Hillsborough, CA Homes for Sale

For the first time in over half a century, this remarkable family estate is opening its doors to a new chapter. Built in 1967 and held by the same family ever since, this is more than just a homeit is a rare opportunity to acquire a residence of incredible character and complete seclusion. The expansive floor plan is thoughtfully designed for both grand entertaining and intimate daily life,

Gina Haggarty Compass

Fully renovated and move-in ready, this 3 bed, 2 bath home offers 2,200 sq ft of thoughtfully updated living space on a beautifully secluded 9,090 sq ft lot. Surrounded by mature trees, the property features multiple private outdoor areas, including a spacious front patio ideal for entertaining and a serene backyard retreat. The home has undergone a complete top-to-bottom renovation, including

James Holt Elevate Group

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 Chen Christie'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

Becky Geller Compass

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

Stanley Lo Green Banker Realty

Located in desirable lower South Hillsborough, 255 Brentwood offers modern design, vaulted ceilings, exceptional natural light throughout, and seamless indoor-outdoor living. A striking front entry opens to a bright, welcoming foyer, leading into thoughtfully designed living spaces filled with natural light. The open kitchen and dining area serves as the heart of the homeperfect for both everyday

The Sharp Group KW Advisors

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

Built in 2011, this exceptional gated residence blends timeless architecture with modern luxury just minutes from Downtown Burlingame and close to acclaimed Hillsborough North Elementary and Crocker Middle School. Designer finishes throughout include Calacatta marble countertops, custom honed limestone fireplaces, hand-painted strié wall finishes, polished nickel Rohl fixtures, oil-rubbed bronze

Max Lo Green Banker Realty

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

Beyond the gates, perched atop a knoll w/ westerly hill views, a remarkable estate in the heart of Hillsborough. Fine luxury living is a timeless Craftsman built in 2009. Opulence begins at the front door to a grand foyer w/ soaring ceilings including a living room, a formal dining room, breakfast room, separate family room, & a gourmet chefs eat-in kitchen w/ custom cabinetry, Viking stainless

Chris Sabido eXp Realty of California Inc

*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

Stanley Lo Green Banker Realty

Occupying a premier setting in one of Hillsboroughs most prestigious enclaves, 260 Robin Road showcases exceptional craftsmanship and timeless design. This completely rebuilt estate offers over 3,800 square feet of refined living space, blending modern luxury with effortless livability. Designed for todays discerning buyer, the home features four luxurious bedroom suites and five beautifully

Denise Laugesen KW Advisors

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 Gilson Golden 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

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

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 Chen Christie's International Real Estate Sereno

A rare and irreplaceable work of art. Designed by renowned architect James H. Mitchell in the dramatic Art Deco/Art Moderne tradition, this is one of the Peninsula's most architecturally significant residences. Bold, streamlined geometry and masterful craftsmanship define every elevation of this striking 5,050± sq ft estate, while expansive wraparound decks and architecturally designed terraces

Jenn Gilson Golden Gate Sotheby's International 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

Nestled in Hillsborough's prestigious Ryan Tract, this exceptional residence blends privacy, convenience, & charm. Just minutes from Downtown Burlingame & Broadway, it offers easy access to Highway 101 and top-rated schools. A welcoming front porch leads into a bright & airy interior w/ hardwood floors, recessed LED lighting, and expansive windows. The elegant dining room features a bow window &

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

Welcome to 45 Calaveras Court, a brand-new modern masterpiece nestled in the Hillsborough hills. Located at the end of a private cul-de-sac on a sizable 4-acre lot, this stunning residence offers approximately 7,000 square feet of elegantly designed living space. Enjoy unobstructed canyon views from every window, providing a breathtaking backdrop to your everyday life. Step inside to discover

Pierre & Alex Buljan Compass

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

Alex Schauffert New Standard Realty

Welcome to this bright top floor condominium residence offering a unique blend of comfort and charm. One bedroom + den has multiple skylights that bathe the living space in sunshine throughout the day. Adjacent to the living room, the den provides an ideal space for home office, reading nook, or guest area. Kitchen, while compact, is efficiently laid out with ample cabinetry, updated appliances,

Louie Kappen Coldwell Banker Realty

Welcome to this bright and inviting 1-bed | 1-bath residence in the heart of coveted Burlingame Park. What an exceptional opportunity to own a piece of Peninsula real estate at an attractive price point with low HOA dues! Bathed in natural light, this thoughtfully designed home offers an airy open-concept layout featuring a timeless mid-century modern built-in workstation and a spacious dining

Heather Lin Compass

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

Light-Filled San Mateo Park Living With Close-In Convenience! Set at the end of a lane in sought-after San Mateo Park, this move-in ready home offers privacy and close-in convenience to shops and restaurants. Lovingly maintained by the same family for more than 40 years, this picture-perfect home is bright and light with fresh interior paint, refinished hardwood floors, and new carpet. Beyond the

Mark Johnson Coldwell Banker Realty

A Once-in-a-Lifetime Baywood Mediterranean | Iconic 1928 Architectural Gem Step inside this stunning 2BD/2BA, 1,310 sqft residence tucked inside one of San Mateo's most iconic 1928 Mediterranean buildings, set behind a lush, manicured courtyard in the coveted Baywood neighborhood. This is the kind of home buyers wait years to find. From the hand-painted Spanish tile entry and wood-beamed ceilings

Kristen Constantino Realty World-S.J.R.-Constantino Team

A quintessential Craftsman residence on one of Burlingames most coveted and picturesque streets, this exceptional property combines timeless architecture, remarkable privacy, and an extraordinary setting just blocks from vibrant Downtown Burlingame. Situated on a rare oversized L-shaped lot, the home is surrounded by enchanting, storybook gardens, mature landscaping, and incredible curb appeal

Pierre & Alex Buljan Compass

Set on a lush terraced hillside in one of San Mateos most desirable neighborhoods, this architecturally distinct 4BD/4BA residence offers a rare blend of privacy, natural beauty, and sophisticated indoor-outdoor living. Designed with a striking vertical layout connected by a newer elevator, the home maximizes both views and usable outdoor space. Expansive living and dining areas open seamlessly

Sophie Tsang Compass

Priced to sell with very motivated sellers, this 2 bedroom condo in prime Burlingame located in close proximity to Burlingame Avenue and downtown! Seller will credit 12 months of HOA dues to buyer. Spanning 993 square feet, this tastefully renovated condo boasts new hardwood floors throughout, updated open kitchen with new appliances, kitchen cabinets and counter tops,light fixtures and breakfast

Pepe Pimentel eRealty

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