$5,100,950Average Value$1,503Average Price per Sq Ft29Homes For Sale
A peaceful enclave in the hills south of San Francisco
Hillsborough is a town of 11,000 people in the foothills of the Santa Cruz Mountains. It offers high-end homes along with peace and privacy. The area was developed as a community of country estates for prominent families, including railroad magnates. Since then, it has continued to attract the rich and famous, including Bing Crosby, William Hearst and Alden Clausen, who was head of the World Bank and Bank of America. Hillsborough and the neighboring city of Burlingame share the 26th wealthiest zip code in the United States.
Despite the prestigious zip code, Hillsborough has a down-to-earth community vibe. “In some other high-end areas, the neighbors don’t know each other. But we have a very tight-knit community that is upheld really well by an online system that binds people together. We also have fundraisers, like an annual car show and a fun run for the kids,” says Milana Ostroy, a Realtor and founder of Milana Real Estate Group who lives in Hillsborough. “We all know each other. I know every one of my neighbors — our dogs even know each other.”
The town of Hillsborough is located south of San Francisco.
Hillsborough is very residential, so locals can enjoy jogging on its wide, winding streets.
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Carolands and other historic mansions center quiet neighborhoods
Historic mansions center several Hillsborough neighborhoods and they range from relatively modest to spectacular. New homes must have a minimum of 2,500 square feet on lots of at least half an acre, but most Hillsborough homes are larger; averaging about 4,000 square feet. In the Tobin Clark Estate neighborhood on the eastern border, ranch-style and mid-century homes up to 6,000 square feet surround the Tobin Clark Tudor mansion, which was built in 1931. The Carolands neighborhood is also named for the historic estate at its center, It has homes around 14,000 square feet, and some have Beaux-Arts architectural elements such as Mansard roofs, grand entrances and bas-relief panels. The Skyfarm neighborhood is named for a 1931 mansion built for the Crocker family. In this neighborhood, stately traditional and Mediterranean revivals with over 5,000 square feet overlook the bay and hills. The median price of a home in Hillsborough is $5.5 million, and the average Hillsborough home value is 9 times the national average.
Lovely landscaping is the norm in Hillsborough.
This two story home in Hillsborough has a unique design.
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Restaurants and shops in nearby Burlingame and San Mateo
When Hillsborough was incorporated, town leaders prohibited businesses. “They were protecting what they referred to as a rural setting,” says Tim Anderson, Director of Building & Planning for Hillsborough. “That meant no post office, no gas station, no corner store, no hair salons and no pubs. Now people are comfortable keeping it residential, and it’s very quiet. With just a half dozen or so stoplights, it’s sometimes called the dark city.”
Today, Hillsborough remains residential with very little buisness in its borders, and most residents go to Burlingame or San Mateo for shopping, dining and entertainment. RASA, an Indian restaurant in Burlingame, and Pausa Bar & Cookery in San Mateo have earned recognition in the Michelin Guide. “Burlingame Avenue has become the go-to place on the Peninsula for people who want to go out but not to the City,” says Ostroy. “It has the trendy restaurants, luxury shopping, a lot of jewelry stores, coffee shops, a post office and an array of grocery store choices. There is also a farmer’s market on Thursdays and the weekend — that’s really popular in suburban life.”
Avocado Toast and 3 bees in are right next door to each other near Hillsborough.
Safeway is the one-stop shopping center for residents of Hillsborough.
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Golfing and hiking in Hillsborough and Crystal Springs areas
Hillsborough golfers have a choice of nearby courses. The Burlingame Country Club, located in central Hillsborough, was built in 1893 and has a private 18-hole golf course with views of the San Francisco Bay. The Crystal Springs Golf Course is integrated into the natural area surrounding the Crystal Springs Reservoir, west of town. Hikers are drawn to the Crystal Springs area — the Sawyer Camp Trailhead is on the southwest tip of the town. Several small parks within Hillsborough have sports facilities and playgrounds.
Burlingame Country Club in Hillsborough has many activities for club members.
Hillsborough is a popular destination for golfers due to its multiple golf courses.
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Schools are rated A-plus with Nueva School a private option
The town is served by the Hillsborough City School District, which is rated A-plus by Niche and the San Mateo Union High School District, also rated A-plus. The Nueva School is a private kindergarten through 12th grade school in Hillsborough, graded A-plus, that requires admissions testing. Crystal Springs is a private middle and high school known for sports and intimate learning. It is also graded A-plus.
The Bridge school serves students living in Hillsborough.
The sprawling campus of Hillsborough High School.
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San Francisco, Palo Alto and San Jose in reach
Interstate 280 connects Hillsborough to San Francisco, 20 miles away. Palo Alto is 20 miles south and San Jose is under 40 miles. The San Francisco International Airport is 6 miles from Hillsborough. The nearest hospital, the Mills Peninsula Medical Center, is under 3 miles away. There is also a BART station in nearby Millbrae.
Hillsborough’s ADUs, wildfires and crime rates
The State of California has expanded requirements for affordable housing, which impacts Hillsborough because of its low-density nature. The Town has relaxed restrictions on Accessory Dwelling Units (ADUs) to encourage homeowners to build them, and the town may rezone two parcels of land for high-density units to meet state requirements. Hillsborough is at risk for wildfires, and the town has taken steps to mitigate the risks by encouraging the establishment of defensible spaces and promoting evacuation preparedness. Property crime in Hillsborough decreased 10% from 2018 to 2023, according to FBI data. Violent crime nearly doubled from 2018 to 2023, but the number of incidents was very low: 9 in 2018 and 17 in 2023.
Written By
Carol Parish
Photography Contributed By
James Breedlove
Video By
Bill Jennings
Interested in learning more about homes in this area?
Reach out to
Timothy Gilmartin,
an experienced agent in this area.
On average, homes in Hillsborough, CA sell after 38 days on the market compared to the national average of 53 days. The median sale price for homes in Hillsborough, CA over the last 12 months is $5,307,500, up 11% from the median home sale price over the previous 12 months.
A rare gem on a quaint street in Lower Hillsborough. This 3-bedroom, 3-bath home features abundant light, oversized windows, and high ceilings on the second level, seamlessly connecting the indoors to the serene outdoor yard. Look for partial bay views from the living and dining rooms. The updated kitchen offers quality appliances, generous counter space, and a cozy dining area overlooking the
A rare opportunity. Located in the coveted lower-Hillsborough Ryan Tract Neighbourhood. 1735 Crockett Lane is an ideal home for entertaining! The home is located on a quiet cul-de-sac. The common area includes a family room, breakfast nook, formal dining room, and formal living room area. This one story 4-bedroom 3 bath home is expansive and private. Plenty of storage space. Located on a private
Remodeled and light-filled two-story home in sought-after San Mateo Park, ideally located between Downtown San Mateo and Burlingame Avenue. Behind private gates, 39 El Cerrito Avenue offers a gracious floor plan with a grand living room, formal dining, and a chefs kitchen, with high-end finishes, overlooking the backyard. The professionally designed gardens are alive with trees, color, and
THE BEST OF THE BEST IN HILLSBOROUGH. Award-Winning architectural design meets timeless farmhouse elegance. Previously featured in Modern Luxury Silicon Valley Magazine, this home was meticulously remodeled & redesigned in 2017 by both an award-winning designer & architect. A stunning blend of modern farmhouse designs and contemporary elements, this exceptional estate is crafted for stylish
Dare to Compare! Highlighting the Best of Foothill Terrace. Pristine family home, cherished by one owner since 1974, sits on an oversized lot in a desirable cul-de-sac offering privacy and easy access. Enchanting curb appeal greets you with mature, colorful landscaping and a brick-accented entry framed by custom aggregate. Inside, gleaming hardwood floors, abundant natural light, and a welcoming
Just steps from downtown Burlingames charming boutiques & cafes, this timeless two-story Mediterranean in sought-after San Mateo Park captures the essence of California living. Graceful curves, a Spanish tile roof, & striking black steel doors create an unforgettable first impression, while mature trees and lush gardens wrap the home in privacy and calm. Inside, sunlight pours across beamed
Welcome to Ryan Tower + Monterey Garden these two landmark buildings are located within the heart of San Mateo’s magnificent, serene and exclusive Baywood District. Both conveniently located just two blocks from downtown San Mateo. Downtown offers shopping, bistros, grocery stores, fine dining, a 12-screen cinema, 24 Hour Fitness, a new public library, Central Park, and lots of other
Luxury Single-Story Estate for Lease in Lower Hillsborough! Experience resort-style living in this exceptional single-story home located in highly sought-after Lower Hillsborough. Originally built in 2004 and beautifully renovated with modern, top-of-the-line finishes, this turn-key property offers elegance, privacy, and convenience in one of the Peninsula's premier neighborhoods. Enjoy high
Conveniently located and recently remodeled apartments with high ceilings that bring an abundance of light and spaciousness to your home.Villa Tuscany is located near Millbrae Bart and Burlingame Avenue. There are many options to commute to work or shop and eat locally. In addition, there are an abundance of highly ranked and safe public schools for all ages K-12.Villa
With views of the San Francisco Bay in the distance, curving roads and woodsy hillsides, Skyfarm is an opulent suburb with multi-million-dollar homes nestled amid the natural scenery of Hillsborough. Located in the northwestern corner of the city, it borders a major highway, making for an easy commute to San Francisco and Silicon Valley. Named for the country mansion that once occupied the area, which still exists today as the private Nueva School, Skyfarm is a sprawling residential area with luxury homes amid lush greenery and rolling hills.
As homebuyers drive up and down the hilly streets of Skyfarm, they’ll notice abundantly lush greenery dividing custom-built mansions. Most properties in the area average more than 5,000 square feet in size. The peaks of these hills allow residents to enjoy panoramic views of the San Francisco Bay. “You’ve got above average square footage, large lots, good privacy and scenic views,” says Realtor Geoffrey Nelson of Coldwell Banker Realty. The neighborhood was built out in the 1970s and 80s with a mix of stately traditional homes and Mediterranean Revival homes. Luxury amenities, backyard swimming pools, dramatic landscaping and grand interior designs are the norm here. Homes typically sell for more than $3 million, although some homes have sold for more than $10 million.
Skyfarm is close to several nearby parks and nature preserves. If travelers follow Skyline Boulevard south, they’ll reach the magnificent Crystal Springs Park, a campsite and trail system that borders the Upper Crystal Springs Reservoir, a basin in the Montara Mountain foothills. The park provides easy access to hiking and nature walks that cut across the wooded countryside. Avid golfers will find it’s only a short trek to the Crystal Springs Golf Course, a picturesque gold course at the edge of the water at the base of scenic Sawyer Ridge. Head the opposite direction and find the Burlingame Country Club, which features a Mediterranean-style club house, a pool and an 18-hole golf course that opened more than a century ago.
The Nueva School’s Hillsborough campus is situated in the heart of Skyfarm. This highly sought-after, private school for gifted children serves Kindergarten through 8th grade students and earns an A-plus on Niche. “The Nueva School is a magnet for that area,” Nelson says, and it's among the best private schools in California, according to Niche. The school occupies the elegant W.H. Crocker Skyfarm mansion, the neighborhood’s namesake. For public schooling, students can attend nearby North Hillsborough Elementary and West Hillsborough Elementary, both highly ranked schools that were listed as California Distinguished Schools in 2023. After graduating, students can attend Crocker Middle School, which scores an A on Niche. Burlingame High is the public high school that serves Skyfarm residents. The school teaches over 1,500 students and gets an A-plus rating from Niche.
There’s no retail or shopping within Skyfarm, but it’s just a few miles from restaurants, shops, grocers and other amenities in downtown Burlingame. There are a variety of fine and casual dining options like Limon, a popular Bay Area tapas restaurant, and Mykonos Meze, which specializes in traditional Greek fare. For coffee and pastries in the a.m., locals enjoy Caffe Central at the corner of Burlingame Avenue and Primrose Road. For groceries, downtown Burlingame has both a Safeway and a Mollie Stone’s Markets, which sells organic and locally grown food.
While this secluded suburb is tucked away in the hills, it's bordered by Interstate 280 making for an easy commute north to San Francisco or south to Silicon Valley. It’s about 20 miles from downtown San Francisco, 20 miles from Palo Alto and under 40 miles from San Jose.
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