$5,213,669Average Value$1,548Average Price per Sq Ft19Homes 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
Nicole Ruccolo,
an experienced agent in this area.
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On average, homes in Hillsborough, CA sell after 40 days on the market compared to the national average of 56 days. The median sale price for homes in Hillsborough, CA over the last 12 months is $5,665,000, up 7% from the median home sale price over the previous 12 months.
Bright, updated condo in Burlingame Park offering a rare opportunity to own in one of the Peninsulas most sought-after neighborhoods with an approachable price point and low HOA. This light-filled home features open, airy living spaces and a well-proportioned layout. The living area is anchored by a custom shiplap accent wall with electric fireplace, creating a natural focal point, while the
Almost fully rebuilt in 2022, this Santa Barbara-style Mediterranean in Hillsborough blends timeless architecture with modern systems and resort-style living. Interior design by JD Bartell creates a truly special & cohesive residence for daily living & entertaining. The home offers up to 6 bedrooms & 6.5 bathrooms with Venetian plaster throughout, custom white oak floors, seamless cabinetry &
Phil ChenChristie's International Real Estate Sereno
Perched in the prestigious Lakeview neighborhood of Hillsborough, this gated residence blends refined living with breathtaking design and panoramic views. A spacious motor court and two-car garage welcome you to a home of distinction. Step into the elegant foyer, where classic columns frame a soaring open-concept living area. Vaulted ceilings with exposed beams and floor-to-ceiling windows flood
Welcome to 24 Mounds Road, a rare offering within an intimate boutique condominium building comprised of just five exclusive residences. Ideally positioned between Downtown San Mateo and Burlingame, and moments from Hillsborough, this prestigious address offers an exceptional blend of privacy and convenience. This rarely available two-bedroom, two-bathroom residence offers approximately 2,100
Prime Hillsborough residence w/4 BR 3.5 BA w/sweeping Bay & San Mateo Bridge views. Expansive great room captures the scenery while overlooking the pool & sunlit deck below creating a natural backdrop for memorable gatherings, everyday living, & effortless entertaining. Main level features 2 primary suites & powder rm, ideal for multi-generational living or flexible use. View-oriented kitchen has
Samia MorganeXp Realty of Northern California, Inc.
Bright, updated condo in Burlingame Park offering a rare opportunity to own in one of the Peninsulas most sought-after neighborhoods with an approachable price point and low HOA. This light-filled home features open, airy living spaces and a well-proportioned layout. The living area is anchored by a custom shiplap accent wall with electric fireplace, creating a natural focal point, while the
Almost fully rebuilt in 2022, this Santa Barbara-style Mediterranean in Hillsborough blends timeless architecture with modern systems and resort-style living. Interior design by JD Bartell creates a truly special & cohesive residence for daily living & entertaining. The home offers up to 6 bedrooms & 6.5 bathrooms with Venetian plaster throughout, custom white oak floors, seamless cabinetry &
Phil ChenChristie's International Real Estate Sereno
Step into ultimate luxury with this spacious 6 BD, 5.5 BA home spanning +/- 4,746 SQFT on over 1/2 an acre of beautifully landscaped grounds. Perfect for entertaining and serene living, this home blends a versatile floorplan with thoughtful updates, including a significant 2017-2018 remodel and expansion. The main level is a showstopper, featuring a chef's kitchen with top-tier appliances, an
Set behind private gates on a 0.645-acre parcel in Hillsborough's prestigious Skyfarm neighborhood, this 9,035 sq ft estate offers sweeping San Francisco Bay views and 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 and vaulted
Modern Sanctuary in Lower South Hillsborough. Welcome to 655 Hayne Road, a newly completed modern residence offering privacy and refined California living in one of Hillsboroughs most desirable neighborhoods. Set behind a gated entrance on a mostly flat, usable parcel, the property is thoughtfully designed for seamless indoor-outdoor living. The main residence flows primarily across a single
*BRAND NEW ADU UNDER CONSTRUCTION, STARTED FEB 2026 W/ FRAMING ALREADY COMPLETED* THIS TROPHY HOME IS A ONE-OF-A-KIND MODERNIZED SMART-HOME MANSION! THE IMPOSSIBLE WAS DONE W/ THESE MULTI-MILLION DOLLAR RENOVATIONS! This magnificent estate perfectly integrates timeless architecture with a modern interior, with all top-of-the-line amenities. An estate fit for royalty! Interior with 100s of
Set on more than 12 secluded acres, Villa de Verano is an ultra-exclusive Hillsborough estate inspired by the elegance of Lake Como. The gated compound offers exceptional privacy, symmetry and scale, with a tree-lined drive leading to a grand motor court & the main residence, guest quarters & sports pavilion. The 12,404 sqft main residence spans 3 levels serviced by an elevator & overlooks the
Jenn GilsonGolden Gate Sotheby's International Realty
Perched in the prestigious Lakeview neighborhood of Hillsborough, this gated residence blends refined living with breathtaking design and panoramic views. A spacious motor court and two-car garage welcome you to a home of distinction. Step into the elegant foyer, where classic columns frame a soaring open-concept living area. Vaulted ceilings with exposed beams and floor-to-ceiling windows flood
Commanding sweeping views of San Francisco, the Bay Bridge, and a glittering skyline, 1340 View Haven is a contemporary Hillsborough retreat designed to showcase its extraordinary vantage point. A private tree lined setting, the home unfolds through a dramatic double-height foyer with a glass-encased staircase and suspended artistic wine display. The house unfolds to expansive, light-filled
Phil ChenChristie's International Real Estate Sereno
Discover a rare opportunity to buy a residential lot zoned R1-A in one of San Mateos most coveted neighborhoods. This just-under-one-acre parcel offers a tranquil, park-like setting with an abundance of mature trees and a "deer shelter" catered to wildlife. Nestled within a quiet neighborhood, the property combines serenity with convenience and offers natural beauty that is increasingly hard to
Bouja & Swenson GroupGolden Gate Sotheby's International Realty
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
Located in Hillsborough, this 3-bedroom, 2-bath home offers approximately 2,110 square feet of living space. The living room features a fireplace, adding a cozy focal point to the area. The kitchen includes an eat-in dining space, ideal for casual meals. Central forced air heating and central air conditioning provide comfort year-round. The property includes a two-car garage. This home is part of
A true urban lifestyle awaits you in downtown Burlingame. Steps from bustling restaurants and boutique shopping, Burlingame Towers offers a haven of convenience and luxury. Located along El Camino Real, the community is adjacent to transit lines that stretch from San Francisco to Menlo Park, and the Silicon Valley. The property includes a fitness room, pool, bbq, and community area.
Discover refined living at 25 Warmwood Way, a stunning residence in Hillsborough's Carolands neighborhood. A long, private driveway leads to an expansive motor court and a 2-car garage, offering ample parking and a grand sense of arrival. Inside, the thoughtfully designed layout flows seamlessly from the foyer. To the left, a formal dining room connects to a sun-drenched breakfast nook and a
Beautiful Blue Bird Haven is a newly built tastefully designed 1 Bedroom 1 Bath apartment with modern amenities for the busy professional: in-unit Laundry, top Suite energy efficient appliances including dishwasher, disposal, oven, microwave, glass top 5 burner stove, refrigerator and windows all around. This bright airy and insulated home sits atop crystal springs with high ceilings, recessed
FULLY FURNISHED 4 BEDROOMS 3 BATHROOMS PLUS OFFICETenant is responsible for all the utilitieswater, garbage, PGampE, high speed internet, and cable, housekeeping, and the gardener.This elegant home in San Mateo neighborhood offers a beautiful views of the bay from the deck. This residence represents modern design, featuring hardwood floors, high end carpets and surround sound system. This house
This exceptional Hillsborough estate is perfect for families seeking luxury and comfort in a warm, inviting home. Ideal for children to grow and explore, the property features soaring ceilings, artisan fireplaces, hand-crafted stained-glass windows, a designer kitchen with newer appliances, and 8.5 updated bathrooms. Smart-home features, including recessed lighting, Sonos sound system, motorized
Spacious 3880sf, 4 bedroom, 3 bath home. Features souring high vaulted ceilings throughout, formal living and dining rooms, separate family/media room, plus loft for office or study, large kitchen with breakfast nook and newer appliances, separate primary suite on lower level with en-suite bath featuring oversized soaking tub, separate vanity area, and huge walk-in closet, junior suite on middle
This bright and beautiful 2 bedroom, 2 bathroom condo is ideally located on West 3rd avenue - 2 blocks from vibrant downtown San Mateo. This lovely top floor unit welcomes you with an abundance of natural light, a spacious floor plan and plentiful closet space. The kitchen has full stainless steel appliances, new countertops and cabinets. Both bathrooms are re-modeled, one with an extra large,
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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