Hillsborough, CA Homes for Sale

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

Michael Haywood Jr. eXp Realty of California Inc

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 Morgan eXp Realty of Northern California, Inc.

Highly desirable cul-de-sac where neighbors are truly neighborly! Homes rarely become available in this park-like setting just moments from vibrant Downtown San Mateo. Step inside to an inviting living room with a cozy fireplace and concealed motorized projector screen for an immersive home theater experience. The open layout flows into the dining area with built-ins, a sunny breakfast nook, and

Miranda Caley Coldwell Banker Realty

Welcome to 1386 Hillside Circle, a timeless Burlingame residence built in 1936, offering approximately 2,340 square feet of living space on a rare 9,082 square foot street-to-street lot. Lovingly owned by the same family for 53 years, this exceptional home blends classic character with everyday comfort. A manicured garden entry opens to warm hardwood floors, an elegant formal dining room,

Alex Hawkins Cronan Real Estate Services, Inc.

Set in San Mateos desirable Baywood Knolls neighborhood, this single-family home offers the warmth, character, and everyday livability that make a home truly special. Hardwood floors, a fireplace, fresh new paint, and well-proportioned living spaces create an inviting setting for relaxing, entertaining, or working from home. The finished lower level adds valuable flexibility for guests, a home

Joe Polyak Rise Homes

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

Anna Wong Compass

*BRAND NEW ADU UNDER CONSTRUCTION, STARTED FEB 2026, TO BE COMPLETED BY END OF AUGUST* 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

Stanley Lo Green Banker Realty

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 Chen Christie'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,

Mike Foor Intero Real Estate Services

*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.

Stanley Lo Green Banker Realty

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

John Pang Realty One Group Extreme

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

Stanley Lo Green Banker Realty

Secluded in the exclusive Country Club Manor neighborhood of Hillsborough, this fully furnished modernist masterpiece, a three story wonder of glass that floats with the forest. Designed by acclaimed, award-winning architect Leonard Ng, this iconic 11,141 sq. ft. retreat is a meditation on minimalism, an extension from the trees that questions where nature ends & home begins. Clear heart cedar

Gina Haggarty Compass

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 Chen Christie's International Real Estate Sereno

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

Madelyn Brown KW Bay Area Estates

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

Gina Haggarty Compass

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

Phil Chen Christie's International Real Estate Sereno

TITLE CLEAR & READY TO CLOSE CREEK HURDLE RESOLVED (RETAINING WALL)! The seller has notified us that the title is clear and the property is ready for an immediate close. The seller is taking full responsibility to pay for, finish, and get final city approval for the creek work. Buyer does NOT have to take over any creek work. This is the absolute best locationquiet street, Ryan Tract, walking

Stanley Lo Green Banker Realty

Situated on a private side street, this grand estate sits on a majestic 2-acres with jaw-dropping panoramic bay views, some of the best in all of Hillsborough. Exquisite architectural detailing and finishes throughout, including inlaid parquet walnut floors, hand carved fireplaces, and walls of glass framing iconic bay views and landscaping. The main level includes a stunning office, billiard

Pierre & Alex Buljan Compass

Welcome to a truly extraordinary Hillsborough estate where elegance, space, and lifestyle come together. Set on nearly 2/3 of an acre, this stunning property offers 7,285 sq ft of refined living space designed to impress and inspire. The main residence spans three beautifully crafted levels, filled with natural light, sophisticated architectural details, and seamless flow throughout. Expansive

Malcolm Lee Nation Home Realty

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

Jenn Gilson Golden Gate Sotheby's International Realty

Finally, an affordable lot to build your dream home in the exclusive city of Hillsboro.

Alex Schauffert New Standard Realty

Prepare to be impressed! Old World charm shines throughout this light filled Baywood condominium, ideally located just a stones throw from the Main Library and vibrant downtown San Mateo with its exceptional shopping, dining, and entertainment. This is a stunning end unit that shares only one common wall and offers the convenience of a desirable first floor location. Timeless details include

Chuck Cochran Coldwell Banker Realty

Welcome to 9 Bel Aire Lane, a rare opportunity to won one of the premier residences within Bel Aire Heights, an exclusive new construction community of just 19 custom-built luxury homes. Perfectly positioned to capture breathtaking, unobstructed water and some San Francisco views, this exceptional residence offers approximately 3908 sq ft of thoughtfully designed living space on an expansive 9500

Denise Laugesen KW Advisors

Welcome to this stunning 4-bedroom, 4-bathroom home in the vibrant city of San Mateo. With an expansive 3,664 sq ft of living space set on a generous 8,115 sq ft lot, this residence offers comfort and style. The spacious kitchen is a culinary enthusiasts dream, featuring a gas cooktop, dishwasher, garbage disposal, island, microwave, and a gas oven. The kitchen seamlessly flows into the family

Denise Laugesen KW Advisors

Brand New Luxury Residence in the highly sought-after Bel Aire Heights community of San Mateo. This exceptional home tryly has it all, nearly 4000 sq ft of thoughtfully designed living space featuring 5 bedrooms and 4.5 bathrooms, including two luxurious primary suites, one on each level, ideal for multi generational living or ultimate flexibility. The open-floor concept floor plan is light

Denise Laugesen KW Advisors

DESIGNER LUXE SONOMA CRAFTSMAN: Perfectly located just one mile from downtown Burlingame Ave, 1021 Cortez tells the story of the Easton Addition. It's no wonder that buyers looking for the ultimate blend of newer construction and timeless character are spellbound by this neighborhood. Built in 2011, this Sonoma Craftsman captures all that magic. Classic front porch sets the tone. New exterior

Geoffrey Nelson Coldwell Banker Realty

Discover the Top of the Mounds, San Mateo's most coveted luxury condominium community. This gorgeous residence offers 2036 sq ft of spacious living with sweeping panoramic Bay and Peninsula views from nearly every room. The generous 2 BR/2BA floor plan features lovely carpet and tile, a beautiful chef's kitchen with ample cabinets and granite countertops, plus spa-like bathrooms. Enjoy the

Janet Russell David Lyng Real Estate

Beautifully remodeled 2/1 bath condo in the sought after area of Baywood. Private entrance and attached garage allow for privacy and security in this wonderful neighborhood. Proximate to downtown San Mateo with its vibrancy and restaurants. Easy access to highways 280 and 101. Excellent for executives and families alike.

David Cauchi Compass