Hillsborough Real Estate

Hillsborough: A Picturesque City in San Mateo County, California

Nestled in the heart of San Mateo County, California, lies the charming city of Hillsborough. Known for its stunning landscapes, grand mansions, and a close-knit community, Hillsborough offers residents a tranquil and luxurious lifestyle.

Located just south of San Francisco, Hillsborough boasts a prime location that combines the best of both worlds. The city is surrounded by lush green hills, providing a serene escape from the bustling city life, while still being within easy reach of the vibrant cultural and economic opportunities of the Bay Area.

One of the defining features of Hillsborough is its architectural beauty. The city is renowned for its sprawling mansions, many of which were built in the early 20th century. These grand estates showcase a variety of architectural styles, from Spanish Colonial Revival to Tudor and Mediterranean. The picturesque streets of Hillsborough are lined with towering trees and manicured gardens, creating a truly enchanting atmosphere.

In addition to its natural and architectural beauty, Hillsborough offers a range of amenities and recreational opportunities. The city is home to several parks and open spaces, providing ample opportunities for outdoor activities such as hiking, biking, and picnicking. The Hillsborough Recreation Department also offers a variety of programs and classes for residents of all ages, fostering a strong sense of community.

With its idyllic setting, luxurious homes, and strong community spirit, Hillsborough is undoubtedly a highly sought-after place to call home. Whether you're looking for a peaceful retreat or a place to raise a family, Hillsborough offers a lifestyle that is second to none.

Newest Listings in Hillsborough

$5,988,000

5 Beds ⋅ 5 Baths ⋅ ML82060425 MLS

Set against stunning Bay views, this Ranch style home blends timeless mid-century modern character with spacious, light filled living. Approximately 4,560 square feet of living space offers five bedrooms and four-and-a-half baths, with an inviting combination of formal and informal rooms. The main bedroom wing is thoughtfully arranged with a spacious primary suite, plus two additional bedrooms connected by a bathroom. A guest suite is conveniently located off the kitchen and laundry area, while the lower level -- with its own exterior access offers a potential fifth bedroom and full bath. The lower level provides even more flexibility, with an additional room perfect for an office, second family room or game room. Abundant natural light fills the home, while expansive windows capture the spectacular Bay outlook and create a strong connection to the private, mostly level grounds. The formal dining room and family room both have access to the backyard with a swimming pool and generous outdoor spaces. Architectural character, generous scale, versatile living spaces, privacy, and breathtaking views all paired with top-rated public schools. Perfect Mid-Peninsula location.

860 Longview RD, Hillsborough

Listed by The Dwyer Group, 650-759-1593 from Compass
(If provided) CoList: from

$12,000,000

7 Beds ⋅ 7 Baths ⋅ ML82059857 MLS

Offered as a rare presale opportunity with the ability to personalize select finishes, this modern architectural masterpiece is estimated for completion in Q3 2027. Privately situated on a level half-acre cul-de-sac lot, the residence offers approximately 5,722 square feet of refined living space, including an attached JADU and detached ADU . A dramatic double-height foyer with a full-height porcelain slab feature wall and statement chandelier creates a striking first impression. Soaring ceilings, premium engineered oak flooring, a dramatic floating staircase, and walls of glass create a striking sense of scale and effortless indoor-outdoor living. The showpiece kitchen features custom European-inspired cabinetry with warm natural wood finishes, natural quartzite surfaces, a waterfall island, and premium Miele appliances. A private balcony, spa-inspired primary bath, custom wine display, Control4 automation, and beautifully landscaped grounds complete the residence. Buy early for preferred pricing and design personalization.

20 Castle CT, Hillsborough

Listed by Phil Chen, 415-271-1920 from Christie's International Real Estate Sereno
(If provided) CoList: Axis Elite Team from Aspire Homes

$48,888,000

10 Beds ⋅ 10 Baths ⋅ ML82059451 MLS

A landmark Hillsborough estate of extraordinary scale, privacy, and unparalleled distinction, nestled within the exclusive New Place Road enclave, historically associated with the Gilded Age-era William H. Crocker estate. Arrival begins at the historic William H. Crocker gate posts marking the entrance to New Place Road, winding through the fairways of Burlingame Country Club. 150 New Place Road is an exceptional compound offering refined California living. Private resort-caliber grounds offer gathering areas for relaxation and elegant entertaining in complete privacy. A private detached guest house, panoramic San Francisco Bay views, swimming pool, private tennis and pickleball court, and comprehensive whole-home systems. Sophisticated interior living spaces, generous bedroom suites, theatre room and indoor sauna provide exceptional comfort and recreation. Walls of glass and expansive terraces frame breathtaking San Francisco Bay views and invite seamless indoor-outdoor living. Ideally positioned near San Francisco, Silicon Valley, SFO, and the Peninsula's renowned schools and amenities. Offered at $48,888,000, 150 New Place is an exceptionally rare Hillsborough trophy estate- a landmark private compound where privacy, scale, setting, and a sense of history converge

150 New Place RD, Hillsborough

Listed by Mary Bee, 650-343-9999 from Intero Real Estate Services
(If provided) CoList: from

$4,099,000

4 Beds ⋅ 3 Baths ⋅ ML82059435 MLS

HILLSBOROUGH'S BEST JUST GOT BETTER WITH A NEW PRICE!!! A MUST SEE! Located in the sought-after Lakeview neighborhood, this private and inviting home is surrounded by mature trees and offers an abundance of indoor and outdoor spaces for comfortable living and entertaining. The main level features a spacious living room and family room combination connected to the dining area, with large windows and glass doors filling the home with natural light and creating a seamless connection to the outdoors. The kitchen offers all the essentials for everyday living, while three bedrooms on the main level include a generously sized primary suite. The lower level adds versatility with a recreation room and an additional guest en-suite bedroom. Behind the garage, a separate finished space provides even more flexibility and can serve as a media room, home office, gym, or whatever suits your needs. Outdoors, enjoy multiple patio areas, expansive open spaces, several decks, mature landscaping, and an ice-cold swimming pool / hot tub combo; creating a private setting for relaxing or entertaining. There is so much to offer and only so much space to say it all. Best of all, this exceptional location provides access to some of Californias finest schools & is just a short drive to downtown Burlingame.

1548 Kingswood DR, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

$7,280,000

5 Beds ⋅ 6 Baths ⋅ ML82057580 MLS

$715,000 Price Reduction! Lowest price home in Lower North Hillsborough! Welcome to this exceptional lower North Hillsborough estate that blends timeless architectural charm with sophisticated modern living. Spanning over 5180sf, this 5 bedroom 6 bath home has it all! A welcoming front porch with dormer windows enhance the homes inviting exterior. The chef's kitchen is thoughtfully appointed for both everyday living and entertaining, with two sets of French doors opening to an expansive patio complete with a built-in grill and full-length pergola. The grand room is truly designed to impress, featuring dual fireplaces and multiple French doors. . The abundant natural light throughout the home creates a rich environment for family living and guest entertainment. The primary suite, along with two additional bedrooms on the main level, features vaulted ceilings and custom-designed closets. The lower level provides an exceptional extension of the living space, offering a spacious media room, two additional bedrooms, a butler's pantry, and a dedicated artist studio or gym. Additional luxuries include central air conditioning, backup generator, and a whole-home audio system. Just minutes to downtown Burlingame, North Elementary and Crocker Middle School, this wonderful home has it all!

901 Hillsborough BLVD, Hillsborough

Listed by Nick Corcoleotes, 650-207-2758 from Coldwell Banker Realty
(If provided) CoList: from

$14,995,000

6 Beds ⋅ 9 Baths ⋅ ML82056682 MLS

A rare offering in coveted South Hillsborough, 810 Lombardi Lane is a private, gated estate set on nearly one level acre of beautifully curated grounds at the end of an exclusive cul-de-sac. Timeless architecture, soaring ceilings, custom millwork, and walls of glass create light-filled interiors that flow effortlessly to the resort-inspired outdoor spaces. Designed for both everyday living and grand-scale entertaining, the home features an exceptional chef's kitchen, expansive gathering spaces, and seamless indoor-outdoor living with accordion glass doors opening to a saltwater pool, outdoor kitchen, custom fire pit, and lush architectural landscaping. The luxurious primary suite is a private retreat with a spa-inspired bath and tranquil garden patio, while each additional bedroom offers a beautifully appointed en suite with its own distinctive designer tilework. A detached ADU with dramatic 12-foot wood-beam ceilings overlooks the pool and provides exceptional flexibility for guests, a private office, wellness studio, or multigenerational living. Combining remarkable privacy, timeless craftsmanship, and an unrivaled South Hillsborough location, this exceptional estate embodies luxurious Peninsula living.

810 Lombardi LN, Hillsborough

Listed by The Sharp Group, 650-766-5333 from KW Advisors
(If provided) CoList: from

$5,300,000

ML82056669 MLS

Land + Fully Approved Shovel-Ready Plans Included in the Price. An extraordinary opportunity to build a landmark luxury estate in Hillsborough's prestigious Skyfarm neighborhood. Set on a private 28,648ÃÂ± sf (0.66ÃÂ± acre) parcel, the offering includes plans for an approximately 7,916 sf contemporary residence with 5 bedrooms, 6 full baths, and 1 half bath (per approved plans: gross floor area across three levels totals 8,600 sf [2,609+4,000+1,991], less the 824 sf garage, plus +140 sf of stairs = 7,916 sf ). Designed by an award-winning architect, the design blends timeless elegance with modern sophistication expansive walls of glass, soaring ceilings, and seamless indoor-outdoor living create a light-filled retreat embracing the natural landscape. Dramatic terraces and an infinity-edge pool and spa appear to float above the hillside for a true resort-inspired setting. The plan includes grand living and entertaining spaces, a temperature-controlled wine room, home theater, and luxurious primary suite. Plans have completed ADRB Formal Review with the Town of Hillsborough, streamlining the path to permit and construction to build a one-of-a-kind estate in one of the Peninsula's most prestigious neighborhoods.

68 Eugenia Way, Hillsborough

Listed by John Pang, 650-699-2838 from Realty One Group Extreme
(If provided) CoList: from

$8,999,000

3 Beds ⋅ 4 Baths ⋅ ML82044812 MLS

RARE OPPORTUNITY! Hurry, properties of this caliber, on this size lot, in this location rarely come on the market! You can remodel a home, but you can never recreate this location, this cul-de-sac, or this extraordinary lot. One of Hillsboroughs most sought-after and prestigious streets. Tucked away at the end of a quiet cul-de-sac, this extraordinary estate sits on one of the largest lots in the neighborhood, an exceptionally rare offering that will not become available again for years. Walking distance to vibrant downtown Burlingame and some of California's best public schools. Whether you choose to enjoy this beautiful estate as it is or create your own dream luxury residence, this is truly a once-in-a-lifetime opportunity in an irreplaceable location. Enjoy unmatched privacy surrounded by magnificent mature trees and lush landscaping, creating your own peaceful retreat. DO NOT WAIT, SERIOUSLY!!!

2155 Geri LN, Hillsborough

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

$11,475,000

6 Beds ⋅ 8 Baths ⋅ ML82054575 MLS

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 station, and an adjoining bonus room. Upstairs, a bedroom suite is joined by a multi-purpose room with fireplace, ideal as a gym, bar, or rec space. All mechanical systems replaced, including new roof and four separate HVAC systems for comfort and efficiency. All-new interior finishes and a chef's kitchen with premium appliances, including Sub-Zero. Private rear driveway with automatic gate. Outdoor spaces offer true California entertaining: brand-new pool and spa with automatic safety cover, outdoor kitchen, Trex decking, new hardscape and paver walkways. Ideally suited for social events, with ample parking and a layout that flows seamlessly from indoors to out.

280 Uplands DR, Hillsborough

Listed by Michael Haywood Jr., 650-773-0266 from eXp Realty of California Inc
(If provided) CoList: from

$11,000,000

5 Beds ⋅ 7 Baths ⋅ ML82052749 MLS

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 family room. Additional highlights include built-in speakers, a custom wet bar, dedicated media room, temperature-controlled wine cellar, and laundry rooms on both levels. The luxurious primary suite offers a private office, walk-in closet, and spa-inspired bath with heated floors, towel racks, soaking tub, and dual showers. All secondary bedrooms feature en-suite baths for added comfort and privacy. Designed for seamless indoor-outdoor living, the grounds showcase a pool, spa, fire pit, expansive lawn, outdoor TV, and covered BBQ pavilion with prep space, refrigerator, and ample seating. Conveniently located near top-rated Hillsborough schools, parks, Downtown Burlingame, and transportation, this turnkey estate presents a rare opportunity in one of the Peninsula's most sought-after communities.

433 El Centro RD, Hillsborough

Listed by Phil Chen, 415-271-1920 from Christie's International Real Estate Sereno
(If provided) CoList: from

$28,995,000

11 Beds ⋅ 15 Baths ⋅ ML82038870 MLS

A secluded trophy estate in the heart of highly coveted Lower North Hillsborough, this extraordinary 2.4+ acre property offers rare scale and privacy on one of the towns largest parcels. Originally designed by acclaimed architects John Bakewell Jr. and Ernest Weihe, the French Chateau-inspired residence was once home to Hollywood icon Bing Crosby and is rich with storied provenance, including connections to the legendary Seabiscuit and curated antique details from the Hearst Collection. Thoughtfully updated by the current owner, the home spans four levels and features 11 bedrooms, 10 full baths, and 5 half baths, blending grand architectural presence with a warm, livable layout. Designed for both intimate daily living and elegant entertaining, the floor plan includes multiple salons, a formal dining room, a wood-paneled library, a private office, and a distinct guest wing. The park-like grounds showcase sweeping lawns, a resort-style pool with fountains, and expansive open space, creating a serene and majestic setting. With its remarkable history, refined craftsmanship, and exceptional acreage, this is a truly irreplaceable legacy estate an unparalleled opportunity to own a landmark property from California's Golden Era.

1200 Armsby DR, Hillsborough

Listed by Jenn Gilson, 650-642-6957 from Golden Gate Sotheby's International Realty
(If provided) CoList: Pierre & Alex Buljan from Compass

$5,280,000

5 Beds ⋅ 4 Baths ⋅ ML82053052 MLS

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 formal dining area with a private patio. The primary bedroom features an ensuite bathroom and a walk-in closet. Top-rated West Elementary School and Crocker Middle School. County records show 3,500 SqFt. 4 Bedrooms, 3 Full Baths. Seller converted the home to 5 Bedrooms, 4 Full Baths, which are permitted.

36 Eugenia WAY, Hillsborough

Listed by John Pang, 650-699-2838 from Realty One Group Extreme
(If provided) CoList: from

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than JABEZ REALTY are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.