Hillsborough Homes with San Mateo Union High School district

Hillsborough Homes with San Mateo Union High School district

Welcome to Hillsborough, California – a hidden gem nestled in the heart of San Mateo County. Known for its serene neighborhoods and stunning landscapes, Hillsborough is a place where charm meets sophistication. This affluent residential community is characterized by its tree-lined streets, expansive estates, and a commitment to preserving the natural beauty of the area. With a population that values privacy and tranquility, Hillsborough offers a unique blend of suburban living and proximity to the vibrant culture of the San Francisco Bay Area.

One of the standout features of Hillsborough is its exceptional educational opportunities, particularly within the San Mateo Union High School District. Families are drawn to the area not only for its picturesque surroundings but also for the highly regarded schools that provide a top-notch education. The district is known for its dedicated teachers, innovative programs, and a strong emphasis on academic excellence, making it an ideal choice for families looking to invest in their children's future.

Hillsborough's real estate market reflects its desirability, showcasing an impressive array of homes that cater to a variety of tastes and lifestyles. From sprawling estates with breathtaking views to charming traditional homes, there’s something for everyone in this picturesque enclave. With its close-knit community feel, lush parks, and easy access to shopping and dining, Hillsborough offers a lifestyle that is both peaceful and vibrant.

Explore the allure of Hillsborough, where every day feels like a retreat, and discover the perfect home in this enchanting California community.

Newest Hillsborough Homes with San Mateo Union High School district

$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 Lane, Hillsborough

Listing courtesy of Stanley Lo from Green Banker Realty. 650-373-0007
$6,800,000
4 Beds ⋅ 4 Baths ⋅ ML82055379 MLS
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 with access to a large sun lit flat back yard. The property comes with a two-car garage and is situated within the Hillsborough City Elementary school district. This residence combines functional living spaces with key amenities in a desirable location.

336 Brentwood Road, Hillsborough

Listing courtesy of Max Lo from Green Banker Realty. 650-307-8816
$3,888,000
4 Beds ⋅ 3 Baths ⋅ ML82054648 MLS
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, and primary bedroom suite, all have sweeping views and direct access to the pool and spa. Extra large laundry room on the bedroom level, expansive 3 car garage with additional work spaces and two very large storage rooms attached. For those few who want to start fresh with a complete custom rebuild, this homes highly desirable expansive lot would be exceptional for a dramatic new design! Do not miss out on your rare opportunity to create a custom estate from the ground up in a highly desirable Hillsborough setting!

1176 Tournament Drive, Hillsborough

Listing courtesy of Mike Foor from Intero Real Estate Services. 650-430-6500
$11,800,000
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 Drive, Hillsborough

Listing courtesy of Michael Haywood Jr. from eXp Realty of California Inc. 650-773-0266
$5,995,000
4 Beds ⋅ 7 Baths ⋅ ML82054112 MLS
Offered for the first time in over 40 years, this iconic Hillsborough estate presents a rare opportunity to own a piece of local history. Set within the coveted Lakeview neighborhood on a private cul-de-sac, the home is thoughtfully designed to embrace its breathtaking surroundings, where panoramic Bay and canyon views are showcased through dramatic walls of windows and enjoyed from multiple view decks. Light-filled interiors offer seamless indoor/outdoor living with expansive gathering spaces, four bedrooms, each with an en suite bathroom, a fitness/yoga studio with sauna, and a dedicated media room ready to become the ultimate home theater. Set on an expansive 25,000 sq. ft. lot with over 7,000 sq. ft. of living space, this timeless estate blends privacy, scale, and natural beauty. Ideally located between San Francisco and Silicon Valley, just minutes from SFO, Highway 280, and top-rated public and private schools. A truly rare opportunity to call one of the Peninsula's most prestigious neighborhoods home.

95 Southdown Court, Hillsborough

Listing courtesy of Madelyn Brown from KW Bay Area Estates. 408-761-7776
$11,500,000
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 Road, Hillsborough

Listing courtesy of Phil Chen from Christie's International Real Estate Sereno. 415-271-1920
$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 Drive, Hillsborough

Listing courtesy of Jenn Gilson from Golden Gate Sotheby's International Realty. 650-642-6957
$11,950,000
5 Beds ⋅ 5 Baths ⋅ ML82053151 MLS
Gracefully tucked behind private gates in Lower Hillsborough's premier location, this exceptional contemporary residence offers a rare blend of privacy, sophistication, and effortless indoor-outdoor living. Directly across from the lush fairways of Burlingame Country Club, the home enjoys expansive green views, a majestic redwood grove, and a serene connection to nature. Designed for both relaxed everyday living and elegant entertaining, the residence features five bedrooms, four-and-one-half bathrooms, and light-filled living spaces. Expansive glass doors create a seamless connection to the landscaped grounds, where mature gardens, multiple outdoor entertaining areas, and a sparkling pool create a resort-like retreat. The thoughtfully designed single-level floor plan includes formal and informal living spaces, a spacious family room, and a well-appointed chef's kitchen, all designed for comfort and seamless living. Located moments from Burlingame Avenue, top-rated Hillsborough schools, San Francisco International Airport, and Silicon Valley, this exceptional residence offers an extraordinary Peninsula lifestyle.

1850 Brookvale Road, Hillsborough

Listing courtesy of Phil Chen from Christie's International Real Estate Sereno. 415-271-1920
$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

Listing courtesy of John Pang from Realty One Group Extreme. 650-699-2838
$3,750,000
4 Beds ⋅ 4 Baths ⋅ ML82051481 MLS
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 w/walls of glass overlooking the pool, expansive deck & panoramic viewsan exceptional setting for everyday living & entertaining. Designed for multigenerational living , w/ADU potential, the home offers 2 kitchens, 2 laundry rooms, separate exterior access & living & work-from-home spaces. Main level includes 2 primary suites, powder rm & view kitchen w/stone countertops, generous island, eating area & fireplace. Nearby office offers potential for a 5th BR or primary suite expansion. Lower level includes 2 BRs, full BA, 2nd kit/dining area & flexible bonus room ideal as a 2nd office or craft room. Direct patio, pool & outdoor access makes this level ideal for extended family, guests, caregivers or independent living. Wine cellar, workshop, 2-car garage, oversized driveway & generous storage complete this rare offering w/exceptional views, impressive scale, versatility & unmatched value.

1407 Carlton Road, Hillsborough

Listing courtesy of Samia Morgan from eXp Realty of Northern California, Inc.. 650-678-3633
$14,000,000
ML82050246 MLS

25 Fagan Drive, Hillsborough

Listing courtesy of from Compass. 650-400-1188
$6,998,000
4 Beds ⋅ 4 Baths ⋅ ML82048818 MLS
Sprawling Privacy Meets Elegant Living Hillsborough Welcome to your private estate, a secluded sanctuary tailored for multi-generational family living & spectacular entertaining. Tucked behind a gated driveway on a premier 2-acre lot, this single-family residence offers a blend of luxury, space, & serenity in one of Hillsboroughs most coveted enclaves. Built in 1974, the home spans a generous 3,230 sq. ft. of living space, beautifully designed to celebrate a seamless indoor-outdoor lifestyle amidst lush landscapes. Step inside to discover a bright, expansive floor plan featuring 4 bedrooms, 3 full bathrooms, and 1 half bathroom. Every room offers room to breathe and space to thrive, with large windows inviting natural light and framing views of the verdant, tree-lined grounds. The crown jewel of this estate is its backyard resort. The sprawling, ultra-private acreage features a sparkling pool and outdoor entertaining spaces, creating an idyllic backdrop for weekend barbecues, sophisticated cocktail parties, or quiet mornings listening to the birds.Here, graceful living meets absolute peace of mind. You are minutes from top-rated schools and world-class dining, yet worlds away from the hustle and bustle. Embrace the pinnacle of Hillsborough luxury. Your private sanctuary awaits.

220 Robin Road, Hillsborough

Listing courtesy of Gina Haggarty from Compass. 650-207-5192
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