highlands-Baywood Park to the south, and Interstate 280 to the west.

Hillsborough’s landscape is dominated by large homes; the town zoning and subdivision ordinances require a 2,500-square-foot (230 m2) minimum house size and minimum lot size of 0.5 acres (2,000 m2). As a result, there are no apartments, condominiums or townhouses in the city limits; however, it is not unusual for the homes along the eastern edge of Hillsborough to face condominiums in neighboring Burlingame, sharing the ZIP code 94010.

The town has no commercial zoning and thus no businesses within the town limits; the only non-residential properties are the town’s four public and three private schools, town and county government facilities, a golf course, a country club, and small parks.

Schools

Hillsborough has its own highly regarded and -ranked public elementary and middle school system, but no public high school. High school-aged children can attend one of several schools in the San Mateo Union High School District, generally assigned by residential address. The town is also home to a small number of independent schools. The Hillsborough school district is ranked as the #1 school district in California and one of the top ten school districts in the country.

  • The Nueva School, a nationally recognized independent school serving gifted and talented students.
  • Crocker Middle School, a public middle school, located on Ralston Avenue, named after William H. Crocker.
  • West Elementary School, a public elementary school, located on Barbara Way.
  • South Elementary School, a public elementary, at 303 El Cerrito.
  • North Elementary School, a public elementary, at 545 Eucalyptus Avenue.
  • The Bridge School, a school serving students with physical and speech impairments.
  • Crystal Springs Uplands School, a college preparatory middle and high school.
Landmarks

Primarily a residential suburb of San Francisco, Hillsborough has many mansions and other points of interest within the town’s borders dating from the early 20th century.

  • Carolands — Built by Harriet Pullman Carolan, heiress to the Pullman railway. At 65,000 ft² (6,000 m²), it is one of the largest residences in the United States and is placed on the National Register of Historic Places.
  • ′The Flintstone House′ (a.k.a. the Adobe/Dome/Bubble/Marshmallow/Gumby house) — designed by architect William Nicholson and built in 1976 using sprayed concrete over balloon-shaped forms, now painted a deep/burnt orange color reminiscent of the Golden Gate Bridge’s distinctive hue. The house can be seen to the east from the Doran Memorial Bridge, northbound on Highway 280 between the Bunker Hill and Hayne/Black Mountain exits.
  • Skyfarm — Built by William H. Crocker, namesake of Crocker middle school, and grandson of Charles Crocker of California’s Big Four railroad magnates. Designed by Arthur Brown, Jr., and opened in 1930. Home since the 1960s to The Nueva School.
  • Tobin Clark Estate – Originally designed by the noted architect David Adler for Mrs. Celia Tobin Clark, one of the Peninsula’s most prominent families of the early 20th Century
  • Uplands — Built by Templeton Crocker, as a gift to his fiancée Helène Irwin, heiress to the C&H Sugar family fortune. Designed by Willis Polk; opened in 1912, with interior of 35,000 ft² (3,250 m²). Home since the 1950s to Crystal Springs Uplands School.
  • Western White House — Commissioned by George Randolph Hearst, son of William Randolph Hearst and now privately owned. It, like Hearst Castle was designed by Julia Morgan.
  • Junípero Serra statue — Overlooking Highway 280, the statue was built in honor of Father Junípero Serra.
Climate

December is the coolest month with an average high of 60 degrees, and September is the warmest month with an average high of 78 degrees. Hillsborough has a Mediterranean climate (Köppen climate classification Csa), with the vast majority of the precipitation from the months of November to April. On average, Hillsborough receives 17 inches (430 mm) of rain. With coastal mountains to the west of Hillsborough, it is blocked in the winter from much of the rainfall over Half Moon Bay, and in the summer it is blocked from virtually all the fog of the coast. Hillsborough receives an average of 307 days of sunshine annually, with 52 days of recordable precipitation per year.

Content Courtesy of Wikipedia.org

Hillsborough, California Homes for Sale


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 in residential design. This approx. 8,000 square foot home offers 6 bedrooms, 4 full baths, and 2 half baths, all thoughtfully arranged within a layout that blends timeless design with grand-scale living. Positioned on a broad, level lot, the estate captures sweeping 200° views from San Francisco to San Jose, showcasing city skylines, iconic bridges, and the full expanse of the Bay Area. The Koshland Estate delivers an extraordinary combination of privacy, accessibility, and world-class vistas. A true Peninsula icon. $17,800,000 Active

130 Reservoir Rd Hillsborough, California

6 Beds 6 Baths 7,732 Sq Ft

Located in one of Hillsboroughs most sought-after locations, 130 New Place is a custom-designed contemporary estate on 1.7+ private acres with panoramic views. This 4BR 5BA (plus office and 3 half baths) home blends timeless architecture with contemporary elegance, creating a sophisticated yet inviting retreat.  The interiors by Douglas Durkin Design, offer a harmonious blend of luxury and comfort, featuring bespoke finishes, thoughtful details, and curated spaces that elevate everyday living. Outdoors, the landscape was crafted to bring a seamless indoor-outdoor experience with serene gardens, water features, elegant terraces, and thoughtfully designed outdoor living areas.  Expertly constructed by Peninsula Custom Homes, this residence reflects the highest standards in quality and craftsmanship. Every element has been carefully considered to deliver a home of enduring beauty, function, and presence. Additional features include a roof deck w/hot tub, bonus multipurpose room, elevator, potential pool site, pocket shades, home automation system, Fleetwood windows/doors, radiant heat and solar panels. $17,000,000 Active

130 New Place Rd Hillsborough, California

4 Beds 8 Baths 8,372 Sq Ft

LOWER HILLSBOROUGH'S PREMIER ESTATE! LUXURY, DESIGN, & PRIVACY! Rare listing, a once-in-a-lifetime property w/ one of the LARGEST LOTS in its area -- 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. Detached 5-car garage with a 1br/1ba ADU and private executive office / conference room. Amenities outside include a regulation tennis court, 2 separate spas, in-ground Pebble-Tec pool surrounded by flowering plants, A HUGE LAWN, multiple patios, a terrazzo terrace, vast motor court, statues by legendary sculptor Gaston Rognier, pristine landscaping by renowned designer Thomas Church, multiple gardens / flower beds, AND SO MUCH MORE! Additionally, the electrical, plumbing, heating, air conditioning, roofing, irrigation, retrofitting, & exterior lighting have all been upgraded modernizing this estate. Inside you'll find a large formal living room & dining rooms, a chef's kitchen, elliptical staircase w/ 40ft high entry, many 13ft high ceilings, butlers pantry, garden room, music room, whole house 22kW generator, smart electronic lighting, elevator, roof deck, multiple en-suites, & MORE! Too much to list here! $15,999,000 Active

245 W Santa Inez Ave Hillsborough, California

5 Beds 6 Baths 8,500 Sq Ft

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 hall, and the "Morocco Room" lounge. Upstairs, the large master suite enjoys equally stunning views of the bay, in addition to a luxury spa bath and formal sitting room. A separate in-law suite and wine cellar with tasting room are located on the lower level of the residence. Equally impressive are the surrounding grounds, fully landscaped with grand-scale trees, expanses of manicured lawn, and an elevated terrace overlooking the views and swimming pool. All of this just minutes from shopping, dining, golfing, parks, and top rated Hillsborough schools. (Square Footage Per County Records: 8,629) $14,995,000 Active

3085 Ralston Ave Hillsborough, California

5 Beds 7 Baths 10,495 Sq Ft

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 includes a Thermadorî cooktop, Sub-Zeroî fridge/freezer, wine cooler, and butler's pantry. A separate guest/in-law wing offers 2 en-suite bedrooms, lounge, and private entrance. The expansive primary suite spans half the upper level with dual walk-ins and a spa-like bath. A lower level includes a wine cellar and flexible storage space. Resort-style grounds boast a pool, spa, outdoor kitchen, fire pit, tennis/basketball court, detached en-suite guest studio, and a detached two-car garage currently used as a gym. A 3-car attached garage, paver motor court, solar panels, and modern central HVAC complete this exceptional offering just minutes from downtown Burlingame. $13,490,000 Active

2181 Parkside Ave Hillsborough, California

7 Beds 8 Baths 6,140 Sq Ft

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 SPARED in this one-of-a-kind, showcase home. This Mid-Century home effortlessly blends living, dining, and kitchen areas into one expansive, light-filled space, perfect for both entertaining and everyday living. Each bedroom is designed as a private retreat, complete with its own ensuite bath, offering comfort and convenience w/ a touch of luxury. The property itself sits on a rare, all-flat lot of almost half acre of land, offering both expansive outdoor space and total privacy. This home redefines elegance, standing as one the most luxurious estates in all of Hillsborough. Highlights include: a sparkling pool, outdoor kitchen, wine cellar, game room, office/study, 20 skylights, heated bathroom floors, solar, a chef's kitchen, formal dining room, luxurious primary suite, access to top schools, & SO MUCH MORE - TOO MANY DETAILS TO LIST, this is a MUST SEE in person! $12,280,000 Active

695 Fairway Cir Hillsborough, California

5 Beds 6 Baths 5,057 Sq Ft

A symphony of modern architecture and refined design, 855 Darrell Road is a one-of-a-kind contemporary estate where form meets function in the most breathtaking way. Crafted by Kelland Architects and built by Thorenfeldt Construction, every inch of this 7,370-square-foot residence pulses with innovation, artistry, and intention. From the moment you step inside, youre greeted by soaring ceilings, curated finishes, and dramatic Bay views framed by walls of glass. Five luxurious en suite bedrooms are tucked across three stunning levelseach an immersive experience in elevated living. The kitchen, a true showpiece, features custom walnut cabinetry, bold tile by Moses Hacmon, and a suite of chef-worthy appliances. Outside, a glass-railed deck and covered entertaining patio offer seamless indoor-outdoor flow, while the spa-inspired lower level, yoga studio, and smart-home systems redefine what it means to live well. Discover a modern marvel designed to captivate, inspire, and endure. $11,900,000 Active

855 Darrell Rd Hillsborough, California

5 Beds 6 Baths 7,138 Sq Ft

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 soaring ceilings that create an open and inviting atmosphere, complemented by an abundance of natural light that fills every corner. The expansive first floor features a massive entertainment deck, perfect for hosting gatherings or simply relaxing amidst nature. With a total of 8 bedrooms, including master suites on each level, this exceptional home is perfect for large families or multi-generation living. $11,800,000 Active

45 Calaveras Ct Hillsborough, California

8 Beds 7 Baths 7,132 Sq Ft

A modern sanctuary of luxurious California living, 655 Hayne Road is nestled in Hillsboroughs coveted Lower South neighborhood. Offered pre-completion with an estimated finish date of November, this gated estate sits on a sprawling, fully usable lot and blends sophisticated design with resort-style amenities.   The open-concept main residence level embraces indoor-outdoor living and showcases dramatic canyon vistas. A flexible lower level suits a home theater, gym, or game room. Manicured grounds surround a shimmering pool, while an attached two-bedroom ADU, complete with a spacious great room that functions as a stunning poolside retreat perfect for entertaining or extended living. A generous garage completes the layout.   Designed for both everyday comfort and refined entertaining, the home showcases high-end finishes, smart features, natural light, and a deep connection to the surrounding landscape. Ideally located near top public and private educational options and minutes from downtown Burlingame and San Mateo, with effortless access to major commute routes. This is more than a home, it's a private sanctuary of style and comfort in one of the Peninsulas most distinguished communities.  *Photos are representational renderings $10,500,000 Active

655 Hayne Rd Hillsborough, California

5 Beds 6 Baths 5,316 Sq Ft

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 baths, fully equipped media room, home gym & upstairs sunroom w/ solarium balcony access. The multi-level layout wraps around meticulously designed gardens, offering picturesque views throughout. The exterior features over half an acre of vast garden space. Enjoy the ivy-covered trellis, elevated terrace with heated saltwater pool & spa & rolling grass-covered yards. Garden pathways lead to a charming children's play area. Mature trees surround the property, ensuring complete seclusion and privacy. Located in the prestigious Lower Hillsborough area, this property sits on a private, quiet street w/ no through traffic. Excellent Hillsborough North schools are a significant draw for families, while the proximity to downtown Burlingame & San Mateo ensures you're never far from amenities. Quick connections to international airports, San Francisco, & Silicon Valley add to the convenience. $10,000,000 Active

55 Fagan Dr Hillsborough, California

7 Beds 5 Baths 6,818 Sq Ft

Step into your modern farmhouse masterpiece in the coveted Carolands neighborhood of Hillsborough. Situated on a flat and spacious half-acre lot, this home has undergone a complete renovation and expansion, ensuring a modern and comfortable living experience. The main house offers 4 bedrooms and 4 bathrooms, with the added bonus of a brand new ADU that includes a 5th bedroom and additional bath. Inside, discover 16-foot ceilings, stunning wood floors, abundant natural light, and premium upgrades throughout. The chef's kitchen features Thermador appliances and an 11-foot island, with La Cantina doors creating seamless indoor-outdoor flow. Outside, your private oasis awaitswith a beautiful pool, bocce ball court, and plenty of room to relax or entertain. The 775 sq ft ADU is versatile and perfect for guests, a home office, or extended family. This property perfectly blends modern living, luxury, and space in the sought-after Carolands neighborhood. Welcome home! $9,500,000 Active

588 Craig Rd Hillsborough, California

5 Beds 5 Baths 4,760 Sq Ft

Welcome to Villa De Pinehill an exceptional Mediterranean masterpiece nestled on nearly two acres of enchanting, Italian-inspired gardens. Spanning three stories, this estate is a harmonious blend of timeless elegance and modern sophistication. Inside, exquisite craftsmanship is on full display with custom woodwork, premium natural stone, and globally sourced materials that infuse each space with old-world charm and refined luxury.  A grand entrance sets the tone for the expansive interiors, featuring soaring ceilings, generously scaled rooms, and a chefs kitchen with a large island that flows seamlessly to the outdoor lawn and detached guest house.  The lower level is designed for entertaining, complete with a wine room, full bar, and flexible bonus space. Multiple balconies and terraces overlook the gated, resort-like grounds. Additional amenities include radiant heating, a security system, an outdoor kitchen, three fireplaces, and a hot tub. A private one-bedroom guest house, with its own eat-in kitchen offers an ideal retreat for guests all set within a coveted enclave of equally stunning estates. Main house 7710sqft + guest house 640 sqft $9,500,000 Active

414 Pinehill Rd Hillsborough, California

5 Beds 6 Baths 8,350 Sq Ft

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