$5,419,813Average Value$1,629Average Price per Sq Ft18Homes 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
Susan Gee Berry,
an experienced agent in this area.
GreatSchools:
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On average, homes in Hillsborough, CA sell after 38 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 $6,400,000, up 25% from the median home sale price over the previous 12 months.
Located in a community renowned for exceptional schools, this is a compelling Hillsborough opportunity. Offered at the lowest price per sq. ft. in Hillsborough, it delivers outstanding value in the community & across the Peninsula. Sweeping Bay & San Mateo Bridge views define this home. Recently refreshed & updated, it features newly painted interiors, hardwood floors & a dramatic great room
Samia MorganeXp Realty of Northern California, Inc.
Located in Lower South Hillsborough, this spacious 3,440 sq ft home offers four bedrooms, three full bathrooms and separate office. The living room and an additional area feature wood-burning fireplaces, adding warmth and charm to the space. The home includes a separate family room and multiple dining options, such as a breakfast room, dining area in the living room, and an eat-in kitchen, All
Welcome to 433 El Centro, a newly remodeled luxury estate in Hillsborough. Situated on 0.41 acres, this exceptional property offers refined living designed for entertaining and everyday comfort. The home features 5 bedrooms (including the ADU), 5 full baths, 2 half baths, and a bonus room/den. The gourmet chef's kitchen boasts premium paneled appliances, a wine cooler, and opens to a spacious
Phil ChenChristie's International Real Estate Sereno
Situated in one of the best locations in Hillsborough, 280 Uplands Dr is a rare opportunity on a flat, private, over-half-acre corner lot, steps from Crystal Springs Uplands School & South Elementary. This estate offers 6 bedrooms, 6 full baths & 2 half baths, all en-suite, with attached ADU. A dedicated office with fireplace, home theater with theatrical lighting and built-in refreshment
Located in a community renowned for exceptional schools, this is a compelling Hillsborough opportunity. Offered at the lowest price per sq. ft. in Hillsborough, it delivers outstanding value in the community & across the Peninsula. Sweeping Bay & San Mateo Bridge views define this home. Recently refreshed & updated, it features newly painted interiors, hardwood floors & a dramatic great room
Samia MorganeXp Realty of Northern California, Inc.
This fabulous top floor condo is located in a sought after premier westside neighborhood near downtown San Mateo quietly tucked between Baywood and San Mateo Park. It offers views of both the bay to the east and the quaint hillside views to the west. This unit features two spacious bedrooms and two newly remodeled bathrooms, an updated kitchen with large walk-in pantry, wet bar, wine cooler, an
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
Phil ChenChristie's International Real Estate Sereno
Exceptional location in a coveted community. Captivating views. Prestigious schools. Stunning pool and spa. Perfect for indoor-outdoor living designed for entertaining - feels like your own personal resort. Open floor plan flooded with natural light. 4 bedrooms with 2.5 baths, huge living room with wood burning fireplace, plus big family room and kitchen breakfast area. The family room, kitchen,
*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.
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
Newly subdivided, approximately 1.0 acre parcel in a premier Hillsborough location. Sweeping San Francisco Bay and Skyline views. Existing tennis court on lot.
A rare opportunity to develop a pristine piece of residential land in one of California's most sought after luxury housing markets. The Meadowood Estates project has a tentative map approved for 8 single family homes. This listing represents one half of the overall project. The approved tentative map has two separate cul-de-sacs, one accessible off of Tartan Trail rd, and the other off of Crystal
An exquisite property located in the exclusive Skyfarm neighborhood of Hillsborough. Set on over 0.69 acres, this home offers breathtaking views of the Bay, the airport, and downtown San Francisco. It creates a perfect setting for indoor / outdoor living in Hillsborough. The formal dining room and living room open onto the back deck, while the chef's kitchen combines a family room and an eat-in
Located in Lower South Hillsborough, this spacious 3,440 sq ft home offers four bedrooms, three full bathrooms and separate office. The living room and an additional area feature wood-burning fireplaces, adding warmth and charm to the space. The home includes a separate family room and multiple dining options, such as a breakfast room, dining area in the living room, and an eat-in kitchen, All
SELLER ALREADY PURCHASED AND WOULD LIKE TO REVIEW ALL OFFERS! *MILLION DOLLAR REDUCTION!!!* HILLSBOROUGH'S BEST IN CLASS, THIS IS LUXURY! MUST SEE!!! A BREATHTAKING TROPHY ESTATE BLENDING TIMELESS ELEGANCE WITH RESORT-STYLE LIVING. This architectural masterpiece offers an extraordinary layout designed for both grand entertaining & intimate daily life. Sweeping driveway & motor court lead to 2
Discover the perfect combination of relaxed refinement and urban excitement at Ryan Tower. Our newly renovated community in San Mateo County features pet-friendly studio, one, and two bedroom apartment homes in a superb central location with a plethora of employers, parks, public transit, and more just around the corner. Elevated comfort meets effortless city living at Ryan Tower. From
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.
OPEN HOUSE: This Sunday, July 19th from 2:00 PM – 4:00 PM. Early applications are highly encouraged—you can apply directly through the link on this listing page prior to the open house.AVAILABLE: September 1, 2026 (with flexibility to move in a few days early, subject to current tenant's accommodation).Located in Lower North Hillsborough—widely recognized as the single most
This wonderfully updated home in the Easton Addition of Burlingame is within a short distance to many of the amenities that Burlingame offers. Located on a large "flag" lot, this rental opportunity has 4 Bedrooms, 4 Bathrooms as well as a Formal Living Room, Formal Dining Room, Family Room and Chef's Kitchen. There is also a Laundry Room, a Pool/Spa, an outdoor gas BBQ and Putting Green. Fresh
Situated on a commanding half-acre lot, this inviting home offers over 4,400 sq. ft. of casual elegance in a picturesque setting. A dramatic foyer leads to the elegant living room with a grand fireplace, wall of windows, and access to a huge rear deck. The gracious dining room features oversized windows that frame amazing views of the outdoors. Nearby, the large family room with a fireplace,
Property Id: 2770330 Luxury Baywood Mediterranean Rental | Utilities , Storage, Parking Available and Laundry! Experience timeless architecture and modern comfort at 212 Eaton Road #22, a beautifully preserved 2-bedroom, 2-bath residence offering approximately 1,310 square feet in one of San Mateo's most iconic 1928 Mediterranean buildings. Set behind a lush, manicured courtyard in
*BRAND NEW ADU UNDER CONSTRUCTION, STARTED FEB 2026, TO BE COMPLETED BY END OF AUGUST* 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
Nestled on a quiet, tree-lined street in one of Burlingame's most sought-after neighborhoods, this beautiful 3-bedroom, 1.5-bath residence offers timeless character, conveniences, and an exceptional lifestyle in the heart of the Peninsula.Inside, rich hardwood floors extend throughout the home, creating a warm and inviting ambiance. A sun-filled breakfast nook provides the perfect setting for
Located in lower Hillsborough, this custom, single-story, mid-century modern home blends timeless architecture with the effortless California lifestyle. Set behind mature landscaping and surrounded by exceptional privacy, dramatic walls of glass fill the home with natural light while seamlessly connecting every main living space to the lush backyard and sparkling pool. The living room, dining
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. <br><br>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.<br><br>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.<br><br>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. <br><br>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.<br><br>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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